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Cheap flights Chicago to Boston (Logan)

1 passenger, economy

Cheap flights Chicago to Boston

Compare prices, duration and stops

American Airlines
AA 2294
18:54
Chicago, O'Hare International Airport (ORD)
Mon, 14 sep
2h 41min
Direct
21:35
Boston, Logan (BOS)
Mon, 14 sep
216 S$
Jetblue Airways
B6 1012
01:24
Chicago, O'Hare International Airport (ORD)
Tue, 15 sep
2h 45min
Direct
04:09
Boston, Logan (BOS)
Tue, 15 sep
154 S$
Frontier Airlines
F9 3044
20:50
Chicago, O'Hare International Airport (ORD)
Wed, 16 sep
17h 32min
1 stop
14:22
Boston, Logan (BOS)
Thu, 17 sep +1
193 S$
Southwest Airlines
WN 3094
10:45
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
2h 15min
Direct
13:00
Boston, Logan (BOS)
Thu, 17 sep
152 S$
Jetblue Airways
B6 1012
01:24
Chicago, O'Hare International Airport (ORD)
Fri, 18 sep
2h 45min
Direct
04:09
Boston, Logan (BOS)
Fri, 18 sep
160 S$
Jetblue Airways
B6 1006
15:59
Chicago, O'Hare International Airport (ORD)
Fri, 18 sep
5h 22min
1 stop
21:21
Boston, Logan (BOS)
Fri, 18 sep
136 S$
Frontier Airlines
F9 3044
20:50
Chicago, O'Hare International Airport (ORD)
Fri, 18 sep
18h 1min
1 stop
14:51
Boston, Logan (BOS)
Sat, 19 sep +1
180 S$
American Airlines
AA 2682
01:19
Chicago, O'Hare International Airport (ORD)
Sat, 19 sep
2h 35min
Direct
03:54
Boston, Logan (BOS)
Sat, 19 sep
169 S$
United Airlines
UA 1779
02:40
Chicago, O'Hare International Airport (ORD)
Sat, 19 sep
2h 30min
Direct
05:10
Boston, Logan (BOS)
Sat, 19 sep
132 S$
Southwest Airlines
WN 2681
12:40
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
2h 20min
Direct
15:00
Boston, Logan (BOS)
Sat, 19 sep
131 S$
Frontier Airlines
F9 4064
17:56
Chicago, O'Hare International Airport (ORD)
Sat, 19 sep
8h 44min
1 stop
02:40
Boston, Logan (BOS)
Sun, 20 sep +1
135 S$
Frontier Airlines
F9 3044
20:50
Chicago, O'Hare International Airport (ORD)
Sat, 19 sep
18h 8min
1 stop
14:58
Boston, Logan (BOS)
Sun, 20 sep +1
176 S$
United Airlines
UA 2331
23:24
Chicago, O'Hare International Airport (ORD)
Sat, 19 sep
2h 35min
Direct
01:59
Boston, Logan (BOS)
Sun, 20 sep +1
129 S$
American Airlines
AA 3022
11:00
Chicago, O'Hare International Airport (ORD)
Sun, 20 sep
2h 39min
Direct
13:39
Boston, Logan (BOS)
Sun, 20 sep
211 S$
Southwest Airlines
WN 3094
10:45
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep
2h 15min
Direct
13:00
Boston, Logan (BOS)
Mon, 21 sep
211 S$
Jetblue Airways
B6 1006
15:59
Chicago, O'Hare International Airport (ORD)
Mon, 21 sep
5h 22min
1 stop
21:21
Boston, Logan (BOS)
Mon, 21 sep
184 S$
Jetblue Airways
B6 112 Best price
14:38
Chicago, O'Hare International Airport (ORD)
Tue, 22 sep
2h 28min
Direct
17:06
Boston, Logan (BOS)
Tue, 22 sep
125 S$
Southwest Airlines
WN 4215
23:00
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
2h 25min
Direct
01:25
Boston, Logan (BOS)
Wed, 23 sep +1
226 S$
Jetblue Airways
B6 112
14:38
Chicago, O'Hare International Airport (ORD)
Wed, 23 sep
2h 28min
Direct
17:06
Boston, Logan (BOS)
Wed, 23 sep
126 S$
American Airlines
AA 2294
18:54
Chicago, O'Hare International Airport (ORD)
Wed, 23 sep
2h 41min
Direct
21:35
Boston, Logan (BOS)
Wed, 23 sep
132 S$
Jetblue Airways
B6 864
20:00
Chicago, O'Hare International Airport (ORD)
Thu, 24 sep
7h 39min
1 stop
03:39
Boston, Logan (BOS)
Fri, 25 sep +1
159 S$
Jetblue Airways
B6 1012
01:24
Chicago, O'Hare International Airport (ORD)
Sun, 27 sep
2h 45min
Direct
04:09
Boston, Logan (BOS)
Sun, 27 sep
175 S$
Southwest Airlines
WN 4860
17:50
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
2h 20min
Direct
20:10
Boston, Logan (BOS)
Tue, 29 sep
183 S$
Jetblue Airways
B6 1012
01:24
Chicago, O'Hare International Airport (ORD)
Fri, 2 oct
2h 45min
Direct
04:09
Boston, Logan (BOS)
Fri, 2 oct
147 S$
Southwest Airlines
WN 4535
10:00
Chicago, Chicago Midway International Airport (MDW)
Sun, 4 oct
2h 25min
Direct
12:25
Boston, Logan (BOS)
Sun, 4 oct
167 S$
United Airlines
UA 1365
00:50
Chicago, O'Hare International Airport (ORD)
Mon, 5 oct
2h 34min
Direct
03:24
Boston, Logan (BOS)
Mon, 5 oct
191 S$
Southwest Airlines
WN 2842
14:10
Chicago, Chicago Midway International Airport (MDW)
Wed, 7 oct
2h 20min
Direct
16:30
Boston, Logan (BOS)
Wed, 7 oct
201 S$
American Airlines
AA 2950
11:00
Chicago, O'Hare International Airport (ORD)
Thu, 8 oct
2h 37min
Direct
13:37
Boston, Logan (BOS)
Thu, 8 oct
247 S$
American Airlines
AA 2682
01:00
Chicago, O'Hare International Airport (ORD)
Sat, 10 oct
2h 36min
Direct
03:36
Boston, Logan (BOS)
Sat, 10 oct
211 S$
Jetblue Airways
B6 906
11:10
Chicago, O'Hare International Airport (ORD)
Sat, 10 oct
7h 19min
1 stop
18:29
Boston, Logan (BOS)
Sat, 10 oct
201 S$
United Airlines
UA 1186
11:10
Chicago, O'Hare International Airport (ORD)
Sun, 11 oct
2h 23min
Direct
13:33
Boston, Logan (BOS)
Sun, 11 oct
237 S$
United Airlines
UA 1779
02:24
Chicago, O'Hare International Airport (ORD)
Tue, 13 oct
2h 30min
Direct
04:54
Boston, Logan (BOS)
Tue, 13 oct
419 S$
Southwest Airlines
WN 1687
03:05
Chicago, Chicago Midway International Airport (MDW)
Tue, 13 oct
11h 10min
1 stop
14:15
Boston, Logan (BOS)
Tue, 13 oct
179 S$
Jetblue Airways
B6 1012
01:04
Chicago, O'Hare International Airport (ORD)
Wed, 14 oct
2h 55min
Direct
03:59
Boston, Logan (BOS)
Wed, 14 oct
214 S$
Jetblue Airways
B6 112
14:38
Chicago, O'Hare International Airport (ORD)
Wed, 14 oct
2h 28min
Direct
17:06
Boston, Logan (BOS)
Wed, 14 oct
133 S$
Jetblue Airways
B6 1006
17:38
Chicago, O'Hare International Airport (ORD)
Wed, 14 oct
7h 11min
1 stop
00:49
Boston, Logan (BOS)
Thu, 15 oct +1
168 S$
United Airlines
UA 2296
02:20
Chicago, O'Hare International Airport (ORD)
Tue, 27 oct
2h 26min
Direct
04:46
Boston, Logan (BOS)
Tue, 27 oct
181 S$
United Airlines
UA 1186
11:00
Chicago, O'Hare International Airport (ORD)
Tue, 27 oct
2h 19min
Direct
13:19
Boston, Logan (BOS)
Tue, 27 oct
181 S$
Southwest Airlines
WN 4113
13:50
Chicago, Chicago Midway International Airport (MDW)
Sun, 1 nov
2h 20min
Direct
16:10
Boston, Logan (BOS)
Sun, 1 nov
152 S$
United Airlines
UA 2296
03:20
Chicago, O'Hare International Airport (ORD)
Mon, 2 nov
2h 26min
Direct
05:46
Boston, Logan (BOS)
Mon, 2 nov
160 S$
Southwest Airlines
WN 2902
00:45
Chicago, Chicago Midway International Airport (MDW)
Tue, 24 nov
2h 15min
Direct
03:00
Boston, Logan (BOS)
Tue, 24 nov
147 S$
United Airlines
UA 1117
15:13
Chicago, O'Hare International Airport (ORD)
Thu, 26 nov
2h 33min
Direct
17:46
Boston, Logan (BOS)
Thu, 26 nov
181 S$
United Airlines
UA 2331
00:08
Chicago, O'Hare International Airport (ORD)
Sat, 28 nov
2h 33min
Direct
02:41
Boston, Logan (BOS)
Sat, 28 nov
181 S$
Southwest Airlines
WN 4113
13:50
Chicago, Chicago Midway International Airport (MDW)
Fri, 11 dec
2h 20min
Direct
16:10
Boston, Logan (BOS)
Fri, 11 dec
159 S$
Southwest Airlines
WN 4113
14:30
Chicago, Chicago Midway International Airport (MDW)
Mon, 14 dec
2h 30min
Direct
17:00
Boston, Logan (BOS)
Mon, 14 dec
142 S$
United Airlines
UA 1707
03:20
Chicago, O'Hare International Airport (ORD)
Sun, 20 dec
2h 35min
Direct
05:55
Boston, Logan (BOS)
Sun, 20 dec
160 S$
Southwest Airlines
WN 2901
22:05
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 dec
2h 15min
Direct
00:20
Boston, Logan (BOS)
Tue, 22 dec +1
157 S$
United Airlines
UA 2213
12:50
Chicago, O'Hare International Airport (ORD)
Wed, 23 dec
2h 27min
Direct
15:17
Boston, Logan (BOS)
Wed, 23 dec
140 S$
American Airlines
AA 4572
21:55
Chicago, O'Hare International Airport (ORD)
Wed, 23 dec
2h 40min
Direct
00:35
Boston, Logan (BOS)
Thu, 24 dec +1
184 S$
American Airlines
AA 1457
15:00
Chicago, O'Hare International Airport (ORD)
Thu, 24 dec
2h 51min
Direct
17:51
Boston, Logan (BOS)
Thu, 24 dec
150 S$

Low price calendar

September 2026
Price chart (September 2026)
min: 125 S$ · max: 216 S$
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Sun
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14
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216 S$
15
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154 S$
16
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193 S$
17
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152 S$
18
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136 S$
19
Good deal
129 S$
20
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211 S$
21
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184 S$
22
Good deal
125 S$
23
Good deal
132 S$
24
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159 S$
25
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27
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175 S$
28
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183 S$
30
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Cheap flights Chicago to Boston

Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$125
United Airlines
United Airlines
Mon, Tue, Wed, Thu, Sat, Sun
Price from
S$129
Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$131
Frontier Airlines
Frontier Airlines
Wed, Fri, Sat
Price from
S$176
American Airlines
American Airlines
Mon, Wed, Thu, Sat, Sun
Price from
S$184

Popular destinations from Chicago

All →
CHI
Chicago — Orlando
United States → United States
ORL
from
S$27
CHI
Chicago — Orlando
United States → United States
MCO
from
S$27
CHI
Chicago — Atlanta
United States → United States
ATL
from
S$28
CHI
Chicago — Houston
United States → United States
HOU
from
S$28
CHI
Chicago — Houston
United States → United States
IAH
from
S$28
CHI
Chicago — New York
United States → United States
NYC
from
S$30
CHI
Chicago — Denver
United States → United States
DEN
from
S$30
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
S$31
CHI
Chicago — Miami
United States → United States
MIA
from
S$31

Popular destinations to Boston

All →
ORL
Orlando — Boston
United States → United States
BOS
from
S$35
FLL
Fort Lauderdale — Boston
United States → United States
BOS
from
S$56
WAS
Washington — Boston
United States → United States
BOS
from
S$57
NYC
New York — Boston
United States → United States
BOS
from
S$76
MIA
Miami — Boston
United States → United States
BOS
from
S$86
ATL
Atlanta — Boston
United States → United States
BOS
from
S$94
BUF
Buffalo — Boston
United States → United States
BOS
from
S$97
LAX
Los Angeles — Boston
United States → United States
BOS
from
S$100

Cheap flights Chicago to Boston

Interesting facts about the route

Flight time

2h 34min

Distance

1 389 km

Average price

S$167

Most frequent flight

WN 4113

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

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3 GB

data

30

days

S$11

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2 GB

data

15

days

S$16

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5 GB

data

30

days

S$18

Buy

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3 GB

data

30

days

S$20

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change

5 GB

data

30

days

S$29

Buy

Frequently Asked Questions

The average ticket price Chicago Boston is S$167. The cheapest ticket costs S$154, operated by Jetblue Airways, flight 1012, departing Chicago on 15 September at 01:24, arriving Boston on 15 September at 04:09.
The average flight time is 2 hours 45 minutes. The fastest flight takes 2 hours 41 minutes, flight 2294 operated by American Airlines, departing Chicago on 14 September at 18:54, arriving Boston on 14 September at 21:35.
Flights on the Chicago - Boston route are operated by the following airlines: American Airlines, Jetblue Airways, Frontier Airlines, United Airlines, Southwest Airlines.
The distance from Chicago to Boston is 1389 km.