Chicago, IL CHI to Boston, MA BOS flight with American Airlines

Mon, Feb 02
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Journey information

Overview: Chicago, IL to Boston, MA flight

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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 $140 (€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
$140 (€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 Feb 02

Cheapest price

$281

Average price

$491

Fastest journey

2 h 14 m

Average duration

2 h 19 m

Flights per day

70

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 $491 if you buy it on the day, but the cheapest tickets can be found for only $281.

Fast flights

Of the 70 flights that leave Chicago, IL for Boston, MA onMon, Feb 02, 15 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.

On Mon, Feb 02 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 14 m .

On Mon, Feb 02 the longest flights will take 2 h 23 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.

JetBlue AirwaysB6312
08:55AM2h26
O'Hare International Airport
12:21PMEdward L. Logan International Airport
$2811One-way
0 transfers
Republic AirlinesAA4760
08:45AM2h26
O'Hare International Airport
12:11PMEdward L. Logan International Airport
$2811One-way
0 transfers
Republic AirlinesAA4650
08:18PM2h26
O'Hare International Airport
11:44PMEdward L. Logan International Airport
$2811One-way
0 transfers
American AirlinesAA380
04:30PM2h14
O'Hare International Airport
07:44PMEdward L. Logan International Airport
$2811One-way
0 transfers
American AirlinesAA2121
01:25PM2h18
O'Hare International Airport
04:43PMEdward L. Logan International Airport
$2811One-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

American Airlines

Most popular airline

Amtrak

Most popular train company

Greyhound

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, Sunday, February 1. You can also manually refresh the results below to see updated flight journeys.

Last updated at 10:13 AM
ProviderDepartsDurationArrivesTransfers
Tickets
spirit_airlinesNK1986 · NK223011:15 AM O'Hare International Airport
10h33
9:48 PM Edward L. Logan International Airport1 transfer
unitedUA1606 · UA6177 · UA67312:00 PM O'Hare International Airport
7h17
7:17 PM Edward L. Logan International Airport2 transfers
republic_airlinesAA4551 · AA445412:00 PM O'Hare International Airport
4h41
4:41 PM Edward L. Logan International Airport1 transfer
american_airlinesAA1854+republic_airlinesAA448112:42 PM O'Hare International Airport
4h43
5:25 PM Edward L. Logan International Airport1 transfer
unitedUA791 · UA12321:00 PM O'Hare International Airport
7h37
8:37 PM Edward L. Logan International Airport1 transfer
envoy_airAA37101:00 PM O'Hare International Airport
2h23
3:23 PM Edward L. Logan International Airport0 transfersDirect
unitedUA3433 · UA1701 · UA26301:10 PM O'Hare International Airport
9h04
10:14 PM Edward L. Logan International Airport2 transfers
unitedUA3433 · UA17011:10 PM O'Hare International Airport
10h22
11:32 PM Edward L. Logan International Airport1 transfer
unitedUA563 · UA3661:10 PM O'Hare International Airport
5h03
6:13 PM Edward L. Logan International Airport1 transfer
unitedUA20671:30 PM O'Hare International Airport
2h22
3:52 PM Edward L. Logan International Airport0 transfersDirect
unitedUA1416 · UA15071:35 PM O'Hare International Airport
9h26
11:01 PM Edward L. Logan International Airport1 transfer
jetblue_airwaysB63121:40 PM O'Hare International Airport
2h25
4:05 PM Edward L. Logan International Airport0 transfersDirect
envoy_airAA4178 · AA37492:00 PM O'Hare International Airport
5h13
7:13 PM Edward L. Logan International Airport1 transfer
republic_airlinesAA4389+envoy_airAA33532:26 PM O'Hare International Airport
4h36
7:02 PM Edward L. Logan International Airport1 transfer
jetblue_airwaysB61306 · B622182:45 PM O'Hare International Airport
7h28
10:13 PM Edward L. Logan International Airport1 transfer
republic_airlinesAA47602:45 PM O'Hare International Airport
2h26
5:11 PM Edward L. Logan International Airport0 transfersDirect
jetblue_airwaysB61306 · B66182:45 PM O'Hare International Airport
9h03
11:48 PM Edward L. Logan International Airport1 transfer
jetblue_airwaysB61306 · B64182:45 PM O'Hare International Airport
6h01
8:46 PM Edward L. Logan International Airport1 transfer
republic_airlinesAA4512 · AA44632:50 PM O'Hare International Airport
5h13
8:03 PM Edward L. Logan International Airport1 transfer
republic_airlinesAA4368+envoy_airAA42932:50 PM O'Hare International Airport
5h34
8:24 PM Edward L. Logan International Airport1 transfer
unitedUA1357 · UA6732:52 PM O'Hare International Airport
4h25
7:17 PM Edward L. Logan International Airport1 transfer
unitedUA1633 · UA15072:54 PM O'Hare International Airport
8h07
11:01 PM Edward L. Logan International Airport1 transfer
unitedUA1972 · UA425 · UA17013:00 PM O'Hare International Airport
8h32
11:32 PM Edward L. Logan International Airport2 transfers
unitedUA1972 · UA555 · UA26913:00 PM O'Hare International Airport
11h52
2:52 AM Edward L. Logan International Airport2 transfers
unitedUA1972 · UA425 · UA26303:00 PM O'Hare International Airport
7h14
10:14 PM Edward L. Logan International Airport2 transfers
unitedUA21833:13 PM O'Hare International Airport
2h33
5:46 PM Edward L. Logan International Airport0 transfersDirect
american_airlinesAA1201+republic_airlinesAA43753:54 PM O'Hare International Airport
4h21
8:15 PM Edward L. Logan International Airport1 transfer
unitedUA1848 · UA555 · UA26914:35 PM O'Hare International Airport
10h17
2:52 AM Edward L. Logan International Airport2 transfers
unitedUA1803 · UA5974:40 PM O'Hare International Airport
8h25
1:05 AM Edward L. Logan International Airport1 transfer
unitedUA2164 · UA3633 · UA26914:47 PM O'Hare International Airport
10h05
2:52 AM Edward L. Logan International Airport2 transfers
spirit_airlinesNK1605 · NK2724:48 PM O'Hare International Airport
11h31
4:19 AM Edward L. Logan International Airport1 transfer
unitedUA3995:05 PM O'Hare International Airport
2h24
7:29 PM Edward L. Logan International Airport0 transfersDirect
american_airlinesAA2041+republic_airlinesAA44795:51 PM O'Hare International Airport
4h07
9:58 PM Edward L. Logan International Airport1 transfer
unitedUA1878 · UA26306:00 PM O'Hare International Airport
4h14
10:14 PM Edward L. Logan International Airport1 transfer
spirit_airlinesNK392 · NK2726:44 PM O'Hare International Airport
9h35
4:19 AM Edward L. Logan International Airport1 transfer
american_airlinesAA772 · AA21486:58 PM O'Hare International Airport
5h09
12:07 AM Edward L. Logan International Airport1 transfer
unitedUA1128 · UA17017:00 PM O'Hare International Airport
4h32
11:32 PM Edward L. Logan International Airport1 transfer
unitedUA293 · UA6887:00 PM O'Hare International Airport
4h57
11:57 PM Edward L. Logan International Airport1 transfer
american_airlinesAA21217:25 PM O'Hare International Airport
2h18
9:43 PM Edward L. Logan International Airport0 transfersDirect
republic_airlinesAA4692 · AA47247:45 PM O'Hare International Airport
4h17
12:02 AM Edward L. Logan International Airport1 transfer
unitedUA16937:55 PM O'Hare International Airport
2h24
10:19 PM Edward L. Logan International Airport0 transfersDirect
unitedUA1176 · UA13567:55 PM O'Hare International Airport
8h51
4:46 AM Edward L. Logan International Airport1 transfer
unitedUA1373 · UA10768:12 PM O'Hare International Airport
8h08
4:20 AM Edward L. Logan International Airport1 transfer
unitedUA587 · UA7558:35 PM O'Hare International Airport
8h14
4:49 AM Edward L. Logan International Airport1 transfer
unitedUA2347 · UA13568:36 PM O'Hare International Airport
8h10
4:46 AM Edward L. Logan International Airport1 transfer
american_airlinesAA2840 · AA22268:50 PM O'Hare International Airport
4h40
1:30 AM Edward L. Logan International Airport1 transfer
american_airlinesAA1500+republic_airlinesAA473010:14 PM O'Hare International Airport
5h42
3:56 AM Edward L. Logan International Airport1 transfer
unitedUA2172 · UA269110:15 PM O'Hare International Airport
4h37
2:52 AM Edward L. Logan International Airport1 transfer
unitedUA167710:15 PM O'Hare International Airport
2h24
12:39 AM Edward L. Logan International Airport0 transfersDirect
american_airlinesAA38010:30 PM O'Hare International Airport
2h14
12:44 AM Edward L. Logan International Airport0 transfersDirect
republic_airlinesAA4663 · AA464110:32 PM O'Hare International Airport
4h55
3:27 AM Edward L. Logan International Airport1 transfer
american_airlinesAA1594+republic_airlinesAA434611:05 PM O'Hare International Airport
4h24
3:29 AM Edward L. Logan International Airport1 transfer
republic_airlinesAA4740 · AA472611:25 PM O'Hare International Airport
4h49
4:14 AM Edward L. Logan International Airport1 transfer
american_airlinesAA103311:25 PM O'Hare International Airport
2h20
1:45 AM Edward L. Logan International Airport0 transfersDirect
american_airlinesAA1418 · AA187411:26 PM O'Hare International Airport
4h29
3:55 AM Edward L. Logan International Airport1 transfer
american_airlinesAA1876 · AA329411:32 PM O'Hare International Airport
5h19
4:51 AM Edward L. Logan International Airport1 transfer
republic_airlinesAA4615+envoy_airAA369011:34 PM O'Hare International Airport
4h24
3:58 AM Edward L. Logan International Airport1 transfer
Monday, February 2
unitedUA198912:05 AM O'Hare International Airport
2h33
2:38 AM Edward L. Logan International Airport0 transfersDirect
unitedUA2677 · UA75512:17 AM O'Hare International Airport
4h32
4:49 AM Edward L. Logan International Airport1 transfer
republic_airlinesAA45821:30 AM O'Hare International Airport
2h26
3:56 AM Edward L. Logan International Airport0 transfersDirect
republic_airlinesAA46502:18 AM O'Hare International Airport
2h26
4:44 AM Edward L. Logan International Airport0 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.

Compare 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.

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Why should you book Chicago, IL to Boston, MA flights with Omio?

Spirit Airlines as well as American Airlines, Republic Airlines, United, JetBlue Airways and more offer flights services from Chicago, IL to Boston, MA.
Omio is an official ticket reseller for all your travel options from Chicago, IL to Boston, MA.

Why book with Omio vs Spirit Airlines?

  • Compare with other providers: On Omio, you can not only buy tickets for Spirit Airlines, but also compare tickets for the likes of American Airlines, Republic Airlines, United or JetBlue Airways to find the best option for your trip from Chicago, IL to Boston, MA.
  • 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 Spirit Airlines with all available travel options, which are train, bus and flight to ensure you get the best deal for traveling from Chicago, IL to Boston, MA.

Why book with Omio over Edreams, Kayak or Trip?

  • Compare with other providers: On Omio, you can also compare tickets for the likes of American Airlines, Republic Airlines, United or JetBlue Airways to find the best option for your trip from Chicago, IL to Boston, MA.
  • Multiple modes of transport: Omio allows you to compare travel options including train, bus and flight to find the ideal travel option from Chicago, IL to Boston, MA.

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 $140 (€111). 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 14m
Cheapest Price
$147 (€116)
United frequency
19 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
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
5h 19m
Cheapest Price
$140 (€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.

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
$216 (€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
$161 (€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.

FAQs
Cheap plane tickets from Chicago, IL to Boston, MA can start from as little as $140 (€111) when you book in advance. The average flight ticket price for Chicago, IL to Boston, MA is $227 (€180) ; 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 Chicago, IL to Boston, MA is 2h 26m 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 Chicago, IL to Boston, MA leaves at 12:06 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Chicago, IL to Boston, MA leaves at 10:12 PM.
Yes, there are 9 direct flights a day from Chicago, IL to Boston, MA with American Airlines, United, Republic Airlines. Schedules can vary on holidays or weekends with fewer direct flights.
When taking a flight from Chicago, IL to Boston, MA, you can count on American Airlines, Spirit Airlines, United, Republic Airlines, JetBlue Airways for the best way to get you to Boston, MA. You can also check all possible airlines who offer a service between Chicago, IL and Boston, MA and compare the amenities they offer before buying a plane ticket.
Flights from Chicago, IL to Boston, MA generally leave from O'Hare International Airport and arrive in Edward L. Logan International Airport.O'Hare International Airport is 1 miles (3 km) away from Chicago, IL city centre and Edward L. Logan International Airport is 1 miles (2 km) from Boston, MA city centre.
The cheapest month for a flight from Chicago, IL to Boston, MA is August.
It's helpful to compare your options as there are 3 ways to travel between Chicago, IL and Boston, MA including taking a train, bus, and flight.
Since neither Chicago, IL nor Boston, MA 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 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 season to visit Boston, MA is 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.
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
WifiWifi
ShoppingShopping
ParkingParking
DiningDining
ATMATM
TaxisTaxis
AccessibilityAccessibility
WCWC
HotelHotel
ShowerShower
LoungeLounge
Lost and Found OfficeLost and Found Office
Car RentalCar Rental
information
ticketOfficeHours
Distance to city center
3 km
carConnection
Car connection
I-190, Exit 1
Wifi
Wifi
  • Free Wi-Fi available throughout the airport.
Shopping
Shopping
  • Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics.
Parking
Parking
  • Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour.
Dining
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
Taxis
  • Available outside the terminal.
Accessibility
Accessibility
  • Elevators, ramps, toilets
WC
WC
  • Available throughout the airport.
Hotel
Hotel
  • Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
Shower
Shower
  • Showers are available in some lounges, such as the United Club, but access may require a fee or membership.
Lounge
Lounge
  • Lounges available, including United Club and American Airlines Admirals Club.
Lost and Found Office
Lost and Found Office
  • Lost and Found located in terminal 1, near the baggage claim area.
Car Rental
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

Most popular flights to and from Boston, MA and Chicago, IL

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