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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 S$111 (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
O'Hare International Airport (ORD)
Thu, 22 Oct
S$205
Southwest Airlines
WN 909
22:00
Logan (BOS)
Thu, 22 Oct
2h 40min
Direct
23:40
Chicago Midway International Airport (MDW)
Thu, 22 Oct
S$160
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
S$192
American Airlines
AA 3160
18:16
Logan (BOS)
Fri, 23 Oct
3h 12min
Direct
20:28
O'Hare International Airport (ORD)
Fri, 23 Oct
S$207
Southwest Airlines
WN 1346
16:40
Logan (BOS)
Sat, 24 Oct
2h 35min
Direct
18:15
Chicago Midway International Airport (MDW)
Sat, 24 Oct
S$146
Frontier Airlines
F9 3511
11:42
Logan (BOS)
Sat, 24 Oct
7h 49min
1 stop
18:31
O'Hare International Airport (ORD)
Sat, 24 Oct
S$196
American Airlines
AA 3324
12:54
Logan (BOS)
Sun, 25 Oct
3h 6min
Direct
15:00
O'Hare International Airport (ORD)
Sun, 25 Oct
S$207
Southwest Airlines
WN 805
12:50
Logan (BOS)
Mon, 26 Oct
2h 35min
Direct
14:25
Chicago Midway International Airport (MDW)
Mon, 26 Oct
S$146
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
S$204
Jetblue Airways
B6 111
16:59
Logan (BOS)
Tue, 27 Oct
3h 1min
Direct
19:00
O'Hare International Airport (ORD)
Tue, 27 Oct
S$128
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
S$195
Jetblue Airways
B6 811
00:15
Logan (BOS)
Wed, 28 Oct
3h 14min
Direct
02:29
O'Hare International Airport (ORD)
Wed, 28 Oct
S$143
Jetblue Airways
B6 111
16:59
Logan (BOS)
Wed, 28 Oct
3h 1min
Direct
19:00
O'Hare International Airport (ORD)
Wed, 28 Oct
S$127
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Wed, 28 Oct
6h 37min
1 stop
18:16
O'Hare International Airport (ORD)
Wed, 28 Oct
S$181
Southwest Airlines
WN 807
12:50
Logan (BOS)
Wed, 28 Oct
2h 35min
Direct
14:25
Chicago Midway International Airport (MDW)
Wed, 28 Oct
S$196
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
S$200
United Airlines
UA 375
20:29
Logan (BOS)
Thu, 29 Oct
3h 3min
Direct
22:32
O'Hare International Airport (ORD)
Thu, 29 Oct
S$141
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Fri, 30 Oct
7h 6min
1 stop
18:45
O'Hare International Airport (ORD)
Fri, 30 Oct
S$162
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
S$172
American Airlines
AA 2146
05:43
Logan (BOS)
Sun, 1 Nov
3h 17min
Direct
08:00
O'Hare International Airport (ORD)
Sun, 1 Nov
S$225
American Airlines
AA 947
07:13
Logan (BOS)
Sun, 1 Nov
3h 16min
Direct
09:29
O'Hare International Airport (ORD)
Sun, 1 Nov
S$223
Jetblue Airways
B6 111
17:59
Logan (BOS)
Sun, 1 Nov
3h
Direct
19:59
O'Hare International Airport (ORD)
Sun, 1 Nov
S$227
American Airlines
AA 1951
18:19
Logan (BOS)
Sun, 1 Nov
3h 10min
Direct
20:29
O'Hare International Airport (ORD)
Sun, 1 Nov
S$164
Jetblue Airways
B6 811
17:05
Logan (BOS)
Sun, 1 Nov
3h 12min
Direct
19:17
O'Hare International Airport (ORD)
Sun, 1 Nov
S$248
Jetblue Airways
B6 111
17:59
Logan (BOS)
Mon, 2 Nov
3h 1min
Direct
20:00
O'Hare International Airport (ORD)
Mon, 2 Nov
S$193
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Mon, 2 Nov
7h 6min
1 stop
18:45
O'Hare International Airport (ORD)
Mon, 2 Nov
S$212
Jetblue Airways
B6 811
17:05
Logan (BOS)
Mon, 2 Nov
3h 12min
Direct
19:17
O'Hare International Airport (ORD)
Mon, 2 Nov
S$115
American Airlines
AA 2925
03:40
Logan (BOS)
Tue, 3 Nov
3h 14min
Direct
05:54
O'Hare International Airport (ORD)
Tue, 3 Nov
S$146
American Airlines
AA 2146
13:43
Logan (BOS)
Tue, 3 Nov
3h 17min
Direct
16:00
O'Hare International Airport (ORD)
Tue, 3 Nov
S$146
Frontier Airlines
F9 3511
12:15
Logan (BOS)
Tue, 3 Nov
7h 15min
1 stop
18:30
O'Hare International Airport (ORD)
Tue, 3 Nov
S$171
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
S$138
Jetblue Airways
B6 111 🔥 Hot deal
09:59
Logan (BOS)
Wed, 4 Nov
3h 1min
Direct
12:00
O'Hare International Airport (ORD)
Wed, 4 Nov
S$115
American Airlines
AA 894
20:33
Logan (BOS)
Wed, 4 Nov
3h 7min
Direct
22:40
O'Hare International Airport (ORD)
Wed, 4 Nov
S$206
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Wed, 4 Nov
6h 51min
1 stop
18:30
O'Hare International Airport (ORD)
Wed, 4 Nov
S$160
Jetblue Airways
B6 111
17:59
Logan (BOS)
Thu, 5 Nov
3h
Direct
19:59
O'Hare International Airport (ORD)
Thu, 5 Nov
S$150
United Airlines
UA 1732
19:55
Logan (BOS)
Thu, 5 Nov
3h 4min
Direct
21:59
O'Hare International Airport (ORD)
Thu, 5 Nov
S$124
Jetblue Airways
B6 811
17:05
Logan (BOS)
Fri, 6 Nov
3h 12min
Direct
19:17
O'Hare International Airport (ORD)
Fri, 6 Nov
S$179
Southwest Airlines
WN 816
18:30
Logan (BOS)
Fri, 6 Nov
2h 45min
Direct
20:15
Chicago Midway International Airport (MDW)
Fri, 6 Nov
S$230
American Airlines
AA 2166
18:20
Logan (BOS)
Sat, 7 Nov
3h 9min
Direct
20:29
O'Hare International Airport (ORD)
Sat, 7 Nov
S$146
United Airlines
UA 1414
14:00
Logan (BOS)
Mon, 9 Nov
3h
Direct
16:00
O'Hare International Airport (ORD)
Mon, 9 Nov
S$125
Jetblue Airways
B6 111
19:15
Logan (BOS)
Mon, 9 Nov
3h 5min
Direct
21:20
O'Hare International Airport (ORD)
Mon, 9 Nov
S$170
Jetblue Airways
B6 811
17:05
Logan (BOS)
Mon, 9 Nov
3h 12min
Direct
19:17
O'Hare International Airport (ORD)
Mon, 9 Nov
S$115
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Fri, 13 Nov
7h 6min
1 stop
02:45
O'Hare International Airport (ORD)
Sat, 14 Nov +1
S$187
Southwest Airlines
WN 2758
15:10
Logan (BOS)
Sat, 14 Nov
2h 45min
Direct
16:55
Chicago Midway International Airport (MDW)
Sat, 14 Nov
S$126
United Airlines
UA 1414
06:00
Logan (BOS)
Sun, 15 Nov
3h
Direct
08:00
O'Hare International Airport (ORD)
Sun, 15 Nov
S$151
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
S$174
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Wed, 18 Nov
6h 37min
1 stop
02:16
O'Hare International Airport (ORD)
Thu, 19 Nov +1
S$174
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Thu, 19 Nov
7h 6min
1 stop
02:45
O'Hare International Airport (ORD)
Fri, 20 Nov +1
S$174
American Airlines
AA 751 Best price
20:08
Logan (BOS)
Thu, 26 Nov
3h 12min
Direct
22:20
O'Hare International Airport (ORD)
Thu, 26 Nov
S$111
Southwest Airlines
WN 0813
13:05
Logan (BOS)
Thu, 26 Nov
2h 40min
Direct
14:45
Chicago Midway International Airport (MDW)
Thu, 26 Nov
S$128

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 S$162

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
S$115
Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$126
Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat
Price from
S$131
United Airlines
United Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$151
American Airlines
American Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$205

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 S$167.

  • Southwest Airlines Average price: S$167 · Flights: 9 · Direct: 9
  • United Airlines Average price: S$171 · Flights: 3 · Direct: 3
  • Jetblue Airways Average price: S$174 · Flights: 3 · Direct: 3
  • Frontier Airlines Average price: S$179 · Flights: 3 · Direct: 0
  • American Airlines Average price: S$184 · 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 S$135 + S$147
One weekWed, 4 NovThu, 12 Nov S$115 + S$126
Two weeksWed, 4 NovThu, 19 Nov S$115 + S$117

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 S$115. Days before departure: 13. 4–7 days before departure tickets cost from S$181, 1–3 days before — from S$192.

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
S$86
BOS
Boston — Fort Lauderdale
United States → United States
FLL
from
S$90
BOS
Boston — Washington
United States → United States
WAS
from
S$96
BOS
Boston — Rutland
United States → United States
RUT
from
S$98
BOS
Boston — Orlando
United States → United States
ORL
from
S$122
BOS
Boston — San Jose
United States → United States
SJC
from
S$129

Popular destinations to Chicago

All →
BNA
Nashville — Chicago
United States → United States
CHI
from
S$40
FLL
Fort Lauderdale — Chicago
United States → United States
CHI
from
S$41
ATL
Atlanta — Chicago
United States → United States
CHI
from
S$56
PHL
Philadelphia — Chicago
United States → United States
CHI
from
S$57
DEN
Denver — Chicago
United States → United States
CHI
from
S$66
DFW
Dallas — Chicago
United States → United States
CHI
from
S$67
TPA
Tampa — Chicago
United States → United States
CHI
from
S$68
LAS
Las Vegas — Chicago
United States → United States
CHI
from
S$87
LAX
Los Angeles — Chicago
United States → United States
CHI
from
S$103

Cheap flights Boston to Chicago

Price from
S$115
Average price
S$176
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 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

S$12

Buy

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2 GB

data

15

days

S$16

Buy

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5 GB

data

30

days

S$18

Buy

change

3 GB

data

30

days

S$20

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change

5 GB

data

30

days

S$29

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 S$111.
The average ticket price Boston Chicago is S$176. The cheapest ticket costs S$111, 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: O'Hare International Airport (ORD), Chicago Midway International Airport (MDW). Most flights arrive at O'Hare International Airport. Departure: Logan (BOS).
Based on prices for the coming months, the cheapest month to fly is November: tickets from S$115. The most expensive month is October, with tickets from S$162.
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 S$115. The average price is S$190. Nonstop flights are operated by: American Airlines, United Airlines, Southwest Airlines, Jetblue Airways. All tickets Chicago — Boston