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Journey information
Overview: Boston, MA to Chicago, IL flight
USAUSA
Flights from Boston, MA to Chicago, IL depart on average 53 times per day, taking around 3h 5m. Cheap flight tickets for this journey start at $73 (€59) if you book in advance.
There are 13 flights per day. The earliest flight runs at 00:06, the last at 22:34. The fastest flight covers the 850 miles (1368 km) distance in 2h 54m. July is the cheapest month to fly.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Distance 850 miles (1368 km) |
Average flight duration 3h 5m |
Cheapest ticket price $73 (€59) |
Flights per day 53 |
Direct flights 13 |
Fastest flight 2h 54m |
First flight 12:06 AM |
Last flight 10:34 PM |
Cheapest Month Jul |
Cheapest Day Wed |
High Season Jul - Sep |
Low Season Jan - Mar |
Busiest Day Thu |
Least Busy Day Sun |
Best time to book 6 days |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
The cheapest and fastest flights from Boston, MA to Chicago, IL
Showing times and prices for Aug 24
Cheapest price
$122
Average price
$299
Fastest journey
2 h 51 m
Average duration
2 h 54 m
Flights per day
78
Distance
1368 km
Cheap tickets
The best way to find a cheap flight ticket from Boston, MA to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Boston, MA to Chicago, IL will cost around $299 if you buy it on the day, but the cheapest tickets can be found for only $122.
Fast flights
Of the 78 flights that leave Boston, MA for Chicago, IL onMon, Aug 24, 22 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Mon, Aug 24 the direct flights cover the 1368 km distance in an average of 2 h 54 m but if you time it right, some flights will get you there in just 2 h 51 m .
On Mon, Aug 24 the longest flights will take 2 h 58 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
B63118:15 AM2h56Edward L. Logan International Airport10:11 AMO'Hare International Airport$1221One-way0 transfers- B6317 · B68054:55 PM6h03Edward L. Logan International Airport9:58 PMO'Hare International Airport$1261One-way1 transfer
AA31607:17 PM3h18Edward L. Logan International Airport9:35 PMO'Hare International Airport$1291One-way0 transfers- AA14793:53 PM3h11Edward L. Logan International Airport6:04 PMO'Hare International Airport$1291One-way0 transfers
- AA28375:45 PM3h19Edward L. Logan International Airport8:04 PMO'Hare International Airport$1291One-way0 transfers
UA50310:38 AM2h51Edward L. Logan International Airport12:29 PMO'Hare International Airport$1681One-way0 transfers- UA14753:30 PM2h52Edward L. Logan International Airport5:22 PMO'Hare International Airport$1681One-way0 transfers
- UA47212:27 PM2h53Edward L. Logan International Airport2:20 PMO'Hare International Airport$1681One-way0 transfers
- B63118:15 AM2h56Edward L. Logan International Airport10:11 AMO'Hare International Airport$1221One-way0 transfers
- UA10156:42 PM2h58Edward L. Logan International Airport8:40 PMO'Hare International Airport$1681One-way0 transfers
Travel Information
Compare train, bus, and flight for Boston, MA to Chicago, IL
Omio recommends booking the train as it is the most popular option from Boston, MA to Chicago, IL among Omio's users. If you are prioritising price take the flight with prices starting from $73. For those with little time consider booking a flight which can get you there in 3h 5m. In case you are seeking to minimise your carbon footprint the train is your best bet as it emits only 0.4 - 1.2kg. The ticket price range depends on the travel mode: a flight costs an average of $73, and a train costs an average of $89.
Distance: 850 miles (1368 km)
Compare flight with
| Flight | Most popular Train | Bus | Driving |
|---|---|---|---|
$156 Average price Cheapest | $251 Average price | $167 Average price | $307 Average price (fuel + tolls) |
6h 5m Average total duration Fastest 3h 5m Onboard + 3h 0m Additional time* | 22h 50m Average total duration 22h 20m Onboard + 30m Additional time* | 23h 54m Average total duration 23h 24m Onboard + 30m Additional time* | 14h 45m Average total duration (door-to-door) |
4.1 - 8.2kg CO2 emissions | 0.4 - 1.2kg CO2 emissions Lowest | 1.4 - 3.4kg CO2 emissions | - CO2 emissions |
Most popular airline |  Most popular train company |  Most popular bus company | Your own car or car rental |
Direct Options | Direct Options | Direct Options | Direct Options |
Additional time: Average total travel duration to departure point, security checks and transfers.
The cheapest way to travel from Boston, MA to Chicago, IL is a flight with an average price of $156 (€126).
This is compared to other travel options from Boston, MA to Chicago, IL:
A flight is $10 (€8) less than a bus for this route with tickets for a bus from Boston, MA to Chicago, IL costing on average $167 (€134).
A flight is $95 (€76) less than a train for this route with tickets for a train from Boston, MA to Chicago, IL costing on average $251 (€202).
The fastest way to travel from Boston, MA to Chicago, IL is by flight with an average journey time of 3h 5m.
Other travel options to Chicago, IL take longer:
Train takes on average 22h 20m.
Bus takes on average 23h 24m.
It's helpful to compare your options as there are 3 ways to travel between Boston, MA and Chicago, IL including taking a train, bus, and flight.
We recommend using the train as it is the most popular way to get from Boston, MA to Chicago, IL among Omio's users.
Live departures
Boston, MA to Chicago, IL flight times
The table below shows live departures for Boston, MA to Chicago, IL flights for today, Sunday, August 23. You can also manually refresh the results below to see updated flight journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| UA1734 · UA1252 | 5:45 AM Edward L. Logan International Airport | 7h08 | 11:53 AM O'Hare International Airport | 1 transfer | |
| UA1734 · UA1775 | 5:45 AM Edward L. Logan International Airport | 4h53 | 9:38 AM O'Hare International Airport | 1 transfer | |
| UA1734 · UA6137 · UA1178 | 5:45 AM Edward L. Logan International Airport | 8h19 | 1:04 PM O'Hare International Airport | 2 transfers | |
| UA1734 · UA6137 · UA5381 | 5:45 AM Edward L. Logan International Airport | 10h02 | 2:47 PM O'Hare International Airport | 2 transfers | |
| UA1833 · UA1253 | 6:00 AM Edward L. Logan International Airport | 7h59 | 12:59 PM O'Hare International Airport | 1 transfer | |
 AA4357 · AA4464 | 6:00 AM Edward L. Logan International Airport | 5h30 | 10:30 AM O'Hare International Airport | 1 transfer | |
| AA1540 · AA2095 | 6:00 AM Edward L. Logan International Airport | 6h08 | 11:08 AM O'Hare International Airport | 1 transfer | |
| UA1833 · UA2443 | 6:00 AM Edward L. Logan International Airport | 9h55 | 2:55 PM O'Hare International Airport | 1 transfer | |
| UA1414 | 6:01 AM Edward L. Logan International Airport | 2h59 | 8:00 AM O'Hare International Airport | 0 transfersDirect | |
| AA3324 | 6:14 AM Edward L. Logan International Airport | 3h06 | 8:20 AM O'Hare International Airport | 0 transfersDirect | |
AA4382+ AA3414 | 6:25 AM Edward L. Logan International Airport | 4h35 | 10:00 AM O'Hare International Airport | 1 transfer | |
| UA2631 | 7:05 AM Edward L. Logan International Airport | 2h59 | 9:04 AM O'Hare International Airport | 0 transfersDirect | |
| AA2715 · AA2742 | 7:07 AM Edward L. Logan International Airport | 6h08 | 12:15 PM O'Hare International Airport | 1 transfer | |
| AA1509 | 7:10 AM Edward L. Logan International Airport | 3h06 | 9:16 AM O'Hare International Airport | 0 transfersDirect | |
| AA4385 · AA4412 | 7:15 AM Edward L. Logan International Airport | 4h55 | 11:10 AM O'Hare International Airport | 1 transfer | |
| AA4385+AA1997 | 7:15 AM Edward L. Logan International Airport | 6h26 | 12:41 PM O'Hare International Airport | 1 transfer | |
| UA226 · UA2417 | 7:25 AM Edward L. Logan International Airport | 8h25 | 2:50 PM O'Hare International Airport | 1 transfer | |
| UA647 · UA2865 | 7:45 AM Edward L. Logan International Airport | 8h15 | 3:00 PM O'Hare International Airport | 1 transfer | |
| AA1348 · AA2742 | 8:00 AM Edward L. Logan International Airport | 5h15 | 12:15 PM O'Hare International Airport | 1 transfer | |
| AA2764 · AA865 | 8:00 AM Edward L. Logan International Airport | 5h11 | 12:11 PM O'Hare International Airport | 1 transfer | |
| UA717 | 8:05 AM Edward L. Logan International Airport | 2h59 | 10:04 AM O'Hare International Airport | 0 transfersDirect | |
| AA1239 | 8:27 AM Edward L. Logan International Airport | 3h03 | 10:30 AM O'Hare International Airport | 0 transfersDirect | |
| UA1349 | 9:00 AM Edward L. Logan International Airport | 2h56 | 10:56 AM O'Hare International Airport | 0 transfersDirect | |
| UA662 · UA617 | 9:35 AM Edward L. Logan International Airport | 8h30 | 5:05 PM O'Hare International Airport | 1 transfer | |
| AA547 | 10:28 AM Edward L. Logan International Airport | 3h01 | 12:29 PM O'Hare International Airport | 0 transfersDirect | |
| UA503 | 10:38 AM Edward L. Logan International Airport | 2h51 | 12:29 PM O'Hare International Airport | 0 transfersDirect | |
| UA2213 · UA1209 | 11:00 AM Edward L. Logan International Airport | 10h29 | 8:29 PM O'Hare International Airport | 1 transfer | |
| UA2213 · UA4464 · UA654 | 11:00 AM Edward L. Logan International Airport | 8h33 | 6:33 PM O'Hare International Airport | 2 transfers | |
| AA4687+AA788 | 11:53 AM Edward L. Logan International Airport | 6h05 | 4:58 PM O'Hare International Airport | 1 transfer | |
| UA414 · UA1131 | 11:55 AM Edward L. Logan International Airport | 9h26 | 8:21 PM O'Hare International Airport | 1 transfer | |
| UA414 · UA1023 | 11:55 AM Edward L. Logan International Airport | 8h35 | 7:30 PM O'Hare International Airport | 1 transfer | |
| AA3048 | 11:58 AM Edward L. Logan International Airport | 3h01 | 1:59 PM O'Hare International Airport | 0 transfersDirect | |
| AA4760+AA4143 | 11:59 AM Edward L. Logan International Airport | 5h21 | 4:20 PM O'Hare International Airport | 1 transfer | |
| AA4405+AA3907 | 12:22 PM Edward L. Logan International Airport | 5h01 | 4:23 PM O'Hare International Airport | 1 transfer | |
| UA472 | 12:27 PM Edward L. Logan International Airport | 2h53 | 2:20 PM O'Hare International Airport | 0 transfersDirect | |
| AA2086 · AA470 | 12:56 PM Edward L. Logan International Airport | 5h05 | 5:01 PM O'Hare International Airport | 1 transfer | |
| AA4533 | 1:01 PM Edward L. Logan International Airport | 3h14 | 3:15 PM O'Hare International Airport | 0 transfersDirect | |
| UA1976 · UA2197 | 1:41 PM Edward L. Logan International Airport | 8h51 | 9:32 PM O'Hare International Airport | 1 transfer | |
| AA3711 | 2:00 PM Edward L. Logan International Airport | 3h05 | 4:05 PM O'Hare International Airport | 0 transfersDirect | |
| UA721 · UA2497 | 2:28 PM Edward L. Logan International Airport | 5h09 | 6:37 PM O'Hare International Airport | 1 transfer | |
| AA885 · AA2488 | 2:37 PM Edward L. Logan International Airport | 6h09 | 7:46 PM O'Hare International Airport | 1 transfer | |
| UA2297 · UA2258 | 3:10 PM Edward L. Logan International Airport | 8h36 | 10:46 PM O'Hare International Airport | 1 transfer | |
| UA1475 | 3:30 PM Edward L. Logan International Airport | 2h52 | 5:22 PM O'Hare International Airport | 0 transfersDirect | |
| UA1183 · UA1752 | 3:45 PM Edward L. Logan International Airport | 8h41 | 11:26 PM O'Hare International Airport | 1 transfer | |
| UA411 · UA546 | 4:05 PM Edward L. Logan International Airport | 7h10 | 10:15 PM O'Hare International Airport | 1 transfer | |
| UA411 · UA1225 | 4:05 PM Edward L. Logan International Airport | 5h55 | 9:00 PM O'Hare International Airport | 1 transfer | |
| UA2040 | 5:01 PM Edward L. Logan International Airport | 2h59 | 7:00 PM O'Hare International Airport | 0 transfersDirect | |
| AA4678+AA3570 | 5:22 PM Edward L. Logan International Airport | 5h18 | 9:40 PM O'Hare International Airport | 1 transfer | |
| AA2837 | 5:45 PM Edward L. Logan International Airport | 3h19 | 8:04 PM O'Hare International Airport | 0 transfersDirect | |
| AA4639+AA2057 | 5:53 PM Edward L. Logan International Airport | 5h37 | 10:30 PM O'Hare International Airport | 1 transfer | |
| UA1693 · UA1347 | 6:07 PM Edward L. Logan International Airport | 6h15 | 11:22 PM O'Hare International Airport | 1 transfer | |
| UA1693 · UA546 | 6:07 PM Edward L. Logan International Airport | 5h08 | 10:15 PM O'Hare International Airport | 1 transfer | |
| UA1015 | 6:42 PM Edward L. Logan International Airport | 2h58 | 8:40 PM O'Hare International Airport | 0 transfersDirect | |
| UA371 · UA1347 | 7:00 PM Edward L. Logan International Airport | 5h22 | 11:22 PM O'Hare International Airport | 1 transfer | |
| AA3160 | 7:17 PM Edward L. Logan International Airport | 3h18 | 9:35 PM O'Hare International Airport | 0 transfersDirect | |
| UA2136 · UA421 | 7:23 PM Edward L. Logan International Airport | 5h17 | 11:40 PM O'Hare International Airport | 1 transfer | |
| AA1004+AA4450 | 7:43 PM Edward L. Logan International Airport | 4h54 | 11:37 PM O'Hare International Airport | 1 transfer | |
| UA2229 | 8:31 PM Edward L. Logan International Airport | 2h59 | 10:30 PM O'Hare International Airport | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
How far in advance should I book flight tickets from Boston, MA to Chicago, IL?
The best time to book your flight from Boston, MA to Chicago, IL is 42 days before departure. See how prices for flights change on the Boston, MA to Chicago, IL route.
Prices are for one-way tickets for one passenger from Boston, MA to Chicago, IL per month. Insights are sourced from fares found by Omio users in the last 12 months. Current prices may differ as prices vary depending on the time of day, class or how far in advance you book your flight from Boston, MA to Chicago, IL.
Flights
from $184Trains
from $160Buses
from $113Compare prices and tickets Boston, MA to Chicago, IL by train, bus, or flight
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
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Why should you book Boston, MA to Chicago, IL flights with Omio?
American Airlines as well as United, JetBlue Airways, Spirit Airlines, Republic Airlines and more offer flights services from Boston, MA to Chicago, IL.
Omio is an official ticket reseller for all your travel options from Boston, MA to Chicago, IL.
Why book with Omio vs American Airlines?
- Compare with other providers: On Omio, you can not only buy tickets for American Airlines, but also compare tickets for the likes of United, JetBlue Airways, Spirit Airlines or Republic Airlines to find the best option for your trip from Boston, MA to Chicago, IL.
- Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
- Compare all your options: Omio allows you to compare American Airlines with all available travel options, which are train, bus and flight to ensure you get the best deal for traveling from Boston, MA to Chicago, IL.
Why book with Omio over Trip, Edreams or Skyscanner?
- Compare with other providers: On Omio, you can also compare tickets for the likes of United, JetBlue Airways, Spirit Airlines or Republic Airlines to find the best option for your trip from Boston, MA to Chicago, IL.
- Multiple modes of transport: Omio allows you to compare travel options including train, bus and flight to find the ideal travel option from Boston, MA to Chicago, IL.
Airlines: American Airlines, United, JetBlue Airways, Spirit Airlines, Republic Airlines from Boston, MA to Chicago, ILFind the best flights between Boston, MA to Chicago, IL with Omio's travel partners American Airlines, United, JetBlue Airways, Spirit Airlines, Republic Airlines from $73 (€59). We can find you the best deals, schedules and tickets when comparing and booking the best trip.
United
About
United Airlines, established in 1926, is a major U.S. airline headquartered in Chicago, Illinois. Operating an extensive domestic and international network, United serves more destinations than any other airline, connecting travelers across six continents. The airline's eight hubs include Chicago–O'Hare, Denver, Houston–Intercontinental, Los Angeles, Newark, San Francisco, Washington–Dulles, and Guam. As a founding member of the Star Alliance, United offers a comprehensive range of services, including regional flights through United Express, catering to both leisure and business travelers. The airline is committed to sustainability, investing in sustainable aviation fuel and innovative technologies to reduce its environmental impact.
Luggage & cancellation policy
Average Duration
2h 58m
Cheapest Price
$134 (€108)
United frequency
35 a day
Luggage included
Carry-on baggage allowance is 7kg total (2 pieces max. ) for both Choice and Flex fares on United Airlines and Virgin Australia flights.
Additional luggage
Excess baggage fees apply for additional checked luggage beyond the standard allowance.
Luggage storage
Both airlines provide checked baggage services for storing luggage during flights.
Cancellation Policy
Cancellation fees apply per person, per booking, with specific fees for different fare types.
Refund
Not applicable to flights; however, full refunds are available if flights are canceled by the airline.
Pregnant on board
Pregnant passengers are permitted to travel, with specific guidelines and medical certificates required after a certain gestational period.
Unaccompagned minor
Unaccompanied minors are permitted to travel, with specific age restrictions and services provided.
Amenities on board the airplane
Wifi
Food sold onboard
Meals and snacks are included on international flights operated by United Airlines and Virgin Australia.
Seat reservation
Seat selection may incur additional fees, depending on the fare type and airline.
Toilets
USB plugs
Accessibility
United Airlines and Virgin Australia offer services to and within Australia, providing accessible travel options for passengers with mobility needs.
Bikes
Both airlines permit bicycles onboard, with specific guidelines and fees.
Pets
United Airlines and Virgin Australia allow pets onboard, subject to specific policies and fees.
JetBlue Airways
About
JetBlue Airways is a U.S.-based low-cost airline headquartered in Long Island City, New York. Established in 1998, it operates over 850 daily flights to 86 destinations across the U.S., Caribbean, and Latin America. The airline is known for its customer-friendly services, including complimentary Wi-Fi, free snacks, and spacious seating. JetBlue's fleet comprises various Airbus models, such as the A220, A320, and A321, as well as the Embraer E190. The company is committed to sustainability and has implemented initiatives to reduce its environmental impact. Joanna Geraghty serves as the CEO, leading a team of approximately 23,000 employees.
Luggage & cancellation policy
Average Duration
2h 55m
Cheapest Price
$98 (€79)
JetBlue Airways frequency
5 a day
Luggage included
JetBlue's standard fare includes one checked bag and one carry-on bag.
Additional luggage
Additional luggage can be added for a fee, subject to availability.
Luggage storage
JetBlue offers overhead bin space for carry-on luggage and checked baggage services.
Cancellation Policy
JetBlue allows cancellations within 24 hours of booking for a full refund; after 24 hours, cancellation fees may apply.
Pregnant on board
JetBlue allows pregnant passengers to fly up to 36 weeks gestation without a medical certificate.
Unaccompagned minor
JetBlue allows unaccompanied minors aged 5-13 to travel for a fee, with specific guidelines.
Amenities on board the airplane
Wifi
Food sold onboard
JetBlue offers complimentary snacks and non-alcoholic beverages on all flights.
Seat reservation
JetBlue offers Even More Space seats for an additional fee, providing extra legroom and priority boarding.
Toilets
USB plugs
Accessibility
JetBlue Airways provides accessible services for passengers with disabilities, including wheelchair assistance and priority boarding.
Bikes
JetBlue accepts bicycles as checked baggage for a fee, with specific packaging requirements.
Pets
JetBlue allows pets in the cabin for a fee, with specific guidelines on pet carriers and weight limits.
American Airlines
About
American Airlines is one of the largest airlines in the world, connecting travelers to hundreds of destinations across the United States, Latin America, Europe, Asia, and beyond. Operating from major hubs such as Dallas/Fort Worth, Miami, and Charlotte, American offers a wide range of travel options. Passengers can choose from Economy with affordable fares, Premium Economy with extra space, or Business and First Class featuring flat-bed seats, premium dining, and lounge access. With a modern fleet and membership in the oneworld alliance, American Airlines combines global reach with comfort and reliability.
Luggage & cancellation policy
Average Duration
2h 54m
Cheapest Price
$73 (€59)
American Airlines frequency
18 a day
Luggage included
1 carry-on bag (22 x 14 x 9 inches) and 1 personal item (18 x 14 x 8 inches) included in most fares
Additional luggage
Checked bags fees vary by route. First checked bag typically $30, second $40 on domestic flights
Cancellation Policy
Basic Economy tickets cannot be changed or refunded. Other fares allow changes with fee, refunds subject to fare rules.
Pregnant on board
Passengers can fly up to 36 weeks for single pregnancies, 32 weeks for multiple pregnancies. Medical certificate required within 7 days of departure if within 4 weeks of due date.
Unaccompagned minor
Children ages 5-14 can travel alone using American Airlines Unaccompanied Minor Service. Service fee is $150 each way.
Amenities on board the airplane
Wifi
Food sold onboard
USB plugs
Accessibility
American Airlines provides wheelchair assistance and special services for passengers with disabilities. Assistance must be requested at least 48 hours before departure.
Pets
Small dogs and cats allowed in cabin for $125 fee. Must be in approved carrier under seat. Service animals allowed.
Spirit Airlines
About
Spirit Airlines is an American ultra-low-cost carrier, headquartered in Dania Beach, Florida, operating scheduled flights throughout the United States, the Caribbean, and Latin America. Known for its distinctive bright yellow planes, Spirit's business model traditionally focuses on offering low base fares by unbundling services, allowing passengers to pay only for the amenities they choose, such as baggage and seat selection. As of August 2024, Spirit is evolving its offerings, introducing new fare tiers like "Go Big," "Go Comfy," "Go Savvy," and "Go," which include various bundled perks such as wider seats, extra legroom, priority boarding, and in-flight refreshments. Spirit was the seventh largest passenger carrier in North America as of 2023.
Luggage & cancellation policy
Average Duration
7h 33m
Cheapest Price
$191 (€154)
Spirit Airlines frequency
3 a day
Luggage included
Personal item (18 x 14 x 8 inches) included
Additional luggage
Checked bags: First bag $79-89, Second bag $89-99, Additional bags $105-110
Cancellation Policy
Cancellation within 24 hours of booking is free, after that fees apply based on fare type and timing
Pregnant on board
Up to 7 days before departure with medical certificate. After 28 weeks, medical certificate required
Unaccompagned minor
Ages 5-14 can travel as unaccompanied minors for $100 fee per direction. Service not available on international flights or connecting flights
Amenities on board the airplane
Wifi
Accessibility
Spirit Airlines offers assistance for passengers with disabilities, including wheelchair services and priority boarding. Passengers are encouraged to request assistance at least 48 hours in advance to ensure availability.
Republic Airlines
About
Republic Airways is a major regional airline in the United States, operating as a subsidiary of Republic Airways Holdings. It provides scheduled passenger service for American Airlines (as American Eagle), Delta Air Lines (as Delta Connection), and United Airlines (as United Express) using a fleet of Embraer 170 and 175 regional jets. Headquartered in Indianapolis, Indiana, Republic Airways operates over 900 daily flights to more than 80 cities across the U.S. and Canada. The company is known for its large fleet of Embraer E-Jets and its state-of-the-art training facilities. In April 2025, Republic Airways Holdings announced its acquisition of Mesa Air Group, which is expected to create the second-largest regional carrier in the U.S.
Luggage & cancellation policy
Average Duration
3h 2m
Cheapest Price
$218 (€175)
Republic Airlines frequency
5 a day
Luggage included
One carry-on bag (24 x 16 x 10) and one personal item
Additional luggage
Checked bags for a fee
Cancellation Policy
Tickets are non-refundable but may be cancelled for future flight credit minus applicable fees
Pregnant on board
Passengers can fly up to the end of their 36th week for single pregnancies and the end of their 32nd week for multiple pregnancies
Unaccompagned minor
Unaccompanied minor service is available for children ages 5-14. Must be booked directly with Republic Airlines
Amenities on board the airplane
USB plugs
Accessibility
Republic Airlines offers assistance for passengers with reduced mobility, including wheelchair services and priority boarding. Passengers are advised to request these services in advance to ensure availability and proper arrangements.
Complete guide to Chicago, IL
Things to do in Chicago, IL
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
- Must visit
Field Museum
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
- Must visit
Museum of Science and Industry
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
- Must visit
Millennium Park
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
- Must visit
Magnificent Mile
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
- Must visit
Chicago Riverwalk
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-Dish Pizza
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
Chicago-Style Hot Dog
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian Beef Sandwich
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Johnnie's Beef
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Superdawg Drive-In
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
Alinea
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
US dollar ($)
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Average meal costs
- Budget
- $10-18 for fast food or casual takeout.
- Mid-range
- $20-40 per person for a restaurant meal.
- Fine dining
- $75+ per person for upscale restaurants.
- Coffee
- $3-6 for coffee or cappuccino.
Tipping culture
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
FAQs: Boston, MA to Chicago, IL Flight
Find answers to the most common questions about traveling from Boston, MA to Chicago, IL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.
Cheap plane tickets from Boston, MA to Chicago, IL can start from as little as $73 (€59) when you book in advance. The average flight ticket price for Boston, MA to Chicago, IL is $156 (€126) ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The average journey time by plane from Boston, MA to Chicago, IL is 2h 54m to travel the 850 miles (1368 km) long route. Journey times can vary on weekends and holidays, so use our Journey Planner to search for a specific date.
The earliest flight from Boston, MA to Chicago, IL leaves at 12:06 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Boston, MA to Chicago, IL leaves at 10:34 PM.
Yes, there are 13 direct flights a day from Boston, MA to Chicago, IL with American Airlines, United, JetBlue Airways, Republic Airlines. Schedules can vary on holidays or weekends with fewer direct flights.
When taking a flight from Boston, MA to Chicago, IL, you can count on American Airlines, United, JetBlue Airways, Spirit Airlines, Republic Airlines for the best way to get you to Chicago, IL. You can also check all possible airlines who offer a service between Boston, MA and Chicago, IL and compare the amenities they offer before buying a plane ticket.
Flights from Boston, MA to Chicago, IL generally leave from Edward L. Logan International Airport and arrive in O'Hare International Airport.Edward L. Logan International Airport is 1 miles (2 km) away from Boston, MA city centre and O'Hare International Airport is 1 miles (3 km) from Chicago, IL city centre.
The cheapest month for a flight from Boston, MA to Chicago, IL is July.
It's helpful to compare your options as there are 3 ways to travel between Boston, MA and Chicago, IL including taking a train, bus, and flight.
Since neither Boston, MA nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
There is a time difference of 1 h between Boston, MA and Chicago, IL all year round.
The best events to attend in Chicago, IL include:
- Chicago Air and Water Show, an exhilarating display of military and civilian aircraft performing daring maneuvers over Lake Michigan
- Lollapalooza, a massive music festival featuring top artists across multiple genres in Grant Park
- Chicago Gourmet, a premier culinary event celebrating the city's vibrant food scene with tastings, cooking demonstrations, and wine pairings.
Some of the most interesting sights to explore in Chicago, IL are:
- Millennium Park, a public park known for its modern art installations and the iconic Cloud Gate sculpture
- Art Institute of Chicago, a renowned museum housing an extensive collection of art from around the world
- Navy Pier, a popular entertainment destination featuring rides, restaurants, and lakefront views
- Willis Tower Skydeck, an observation deck offering panoramic views of the city from one of the tallest buildings in the Western Hemisphere
- Field Museum, a natural history museum with vast exhibits including the famous T. rex skeleton, Sue.
The best holidays to experience in Chicago, IL include:
- Memorial Day, the unofficial start of summer with vibrant outdoor activities and events
- Independence Day, spectacular fireworks and festive celebrations throughout the city
- Labor Day, a lively atmosphere with various festivals and pleasant weather.
The best things to do in Chicago, IL include:
- Museum of Science and Industry, an interactive museum featuring exhibits on science, technology, and industry
- Explore the vibrant neighborhoods of Chicago, such as Wicker Park and Lincoln Park, known for their unique shops and eateries
- Take a river cruise to see the city's iconic architecture from a different perspective
- Attend a live performance at the historic Chicago Theatre
- Enjoy a day at Lincoln Park Zoo, one of the oldest zoos in the U.S., offering free admission.
The best season to visit Chicago, IL is Spring or Summer. The best weather to explore Chicago, IL is during May-September.
We recommend using the train as it is the most popular way to get from Boston, MA to Chicago, IL among Omio's users.
For domestic flights we recommend to arrive 1.5 to 2 hours before departure. Please check the website of your departure airport if in doubt. Some airports may offer booking time slots for security checks or offer additional information on when to get there based on time of day.
Most airlines permit carry-on bags that fit within specific dimensions (e.g., 22 x 14 x 9 inches or 56 x 36 x 23 cm), including handles and wheels. Bags must fit in the overhead bin or under the seat in front of you.
Many airlines impose weight limits, commonly ranging between 7 kg (15 lbs) and 12 kg (26 lbs). Typically, passengers are allowed one carry-on bag and one personal item (for example a purse, laptop bag, or backpack). Personal items must fit under the seat in front of you. Budget Airlines (like Ryanair or Wizz Air) have stricter size and weight limits, often requiring fees for larger carry-ons. Full-Service Airlines have more lenient policies, sometimes including more spacious dimensions or higher weight limits depending on your ticket class.
The list of items prohibited on an airplane varies by country and airline, but in general, the following items are not allowed in carry-on or checked baggage: Weapons and self-defence items, sharp objects, flammable materials, explosives, toxic substances, or liquids over 100ml (except for medications and baby essentials). In checked baggage, firearms (without authorization), explosives, large lithium batteries, and hazardous chemicals are prohibited. Electronic cigarettes must be in carry-on bags, while alcohol and dry ice have restrictions. Always check with your airline for specific regulations.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
popular airports
Popular airports from Boston, MA to Chicago, IL
Most Boston, MA to Chicago, IL flights use the Edward L. Logan International Airport to O'Hare International Airport airport pair. Use this guide to compare Boston, MA and Chicago, IL airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
Departure airports in Boston
Arrival airports in Chicago
Which Boston, MA airport do flights to Chicago, IL leave from?
Flights from Boston, MA to Chicago, IL depart from Edward L. Logan International Airport. The airport is 1 miles (3 km) from Boston, MA city centre at 1 Harborside Dr, Boston, MA 02128, USA.
Edward L. Logan International Airport (BOS)1 Harborside Dr, Boston, MA 02128, USA
City-centre transport
Getting to Edward L. Logan International Airport from Boston city centre
Edward L. Logan International Airport is 2 km from Boston city centre. Public transport options include:
Bus22, 221, 551, 55, 552 · 6m · $10 · every ~66 min
Southbound · 14m · $5 · every ~1 min
Bb · 14m · $10 · every ~4 min
Sl1 · 15m · $5 · every ~15 min
Hanover, Boston South Station · 15m · $1 · every ~1 min
Hyannis - South Shore to Logan Airport, Woods Hole to Boston/Logan Airport · 25m · $11 · every ~2 min
Edward L. Logan International Airport airport facilities and services
Edward L. Logan International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food and drink
Food options include: Restaurants are available in all terminals, including Legal Sea Foods (seafood) and Wahlburgers (American).
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located throughout the airport, near gates and publicas.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at Edward L. Logan International Airport: Parking, Taxis, WC.
Bike and car services
Available at Edward L. Logan International Airport: Car Rental.
Accessibility
Accessibility facilities are available at Edward L. Logan International Airport: Elevators, ramps.
Shops, hotels and contact
Nearby hotels include Hotels within walking distance, including Hilton Boston Logan Airport..
Which Chicago, IL airport do flights from Boston, MA arrive at?
Flights from Boston, MA to Chicago, IL arrive at O'Hare International Airport. O'Hare International Airport is 2 miles (4 km) from Chicago, IL city centre.
O'Hare International Airport (ORD)10000 W O'Hare Ave, Chicago, IL 60666, USA
City-centre transport
Getting to O'Hare International Airport from Chicago city centre
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
SubwayBlue Line · 1h 7m · $6 · every ~23 min
O'Hare International Airport airport facilities and services
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food and drink
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at O'Hare International Airport: Parking, Taxis, WC.
Bike and car services
Available at O'Hare International Airport: Car Rental.
Accessibility
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Shops, hotels and contact
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
More options for your journey from Boston, MA to Chicago, IL
Here are some other resources that might have the information you need
Most popular flights to and from Chicago, IL and Boston, MA
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