Airfare Deals Boston to Chicago

On HolidayPrice.com you will find 6 direct and 4 connecting flights from Boston to Chicago at a price of from $46. You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out BOS - CHI flight schedule to find best flight time, convenient departure and arrival airports.

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The cost of airline tickets from Boston to Chicago (United States) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to Chicago.

One way flight from Boston to Chicago

Below are the prices of tickets for direct one-way flights from Boston to Chicago. The cheapest flight from Boston to Chicago starts from $ 46 – the departure date for this flight is 27 October 2021.

Sort by: Departure dateCheap flightsFast flightsDirect flights
30.11.2021 Tuesday
from $ 47 Trip.com
Economy Found today
Nonstop 3 hours 3 min
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16.11.2021 Tuesday
from $ 58 Tickets.ua
Economy Found 2021-10-05
1 Stopover 29 hours 42 min
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16.11.2021 Tuesday
from $ 61 Tickets.ua
Economy Found 2021-10-05
Nonstop 3 hours 2 min
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30.11.2021 Tuesday
from $ 66 Aviakassa
Economy Found today
1 Stopover 25 hours 23 min
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06.11.2021 Saturday
from $ 67 KupiBilet.ru
Economy Found 2021-10-04
Nonstop 2 hours 59 min
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06.11.2021 Saturday
from $ 71 MEGO.travel
Economy Found 2021-10-04
1 Stopover 4 hours 44 min
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06.11.2021 Saturday
from $ 77 Kiwi.com
Economy Found 2021-10-04
2 Stopovers 13 hours 28 min
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06.11.2021 Saturday
from $ 81 SuperSaver
Economy Found 2021-10-04
3 Stopovers 23 hours 30 min
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30.11.2021 Tuesday
from $ 84 Aviakassa
Economy Found today
2 Stopovers 39 hours 32 min
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16.11.2021 Tuesday
from $ 91 Tickets.ua
Economy Found 2021-10-05
2 Stopovers 23 hours 19 min
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16.11.2021 Tuesday
from $ 140 Tickets.ua
Economy Found 2021-10-05
3 Stopovers 49 hours 26 min
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06.11.2021 Saturday
from $ 152 SuperSaver
Economy Found 2021-10-04
4 Stopovers 28 hours 8 min
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30.11.2021 Tuesday
from $ 159 Aviakassa
Economy Found today
3 Stopovers 50 hours 58 min
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*Prices include: baggage, hand luggage, airline fees and charges.

Flights from Boston to Chicago are most popular in August, September, October. During this period, the average price of fly tickets is from $ 70. In the low season in February, March, April, air tickets become cheaper and the average price will be from $ 33 one way.

Round trip from Boston to Chicago

You can buy a round-trip ticket from Boston to Chicago (United States) and back using the table below. The best offer starts from $ 77, the flight dates are: there on 23 October 2021 year and back on 25 October 2021 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Spirit Airlines NK 615 Evening flight
Departure 23.10.21 21:32, Sa
1 Stopover Trip 2 days
Return 25.10.21 12:00, Mo
Spirit Airlines NK 609 Morning flight
Departure 13.10.21 10:11, We
1 Stopover Trip 7 days
Return 20.10.21 00:10, We
American Airlines AA 2265 Morning flight
Departure 15.11.21 10:00, Mo
Direct Trip 2 days
Return 17.11.21 14:05, We
Frontier Airlines F9 1239 Day flight
Departure 02.11.21 13:59, Tu
1 Stopover Trip 2 days
Return 04.11.21 14:46, Th
American Airlines AA 1509 Day flight
Departure 12.11.21 12:30, Fr
1 Stopover Trip 3 days
Return 15.11.21 13:00, Mo
American Airlines AA 2265 Morning flight
Departure 09.12.21 10:00, Th
Direct Trip 4 days
Return 13.12.21 00:50, Mo
JetBlue Airways B6 311 Day flight
Departure 07.11.21 12:00, Su
Direct Trip 4 days
Return 11.11.21 00:25, Th
JetBlue Airways B6 2569 Evening flight
Departure 22.10.21 23:55, Fr
1 Stopover Trip 3 days
Return 25.10.21 12:00, Mo
American Airlines AA 2265 Morning flight
Departure 29.10.21 09:00, Fr
1 Stopover Trip 2 days
Return 31.10.21 10:10, Su
United Airlines UA 1564 Evening flight
Departure 18.11.21 17:00, Th
Direct Trip 3 days
Return 22.11.21 03:10, Mo
American Airlines AA 2269 Evening flight
Departure 19.01.22 22:15, We
Direct Trip 6 days
Return 25.01.22 16:30, Tu
Spirit Airlines NK 2834 Evening flight
Departure 15.10.21 23:00, Fr
1 Stopover Trip 3 days
Return 19.10.21 00:52, Tu
American Airlines AA 2118 Evening flight
Departure 05.11.21 18:00, Fr
1 Stopover Trip 2 days
Return 07.11.21 10:55, Su
Spirit Airlines NK 3151 Day flight
Departure 23.11.21 13:45, Tu
1 Stopover Trip 8 days
Return 02.12.21 00:50, Th
United Airlines UA 748 Day flight
Departure 26.12.21 11:05, Su
1 Stopover Trip 9 days
Return 04.01.22 15:04, Tu
American Airlines AA 2146 Evening flight
Departure 24.12.21 21:00, Fr
1 Stopover Trip 9 days
Return 03.01.22 03:45, Mo
Delta Air Lines DL 826 Morning flight
Departure 17.10.21 09:30, Su
1 Stopover Trip 2 days
Return 19.10.21 00:59, Tu
Southwest Airlines WN 113 Morning flight
Departure 07.10.21 09:35, Th
Direct Trip 3 days
Return 10.10.21 13:10, Su
JetBlue Airways B6 1117 Night flight
Departure 25.11.21 03:00, Th
1 Stopover Trip 3 days
Return 28.11.21 05:59, Su
Southwest Airlines WN 1187 Evening flight
Departure 25.11.21 23:20, Th
1 Stopover Trip 3 days
Return 29.11.21 03:45, Mo
United Airlines UA 748 Morning flight
Departure 08.10.21 10:00, Fr
1 Stopover Trip 2 days
Return 10.10.21 11:00, Su
Southwest Airlines WN 2865 Evening flight
Departure 09.10.21 21:40, Sa
2 Stopovers Trip 2 days
Return 12.10.21 01:51, Tu
*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 low-cost airlines.

Flight Information

Flying to Chicago from Boston takes 02:20 minutes (excluding transfers). The distance between Boston and Chicago is 847 miles (1364 kilometers). Planes depart from Boston between 00:00 and 23:55. The fastest flight from the company United Airlines with flight number UA 789. Flies for just 02:16 minutes with departure from Boston RT128 Railway and arrival in O'Hare.

time

Average 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

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.

*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

Airports serving the air communication between Boston and Chicago. You can fly to Chicago from 1 Boston airports. Planes arrive at 2 airport in Chicago.

Boston airports:

Boston RT128 Railway  ~ 4 km*

Chicago airports:

O'Hare  ~ 25 km* from $ 63Chicago Midway  ~ 14 km* from $ 71

*Distance from the airport to the city center

Aircraft

You can fly from Boston to Chicago on board of 6 airlines that utilize 13 aircraft models.

  • 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 to Chicago from Boston. 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 HolidayPrice.com 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 $ 26
14 November 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 $ 42
27 October 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 $ 26
14 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 $ 46
27 October 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 $ 107
21 November 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 $ 32
03 November 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 $ 27
03 November 2021
Miami - Chicago AA 2796 American Airlines Boeing 767-300
17:05 Miami
in a way 2 hours 55 min Direct
20:00 O'Hare
Flights
from $ 21
14 October 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 $ 54
07 December 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 $ 46
27 October 2021

All flights to Chicago

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 city

To start searching for tickets, Specify dates.

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