Cheap flights Chicago to Boston (Logan)

From

To

Depart

Return

Passengers

1 passenger, economy

Cheap flights Chicago to Boston

Compare prices, duration and stops

Filters

Stops

Direct only 1 stop

Price

98 $ 373 $ 373 $

Airlines

American Airlines Frontier Airlines Jetblue Airways Southwest Airlines United Airlines

WN 3315

13:45

Chicago, Чикаго-Мидвей (MDW)

Tue, 15 sep

2h 30min

Direct

16:15

Boston, Logan (BOS)

Tue, 15 sep

203 $

F9 3044

20:50

Chicago, О'Хара (ORD)

Wed, 16 sep

17h 32min

1 stop

14:22

Boston, Logan (BOS)

Thu, 17 sep +1

165 $

WN 3094

10:45

Chicago, Чикаго-Мидвей (MDW)

Thu, 17 sep

2h 15min

Direct

13:00

Boston, Logan (BOS)

Thu, 17 sep

119 $

B6 1012

01:24

Chicago, О'Хара (ORD)

Fri, 18 sep

2h 45min

Direct

04:09

Boston, Logan (BOS)

Fri, 18 sep

126 $

B6 1006

15:59

Chicago, О'Хара (ORD)

Fri, 18 sep

5h 22min

1 stop

21:21

Boston, Logan (BOS)

Fri, 18 sep

107 $

F9 3044

20:50

Chicago, О'Хара (ORD)

Fri, 18 sep

18h 1min

1 stop

14:51

Boston, Logan (BOS)

Sat, 19 sep +1

142 $

AA 2682

01:19

Chicago, О'Хара (ORD)

Sat, 19 sep

2h 35min

Direct

03:54

Boston, Logan (BOS)

Sat, 19 sep

133 $

UA 1779

02:40

Chicago, О'Хара (ORD)

Sat, 19 sep

2h 30min

Direct

05:10

Boston, Logan (BOS)

Sat, 19 sep

104 $

WN 2681

12:40

Chicago, Чикаго-Мидвей (MDW)

Sat, 19 sep

2h 20min

Direct

15:00

Boston, Logan (BOS)

Sat, 19 sep

103 $

F9 4064

17:56

Chicago, О'Хара (ORD)

Sat, 19 sep

8h 44min

1 stop

02:40

Boston, Logan (BOS)

Sun, 20 sep +1

107 $

F9 3044

20:50

Chicago, О'Хара (ORD)

Sat, 19 sep

18h 8min

1 stop

14:58

Boston, Logan (BOS)

Sun, 20 sep +1

139 $

UA 2331

23:24

Chicago, О'Хара (ORD)

Sat, 19 sep

2h 35min

Direct

01:59

Boston, Logan (BOS)

Sun, 20 sep +1

102 $

AA 3022

11:00

Chicago, О'Хара (ORD)

Sun, 20 sep

2h 39min

Direct

13:39

Boston, Logan (BOS)

Sun, 20 sep

166 $

WN 3094

10:45

Chicago, Чикаго-Мидвей (MDW)

Mon, 21 sep

2h 15min

Direct

13:00

Boston, Logan (BOS)

Mon, 21 sep

167 $

B6 1006

15:59

Chicago, О'Хара (ORD)

Mon, 21 sep

5h 22min

1 stop

21:21

Boston, Logan (BOS)

Mon, 21 sep

145 $

B6 112

14:38

Chicago, О'Хара (ORD)

Tue, 22 sep

2h 28min

Direct

17:06

Boston, Logan (BOS)

Tue, 22 sep

99 $

WN 4215

23:00

Chicago, Чикаго-Мидвей (MDW)

Tue, 22 sep

2h 25min

Direct

01:25

Boston, Logan (BOS)

Wed, 23 sep +1

178 $

WN 1677

11:40

Chicago, Чикаго-Мидвей (MDW)

Wed, 23 sep

2h 15min

Direct

13:55

Boston, Logan (BOS)

Wed, 23 sep

178 $

B6 112

14:38

Chicago, О'Хара (ORD)

Wed, 23 sep

2h 28min

Direct

17:06

Boston, Logan (BOS)

Wed, 23 sep

100 $

AA 2294

18:54

Chicago, О'Хара (ORD)

Wed, 23 sep

2h 41min

Direct

21:35

Boston, Logan (BOS)

Wed, 23 sep

104 $

B6 112

14:38

Chicago, О'Хара (ORD)

Thu, 24 sep

2h 28min

Direct

17:06

Boston, Logan (BOS)

Thu, 24 sep

180 $

B6 864

20:00

Chicago, О'Хара (ORD)

Thu, 24 sep

7h 39min

1 stop

03:39

Boston, Logan (BOS)

Fri, 25 sep +1

125 $

B6 1012

01:24

Chicago, О'Хара (ORD)

Sun, 27 sep

2h 45min

Direct

04:09

Boston, Logan (BOS)

Sun, 27 sep

138 $

WN 4860

17:50

Chicago, Чикаго-Мидвей (MDW)

Tue, 29 sep

2h 20min

Direct

20:10

Boston, Logan (BOS)

Tue, 29 sep

144 $

B6 1012

01:24

Chicago, О'Хара (ORD)

Thu, 1 oct

2h 45min

Direct

04:09

Boston, Logan (BOS)

Thu, 1 oct

133 $

F9 3044

20:50

Chicago, О'Хара (ORD)

Thu, 1 oct

18h 1min

1 stop

14:51

Boston, Logan (BOS)

Fri, 2 oct +1

150 $

B6 1012

01:24

Chicago, О'Хара (ORD)

Fri, 2 oct

2h 45min

Direct

04:09

Boston, Logan (BOS)

Fri, 2 oct

116 $

WN 4535

10:00

Chicago, Чикаго-Мидвей (MDW)

Sun, 4 oct

2h 25min

Direct

12:25

Boston, Logan (BOS)

Sun, 4 oct

131 $

UA 1365

00:50

Chicago, О'Хара (ORD)

Mon, 5 oct

2h 34min

Direct

03:24

Boston, Logan (BOS)

Mon, 5 oct

150 $

WN 2842

14:10

Chicago, Чикаго-Мидвей (MDW)

Wed, 7 oct

2h 20min

Direct

16:30

Boston, Logan (BOS)

Wed, 7 oct

157 $

AA 2950

11:00

Chicago, О'Хара (ORD)

Thu, 8 oct

2h 37min

Direct

13:37

Boston, Logan (BOS)

Thu, 8 oct

242 $

UA 1779

02:24

Chicago, О'Хара (ORD)

Fri, 9 oct

2h 30min

Direct

04:54

Boston, Logan (BOS)

Fri, 9 oct

230 $

AA 3107

00:03

Chicago, О'Хара (ORD)

Sat, 10 oct

2h 34min

Direct

02:37

Boston, Logan (BOS)

Sat, 10 oct

158 $

AA 2682

01:00

Chicago, О'Хара (ORD)

Sat, 10 oct

2h 36min

Direct

03:36

Boston, Logan (BOS)

Sat, 10 oct

157 $

B6 906

11:10

Chicago, О'Хара (ORD)

Sat, 10 oct

7h 19min

1 stop

18:29

Boston, Logan (BOS)

Sat, 10 oct

158 $

AA 3107

00:03

Chicago, О'Хара (ORD)

Sun, 11 oct

2h 34min

Direct

02:37

Boston, Logan (BOS)

Sun, 11 oct

157 $

B6 1012 Best price

01:04

Chicago, О'Хара (ORD)

Sun, 11 oct

2h 55min

Direct

03:59

Boston, Logan (BOS)

Sun, 11 oct

98 $

UA 1186

11:10

Chicago, О'Хара (ORD)

Sun, 11 oct

2h 23min

Direct

13:33

Boston, Logan (BOS)

Sun, 11 oct

187 $

AA 2511

12:00

Chicago, О'Хара (ORD)

Sun, 11 oct

2h 33min

Direct

14:33

Boston, Logan (BOS)

Sun, 11 oct

196 $

B6 112

14:38

Chicago, О'Хара (ORD)

Sun, 11 oct

2h 28min

Direct

17:06

Boston, Logan (BOS)

Sun, 11 oct

161 $

WN 2851

01:55

Chicago, Чикаго-Мидвей (MDW)

Tue, 13 oct

10h 55min

1 stop

12:50

Boston, Logan (BOS)

Tue, 13 oct

353 $

UA 1779

02:24

Chicago, О'Хара (ORD)

Tue, 13 oct

2h 30min

Direct

04:54

Boston, Logan (BOS)

Tue, 13 oct

373 $

WN 1687

03:05

Chicago, Чикаго-Мидвей (MDW)

Tue, 13 oct

11h 10min

1 stop

14:15

Boston, Logan (BOS)

Tue, 13 oct

141 $

B6 1012 Best price

01:04

Chicago, О'Хара (ORD)

Wed, 14 oct

2h 55min

Direct

03:59

Boston, Logan (BOS)

Wed, 14 oct

98 $

B6 112

14:38

Chicago, О'Хара (ORD)

Wed, 14 oct

2h 28min

Direct

17:06

Boston, Logan (BOS)

Wed, 14 oct

105 $

B6 1006

17:38

Chicago, О'Хара (ORD)

Wed, 14 oct

7h 11min

1 stop

00:49

Boston, Logan (BOS)

Thu, 15 oct +1

133 $

B6 1012 Best price

01:04

Chicago, О'Хара (ORD)

Thu, 15 oct

2h 55min

Direct

03:59

Boston, Logan (BOS)

Thu, 15 oct

98 $

UA 2296

02:20

Chicago, О'Хара (ORD)

Tue, 27 oct

2h 26min

Direct

04:46

Boston, Logan (BOS)

Tue, 27 oct

142 $

UA 1186

11:00

Chicago, О'Хара (ORD)

Tue, 27 oct

2h 19min

Direct

13:19

Boston, Logan (BOS)

Tue, 27 oct

142 $

WN 4113

13:50

Chicago, Чикаго-Мидвей (MDW)

Sun, 1 nov

2h 20min

Direct

16:10

Boston, Logan (BOS)

Sun, 1 nov

120 $

Low price calendar

September 2026

Price chart (September 2026)

min: 99 $ · max: 203 $

Mon

Tue

Wed

Thu

Fri

Sat

Sun

1

placeholder

no data

2

placeholder

no data

3

placeholder

no data

4

placeholder

no data

5

placeholder

no data

6

placeholder

no data

7

placeholder

no data

8

placeholder

no data

9

placeholder

no data

10

placeholder

no data

11

placeholder

no data

12

placeholder

no data

13

placeholder

no data

14

placeholder

no data

15

placeholder

203 $

16

placeholder

165 $

17

placeholder

119 $

18

Good deal

107 $

19

Good deal

102 $

20

placeholder

166 $

21

placeholder

145 $

22

Good deal

99 $

23

placeholder

178 $

24

placeholder

180 $

25

placeholder

no data

26

placeholder

no data

27

placeholder

138 $

28

placeholder

no data

29

placeholder

144 $

30

placeholder

no data

Cheap flights Chicago to Boston

Jetblue Airways

Mon, Tue, Wed, Thu, Fri, Sat, Sun

Price from

$98

United Airlines

Mon, Tue, Wed, Thu, Fri, Sat, Sun

Price from

$102

Southwest Airlines

Mon, Tue, Wed, Thu, Fri, Sat, Sun

Price from

$103

Frontier Airlines

Wed, Thu, Fri, Sat

Price from

$139

American Airlines

Wed, Thu, Sat, Sun

Price from

$145

Popular destinations from Chicago

All →

CHI

Chicago — Orlando

United States → United States

ORL

from

$21

CHI

Chicago — Orlando

United States → United States

MCO

from

$21

CHI

Chicago — Atlanta

United States → United States

ATL

from

$22

CHI

Chicago — Houston

United States → United States

IAH

from

$22

CHI

Chicago — Houston

United States → United States

HOU

from

$22

CHI

Chicago — New York

United States → United States

NYC

from

$23

CHI

Chicago — Denver

United States → United States

DEN

from

$24

CHI

Chicago — Fort Lauderdale

United States → United States

FLL

from

$24

CHI

Chicago — Miami

United States → United States

MIA

from

$25

Popular destinations to Boston

All →

ORL

Orlando — Boston

United States → United States

BOS

from

$27

FLL

Fort Lauderdale — Boston

United States → United States

BOS

from

$44

WAS

Washington — Boston

United States → United States

BOS

from

$45

NYC

New York — Boston

United States → United States

BOS

from

$60

MIA

Miami — Boston

United States → United States

BOS

from

$68

ATL

Atlanta — Boston

United States → United States

BOS

from

$74

BUF

Buffalo — Boston

United States → United States

BOS

from

$77

LAX

Los Angeles — Boston

United States → United States

BOS

from

$78

Cheap flights Chicago to Boston

Interesting facts about the route

Flight time

2h 33min

Distance

1 389 km

Average price

$139

Most frequent flight

B6 1012

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

change

3 GB

data

30

days

$9

change

2 GB

data

15

days

$13

change

5 GB

data

30

days

$14

change

3 GB

data

30

days

$16

change

5 GB

data

30

days

$23

Frequently Asked Questions

The average ticket price Chicago Boston is $139. The cheapest ticket costs $107, operated by Jetblue Airways, flight 1006, departing Chicago on 18 September at 15:59, arriving Boston on 18 September at 21:21.

The average flight time is 5 hours 22 minutes. The fastest flight takes 2 hours 15 minutes, flight 3094 operated by Southwest Airlines, departing Chicago on 17 September at 10:45, arriving Boston on 17 September at 13:00.

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.