Journey information
Overview: Boston, MA to Chicago, IL flight
Flights from Boston, MA to Chicago, IL depart on average 43 times per day, taking around 3h 9m. Cheap flight tickets for this journey start at £48 if you book in advance.
There are 10 flights per day. The earliest flight runs at 00:06, the last at 22:34. The fastest flight covers the 1368 km distance in 3h 0m. May is the cheapest month to fly.
Distance 1368 km |
Average flight duration 3h 9m |
Cheapest ticket price £48 |
Flights per day 43 |
Direct flights 10 |
Fastest flight 3h 0m |
Cheapest month to travel May |
First flight 00:06 |
Last flight 22:34 |
The cheapest and fastest flights from Boston, MA to Chicago, IL
Cheapest price
£227
Average price
£393
Fastest journey
3 h
Average duration
3 h 4 m
Flights per day
65
Distance
1368 km
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 travelling at rush hour.
The average ticket from Boston, MA to Chicago, IL will cost around £393 if you buy it on the day, but you can find cheap flight tickets today for only £227.
Of the 65 flights that leave Boston, MA for Chicago, IL every day 13 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
These direct flights cover the 1368 km distance in an average of 3 h 4 m but if you time it right, some flights will get you there in just 3 h .
The slowest flights will take 3 h 6 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.
AA1174
AA1328
B6311
AA3346
AA3712
UA1414
UA503
UA1349
UA2040
AA1174Travel Information
Compare train, coach 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 £48. For those with little time consider booking a flight which can get you there in 3h 9m. 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 £48, and a train costs an average of £66.
Distance: 1368 km
Compare flight with
| Flight | Most popular Train | Coach |
|---|---|---|
£155 Average Price Cheapest | £248 Average Price | £168 Average Price |
6h 9m Average total duration Fastest 3h 9m Onboard + 3h 0m Additional time* | 22h 57m Average total duration 22h 27m Onboard + 30m Additional time* | 25h 29m Average total duration 24h 59m 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
Boston, MA to Chicago, IL flight times
The table below shows live departures for Boston, MA to Chicago, IL flights for today, Friday 6 March. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Changes | Tickets |
|---|---|---|---|---|---|
UA1734 · UA1775 | 10:45 Edward L. Logan International Airport | 5h05 | 15:50 O'Hare International Airport | 1 change | |
AA2096 · AA1250 | 10:49 Edward L. Logan International Airport | 5h23 | 16:12 O'Hare International Airport | 1 change | |
AA1253 · AA1200 | 11:00 Edward L. Logan International Airport | 5h57 | 16:57 O'Hare International Airport | 1 change | |
UA1833 · UA3578 · UA1531 | 11:00 Edward L. Logan International Airport | 12h02 | 23:02 O'Hare International Airport | 2 changes | |
AA4424+ AA3234 | 11:00 Edward L. Logan International Airport | 5h54 | 16:54 O'Hare International Airport | 1 change | |
UA1414 | 11:00 Edward L. Logan International Airport | 3h00 | 14:00 O'Hare International Airport | 0 changesdirect | |
UA1833 · UA1525 | 11:00 Edward L. Logan International Airport | 5h51 | 16:51 O'Hare International Airport | 1 change | |
B6117 · B62105 | 11:10 Edward L. Logan International Airport | 6h38 | 17:48 O'Hare International Airport | 1 change | |
AA1328 | 11:52 Edward L. Logan International Airport | 3h11 | 15:03 O'Hare International Airport | 0 changesdirect | |
AA1475 · AA1200 | 12:00 Edward L. Logan International Airport | 4h57 | 16:57 O'Hare International Airport | 1 change | |
UA647 · UA2865 | 12:00 Edward L. Logan International Airport | 8h50 | 20:50 O'Hare International Airport | 1 change | |
B6311 | 12:00 Edward L. Logan International Airport | 3h10 | 15:10 O'Hare International Airport | 0 changesdirect | |
UA570 · UA1883 | 12:05 Edward L. Logan International Airport | 5h55 | 18:00 O'Hare International Airport | 1 change | |
UA226 · UA1327 | 12:15 Edward L. Logan International Airport | 10h50 | 23:05 O'Hare International Airport | 1 change | |
UA226 · UA2417 | 12:15 Edward L. Logan International Airport | 8h29 | 20:44 O'Hare International Airport | 1 change | |
UA2488 | 12:16 Edward L. Logan International Airport | 3h06 | 15:22 O'Hare International Airport | 0 changesdirect | |
AA1004 · AA1983 | 12:40 Edward L. Logan International Airport | 5h55 | 18:35 O'Hare International Airport | 1 change | |
AA690 · AA1854 | 13:00 Edward L. Logan International Airport | 5h05 | 18:05 O'Hare International Airport | 1 change | |
UA1349 | 13:15 Edward L. Logan International Airport | 3h05 | 16:20 O'Hare International Airport | 0 changesdirect | |
UA1307 · UA2345 · UA1046 | 13:45 Edward L. Logan International Airport | 12h33 | 02:18 O'Hare International Airport | 2 changes | |
UA1307 · UA1875 | 13:45 Edward L. Logan International Airport | 5h30 | 19:15 O'Hare International Airport | 1 change | |
AA2153 · AA1944 | 14:00 Edward L. Logan International Airport | 5h19 | 19:19 O'Hare International Airport | 1 change | |
UA662 · UA617 | 14:20 Edward L. Logan International Airport | 8h40 | 23:00 O'Hare International Airport | 1 change | |
AA1688 · AA2319 | 14:25 Edward L. Logan International Airport | 5h51 | 20:16 O'Hare International Airport | 1 change | |
UA2098 · UA2331 | 14:30 Edward L. Logan International Airport | 6h03 | 20:33 O'Hare International Airport | 1 change | |
UA230 · UA1327 | 14:32 Edward L. Logan International Airport | 8h33 | 23:05 O'Hare International Airport | 1 change | |
AA4398+ AA3005 | 14:57 Edward L. Logan International Airport | 4h55 | 19:52 O'Hare International Airport | 1 change | |
AA4561+ AA647 | 15:00 Edward L. Logan International Airport | 4h57 | 19:57 O'Hare International Airport | 1 change | |
AA4794 | 15:24 Edward L. Logan International Airport | 3h11 | 18:35 O'Hare International Airport | 0 changesdirect | |
UA2394 · UA2376 · UA1046 | 15:30 Edward L. Logan International Airport | 10h48 | 02:18 O'Hare International Airport | 2 changes | |
UA2394 · UA2233 · UA2155 | 15:30 Edward L. Logan International Airport | 9h25 | 00:55 O'Hare International Airport | 2 changes | |
UA2394 · UA2345 · UA1046 | 15:30 Edward L. Logan International Airport | 10h48 | 02:18 O'Hare International Airport | 2 changes | |
UA2394 · UA3672 · UA1237 | 15:30 Edward L. Logan International Airport | 10h56 | 02:26 O'Hare International Airport | 2 changes | |
AA2476 · AA725 | 15:56 Edward L. Logan International Airport | 5h25 | 21:21 O'Hare International Airport | 1 change | |
AA4366 · AA4731 | 15:59 Edward L. Logan International Airport | 5h18 | 21:17 O'Hare International Airport | 1 change | |
AA4717+ AA1452 | 16:00 Edward L. Logan International Airport | 5h08 | 21:08 O'Hare International Airport | 1 change | |
UA414 · UA1023 | 16:00 Edward L. Logan International Airport | 8h45 | 00:45 O'Hare International Airport | 1 change | |
UA503 | 16:02 Edward L. Logan International Airport | 3h05 | 19:07 O'Hare International Airport | 0 changesdirect | |
AA4582 | 16:19 Edward L. Logan International Airport | 3h11 | 19:30 O'Hare International Airport | 0 changesdirect | |
UA533 | 17:07 Edward L. Logan International Airport | 5h54 | 23:01 O'Hare International Airport | 0 changesdirect | |
UA533 · UA2376 · UA1046 | 17:07 Edward L. Logan International Airport | 9h11 | 02:18 O'Hare International Airport | 2 changes | |
UA533 · UA3672 · UA1237 | 17:07 Edward L. Logan International Airport | 9h19 | 02:26 O'Hare International Airport | 2 changes | |
UA533 · UA2233 · UA2155 | 17:07 Edward L. Logan International Airport | 7h48 | 00:55 O'Hare International Airport | 2 changes | |
AA1283 | 17:09 Edward L. Logan International Airport | 3h06 | 20:15 O'Hare International Airport | 0 changesdirect | |
UA1732 | 17:10 Edward L. Logan International Airport | 3h05 | 20:15 O'Hare International Airport | 0 changesdirect | |
UA1976 · UA2197 | 18:20 Edward L. Logan International Airport | 9h18 | 03:38 O'Hare International Airport | 1 change | |
UA1976 · UA1752 | 18:20 Edward L. Logan International Airport | 10h48 | 05:08 O'Hare International Airport | 1 change | |
NK3021 · NK1 | 18:59 Edward L. Logan International Airport | 10h48 | 05:47 O'Hare International Airport | 1 change | |
NK3021 · NK581 | 18:59 Edward L. Logan International Airport | 8h14 | 03:13 O'Hare International Airport | 1 change | |
AA5902+ AA4175 | 19:10 Edward L. Logan International Airport | 5h00 | 00:10 O'Hare International Airport | 1 change | |
UA721 · UA2497 | 19:15 Edward L. Logan International Airport | 5h36 | 00:51 O'Hare International Airport | 1 change | |
AA4648 · AA4603 | 19:50 Edward L. Logan International Airport | 5h44 | 01:34 O'Hare International Airport | 1 change | |
AA3658 · AA3520 | 20:03 Edward L. Logan International Airport | 6h02 | 02:05 O'Hare International Airport | 1 change | |
AA3711 | 20:51 Edward L. Logan International Airport | 3h15 | 00:06 O'Hare International Airport | 0 changesdirect | |
UA1807 · UA546 | 21:28 Edward L. Logan International Airport | 6h06 | 03:34 O'Hare International Airport | 1 change | |
UA2040 | 21:30 Edward L. Logan International Airport | 3h05 | 00:35 O'Hare International Airport | 0 changesdirect | |
AA3712 | 21:49 Edward L. Logan International Airport | 3h16 | 01:05 O'Hare International Airport | 0 changesdirect | |
UA800 · UA377 | 21:50 Edward L. Logan International Airport | 8h02 | 05:52 O'Hare International Airport | 1 change | |
AA2468 · AA3296 | 22:00 Edward L. Logan International Airport | 5h24 | 03:24 O'Hare International Airport | 1 change | |
AA1174 | 22:31 Edward L. Logan International Airport | 3h17 | 01:48 O'Hare International Airport | 0 changesdirect | |
B6717 · B61305 | 22:32 Edward L. Logan International Airport | 6h28 | 05:00 O'Hare International Airport | 1 change | |
UA1015 | 23:23 Edward L. Logan International Airport | 3h02 | 02:25 O'Hare International Airport | 0 changesdirect | |
UA1693 · UA1981 | 23:30 Edward L. Logan International Airport | 5h43 | 05:13 O'Hare International Airport | 1 change | |
| Saturday 7 March | |||||
AA1270 | 00:16 Edward L. Logan International Airport | 3h14 | 03:30 O'Hare International Airport | 0 changesdirect | |
UA2136 · UA1738 | 00:34 Edward L. Logan International Airport | 5h10 | 05:44 O'Hare International Airport | 1 change | |
Find all the dates and times for this journey
How far in advance should I book flight tickets from Boston, MA to Chicago, IL?
Compare prices and tickets Boston, MA to Chicago, IL by train, coach or flight
Compare train, coach 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?
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 £48. We can find you the best deals, schedules and tickets when comparing and booking the best trip.
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FAQs: Boston, MA to Chicago, IL flights
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.

popular airports
Important Stations and Airports in Boston, MA and Chicago, IL
- Free Wi-Fi available throughout the airport.
- Shops are located in all terminals, including Duty-Free and Hudson News.
- Parking available in Central Parking Garage, Economy Parking, and terminal B Garage, approximately 7.6€ ($8) per hour.
- Restaurants are available in all terminals, including Legal Sea Foods (seafood) and Wahlburgers (American).
- Available outside the terminal.
- Elevators, ramps
- Available throughout the airport.
- Hotels within walking distance, including Hilton Boston Logan Airport.
- Showers are available in some lounges; access may require a lounge pass or membership.
- Lounges available, including The Club and Delta Sky Club.
- Lost and Found located in the Lost & Found Office in terminal C.
- Car rental services are available at the Rental Car Center, accessible by shuttle.
- MBTA Blue Line, Airport Station, 5 km
- Free Wi-Fi available throughout the airport.
- Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics.
- Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour.
- Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
- Available outside the terminal.
- Elevators, ramps, toilets
- Available throughout the airport.
- Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
- Showers are available in some lounges, such as the United Club, but access may require a fee or membership.
- Lounges available, including United Club and American Airlines Admirals Club.
- Lost and Found located in terminal 1, near the baggage claim area.
- Car rental services are available at the Multi-Modal Facility, with companies like Hertz and Avis.
- CTA Blue Line, O'Hare Station, 45 minutes to city center
Most popular flights from Boston, MA
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