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Journey information
Overview: Chicago, IL to Boston, MA flight
USAUSA
Flights from Chicago, IL to Boston, MA depart on average 33 times per day, taking around 2h 35m. Cheap flight tickets for this journey start at $137 (€111) if you book in advance.
There are 9 flights per day. The earliest flight runs at 00:06, the last at 22:12. The fastest flight covers the 850 miles (1368 km) distance in 2h 26m. August 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 2h 35m |
Cheapest ticket price $137 (€111) |
Flights per day 33 |
Direct flights 9 |
Fastest flight 2h 26m |
Cheapest month to travel August |
First flight 00:06 |
Last flight 22:12 |
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 Chicago, IL to Boston, MA
Showing times and prices for Nov 14
Cheapest price
$235
Average price
$464
Fastest journey
2 h 15 m
Average duration
2 h 19 m
Flights per day
66
Distance
1368 km
Cheap tickets
The best way to find a cheap flight ticket from Chicago, IL to Boston, MA is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Boston, MA will cost around $464 if you buy it on the day, but the cheapest tickets can be found for only $235.
Fast flights
Of the 66 flights that leave Chicago, IL for Boston, MA onFri, Nov 14, 19 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Fri, Nov 14 the direct flights cover the 1368 km distance in an average of 2 h 19 m but if you time it right, some flights will get you there in just 2 h 15 m .
On Fri, Nov 14 the longest flights will take 2 h 20 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.
AA250403:08PM2h21
O'Hare International Airport06:29PMEdward L. Logan International Airport
$2351One-way
0 transfers
AA460606:51AM2h27
O'Hare International Airport10:18AMEdward L. Logan International Airport
$2351One-way
0 transfers
AA438407:12PM2h32
O'Hare International Airport10:44PMEdward L. Logan International Airport
$2351One-way
0 transfers
AA46905:10PM2h20
O'Hare International Airport08:30PMEdward L. Logan International Airport
$2351One-way
0 transfers
AA144301:04PM2h28
O'Hare International Airport04:32PMEdward L. Logan International Airport
$2351One-way
0 transfers
UA210406:15AM2h15
O'Hare International Airport09:30AMEdward L. Logan International Airport
$2821One-way
0 transfers
UA206707:15AM2h19
O'Hare International Airport10:34AMEdward L. Logan International Airport
$2821One-way
0 transfers
AA46905:10PM2h20
O'Hare International Airport08:30PMEdward L. Logan International Airport
$2351One-way
0 transfers
UA169301:55PM2h20
O'Hare International Airport05:15PMEdward L. Logan International Airport
$2821One-way
0 transfers
UA167704:00PM2h20
O'Hare International Airport07:20PMEdward L. Logan International Airport
$2821One-way
0 transfers
Travel Information
Compare train, bus, and flight for Chicago, IL to Boston, MA
Omio recommends booking the train as it is the most popular option from Chicago, IL to Boston, MA among Omio's users. If you are prioritising price take the bus with prices starting from €119. For those with little time consider booking a flight which can get you there in 2h 35m. 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 bus costs an average of €119, and a train costs an average of €458.
Distance: 850 miles (1368 km)
Compare flight with
| Flight | Most popular Train | Bus |
|---|---|---|
€180 Average price | €543 Average price | €172 Average price Cheapest |
5h 35m Average total duration Fastest 2h 35m Onboard + 3h 0m Additional time* | 22h 38m Average total duration 22h 8m Onboard + 30m Additional time* | 25h 35m Average total duration 25h 5m Onboard + 30m Additional time* |
4.1 - 8.2kg CO2 emissions | 0.4 - 1.2kg CO2 emissions Lowest | 1.4 - 3.4kg CO2 emissions |
Most popular airline |  Most popular train company |  Most popular bus company |
Direct Options | Direct Options | Direct Options |
Additional time: Average total travel duration to departure point, security checks and transfers.
Live departures
Chicago, IL to Boston, MA flight times
The table below shows live departures for Chicago, IL to Boston, MA flights for today, Thursday, November 13. You can also manually refresh the results below to see updated flight journeys.
Last updated at 3:38 AM
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| UA2066 · UA1429 | 12:00 PM O'Hare International Airport | 7h29 | 7:29 PM Edward L. Logan International Airport | 1 transfer | |
| UA1658 · UA593 | 12:02 PM O'Hare International Airport | 5h26 | 5:28 PM Edward L. Logan International Airport | 1 transfer | |
 AA3710 | 12:05 PM O'Hare International Airport | 2h24 | 2:29 PM Edward L. Logan International Airport | 0 transfersDirect | |
| UA2104 | 12:15 PM O'Hare International Airport | 2h15 | 2:30 PM Edward L. Logan International Airport | 0 transfersDirect | |
| AA3019+AA4454 | 12:25 PM O'Hare International Airport | 4h01 | 4:26 PM Edward L. Logan International Airport | 1 transfer | |
 B62106 · B6418 | 12:45 PM O'Hare International Airport | 7h15 | 8:00 PM Edward L. Logan International Airport | 1 transfer | |
| AA1854 · AA2615 | 12:50 PM O'Hare International Airport | 4h32 | 5:22 PM Edward L. Logan International Airport | 1 transfer | |
| AA4606 | 12:51 PM O'Hare International Airport | 2h27 | 3:18 PM Edward L. Logan International Airport | 0 transfersDirect | |
| UA791 · UA2461 | 1:10 PM O'Hare International Airport | 7h32 | 8:42 PM Edward L. Logan International Airport | 1 transfer | |
| UA2067 | 1:15 PM O'Hare International Airport | 2h19 | 3:34 PM Edward L. Logan International Airport | 0 transfersDirect | |
| UA563 · UA593 | 1:15 PM O'Hare International Airport | 4h13 | 5:28 PM Edward L. Logan International Airport | 1 transfer | |
| UA1195 · UA1701 | 1:30 PM O'Hare International Airport | 10h02 | 11:32 PM Edward L. Logan International Airport | 1 transfer | |
| AA1242+AA4103 | 2:02 PM O'Hare International Airport | 4h00 | 6:02 PM Edward L. Logan International Airport | 1 transfer | |
| AA3600 | 2:05 PM O'Hare International Airport | 2h28 | 4:33 PM Edward L. Logan International Airport | 0 transfersDirect | |
| AA2814 · AA821 | 2:20 PM O'Hare International Airport | 5h13 | 7:33 PM Edward L. Logan International Airport | 1 transfer | |
| UA2638 · UA350 | 2:50 PM O'Hare International Airport | 7h53 | 10:43 PM Edward L. Logan International Airport | 1 transfer | |
| UA1357 · UA1709 | 2:50 PM O'Hare International Airport | 4h39 | 7:29 PM Edward L. Logan International Airport | 1 transfer | |
| UA2301 · UA577 | 3:15 PM O'Hare International Airport | 5h07 | 8:22 PM Edward L. Logan International Airport | 1 transfer | |
| UA618 | 3:20 PM O'Hare International Airport | 2h24 | 5:44 PM Edward L. Logan International Airport | 0 transfersDirect | |
| AA1457 | 3:20 PM O'Hare International Airport | 2h28 | 5:48 PM Edward L. Logan International Airport | 0 transfersDirect | |
| AA4778+AA3243 | 3:53 PM O'Hare International Airport | 5h45 | 9:38 PM Edward L. Logan International Airport | 1 transfer | |
| UA1803 · UA597 | 4:40 PM O'Hare International Airport | 8h15 | 12:55 AM Edward L. Logan International Airport | 1 transfer | |
| UA399 | 4:48 PM O'Hare International Airport | 2h20 | 7:08 PM Edward L. Logan International Airport | 0 transfersDirect | |
 NK2049 · NK850 | 4:52 PM O'Hare International Airport | 12h07 | 4:59 AM Edward L. Logan International Airport | 1 transfer | |
| UA2389 · UA1697 · UA1701 | 4:55 PM O'Hare International Airport | 6h37 | 11:32 PM Edward L. Logan International Airport | 2 transfers | |
| UA2467 · UA3701 · UA2001 | 4:55 PM O'Hare International Airport | 9h25 | 2:20 AM Edward L. Logan International Airport | 2 transfers | |
| UA2467 · UA6190 · UA688 | 4:55 PM O'Hare International Airport | 6h53 | 11:48 PM Edward L. Logan International Airport | 2 transfers | |
| UA2467 · UA3701 · UA1701 | 4:55 PM O'Hare International Airport | 6h37 | 11:32 PM Edward L. Logan International Airport | 2 transfers | |
| UA1126 · UA2630 | 5:01 PM O'Hare International Airport | 5h21 | 10:22 PM Edward L. Logan International Airport | 1 transfer | |
| B6312 | 5:20 PM O'Hare International Airport | 2h24 | 7:44 PM Edward L. Logan International Airport | 0 transfersDirect | |
| AA3159+AA4599 | 5:20 PM O'Hare International Airport | 4h01 | 9:21 PM Edward L. Logan International Airport | 1 transfer | |
| AA603 · AA3243 | 5:40 PM O'Hare International Airport | 3h58 | 9:38 PM Edward L. Logan International Airport | 1 transfer | |
| AA603 · AA2493 | 5:40 PM O'Hare International Airport | 4h44 | 10:24 PM Edward L. Logan International Airport | 1 transfer | |
| AA2254+AA4724 | 5:40 PM O'Hare International Airport | 4h42 | 10:22 PM Edward L. Logan International Airport | 1 transfer | |
| UA1205 · UA2630 | 5:50 PM O'Hare International Airport | 4h32 | 10:22 PM Edward L. Logan International Airport | 1 transfer | |
 AA6332+AA3416 | 6:13 PM O'Hare International Airport | 5h15 | 11:28 PM Edward L. Logan International Airport | 1 transfer | |
| UA2657 · UA2439 | 6:45 PM O'Hare International Airport | 7h50 | 2:35 AM Edward L. Logan International Airport | 1 transfer | |
| UA1262 | 6:50 PM O'Hare International Airport | 2h20 | 9:10 PM Edward L. Logan International Airport | 0 transfersDirect | |
| UA3601 · UA3433 · UA2001 | 6:59 PM O'Hare International Airport | 7h21 | 2:20 AM Edward L. Logan International Airport | 2 transfers | |
| UA3601 · UA2645 · UA2001 | 6:59 PM O'Hare International Airport | 7h21 | 2:20 AM Edward L. Logan International Airport | 2 transfers | |
| UA2090 · UA716 | 7:00 PM O'Hare International Airport | 7h50 | 2:50 AM Edward L. Logan International Airport | 1 transfer | |
| UA2746 · UA688 | 7:00 PM O'Hare International Airport | 4h48 | 11:48 PM Edward L. Logan International Airport | 1 transfer | |
| AA1443 | 7:04 PM O'Hare International Airport | 2h28 | 9:32 PM Edward L. Logan International Airport | 0 transfersDirect | |
| AA2345 · AA2148 | 7:15 PM O'Hare International Airport | 4h45 | 12:00 AM Edward L. Logan International Airport | 1 transfer | |
| UA1693 | 7:55 PM O'Hare International Airport | 2h20 | 10:15 PM Edward L. Logan International Airport | 0 transfersDirect | |
| UA310 · UA3420 · UA278 | 8:20 PM O'Hare International Airport | 7h28 | 3:48 AM Edward L. Logan International Airport | 2 transfers | |
| UA2091 · UA1929 · UA278 | 8:20 PM O'Hare International Airport | 7h28 | 3:48 AM Edward L. Logan International Airport | 2 transfers | |
| UA310 · UA6362 · UA755 | 8:20 PM O'Hare International Airport | 8h22 | 4:42 AM Edward L. Logan International Airport | 2 transfers | |
| UA2091 · UA2645 · UA2001 | 8:20 PM O'Hare International Airport | 6h00 | 2:20 AM Edward L. Logan International Airport | 2 transfers | |
| UA1373 · UA1076 | 8:21 PM O'Hare International Airport | 7h54 | 4:15 AM Edward L. Logan International Airport | 1 transfer | |
| UA587 · UA755 | 8:39 PM O'Hare International Airport | 8h03 | 4:42 AM Edward L. Logan International Airport | 1 transfer | |
| UA1485 · UA1587 | 8:40 PM O'Hare International Airport | 7h59 | 4:39 AM Edward L. Logan International Airport | 1 transfer | |
| AA2840 · AA2990 | 8:50 PM O'Hare International Airport | 4h32 | 1:22 AM Edward L. Logan International Airport | 1 transfer | |
AA4680+ AA5928 | 9:01 PM O'Hare International Airport | 3h58 | 12:59 AM Edward L. Logan International Airport | 1 transfer | |
| AA2504 | 9:08 PM O'Hare International Airport | 2h21 | 11:29 PM Edward L. Logan International Airport | 0 transfersDirect | |
| NK1333 · NK850 | 9:26 PM O'Hare International Airport | 7h33 | 4:59 AM Edward L. Logan International Airport | 1 transfer | |
| AA444 · AA1728 | 9:50 PM O'Hare International Airport | 5h32 | 3:22 AM Edward L. Logan International Airport | 1 transfer | |
| UA1677 | 10:00 PM O'Hare International Airport | 2h20 | 12:20 AM Edward L. Logan International Airport | 0 transfersDirect | |
| AA1624+AA4397 | 10:06 PM O'Hare International Airport | 5h41 | 3:47 AM Edward L. Logan International Airport | 1 transfer | |
| AA469 | 11:10 PM O'Hare International Airport | 2h20 | 1:30 AM Edward L. Logan International Airport | 0 transfersDirect | |
| AA4615+AA3586 | 11:54 PM O'Hare International Airport | 4h48 | 4:42 AM Edward L. Logan International Airport | 1 transfer | |
| Friday, November 14 | |||||
| UA426 · UA755 | 12:20 AM O'Hare International Airport | 4h22 | 4:42 AM Edward L. Logan International Airport | 1 transfer | |
| UA1989 | 12:21 AM O'Hare International Airport | 2h28 | 2:49 AM Edward L. Logan International Airport | 0 transfersDirect | |
| B61012 | 12:55 AM O'Hare International Airport | 2h32 | 3:27 AM Edward L. Logan International Airport | 0 transfersDirect | |
| AA4384 | 1:12 AM O'Hare International Airport | 2h32 | 3:44 AM Edward L. Logan International Airport | 0 transfersDirect | |
| AA4650 | 2:11 AM O'Hare International Airport | 2h32 | 4:43 AM Edward L. Logan International Airport | 0 transfersDirect | |
| UA1779 | 3:25 AM O'Hare International Airport | 2h20 | 5:45 AM Edward L. Logan 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 Chicago, IL to Boston, MA?
The best time to book your flight from Chicago, IL to Boston, MA is 84 days before departure. See how prices for flights change on the Chicago, IL to Boston, MA route.
Prices are for one-way tickets for one passenger from Chicago, IL to Boston, MA 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 Chicago, IL to Boston, MA.
Flights
from $191Trains
from $131Buses
from $151Compare prices and tickets Chicago, IL to Boston, MA 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.
Fri
Nov 14
Nov 14
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Nov 15
Nov 15
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Nov 16
Nov 16
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Nov 17
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Nov 19
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Nov 20
Nov 20
Airlines: American Airlines, Spirit Airlines, United, Republic Airlines, JetBlue Airways from Chicago, IL to Boston, MAFind the best flights between Chicago, IL to Boston, MA with Omio's travel partners American Airlines, Spirit Airlines, United, Republic Airlines, JetBlue Airways from $137 (€111). We can find you the best deals, schedules and tickets when comparing and booking the best trip.
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
5h 19m
Cheapest Price
$137 (€111)
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.
Entertaiment on board
United
About
United Airlines is one of the USA’s leading carriers, operating both domestic and international routes. For your next trip, you can choose from Economy, Premium Economy, and Business Class fares.
Luggage & cancellation policy
Average Duration
2h 14m
Cheapest Price
$143 (€116)
United frequency
19 a day
Luggage included
One carry-on bag (9 x 14 x 22 inches) and one personal item (9 x 10 x 17 inches)
Additional luggage
Checked baggage fees vary by route and fare class. Most economy tickets allow purchase of up to 2 checked bags
Cancellation Policy
Basic Economy tickets are non-refundable, other fares allow changes/cancellations with fee depending on fare type and elite status
Pregnant on board
Passengers can fly through the end of their 36th week for single pregnancies, 32nd week for multiple pregnancies. Medical certificate required within 4 weeks of flight
Unaccompagned minor
Children ages 5-14 can travel as unaccompanied minors with mandatory service. Ages 15-17 optional service available
Amenities on board the airplane
Wifi
USB plugs
Accessibility
United provides assistance for passengers with disabilities, including wheelchair assistance and support for passengers with visual or hearing impairments
Pets
Small dogs and cats in cabin, service animals allowed. Pets must be in approved carriers and booked in advance
Entertaiment on board
JetBlue Airways
About
JetBlue Airways is an American low-cost airline headquartered in Long Island City, New York City. Founded in 1998, JetBlue began operations in 2000, aiming to offer affordable travel with distinguishing amenities. The airline operates a point-to-point network with focus cities including its main hub at New York City's John F. Kennedy International Airport, and serves over 100 destinations across the Americas and Europe. JetBlue is known for its customer-centric approach, offering features like complimentary Wi-Fi, free live TV and movies on seatback screens, and the most legroom in coach among U.S. airlines. They also provide free snacks and non-alcoholic drinks on all flights, with full meal service on transatlantic routes. In 2024, JetBlue launched "Blueprint by JetBlue," a personalized in-flight experience platform with features such as watch parties and content recommendations.
Luggage & cancellation policy
Luggage included
One personal item (17L x 13W x 8H) and one carry-on bag (22L x 14W x 9H)
Additional luggage
Checked bags up to 62 linear inches and 50 pounds for a fee
Cancellation Policy
Full refund if cancelled within 24 hours of booking. Blue Basic non-refundable, other fares offer credit valid for 12 months
Pregnant on board
Pregnant women can travel up to 7 days before due date. Medical certificate required after 36 weeks
Unaccompagned minor
Children ages 5-14 can travel alone. Service fee applies. Must be booked by phone
Amenities on board the airplane
Wifi
USB plugs
Accessibility
JetBlue provides wheelchair assistance and special services for passengers with disabilities
Pets
Small dogs and cats allowed in cabin for a fee of $125 each way
Entertaiment on board
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
15h 0m
Cheapest Price
$211 (€171)
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
2h 27m
Cheapest Price
$158 (€128)
Republic Airlines frequency
2 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.
FAQs: Chicago, IL to Boston, MA Flight
Find answers to the most common questions about traveling from Chicago, IL to Boston, MA 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 Boston, MA, this guide helps you travel smarter and with confidence.
Cheap plane tickets from Chicago, IL to Boston, MA can start from as little as $27 (€22) when you book in advance. The average flight ticket price for Chicago, IL to Boston, MA is $136 (€110); however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The flight time from Chicago, IL to Boston, MA is on average 2 h 14 min for the 848 mile (1367 km) long journey, but the time it takes to go to Boston, MA from Chicago, IL by flight can vary depending on specific dates or if traveling on weekends and holidays.
The earliest flight from Chicago, IL to Boston, MA leaves at 5: 00AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Chicago, IL to Boston, MA leaves at 10: 14PM.
There are 29 flights a day from Chicago, IL to Boston, MA which require at least one change with American Airlines, United, Spirit Airlines or Republic Airlines. Schedules can vary on holidays or weekends with fewer flights.
For the best Chicago, IL to Boston, MA flight to buy, you can travel safely and comfortably with American Airlines, United, Spirit Airlines or Republic Airlines. However, it's always good to check all possible airlines with services to Boston, MA from Chicago, IL to compare what amenities they may offer.
The cheapest month for a flight from Chicago, IL to Boston, MA is September.
You have options as you can travel between Chicago, IL and Boston, MA 3 different ways: train, bus or flight.
Since neither Chicago, IL nor Boston, MA are in the Schengen Area, passport requirements depend on the specific immigration rules of USA and USA. 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 Chicago, IL and Boston, MA all year round.
The best events to attend in Boston, MA include:
- Boston Marathon, the world's oldest annual marathon attracting elite runners and thousands of spectators
- Boston Calling Music Festival, a three-day music festival featuring top artists across various genres
- Independence Day Celebration on the Esplanade, a spectacular fireworks display and concert celebrating America's birthday along the Charles River.
The best holidays to experience in Boston, MA include:
- Patriot's Day, commemorates the start of the American Revolution with reenactments and parades
- Memorial Day, marks the unofficial start of summer with vibrant outdoor activities and events
- Labor Day, offers pleasant weather and a chance to enjoy the city's parks and waterfront.
The best seasons to visit Boston, MA are Spring or Fall. The best weather to explore Boston, MA is during May-June or September-October.
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.
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.
popular airports
Popular airports from Chicago, IL to Boston, MA
Chicago
Boston
The major airport for departures in Chicago is O'Hare International Airport. Find all the information you need to know about services, amenities and connections at O'Hare International Airport for your trip from Chicago to Boston.
Amenities at airport
Wifi
Shopping
Parking
Dining
ATM
Taxis
Accessibility
WC
Hotel
Shower
Lounge
Lost and Found Office
Car Rentalinformation
Distance to city center
3 km
Car connection
I-190, Exit 1Wifi
- Free Wi-Fi available throughout the airport.
Shopping
- Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics.
Parking
- Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour.
Dining
- Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Taxis
- Available outside the terminal.
Accessibility
- Elevators, ramps, toilets
WC
- Available throughout the airport.
Hotel
- Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
Shower
- Showers are available in some lounges, such as the United Club, but access may require a fee or membership.
Lounge
- Lounges available, including United Club and American Airlines Admirals Club.
Lost and Found Office
- Lost and Found located in terminal 1, near the baggage claim area.
Car Rental
- Car rental services are available at the Multi-Modal Facility, with companies like Hertz and Avis.
Public transit options for O'Hare International Airport
- CTA Blue Line, O'Hare Station, 45 minutes to city center
The major airport for arrivals in Boston is Edward L. Logan International Airport. Find all the information you need to know about services, amenities and connections at Edward L. Logan International Airport for your journey to Boston from Chicago.
Amenities at airport
WifiShoppingParkingDiningATMTaxisAccessibilityWCHotelShowerLoungeLost and Found OfficeCar Rentalinformation
Distance to city center
2 kmCar connection
I-90, Exit 26Wifi
- Free Wi-Fi available throughout the airport.
Shopping
- Shops are located in all terminals, including Duty-Free and Hudson News.
Parking
- Parking available in Central Parking Garage, Economy Parking, and terminal B Garage, approximately 7.6€ ($8) per hour.
Dining
- Restaurants are available in all terminals, including Legal Sea Foods (seafood) and Wahlburgers (American).
Taxis
- Available outside the terminal.
Accessibility
- Elevators, ramps
WC
- Available throughout the airport.
Hotel
- Hotels within walking distance, including Hilton Boston Logan Airport.
Shower
- Showers are available in some lounges; access may require a lounge pass or membership.
Lounge
- Lounges available, including The Club and Delta Sky Club.
Lost and Found Office
- Lost and Found located in the Lost & Found Office in terminal C.
Car Rental
- Car rental services are available at the Rental Car Center, accessible by shuttle.
Public transit options for Edward L. Logan International Airport
- MBTA Blue Line, Airport Station, 5 km
More options for your journey from Chicago, IL to Boston, MA
Here are some other resources that might have the information you need
Most popular flights to and from Boston, MA and Chicago, IL
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