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Cheap flights Boston (Logan) to Chicago

1 passenger, economy

Nonstop flights from Boston to Chicago: American Airlines, Southwest Airlines, Jetblue Airways and 1 more. Nonstop flights per week: 57. Flight time: 3 hours 5 minutes. Distance: 1389 km. Tickets from R1 460 (departure 26 November).

Prices updated on 23 October at 11:04

See also: Chicago — Boston (Logan)Flights from Boston (Logan)Flights to Chicago

Cheap flights Boston to Chicago

Compare prices, duration and stops

American Airlines
AA 3160
18:16
Logan (BOS)
Fri, 23 Oct
3h 12min
Direct
20:28
Chicago O'Hare International Airport (ORD)
Fri, 23 Oct
R2 726
American Airlines
AA 927
19:23
Logan (BOS)
Fri, 23 Oct
3h 6min
Direct
21:29
Chicago O'Hare International Airport (ORD)
Fri, 23 Oct
R2 695
Southwest Airlines
WN 1346
16:40
Logan (BOS)
Sat, 24 Oct
2h 35min
Direct
18:15
Chicago Midway International Airport (MDW)
Sat, 24 Oct
R1 929
Frontier Airlines
F9 3511
11:42
Logan (BOS)
Sat, 24 Oct
7h 49min
1 stop
18:31
Chicago O'Hare International Airport (ORD)
Sat, 24 Oct
R2 588
American Airlines
AA 3324
12:54
Logan (BOS)
Sun, 25 Oct
3h 6min
Direct
15:00
Chicago O'Hare International Airport (ORD)
Sun, 25 Oct
R2 734
Southwest Airlines
WN 805
12:50
Logan (BOS)
Mon, 26 Oct
2h 35min
Direct
14:25
Chicago Midway International Airport (MDW)
Mon, 26 Oct
R1 929
Frontier Airlines
F9 3511
12:57
Logan (BOS)
Mon, 26 Oct
11h 46min
1 stop
23:43
Chicago Midway International Airport (MDW)
Mon, 26 Oct
R2 693
Jetblue Airways
B6 111
16:59
Logan (BOS)
Tue, 27 Oct
3h 1min
Direct
19:00
Chicago O'Hare International Airport (ORD)
Tue, 27 Oct
R1 683
Frontier Airlines
F9 3511
11:12
Logan (BOS)
Tue, 27 Oct
7h 15min
1 stop
17:27
Chicago Midway International Airport (MDW)
Tue, 27 Oct
R2 571
Jetblue Airways
B6 811
00:15
Logan (BOS)
Wed, 28 Oct
3h 14min
Direct
02:29
Chicago O'Hare International Airport (ORD)
Wed, 28 Oct
R1 884
Jetblue Airways
B6 111
16:59
Logan (BOS)
Wed, 28 Oct
3h 1min
Direct
19:00
Chicago O'Hare International Airport (ORD)
Wed, 28 Oct
R1 677
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Wed, 28 Oct
6h 37min
1 stop
18:16
Chicago O'Hare International Airport (ORD)
Wed, 28 Oct
R2 382
Southwest Airlines
WN 807
12:50
Logan (BOS)
Wed, 28 Oct
2h 35min
Direct
14:25
Chicago Midway International Airport (MDW)
Wed, 28 Oct
R2 582
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Thu, 29 Oct
12h 8min
1 stop
23:47
Chicago Midway International Airport (MDW)
Thu, 29 Oct
R2 638
United Airlines
UA 375
20:29
Logan (BOS)
Thu, 29 Oct
3h 3min
Direct
22:32
Chicago O'Hare International Airport (ORD)
Thu, 29 Oct
R1 862
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Fri, 30 Oct
7h 6min
1 stop
18:45
Chicago O'Hare International Airport (ORD)
Fri, 30 Oct
R2 139
Frontier Airlines
F9 3511
11:27
Logan (BOS)
Sat, 31 Oct
7h 20min
1 stop
17:47
Chicago Midway International Airport (MDW)
Sat, 31 Oct
R2 263
American Airlines
AA 2146
05:43
Logan (BOS)
Sun, 1 Nov
3h 17min
Direct
08:00
Chicago O'Hare International Airport (ORD)
Sun, 1 Nov
R2 965
American Airlines
AA 947
07:13
Logan (BOS)
Sun, 1 Nov
3h 16min
Direct
09:29
Chicago O'Hare International Airport (ORD)
Sun, 1 Nov
R2 936
Jetblue Airways
B6 111
17:59
Logan (BOS)
Sun, 1 Nov
3h
Direct
19:59
Chicago O'Hare International Airport (ORD)
Sun, 1 Nov
R2 998
American Airlines
AA 1951
18:19
Logan (BOS)
Sun, 1 Nov
3h 10min
Direct
20:29
Chicago O'Hare International Airport (ORD)
Sun, 1 Nov
R2 170
Jetblue Airways
B6 811
17:05
Logan (BOS)
Sun, 1 Nov
3h 12min
Direct
19:17
Chicago O'Hare International Airport (ORD)
Sun, 1 Nov
R3 277
Jetblue Airways
B6 111
17:59
Logan (BOS)
Mon, 2 Nov
3h 1min
Direct
20:00
Chicago O'Hare International Airport (ORD)
Mon, 2 Nov
R2 552
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Mon, 2 Nov
7h 6min
1 stop
18:45
Chicago O'Hare International Airport (ORD)
Mon, 2 Nov
R2 793
Jetblue Airways
B6 811
17:05
Logan (BOS)
Mon, 2 Nov
3h 12min
Direct
19:17
Chicago O'Hare International Airport (ORD)
Mon, 2 Nov
R1 523
American Airlines
AA 2925
03:40
Logan (BOS)
Tue, 3 Nov
3h 14min
Direct
05:54
Chicago O'Hare International Airport (ORD)
Tue, 3 Nov
R1 929
American Airlines
AA 2146
13:43
Logan (BOS)
Tue, 3 Nov
3h 17min
Direct
16:00
Chicago O'Hare International Airport (ORD)
Tue, 3 Nov
R1 929
Frontier Airlines
F9 3511
12:15
Logan (BOS)
Tue, 3 Nov
7h 15min
1 stop
18:30
Chicago O'Hare International Airport (ORD)
Tue, 3 Nov
R2 274
Southwest Airlines
WN 816 🔥 Hot deal
17:55
Logan (BOS)
Tue, 3 Nov
2h 45min
Direct
19:40
Chicago Midway International Airport (MDW)
Tue, 3 Nov
R1 824
Jetblue Airways
B6 111 🔥 Hot deal
09:59
Logan (BOS)
Wed, 4 Nov
3h 1min
Direct
12:00
Chicago O'Hare International Airport (ORD)
Wed, 4 Nov
R1 519
American Airlines
AA 894
20:33
Logan (BOS)
Wed, 4 Nov
3h 7min
Direct
22:40
Chicago O'Hare International Airport (ORD)
Wed, 4 Nov
R2 723
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Wed, 4 Nov
6h 51min
1 stop
18:30
Chicago O'Hare International Airport (ORD)
Wed, 4 Nov
R2 116
Jetblue Airways
B6 111
17:59
Logan (BOS)
Thu, 5 Nov
3h
Direct
19:59
Chicago O'Hare International Airport (ORD)
Thu, 5 Nov
R1 985
United Airlines
UA 1732
19:55
Logan (BOS)
Thu, 5 Nov
3h 4min
Direct
21:59
Chicago O'Hare International Airport (ORD)
Thu, 5 Nov
R1 634
Jetblue Airways
B6 811
17:05
Logan (BOS)
Fri, 6 Nov
3h 12min
Direct
19:17
Chicago O'Hare International Airport (ORD)
Fri, 6 Nov
R2 362
Southwest Airlines
WN 816
18:30
Logan (BOS)
Fri, 6 Nov
2h 45min
Direct
20:15
Chicago Midway International Airport (MDW)
Fri, 6 Nov
R3 038
American Airlines
AA 2166
18:20
Logan (BOS)
Sat, 7 Nov
3h 9min
Direct
20:29
Chicago O'Hare International Airport (ORD)
Sat, 7 Nov
R1 929
United Airlines
UA 1414
14:00
Logan (BOS)
Mon, 9 Nov
3h
Direct
16:00
Chicago O'Hare International Airport (ORD)
Mon, 9 Nov
R1 651
Jetblue Airways
B6 111
19:15
Logan (BOS)
Mon, 9 Nov
3h 5min
Direct
21:20
Chicago O'Hare International Airport (ORD)
Mon, 9 Nov
R2 249
Jetblue Airways
B6 811
17:05
Logan (BOS)
Mon, 9 Nov
3h 12min
Direct
19:17
Chicago O'Hare International Airport (ORD)
Mon, 9 Nov
R1 519
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Fri, 13 Nov
7h 6min
1 stop
02:45
Chicago O'Hare International Airport (ORD)
Sat, 14 Nov +1
R2 473
Southwest Airlines
WN 2758
15:10
Logan (BOS)
Sat, 14 Nov
2h 45min
Direct
16:55
Chicago Midway International Airport (MDW)
Sat, 14 Nov
R1 668
United Airlines
UA 1414
06:00
Logan (BOS)
Sun, 15 Nov
3h
Direct
08:00
Chicago O'Hare International Airport (ORD)
Sun, 15 Nov
R1 987
American Airlines
AA 2779
15:21
Logan (BOS)
Sun, 15 Nov
3h 15min
Direct
17:36
Chicago O'Hare International Airport (ORD)
Sun, 15 Nov
R1 937
Frontier Airlines
F9 3511
20:15
Logan (BOS)
Tue, 17 Nov
6h 32min
1 stop
01:47
Chicago Midway International Airport (MDW)
Wed, 18 Nov +1
R2 298
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Wed, 18 Nov
6h 37min
1 stop
02:16
Chicago O'Hare International Airport (ORD)
Thu, 19 Nov +1
R2 298
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Thu, 19 Nov
7h 6min
1 stop
02:45
Chicago O'Hare International Airport (ORD)
Fri, 20 Nov +1
R2 298
American Airlines
AA 751 Best price
20:08
Logan (BOS)
Thu, 26 Nov
3h 12min
Direct
22:20
Chicago O'Hare International Airport (ORD)
Thu, 26 Nov
R1 460
Southwest Airlines
WN 0813
13:05
Logan (BOS)
Thu, 26 Nov
2h 40min
Direct
14:45
Chicago Midway International Airport (MDW)
Thu, 26 Nov
R1 692
Southwest Airlines
WN 2185
07:05
Logan (BOS)
Fri, 27 Nov
2h 45min
Direct
08:50
Chicago Midway International Airport (MDW)
Fri, 27 Nov
R2 637

Direct flight schedule Boston — Chicago

Direct flights: 12 · Airlines: 4 · First departure: 05:43 · Last departure: 20:29

Departure → arrivalFlightAirport DaysDurationPrice
05:43→08:00 American Airlines AA 2146 LoganBOS MonTueWedThuFriSatSun 3h 17min
07:05→08:50 Southwest Airlines WN 2185 LoganBOS MonTueWedThuFriSatSun 2h 45min
07:13→09:26 American Airlines AA 947 LoganBOS MonTueWedThuFriSatSun 3h 13min
08:00→10:10 Jetblue Airways B6 311 LoganBOS MonTueWedThuFriSatSun 3h 10min
12:45→14:30 Southwest Airlines WN 813 LoganBOS MonTueWedThuFriSatSun 2h 45min
13:45→15:51 United Airlines UA 1414 LoganBOS MonTueWedThuFriSatSun 3h 6min
15:10→16:55 Southwest Airlines WN 2758 LoganBOS MonTueWedThuFriSatSun 2h 45min
15:21→17:34 American Airlines AA 2779 LoganBOS MonTueWedThuFriSatSun 3h 13min
Local time: departure at the departure airport, arrival at the arrival airport. Days and prices are based on tickets found for the coming months.

Low price calendar

From
To
Lowest price of the month Fri, 30 Oct · One way from R2 139

Prices as of 23 October, 11:05 Moscow time

Cheap flights Boston to Chicago

Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Fri, Sun
Price from
R1 519
Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
R1 668
American Airlines
American Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
R1 937
United Airlines
United Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
R1 987
Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat
Price from
R2 116

Which airlines offer the cheapest flights from Boston to Chicago?

Based on collected data, the cheapest flights are offered by Southwest Airlines with an average ticket price of R2 204.

  • Southwest Airlines Average price: R2 204 · Flights: 8 · Direct: 8
  • United Airlines Average price: R2 261 · Flights: 3 · Direct: 3
  • Jetblue Airways Average price: R2 300 · Flights: 3 · Direct: 3
  • Frontier Airlines Average price: R2 366 · Flights: 3 · Direct: 0
  • American Airlines Average price: R2 405 · Flights: 17 · Direct: 17

Which airlines fly most often from Boston to Chicago?

The most flight options on this route are offered by American Airlines — options found: 17.

  • American Airlines Flights: 17 · Direct: 17
  • Southwest Airlines Flights: 8 · Direct: 8
  • United Airlines Flights: 3 · Direct: 3
  • Jetblue Airways Flights: 3 · Direct: 3
  • Frontier Airlines Flights: 3 · Direct: 0

Round trip Boston — Chicago

TripOutboundReturnOutbound + returnTotal
Weekend tripSat, 12 DecMon, 14 Dec R1 787 + R1 945
One weekWed, 4 NovThu, 12 Nov R1 519 + R1 668
Two weeksWed, 4 NovThu, 19 Nov R1 519 + R1 550

Two one-way tickets combined, price per adult. Tap a price to search these dates.

Prices as of 23 October, 11:05 Moscow time

How many days before departure is it cheapest to buy a Boston — Chicago ticket?

The cheapest departure right now is Wed, 4 Nov — from R1 519. Days before departure: 11. 4–7 days before departure tickets cost from R2 139, 1–3 days before — from R2 571.

Before departureDeparture dateDifference from lowestPrice
1–3 days Tue, 27 Oct 69% more
4–7 days Fri, 30 Oct 41% more
8–14 days Wed, 4 Nov cheapest
15–21 days Mon, 9 Nov cheapest
22–30 days Sun, 15 Nov 28% more

Lowest prices for departures in the next 30 days.

How many flights per day operate from Boston to Chicago?

Most flights operate on Thu (12), the fewest on Sat (5).

  • Mon Flights: 11 · Direct: 9
  • Tue Flights: 9 · Direct: 8
  • Wed Flights: 11 · Direct: 10
  • Thu Flights: 12 · Direct: 10
  • Fri Flights: 9 · Direct: 7
  • Sat Flights: 5 · Direct: 4
  • Sun Flights: 9 · Direct: 9

Popular destinations from Boston

All →
BOS
Boston — Lebanon
United States → United States
LEB
from
R1 132
BOS
Boston — Rutland
United States → United States
RUT
from
R1 287
BOS
Boston — Washington
United States → United States
WAS
from
R1 320
BOS
Boston — Philadelphia
United States → United States
PHL
from
R1 583
BOS
Boston — Orlando
United States → United States
ORL
from
R1 615
BOS
Boston — San Jose
United States → United States
SJC
from
R1 702

Popular destinations to Chicago

All →
PHL
Philadelphia — Chicago
United States → United States
CHI
from
R320
BNA
Nashville — Chicago
United States → United States
CHI
from
R534
FLL
Fort Lauderdale — Chicago
United States → United States
CHI
from
R545
ATL
Atlanta — Chicago
United States → United States
CHI
from
R743
DEN
Denver — Chicago
United States → United States
CHI
from
R865
DFW
Dallas — Chicago
United States → United States
CHI
from
R883
TPA
Tampa — Chicago
United States → United States
CHI
from
R900
LAS
Las Vegas — Chicago
United States → United States
CHI
from
R1 151
LAX
Los Angeles — Chicago
United States → United States
CHI
from
R1 435

Cheap flights Boston to Chicago

Price from
R1 519
Average price
R2 298
Flight time
3 hours 5 minutes
Distance
1 389 km
Рейсов в неделю
57
Airlines
5
Most frequent flight
AA 2146

Prices as of 23 October, 11:04 Moscow time

Airports on the Boston — Chicago route

From → to Flights Direct Airlines Price from
LoganBOS Chicago O'Hare International AirportORD Cheapest
24224
LoganBOS Chicago Midway International AirportMDW
1082

Departure airports · Boston

Arrival airports · Chicago

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

change

3 GB

data

30

days

R149

Buy

change

2 GB

data

15

days

R207

Buy

change

5 GB

data

30

days

R232

Buy

change

3 GB

data

30

days

R265

Buy

change

5 GB

data

30

days

R373

Buy

Frequently Asked Questions

Yes. Nonstop flights from Boston to Chicago are operated by: American Airlines, Southwest Airlines, Jetblue Airways, United Airlines. A nonstop flight takes 3 hours 5 minutes on average. Nonstop tickets start at R1 460.
The average ticket price Boston Chicago is R2 298. The cheapest ticket costs R1 460, operated by American Airlines, flight AA 751, departing Boston on 26 November at 20:08, arriving Chicago on 26 November at 22:20. Prices as of 23 October.
A nonstop flight takes 3 hours 5 minutes on average. The fastest is WN 1346 Southwest Airlines: 2 hours 35 minutes. With a connection: from 6 hours 32 minutes, usually about 7 hours.
Flights from Boston to Chicago arrive at these airports: Chicago O'Hare International Airport (ORD), Chicago Midway International Airport (MDW). Most flights arrive at Chicago O'Hare International Airport. Departure: Logan (BOS).
Based on prices for the coming months, the cheapest month to fly is November: tickets from R1 519. The most expensive month is October, with tickets from R2 139.
Tickets from Boston to Chicago are sold by: American Airlines, Southwest Airlines, Jetblue Airways, Frontier Airlines, United Airlines. Nonstop: American Airlines, Southwest Airlines, Jetblue Airways, United Airlines.
The distance from Boston to Chicago is 1389 km.
Tickets from Chicago to Boston start at R1 519. The average price is R2 505. Nonstop flights are operated by: American Airlines, United Airlines, Southwest Airlines, Jetblue Airways. All tickets Chicago — Boston