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 $53. 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 $53 – the departure date for this flight is 01 May 2024.

Sort by: Departure dateCheap flightsFast flightsDirect flights
26.03.2024 Tuesday
from $48
Economy Found 2024-02-09
Nonstop 3 hours 0 min
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12.03.2024 Tuesday
from $48
Economy Found 2024-02-09
Nonstop 3 hours 0 min
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24.03.2024 Sunday
from $63
Economy Found 2 days
Nonstop 3 hours 0 min
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23.03.2024 Saturday
from $63
Economy Found 2 days
Nonstop 3 hours 0 min
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12.03.2024 Tuesday
from $64
Economy Found 2024-02-09
1 Stopover 6 hours 8 min
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19.03.2024 Tuesday
from $64
Economy Found yesterday
1 Stopover 6 hours 8 min
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27.03.2024 Wednesday
from $70
Economy Found 2024-02-09
1 Stopover 9 hours 40 min
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13.03.2024 Wednesday
from $70
Economy Found 2024-02-09
1 Stopover 9 hours 40 min
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18.03.2024 Monday
from $91
Economy Found 2024-02-09
1 Stopover 9 hours 50 min
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05.03.2024 Tuesday
from $91
Economy Found 2 days
1 Stopover 9 hours 44 min
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21.03.2024 Thursday
from $92
Economy Found yesterday
1 Stopover 6 hours 38 min
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25.03.2024 Monday
from $102
Economy Found 2 days
Nonstop 3 hours 8 min
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04.03.2024 Monday
from $102
Economy Found 2 days
Nonstop 3 hours 12 min
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08.03.2024 Friday
from $109
Economy Found yesterday
Nonstop 3 hours 0 min
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20.03.2024 Wednesday
from $118
Economy Found yesterday
1 Stopover 11 hours 31 min
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01.03.2024 Friday
from $119
Economy Found 2 days
Nonstop 3 hours 0 min
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13.03.2024 Wednesday
from $131
Economy Found 2024-02-09
2 Stopovers 20 hours 31 min
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01.03.2024 Friday
from $131
Economy Found 2 days
1 Stopover 14 hours 57 min
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17.03.2024 Sunday
from $138
Economy Found yesterday
1 Stopover 16 hours 55 min
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16.03.2024 Saturday
from $138
Economy Found yesterday
1 Stopover 16 hours 55 min
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26.03.2024 Tuesday
from $142
Economy Found 2024-02-09
2 Stopovers 21 hours 9 min
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14.03.2024 Thursday
from $153
Economy Found 2 days
1 Stopover 6 hours 38 min
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29.03.2024 Friday
from $179
Economy Found yesterday
1 Stopover 9 hours 40 min
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30.03.2024 Saturday
from $203
Economy Found 2 days
1 Stopover 6 hours 21 min
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27.03.2024 Wednesday
from $221
Economy Found 2024-02-09
2 Stopovers 11 hours 26 min
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01.03.2024 Friday
from $271
Economy Found 2 days
2 Stopovers 17 hours 51 min
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22.03.2024 Friday
from $309
Economy Found yesterday
2 Stopovers 34 hours 22 min
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09.03.2024 Saturday
from $309
Economy Found yesterday
2 Stopovers 26 hours 3 min
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06.03.2024 Wednesday
from $383
Economy Found 2024-02-09
2 Stopovers 10 hours 10 min
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11.03.2024 Monday
from $400
Economy Found 2024-02-09
2 Stopovers 7 hours 22 min
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*Prices include: baggage, hand luggage, airline fees and charges.

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 $248, the flight dates are: there on 14 June 2024 year and back on 18 June 2024 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Frontier Airlines F9 2167 Day flight
Departure 03.04.24 12:21, We
1 Stopover Trip 8 days
Return 11.04.24 22:56, Th
JetBlue Airways B6 311 Day flight
Departure 27.02.24 11:30, Tu
Direct Trip 6 hours
Return 27.02.24 17:03, Tu
JetBlue Airways B6 311 Day flight
Departure 28.02.24 11:30, We
Direct Trip 6 hours
Return 28.02.24 17:32, We
JetBlue Airways B6 311 Day flight
Departure 29.02.24 11:30, Th
Direct Trip 6 hours
Return 29.02.24 17:32, Th
JetBlue Airways B6 311 Day flight
Departure 06.03.24 11:38, We
Direct Trip 7 days
Return 13.03.24 00:55, We
JetBlue Airways B6 2311 Evening flight
Departure 11.05.24 19:57, Sa
Direct Trip 3 days
Return 14.05.24 23:38, Tu
JetBlue Airways B6 311 Morning flight
Departure 13.03.24 10:38, We
Direct Trip 1 day
Return 14.03.24 16:32, Th
JetBlue Airways B6 311 Morning flight
Departure 02.04.24 10:00, Tu
Direct Trip 1 day
Return 03.04.24 13:38, We
JetBlue Airways B6 311 Morning flight
Departure 06.05.24 10:00, Mo
Direct Trip 3 days
Return 08.05.24 23:38, We
JetBlue Airways B6 311 Day flight
Departure 24.02.24 11:30, Sa
Direct Trip 3 days
Return 27.02.24 17:03, Tu
Delta Air Lines DL 1088 Morning flight
Departure 07.05.24 10:30, Tu
Direct Trip 2 days
Return 09.05.24 01:20, Th
JetBlue Airways B6 611 Evening flight
Departure 19.03.24 21:10, Tu
Direct Trip 7 days
Return 27.03.24 00:55, We
JetBlue Airways B6 1225 Evening flight
Departure 30.04.24 19:20, Tu
Direct Trip 7 days
Return 07.05.24 13:28, Tu
JetBlue Airways B6 2311 Evening flight
Departure 01.05.24 19:57, We
Direct Trip 14 days
Return 15.05.24 23:38, We
JetBlue Airways B6 311 Day flight
Departure 09.04.24 12:10, Tu
Direct Trip 1 day
Return 10.04.24 15:55, We
JetBlue Airways B6 311 Day flight
Departure 10.04.24 12:10, We
Direct Trip 1 day
Return 11.04.24 23:10, Th
JetBlue Airways B6 311 Morning flight
Departure 21.03.24 10:38, Th
Direct Trip 7 days
Return 28.03.24 00:55, Th
Delta Air Lines DL 2631 Day flight
Departure 04.05.24 16:20, Sa
Direct Trip 2 days
Return 07.05.24 01:15, Tu
JetBlue Airways B6 311 Day flight
Departure 05.03.24 11:38, Tu
Direct Trip 1 day
Return 06.03.24 17:32, We
JetBlue Airways B6 1225 Evening flight
Departure 24.04.24 19:20, We
Direct Trip 7 days
Return 01.05.24 23:38, We
JetBlue Airways B6 611 Evening flight
Departure 12.03.24 21:10, Tu
Direct Trip 1 day
Return 13.03.24 16:32, We
JetBlue Airways B6 311 Morning flight
Departure 08.05.24 10:00, We
Direct Trip 7 days
Return 14.05.24 23:38, Tu
JetBlue Airways B6 311 Morning flight
Departure 11.03.24 10:38, Mo
Direct Trip 3 days
Return 14.03.24 16:32, Th
Delta Air Lines DL 1417 Morning flight
Departure 26.03.24 10:15, Tu
Direct Trip 2 days
Return 28.03.24 11:25, Th
Delta Air Lines DL 1715 Day flight
Departure 27.04.24 12:05, Sa
Direct Trip 4 days
Return 01.05.24 01:15, We
JetBlue Airways B6 311 Day flight
Departure 23.04.24 12:10, Tu
Direct Trip 7 days
Return 30.04.24 15:55, Tu
JetBlue Airways B6 311 Day flight
Departure 26.02.24 11:30, Mo
Direct Trip 1 day
Return 27.02.24 17:03, Tu
JetBlue Airways B6 311 Morning flight
Departure 27.03.24 10:38, We
Direct Trip 4 days
Return 31.03.24 00:55, Su
Delta Air Lines DL 5595 Day flight
Departure 07.03.24 11:15, Th
Direct Trip 6 days
Return 13.03.24 00:59, We
JetBlue Airways B6 311 Day flight
Departure 25.02.24 11:30, Su
Direct Trip 3 days
Return 28.02.24 17:32, We
JetBlue Airways B6 311 Day flight
Departure 03.03.24 11:38, Su
Direct Trip 3 days
Return 06.03.24 01:50, We
JetBlue Airways B6 311 Morning flight
Departure 24.03.24 10:38, Su
Direct Trip 4 days
Return 28.03.24 00:55, Th
JetBlue Airways B6 311 Morning flight
Departure 23.03.24 10:38, Sa
Direct Trip 7 days
Return 30.03.24 00:55, Sa
JetBlue Airways B6 311 Day flight
Departure 02.03.24 11:38, Sa
Direct Trip 6 hours
Return 02.03.24 17:27, Sa
Delta Air Lines DL 1417 Morning flight
Departure 22.03.24 10:15, Fr
Direct Trip 5 days
Return 27.03.24 22:05, We
Delta Air Lines DL 1088 Morning flight
Departure 09.05.24 10:30, Th
Direct Trip 6 days
Return 15.05.24 01:20, We
JetBlue Airways B6 1225 Evening flight
Departure 06.04.24 19:20, Sa
Direct Trip 2 days
Return 08.04.24 23:10, Mo
Delta Air Lines DL 1417 Morning flight
Departure 04.04.24 10:15, Th
Direct Trip 6 days
Return 10.04.24 18:00, We
JetBlue Airways B6 311 Day flight
Departure 29.04.24 12:10, Mo
Direct Trip 1 day
Return 30.04.24 15:55, Tu
JetBlue Airways B6 311 Morning flight
Departure 05.05.24 10:00, Su
Direct Trip 4 days
Return 08.05.24 23:38, We
JetBlue Airways B6 311 Morning flight
Departure 12.05.24 10:00, Su
Direct Trip 2 days
Return 14.05.24 13:28, Tu
JetBlue Airways B6 311 Morning flight
Departure 10.03.24 10:38, Su
Direct Trip 3 days
Return 13.03.24 16:32, We
JetBlue Airways B6 1225 Evening flight
Departure 20.04.24 19:20, Sa
Direct Trip 4 days
Return 24.04.24 16:06, We
JetBlue Airways B6 311 Day flight
Departure 08.04.24 12:10, Mo
Direct Trip 7 days
Return 15.04.24 23:10, Mo
JetBlue Airways B6 311 Morning flight
Departure 18.05.24 10:00, Sa
Direct Trip 8 days
Return 25.05.24 23:38, Sa
JetBlue Airways B6 311 Day flight
Departure 22.04.24 12:10, Mo
Direct Trip 7 days
Return 29.04.24 23:10, Mo
JetBlue Airways B6 617 Evening flight
Departure 04.03.24 23:25, Mo
1 Stopover Trip 3 days
Return 07.03.24 17:32, Th
JetBlue Airways B6 217 Morning flight
Departure 25.03.24 09:30, Mo
1 Stopover Trip 2 days
Return 27.03.24 00:55, We
JetBlue Airways B6 311 Morning flight
Departure 15.05.24 10:00, We
1 Stopover Trip 7 days
Return 21.05.24 22:32, Tu
Delta Air Lines DL 1417 Morning flight
Departure 02.05.24 10:30, Th
Direct Trip 5 days
Return 07.05.24 01:15, Tu
Frontier Airlines F9 1098 Day flight
Departure 05.04.24 13:45, Fr
1 Stopover Trip 3 days
Return 08.04.24 20:02, Mo
JetBlue Airways B6 311 Morning flight
Departure 13.05.24 10:00, Mo
Direct Trip 2 days
Return 14.05.24 23:38, Tu
JetBlue Airways B6 311 Day flight
Departure 09.03.24 11:38, Sa
Direct Trip 4 days
Return 13.03.24 00:55, We
JetBlue Airways B6 317 Night flight
Departure 02.03.24 01:55, Sa
1 Stopover Trip 4 days
Return 06.03.24 01:50, We
JetBlue Airways B6 317 Night flight
Departure 09.03.24 02:37, Sa
1 Stopover Trip 4 days
Return 13.03.24 00:55, We
JetBlue Airways B6 917 Morning flight
Departure 03.05.24 09:45, Fr
1 Stopover Trip 5 days
Return 07.05.24 23:38, Tu
United Airlines UA 408 Day flight
Departure 13.02.24 14:25, Tu
Direct Trip 2 days
Return 15.02.24 17:00, Th
JetBlue Airways B6 311 Morning flight
Departure 14.05.24 10:00, Tu
1 Stopover Trip 7 days
Return 20.05.24 22:32, Mo
Spirit Airlines NK 495 Day flight
Departure 17.04.24 15:30, We
1 Stopover Trip 7 days
Return 24.04.24 15:45, We
JetBlue Airways B6 311 Day flight
Departure 07.04.24 12:10, Su
Direct Trip 3 days
Return 10.04.24 15:55, We
JetBlue Airways B6 311 Morning flight
Departure 18.03.24 10:38, Mo
Direct Trip 10 days
Return 28.03.24 00:55, Th
JetBlue Airways B6 311 Morning flight
Departure 21.05.24 10:00, Tu
Direct Trip 5 days
Return 26.05.24 13:28, Su
Delta Air Lines DL 1417 Morning flight
Departure 18.04.24 10:30, Th
Direct Trip 6 days
Return 24.04.24 01:15, We
Delta Air Lines DL 5603 Night flight
Departure 20.04.24 00:55, Sa
Direct Trip 7 days
Return 27.04.24 01:15, Sa
Frontier Airlines F9 3347 Day flight
Departure 19.05.24 14:34, Su
1 Stopover Trip 2 days
Return 21.05.24 10:01, Tu
Frontier Airlines F9 1098 Day flight
Departure 16.03.24 13:45, Sa
1 Stopover Trip 3 days
Return 20.03.24 00:58, We
JetBlue Airways B6 311 Day flight
Departure 11.04.24 12:10, Th
Direct Trip 4 days
Return 15.04.24 23:10, Mo
JetBlue Airways B6 217 Day flight
Departure 10.05.24 14:28, Fr
1 Stopover Trip 4 days
Return 14.05.24 23:38, Tu
JetBlue Airways B6 917 Morning flight
Departure 20.05.24 09:45, Mo
1 Stopover Trip 6 days
Return 25.05.24 23:38, Sa
JetBlue Airways B6 217 Morning flight
Departure 28.04.24 09:08, Su
1 Stopover Trip 4 days
Return 01.05.24 23:38, We
Frontier Airlines F9 2167 Day flight
Departure 01.04.24 12:21, Mo
1 Stopover Trip 3 days
Return 04.04.24 01:43, Th
JetBlue Airways B6 311 Day flight
Departure 21.04.24 12:10, Su
Direct Trip 3 days
Return 24.04.24 23:10, We
JetBlue Airways B6 311 Day flight
Departure 15.04.24 12:10, Mo
Direct Trip 1 day
Return 16.04.24 15:55, Tu
Frontier Airlines F9 3347 Day flight
Departure 25.04.24 14:34, Th
1 Stopover Trip 3 days
Return 28.04.24 21:48, Su
Spirit Airlines NK 836 Evening flight
Departure 26.04.24 18:37, Fr
1 Stopover Trip 7 days
Return 03.05.24 14:25, Fr
Frontier Airlines F9 2167 Day flight
Departure 17.03.24 12:21, Su
1 Stopover Trip 1 day
Return 18.03.24 00:48, Mo
Frontier Airlines F9 3347 Day flight
Departure 16.05.24 14:34, Th
1 Stopover Trip 2 days
Return 18.05.24 22:42, Sa
JetBlue Airways B6 317 Night flight
Departure 21.02.24 02:09, We
1 Stopover Trip 7 days
Return 28.02.24 02:10, We
Delta Air Lines DL 1417 Morning flight
Departure 15.03.24 10:15, Fr
Direct Trip 12 days
Return 27.03.24 00:59, We
JetBlue Airways B6 311 Morning flight
Departure 29.03.24 10:38, Fr
Direct Trip 2 days
Return 31.03.24 00:55, Su
Southwest Airlines WN 1726 Evening flight
Departure 22.02.24 17:35, Th
Direct Trip 4 days
Return 27.02.24 00:20, Tu
Delta Air Lines DL 735 Morning flight
Departure 30.03.24 09:45, Sa
1 Stopover Trip 3 days
Return 02.04.24 11:25, Tu
United Airlines UA 567 Morning flight
Departure 20.03.24 10:00, We
Direct Trip 4 days
Return 24.03.24 11:00, Su
Frontier Airlines F9 1893 Day flight
Departure 28.03.24 12:21, Th
1 Stopover Trip 4 days
Return 01.04.24 02:50, Mo
United Airlines UA 2341 Day flight
Departure 14.03.24 11:30, Th
Direct Trip 3 days
Return 17.03.24 11:00, Su
Delta Air Lines DL 5596 Day flight
Departure 12.02.24 15:32, Mo
Direct Trip 7 days
Return 19.02.24 12:15, Mo
JetBlue Airways B6 311 Day flight
Departure 14.04.24 12:10, Su
Direct Trip 1 day
Return 15.04.24 23:10, Mo
Frontier Airlines F9 3011 Day flight
Departure 31.03.24 15:23, Su
1 Stopover Trip 3 days
Return 04.04.24 01:43, Th
Spirit Airlines NK 1911 Evening flight
Departure 16.04.24 20:30, Tu
1 Stopover Trip 8 days
Return 24.04.24 15:45, We
Delta Air Lines DL 1088 Morning flight
Departure 17.05.24 10:30, Fr
Direct Trip 5 days
Return 22.05.24 01:20, We
American Airlines AA 2951 Day flight
Departure 15.02.24 13:56, Th
1 Stopover Trip 4 days
Return 19.02.24 02:39, Mo
American Airlines AA 1239 Day flight
Departure 23.02.24 13:37, Fr
1 Stopover Trip 2 days
Return 25.02.24 14:14, Su
JetBlue Airways B6 217 Morning flight
Departure 19.02.24 10:38, Mo
1 Stopover Trip 2 days
Return 21.02.24 17:32, We
American Airlines AA 1414 Day flight
Departure 16.02.24 12:10, Fr
1 Stopover Trip 2 days
Return 18.02.24 12:44, Su
Delta Air Lines DL 1417 Morning flight
Departure 12.04.24 10:30, Fr
Direct Trip 4 days
Return 16.04.24 01:15, Tu
JetBlue Airways B6 311 Day flight
Departure 14.02.24 13:40, We
Direct Trip 2 days
Return 16.02.24 17:03, Fr
Delta Air Lines DL 5605 Day flight
Departure 13.04.24 12:05, Sa
Direct Trip 3 days
Return 16.04.24 01:15, Tu
Spirit Airlines NK 299 Night flight
Departure 19.02.24 02:46, Mo
1 Stopover Trip 2 days
Return 21.02.24 12:15, We
Delta Air Lines DL 5814 Night flight
Departure 18.02.24 00:15, Su
1 Stopover Trip 3 days
Return 20.02.24 12:15, Tu
Spirit Airlines NK 299 Night flight
Departure 22.02.24 02:46, Th
1 Stopover Trip 4 days
Return 25.02.24 16:20, Su
*Prices include: baggage, hand luggage, airline fees and charges.
From Boston to Chicago from $86! Airfare Deals by Southwest Airlines
from $86 left 13 days
Sales dates 01 February 2024 Flight dates: 25 February 2024
Boston - Chicago One way, Economy - from $86
Find flights

Flight Schedule Boston to Chicago 2024

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 14 flights every day, from 2hours 40min. Local departure and arrival times are indicated.
06:0007:57
United Airlines UA567 United Airlines UA567
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
06:0508:04
Delta Air Lines DL2320 Delta Air Lines DL2320
BOS → ORD
Mo Tu We Th Fr - -
Check price
06:1508:28
American Airlines AA1509 American Airlines AA1509
BOS → ORD
- - - - - Sa -
Check price
06:5008:54
American Airlines AA2672 American Airlines AA2672
BOS → ORD
- Tu We Th - - Su
Check price
06:5008:54
American Airlines AA1509 American Airlines AA1509
BOS → ORD
Mo - - - Fr - -
Check price
06:5008:45
Southwest Airlines WN3677 Southwest Airlines WN3677
BOS → MDW
- - - - - Sa -
Check price
07:0008:59
JetBlue Airways B6311 JetBlue Airways B6311
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
07:1509:05
Southwest Airlines WN533 Southwest Airlines WN533
BOS → MDW
Mo Tu We Th Fr - Su
Check price
07:5009:57
American Airlines AA1239 American Airlines AA1239
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
09:1513:00
Southwest Airlines WN892 Southwest Airlines WN892
BOS → ORD
Mo Tu We Th Fr - Su
Check price
09:3511:33
Delta Air Lines DL1429 Delta Air Lines DL1429
BOS → ORD
- - - - - Sa -
Check price
09:4611:43
United Airlines UA408 United Airlines UA408
BOS → ORD
Mo Tu We Th Fr Sa Su
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 $52
13 February 2024
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 $114
20 February 2024
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 $37
05 March 2024
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 $53
01 May 2024
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 $91
04 March 2024

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 $44
11 March 2024
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 $61
22 April 2024
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 $37
22 February 2024
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 $51
07 March 2024
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 $53
01 May 2024

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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