Airfare Deals from Boston to Chicago

Find cheap flights from Boston to Chicago at Tripsta.co.uk in just 5 minutes. On the site you can compare flight prices on this route, buy airline tickets costing from £23 and see the aircraft schedule.

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The cheapest flight ticket from Boston to Chicago was found 5 days ago. Its one way cost starts from £23, the departure date is 29 September 2021. The minimum price for a round trip flight starts from £53. This flight fare was found 6 days ago, with the following departure dates: Boston on 18 September 2021 year, and back from Chicago on 25 September 2021 year.

Plane tickets from Boston to Chicago, one way

The table shows the prices of direct flight plane tickets to Chicago from Boston. If you find an interesting air travel offer, do not delay your purchase, last minute offers run out very quickly.

Sort by: Departure dateCheap flightsFast flightsDirect flights
11.10.2021 Monday
from £43 Kiwi.com
Economy Found 2021-09-14
1 Stopover 18 hours 32 min
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11.10.2021 Monday
from £65 Kiwi.com
Economy Found 2021-09-14
2 Stopovers 23 hours 9 min
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11.10.2021 Monday
from £75 FlyFar
Economy Found 2021-09-14
3 Stopovers 26 hours 23 min
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11.10.2021 Monday
from £84 Myflightsbuddy
Economy Found 2021-09-14
Nonstop 2 hours 47 min
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Flights from Boston to Chicago are most popular in August, September, October. During this period, the average price of fly tickets is from £50. In the low season in February, March, April, air tickets become cheaper and the average price will be from £24 one way.

Best Flights: Boston to Chicago and back

The cost of a round trip flight on the Boston - Chicago (United States) route. The cheapest ticket was purchased 6 days ago, its price was from £53. It flies to Chicago on 18 September 2021 year and returns to Boston on 25 September 2021 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Spirit Airlines NK 615 Evening flight
Departure 18.09.21 20:53, Sa
1 Stopover Trip 7 days
Return 25.09.21 12:45, Sa
United Airlines UA 380 Day flight
Departure 13.10.21 11:30, We
1 Stopover Trip 7 days
Return 20.10.21 00:10, We
Spirit Airlines NK 615 Evening flight
Departure 23.09.21 20:53, Th
1 Stopover Trip 2 days
Return 25.09.21 12:45, Sa
Spirit Airlines NK 615 Evening flight
Departure 09.10.21 21:20, Sa
1 Stopover Trip 2 days
Return 12.10.21 00:10, Tu
American Airlines AA 1509 Morning flight
Departure 22.09.21 10:45, We
1 Stopover Trip 3 days
Return 25.09.21 12:45, Sa
Spirit Airlines NK 615 Evening flight
Departure 02.10.21 20:53, Sa
1 Stopover Trip 2 days
Return 04.10.21 13:00, Mo
JetBlue Airways B6 311 Day flight
Departure 19.10.21 11:37, Tu
Direct Trip 2 days
Return 21.10.21 15:19, Th
American Airlines AA 2265 Morning flight
Departure 21.10.21 09:00, Th
Direct Trip 4 days
Return 25.10.21 15:19, Mo
United Airlines UA 748 Morning flight
Departure 29.10.21 10:00, Fr
1 Stopover Trip 1 day
Return 30.10.21 00:10, Sa
American Airlines AA 2265 Morning flight
Departure 16.10.21 09:00, Sa
1 Stopover Trip 3 days
Return 19.10.21 00:10, Tu
United Airlines UA 748 Morning flight
Departure 14.10.21 10:00, Th
1 Stopover Trip 4 days
Return 18.10.21 00:10, Mo
American Airlines AA 2265 Morning flight
Departure 19.01.22 10:45, We
Direct Trip 6 days
Return 25.01.22 19:12, Tu
Spirit Airlines NK 609 Morning flight
Departure 16.09.21 09:15, Th
1 Stopover Trip 1 day
Return 17.09.21 13:00, Fr
United Airlines UA 748 Morning flight
Departure 22.10.21 10:00, Fr
1 Stopover Trip 2 days
Return 24.10.21 21:51, Su
American Airlines AA 2269 Evening flight
Departure 17.09.21 21:35, Fr
1 Stopover Trip 2 days
Return 19.09.21 21:40, Su
United Airlines UA 380 Day flight
Departure 07.10.21 11:30, Th
1 Stopover Trip 5 days
Return 12.10.21 00:10, Tu
Southwest Airlines WN 372 Morning flight
Departure 08.10.21 09:35, Fr
1 Stopover Trip 3 days
Return 11.10.21 20:19, Mo
Spirit Airlines NK 609 Morning flight
Departure 22.11.21 10:45, Mo
1 Stopover Trip 7 days
Return 29.11.21 16:23, Mo

*Prices include: baggage, hand luggage, airline fees and charges.

Flight Schedule Boston to Chicago 2021

The current flight schedule for the route from Boston to Chicago for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.

More than 15 flights every day, from 2hours 35min. Local departure and arrival times are indicated.
05:3507:10
Southwest Airlines WN4409 Southwest Airlines WN4409
BOS → MDW
- - - - - - Su
Check price
05:4507:25
Southwest Airlines WN1318 Southwest Airlines WN1318
BOS → MDW
Mo - - Th Fr Sa -
Check price
05:5007:30
Southwest Airlines WN4370 Southwest Airlines WN4370
BOS → MDW
- Tu We - - - -
Check price
06:0008:00
United Airlines UA449 United Airlines UA449
BOS → ORD
Mo Tu We Th Fr - Su
Check price
06:4508:48
JetBlue Airways B64198 JetBlue Airways B64198
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
07:3009:27
American Airlines AA9442 American Airlines AA9442
BOS → ORD
Mo Tu We Th Fr - Su
Check price
07:3009:27
JetBlue Airways B6311 JetBlue Airways B6311
BOS → ORD
Mo Tu We Th Fr - Su
Check price
08:0509:59
Delta Air Lines DL5708 Delta Air Lines DL5708
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
08:4010:35
American Airlines AA1239 American Airlines AA1239
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
08:4010:35
JetBlue Airways B64162 JetBlue Airways B64162
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
10:2012:04
United Airlines UA1251 United Airlines UA1251
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
12:1513:50
Southwest Airlines WN3287 Southwest Airlines WN3287
BOS → MDW
- - - - - Sa -
Check price
Show all

*Schedule is indicated only for direct scheduled flights and lowcost airlines.

Flight information

It takes 02:20 minutes to fly from Boston to Chicago excluding transfers. The distance between the cities is 1364 km or 847 miles. The earliest morning plane from Boston leaves for Chicago at 00:00. And the latest evening flight departs at 23:55.

time

Non-stop flight time

02:20 min

distance

Distance

847 mi

The earliest flight

The earliest flight

00:00

The latest flight

The latest flight

23:55

Airplane

The fastest flight

02:16

The fastest Boston - Chicago flight ticket is provided by United Airlines, the flight number is UA 789. It is in the air for 02:16 mins, departing from Boston RT128 Railway at 02:44 and arriving at 05:00 in O'Hare. This flight is carried out on a modern Boeing 737-900 airliner.

Airlines

Direct flight

There are 6 airlines that fly directly from Boston to Chicago. The most popular company carrying out non-stop flights is United Airlines.

  • United Airlines: UA 203, UA 2214, UA 375
  • American Airlines: AA 1427, AA 2178, AA 2265
  • Southwest Airlines: WN 1381, WN 4496, WN 2556
  • JetBlue Airways: B6 111, B6 311, B6 1711
  • Delta Air Lines: DL 5904, DL 5984, DL 6075
  • Spirit Airlines: NK 773

*Flight number

Flights with Transfers

Flights with transfers from Boston to Chicago can be bought from 4 airlines:

  • Southwest Airlines: Baltimore
  • JetBlue Airways: Cleveland, Baltimore, Pittsburgh
  • Delta Air Lines: New York
  • Air Canada: Hamilton

*Transit cities

Airports

Airfare from airports. In Boston, 1 airports serve all air communications with Chicago. Airplanes arrive at 2 airport in Chicago.

Boston airports:

Boston RT128 Railway  ~ 4 km*

Chicago airports:

O'Hare  ~ 25 km* from £34Chicago Midway  ~ 14 km* from £50

*Distance from the airport to the city center

Airplanes

13 aircraft models from 6 airlines fly on the Boston - Chicago route. The fastest airliner is the Boeing 737-900, from the company United Airlines.

  • Airbus A319
  • Airbus A320
  • Airbus A321
  • Boeing 737
  • Boeing 737-700
  • Boeing 737-800
  • Boeing 737-900
  • Boeing 757-200
  • Boeing 757-300
  • Embraer 170
  • Embraer 175
  • Embraer 190
  • Embraer EMB 175

Connecting cities

The list of cities on transfer flights from Boston to Chicago. The best options are to fly through: Baltimore, Cleveland, New York, Hamilton, Pittsburgh, Detroit.

Cheap airline tickets from Boston to United States

Here is a list of flights from Boston to United States purchased on Tripsta.co.uk in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.

Boston - New York B6 917 JetBlue Airways Embraer 190
12:10 Boston RT128 Railway
in a way 0 hours 50 min Direct
13:00 John F. Kennedy
Flights
from £14
23 September 2021
Boston - Los Angeles UA 2145 United Airlines Boeing 757-200
16:45 Boston RT128 Railway
in a way 6 hours 0 min Direct
22:45 Los Angeles
Flights
from £31
29 September 2021
Boston - Miami B6 221 JetBlue Airways Airbus A320
03:50 Boston RT128 Railway
in a way 3 hours 8 min Direct
06:58 Palm Beach
Flights
from £15
07 November 2021
Boston - Chicago UA 789 United Airlines Boeing 737-900
02:44 Boston RT128 Railway
in a way 2 hours 16 min Direct
05:00 O'Hare
Flights
from £23
29 September 2021
Boston - San Francisco B6 133 JetBlue Airways Airbus A318/319/320/321
13:52 Boston RT128 Railway
in a way 6 hours 8 min Direct
20:00 San Francisco
Flights
from £58
12 October 2021

All flights from Boston

Flights from United States to Chicago

Here are the cheapest flight bookings from United States to Chicago made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

New York - Chicago UA 761 United Airlines Boeing 737-800
13:00 LaGuardia
in a way 2 hours 0 min Direct
15:00 O'Hare
Flights
from £24
06 October 2021
Los Angeles - Chicago UA 910 United Airlines Boeing 737-800
10:23 Los Angeles
in a way 3 hours 37 min Direct
14:00 O'Hare
Flights
from £20
07 October 2021
Miami - Chicago AA 2796 American Airlines Boeing 767-300
17:05 Miami International Airport
in a way 2 hours 55 min Direct
20:00 O'Hare International Airport
Flights
from £16
23 September 2021
San Francisco - Chicago UA 1800 United Airlines Airbus A319
04:15 San Francisco
in a way 3 hours 45 min Direct
08:00 O'Hare
Flights
from £37
27 September 2021
Boston - Chicago UA 789 United Airlines Boeing 737-900
02:44 Boston RT128 Railway
in a way 2 hours 16 min Direct
05:00 O'Hare
Flights
from £23
29 September 2021

All flights to Chicago

Frequently asked question

How much does a plane ticket from Boston to Chicago cost?

The cost of the cheapest one-way flight from Boston to Chicago starts from £23. The departure date of that flight is 29 September 2021.

Round trip costs start from £53, with the departure date there being on 18 September 2021 year, and back on 25 September 2021 year.

Which airlines fly on the Boston - Chicago route?

There are 6 airlines flying directly from Boston to Chicago: United Airlines, American Airlines, Southwest Airlines, JetBlue Airways, Delta Air Lines, Spirit Airlines

And 4 airlines fly with transfers: Southwest Airlines, JetBlue Airways, Delta Air Lines, Air Canada

How long does it take to fly from Boston to Chicago?

The flight time from Boston to Chicago averages 02:20 mins.

Which planes fly to Chicago from Boston?

13 aircraft models fly from Boston to Chicago, overcoming 847 miles in an average of 02:20 mins. The fastest aircraft on this route is Boeing 737-900 from United Airlines, it flies for 02:16 min.

  • Airbus A319
  • Airbus A320
  • Airbus A321
  • Boeing 737
  • Boeing 737-700
  • Boeing 737-800
  • Boeing 737-900
  • Boeing 757-200
  • Boeing 757-300
  • Embraer 170
  • Embraer 175
  • Embraer 190
  • Embraer EMB 175

Tips for buying a ticket

Boston – Chicago – Boston round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Boston to Chicago
Chicago

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