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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 4 minutes. Distance: 1389 km. Tickets from KSh10 789 (departure 26 November).

Prices updated on 22 October at 11:05

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 3324
05:54
Logan (BOS)
Thu, 22 Oct
3h 6min
Direct
08:00
Chicago O'Hare International Airport (ORD)
Thu, 22 Oct
KSh19 957
Southwest Airlines
WN 909
22:00
Logan (BOS)
Thu, 22 Oct
2h 40min
Direct
23:40
Chicago Midway International Airport (MDW)
Thu, 22 Oct
KSh15 580
Frontier Airlines
F9 3511
12:57
Logan (BOS)
Fri, 23 Oct
11h 46min
1 stop
23:43
Chicago Midway International Airport (MDW)
Fri, 23 Oct
KSh18 703
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
KSh20 138
Southwest Airlines
WN 1346
16:40
Logan (BOS)
Sat, 24 Oct
2h 35min
Direct
18:15
Chicago Midway International Airport (MDW)
Sat, 24 Oct
KSh14 251
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
KSh19 117
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
KSh20 196
Southwest Airlines
WN 805
12:50
Logan (BOS)
Mon, 26 Oct
2h 35min
Direct
14:25
Chicago Midway International Airport (MDW)
Mon, 26 Oct
KSh14 251
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
KSh19 897
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
KSh12 432
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
KSh18 993
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
KSh13 918
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
KSh12 387
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
KSh17 595
Southwest Airlines
WN 807
12:50
Logan (BOS)
Wed, 28 Oct
2h 35min
Direct
14:25
Chicago Midway International Airport (MDW)
Wed, 28 Oct
KSh19 078
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
KSh19 486
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
KSh13 759
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
KSh15 799
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
KSh16 715
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
KSh21 901
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
KSh21 691
Jetblue Airways
B6 111
17:59
Logan (BOS)
Sun, 1 Nov
3h
Direct
19:59
Chicago O'Hare International Airport (ORD)
Sun, 1 Nov
KSh22 151
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
KSh16 030
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
KSh24 211
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
KSh18 851
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
KSh20 631
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
KSh11 249
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
KSh14 251
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
KSh14 251
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
KSh16 647
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
KSh13 475
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
KSh11 218
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
KSh20 117
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
KSh15 634
Jetblue Airways
B6 111
17:59
Logan (BOS)
Thu, 5 Nov
3h
Direct
19:59
Chicago O'Hare International Airport (ORD)
Thu, 5 Nov
KSh14 663
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
KSh12 068
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
KSh17 449
Southwest Airlines
WN 816
18:30
Logan (BOS)
Fri, 6 Nov
2h 45min
Direct
20:15
Chicago Midway International Airport (MDW)
Fri, 6 Nov
KSh22 446
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
KSh14 251
United Airlines
UA 1414
14:00
Logan (BOS)
Mon, 9 Nov
3h
Direct
16:00
Chicago O'Hare International Airport (ORD)
Mon, 9 Nov
KSh12 198
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
KSh16 613
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
KSh11 218
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
KSh18 273
Southwest Airlines
WN 2758
15:10
Logan (BOS)
Sat, 14 Nov
2h 45min
Direct
16:55
Chicago Midway International Airport (MDW)
Sat, 14 Nov
KSh12 325
United Airlines
UA 1414
06:00
Logan (BOS)
Sun, 15 Nov
3h
Direct
08:00
Chicago O'Hare International Airport (ORD)
Sun, 15 Nov
KSh14 682
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
KSh16 975
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
KSh16 975
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
KSh16 975
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
KSh10 789
Southwest Airlines
WN 0813
13:05
Logan (BOS)
Thu, 26 Nov
2h 40min
Direct
14:45
Chicago Midway International Airport (MDW)
Thu, 26 Nov
KSh12 496

Direct flight schedule Boston — Chicago

Direct flights: 11 · 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
17:05→19:17 Jetblue Airways B6 811 LoganBOS MonTueWedThuFriSatSun 3h 12min
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 KSh15 799

Prices as of 22 October, 11:06 Moscow time

Cheap flights Boston to Chicago

Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Fri, Sun
Price from
KSh11 218
Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
KSh12 325
Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat
Price from
KSh12 803
United Airlines
United Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
KSh14 682
American Airlines
American Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
KSh19 957

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 KSh16 240.

  • Southwest Airlines Average price: KSh16 240 · Flights: 9 · Direct: 9
  • United Airlines Average price: KSh16 706 · Flights: 3 · Direct: 3
  • Jetblue Airways Average price: KSh16 995 · Flights: 3 · Direct: 3
  • Frontier Airlines Average price: KSh17 475 · Flights: 3 · Direct: 0
  • American Airlines Average price: KSh17 955 · Flights: 16 · Direct: 16

Which airlines fly most often from Boston to Chicago?

The most flight options on this route are offered by American Airlines — options found: 16.

  • American Airlines Flights: 16 · Direct: 16
  • Southwest Airlines Flights: 9 · Direct: 9
  • 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 KSh13 201 + KSh14 368
One weekWed, 4 NovThu, 12 Nov KSh11 218 + KSh12 325
Two weeksWed, 4 NovThu, 19 Nov KSh11 218 + KSh11 448

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

Prices as of 22 October, 11:06 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 KSh11 218. Days before departure: 13. 4–7 days before departure tickets cost from KSh17 595, 1–3 days before — from KSh18 703.

Before departureDeparture dateDifference from lowestPrice
1–3 days Fri, 23 Oct 67% more
4–7 days Wed, 28 Oct 57% more
8–14 days Wed, 4 Nov cheapest
15–21 days Mon, 9 Nov cheapest
22–30 days Sat, 14 Nov 10% 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 (14), the fewest on Sat (5).

  • Mon Flights: 11 · Direct: 9
  • Tue Flights: 9 · Direct: 8
  • Wed Flights: 11 · Direct: 10
  • Thu Flights: 14 · Direct: 12
  • Fri Flights: 8 · Direct: 6
  • Sat Flights: 5 · Direct: 4
  • Sun Flights: 8 · Direct: 8

Popular destinations from Boston

All →
BOS
Boston — Lebanon
United States → United States
LEB
from
KSh8 359
BOS
Boston — Fort Lauderdale
United States → United States
FLL
from
KSh8 754
BOS
Boston — Washington
United States → United States
WAS
from
KSh9 369
BOS
Boston — Rutland
United States → United States
RUT
from
KSh9 506
BOS
Boston — Orlando
United States → United States
ORL
from
KSh11 934
BOS
Boston — San Jose
United States → United States
SJC
from
KSh12 574

Popular destinations to Chicago

All →
BNA
Nashville — Chicago
United States → United States
CHI
from
KSh3 946
FLL
Fort Lauderdale — Chicago
United States → United States
CHI
from
KSh4 025
ATL
Atlanta — Chicago
United States → United States
CHI
from
KSh5 489
PHL
Philadelphia — Chicago
United States → United States
CHI
from
KSh5 567
DEN
Denver — Chicago
United States → United States
CHI
from
KSh6 390
DFW
Dallas — Chicago
United States → United States
CHI
from
KSh6 521
TPA
Tampa — Chicago
United States → United States
CHI
from
KSh6 647
LAS
Las Vegas — Chicago
United States → United States
CHI
from
KSh8 453
LAX
Los Angeles — Chicago
United States → United States
CHI
from
KSh10 005

Cheap flights Boston to Chicago

Price from
KSh11 218
Average price
KSh17 194
Flight time
3 hours 4 minutes
Distance
1 389 km
Рейсов в неделю
57
Airlines
5
Most frequent flight
B6 811

Prices as of 22 October, 11:05 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
1192

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

KSh1 121

Buy

change

2 GB

data

15

days

KSh1 557

Buy

change

5 GB

data

30

days

KSh1 744

Buy

change

3 GB

data

30

days

KSh1 993

Buy

change

5 GB

data

30

days

KSh2 802

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 4 minutes on average. Nonstop tickets start at KSh10 789.
The average ticket price Boston Chicago is KSh17 194. The cheapest ticket costs KSh10 789, 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 22 October.
A nonstop flight takes 3 hours 4 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 KSh11 218. The most expensive month is October, with tickets from KSh15 799.
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 KSh11 218. The average price is KSh18 551. Nonstop flights are operated by: American Airlines, United Airlines, Southwest Airlines, Jetblue Airways. All tickets Chicago — Boston