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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
235 C$
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
168 C$
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
211 C$
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
165 C$
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
174 C$
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
148 C$
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
196 C$
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
185 C$
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
143 C$
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
142 C$
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
147 C$
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
192 C$
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
141 C$
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
230 C$
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
230 C$
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
137 C$
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
138 C$
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
144 C$
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
173 C$
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
191 C$
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
199 C$
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
160 C$
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
182 C$
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
208 C$
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
219 C$
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
269 C$
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
229 C$
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
219 C$
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
259 C$
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
457 C$
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
195 C$
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
233 C$
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
145 C$
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
183 C$
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
197 C$
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
197 C$
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
166 C$
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
175 C$
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
160 C$
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
197 C$
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
197 C$
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
173 C$
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
155 C$
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
174 C$
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
171 C$
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
152 C$
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
201 C$
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
164 C$
United Airlines
UA 2213
12:50
Chicago, O'Hare International Airport (ORD)
Wed, 30 dec
2h 27min
Direct
15:17
Boston, Logan (BOS)
Wed, 30 dec
165 C$
Southwest Airlines
WN 4113
14:30
Chicago, Chicago Midway International Airport (MDW)
Tue, 5 jan
2h 30min
Direct
17:00
Boston, Logan (BOS)
Tue, 5 jan
200 C$

Low price calendar

September 2026
Price chart (September 2026)
min: 137 C$ · max: 235 C$
01.09.2026 — no data 02.09.2026 — no data 03.09.2026 — no data 04.09.2026 — no data 05.09.2026 — no data 06.09.2026 — no data 07.09.2026 — no data 08.09.2026 — no data 09.09.2026 — no data 10.09.2026 — no data 11.09.2026 — no data 12.09.2026 — 144 C$ 13.09.2026 — no data 14.09.2026 — 235 C$ 15.09.2026 — 168 C$ 16.09.2026 — 211 C$ 17.09.2026 — 165 C$ 18.09.2026 — 148 C$ 19.09.2026 — 141 C$ 20.09.2026 — 230 C$ 21.09.2026 — 230 C$ 22.09.2026 — 137 C$ 23.09.2026 — 144 C$ 24.09.2026 — 173 C$ 25.09.2026 — no data 26.09.2026 — no data 27.09.2026 — 191 C$ 28.09.2026 — no data 29.09.2026 — 199 C$ 30.09.2026 — no data 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
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Tue
Wed
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Fri
Sat
Sun
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144 C$
13
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14
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235 C$
15
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168 C$
16
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211 C$
17
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165 C$
18
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148 C$
19
Good deal
141 C$
20
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230 C$
21
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230 C$
22
Good deal
137 C$
23
Good deal
144 C$
24
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173 C$
25
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26
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27
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191 C$
28
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29
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199 C$
30
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Cheap flights Chicago to Boston

Jetblue Airways
Jetblue Airways
Tue, Wed, Thu, Fri, Sat, Sun
Price from
C$137
United Airlines
United Airlines
Mon, Tue, Wed, Thu, Sat, Sun
Price from
C$141
Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
C$142
Frontier Airlines
Frontier Airlines
Wed, Fri, Sat
Price from
C$192
American Airlines
American Airlines
Mon, Wed, Thu, Sat, Sun
Price from
C$201

Popular destinations from Chicago

All →
CHI
Chicago — Orlando
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ORL
from
C$30
CHI
Chicago — Orlando
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MCO
from
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Chicago — Atlanta
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from
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Chicago — Houston
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from
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Chicago — Houston
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from
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Chicago — New York
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NYC
from
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CHI
Chicago — Denver
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from
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CHI
Chicago — Fort Lauderdale
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from
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CHI
Chicago — Miami
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from
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Popular destinations to Boston

All →
ORL
Orlando — Boston
United States → United States
BOS
from
C$38
FLL
Fort Lauderdale — Boston
United States → United States
BOS
from
C$61
WAS
Washington — Boston
United States → United States
BOS
from
C$62
NYC
New York — Boston
United States → United States
BOS
from
C$83
MIA
Miami — Boston
United States → United States
BOS
from
C$94
ATL
Atlanta — Boston
United States → United States
BOS
from
C$103
BUF
Buffalo — Boston
United States → United States
BOS
from
C$106
LAX
Los Angeles — Boston
United States → United States
BOS
from
C$109

Cheap flights Chicago to Boston

Interesting facts about the route

Flight time

2h 35min

Distance

1 389 km

Average price

C$175

Most frequent flight

AA 2682

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

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3 GB

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30

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C$12

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2 GB

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15

days

C$17

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5 GB

data

30

days

C$19

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3 GB

data

30

days

C$22

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5 GB

data

30

days

C$31

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Frequently Asked Questions

The average ticket price Chicago Boston is C$175. The cheapest ticket costs C$168, 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.