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

84 € 322 € 322 €

Airlines

American Airlines Frontier Airlines Jetblue Airways Southwest Airlines United Airlines

WN 3315

13:45

Chicago, Chicago Midway International Airport (MDW)

Tue, 15 sep

2h 30min

Direct

16:15

Boston, Logan (BOS)

Tue, 15 sep

175 €

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

143 €

WN 3094

10:45

Chicago, Chicago Midway International Airport (MDW)

Thu, 17 sep

2h 15min

Direct

13:00

Boston, Logan (BOS)

Thu, 17 sep

103 €

B6 1012

01:24

Chicago, O'Hare International Airport (ORD)

Fri, 18 sep

2h 45min

Direct

04:09

Boston, Logan (BOS)

Fri, 18 sep

108 €

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

92 €

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

122 €

AA 2682

01:19

Chicago, O'Hare International Airport (ORD)

Sat, 19 sep

2h 35min

Direct

03:54

Boston, Logan (BOS)

Sat, 19 sep

115 €

UA 1779

02:40

Chicago, O'Hare International Airport (ORD)

Sat, 19 sep

2h 30min

Direct

05:10

Boston, Logan (BOS)

Sat, 19 sep

89 €

WN 2681

12:40

Chicago, Chicago Midway International Airport (MDW)

Sat, 19 sep

2h 20min

Direct

15:00

Boston, Logan (BOS)

Sat, 19 sep

89 €

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

92 €

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

120 €

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

88 €

AA 3022

11:00

Chicago, O'Hare International Airport (ORD)

Sun, 20 sep

2h 39min

Direct

13:39

Boston, Logan (BOS)

Sun, 20 sep

143 €

WN 3094

10:45

Chicago, Chicago Midway International Airport (MDW)

Mon, 21 sep

2h 15min

Direct

13:00

Boston, Logan (BOS)

Mon, 21 sep

144 €

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

125 €

B6 112

14:38

Chicago, O'Hare International Airport (ORD)

Tue, 22 sep

2h 28min

Direct

17:06

Boston, Logan (BOS)

Tue, 22 sep

85 €

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

153 €

WN 1677

11:40

Chicago, Chicago Midway International Airport (MDW)

Wed, 23 sep

2h 15min

Direct

13:55

Boston, Logan (BOS)

Wed, 23 sep

154 €

B6 112

14:38

Chicago, O'Hare International Airport (ORD)

Wed, 23 sep

2h 28min

Direct

17:06

Boston, Logan (BOS)

Wed, 23 sep

86 €

AA 2294

18:54

Chicago, O'Hare International Airport (ORD)

Wed, 23 sep

2h 41min

Direct

21:35

Boston, Logan (BOS)

Wed, 23 sep

90 €

B6 112

14:38

Chicago, O'Hare International Airport (ORD)

Thu, 24 sep

2h 28min

Direct

17:06

Boston, Logan (BOS)

Thu, 24 sep

156 €

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

108 €

B6 1012

01:24

Chicago, O'Hare International Airport (ORD)

Sun, 27 sep

2h 45min

Direct

04:09

Boston, Logan (BOS)

Sun, 27 sep

119 €

WN 4860

17:50

Chicago, Chicago Midway International Airport (MDW)

Tue, 29 sep

2h 20min

Direct

20:10

Boston, Logan (BOS)

Tue, 29 sep

124 €

B6 1012

01:24

Chicago, O'Hare International Airport (ORD)

Thu, 1 oct

2h 45min

Direct

04:09

Boston, Logan (BOS)

Thu, 1 oct

114 €

F9 3044

20:50

Chicago, O'Hare International Airport (ORD)

Thu, 1 oct

18h 1min

1 stop

14:51

Boston, Logan (BOS)

Fri, 2 oct +1

129 €

B6 1012

01:24

Chicago, O'Hare International Airport (ORD)

Fri, 2 oct

2h 45min

Direct

04:09

Boston, Logan (BOS)

Fri, 2 oct

100 €

WN 4535

10:00

Chicago, Chicago Midway International Airport (MDW)

Sun, 4 oct

2h 25min

Direct

12:25

Boston, Logan (BOS)

Sun, 4 oct

113 €

UA 1365

00:50

Chicago, O'Hare International Airport (ORD)

Mon, 5 oct

2h 34min

Direct

03:24

Boston, Logan (BOS)

Mon, 5 oct

130 €

WN 2842

14:10

Chicago, Chicago Midway International Airport (MDW)

Wed, 7 oct

2h 20min

Direct

16:30

Boston, Logan (BOS)

Wed, 7 oct

135 €

AA 2950

11:00

Chicago, O'Hare International Airport (ORD)

Thu, 8 oct

2h 37min

Direct

13:37

Boston, Logan (BOS)

Thu, 8 oct

209 €

UA 1779

02:24

Chicago, O'Hare International Airport (ORD)

Fri, 9 oct

2h 30min

Direct

04:54

Boston, Logan (BOS)

Fri, 9 oct

198 €

AA 3107

00:03

Chicago, O'Hare International Airport (ORD)

Sat, 10 oct

2h 34min

Direct

02:37

Boston, Logan (BOS)

Sat, 10 oct

136 €

AA 2682

01:00

Chicago, O'Hare International Airport (ORD)

Sat, 10 oct

2h 36min

Direct

03:36

Boston, Logan (BOS)

Sat, 10 oct

136 €

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

137 €

AA 3107

00:03

Chicago, O'Hare International Airport (ORD)

Sun, 11 oct

2h 34min

Direct

02:37

Boston, Logan (BOS)

Sun, 11 oct

136 €

B6 1012 Best price

01:04

Chicago, O'Hare International Airport (ORD)

Sun, 11 oct

2h 55min

Direct

03:59

Boston, Logan (BOS)

Sun, 11 oct

84 €

UA 1186

11:10

Chicago, O'Hare International Airport (ORD)

Sun, 11 oct

2h 23min

Direct

13:33

Boston, Logan (BOS)

Sun, 11 oct

161 €

AA 2511

12:00

Chicago, O'Hare International Airport (ORD)

Sun, 11 oct

2h 33min

Direct

14:33

Boston, Logan (BOS)

Sun, 11 oct

169 €

B6 112

14:38

Chicago, O'Hare International Airport (ORD)

Sun, 11 oct

2h 28min

Direct

17:06

Boston, Logan (BOS)

Sun, 11 oct

139 €

WN 2851

01:55

Chicago, Chicago Midway International Airport (MDW)

Tue, 13 oct

10h 55min

1 stop

12:50

Boston, Logan (BOS)

Tue, 13 oct

305 €

UA 1779

02:24

Chicago, O'Hare International Airport (ORD)

Tue, 13 oct

2h 30min

Direct

04:54

Boston, Logan (BOS)

Tue, 13 oct

322 €

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

121 €

B6 1012 Best price

01:04

Chicago, O'Hare International Airport (ORD)

Wed, 14 oct

2h 55min

Direct

03:59

Boston, Logan (BOS)

Wed, 14 oct

84 €

B6 112

14:38

Chicago, O'Hare International Airport (ORD)

Wed, 14 oct

2h 28min

Direct

17:06

Boston, Logan (BOS)

Wed, 14 oct

91 €

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

114 €

B6 1012 Best price

01:04

Chicago, O'Hare International Airport (ORD)

Thu, 15 oct

2h 55min

Direct

03:59

Boston, Logan (BOS)

Thu, 15 oct

84 €

UA 2296

02:20

Chicago, O'Hare International Airport (ORD)

Tue, 27 oct

2h 26min

Direct

04:46

Boston, Logan (BOS)

Tue, 27 oct

123 €

UA 1186

11:00

Chicago, O'Hare International Airport (ORD)

Tue, 27 oct

2h 19min

Direct

13:19

Boston, Logan (BOS)

Tue, 27 oct

123 €

WN 4113

13:50

Chicago, Chicago Midway International Airport (MDW)

Sun, 1 nov

2h 20min

Direct

16:10

Boston, Logan (BOS)

Sun, 1 nov

104 €

Low price calendar

September 2026

Price chart (September 2026)

min: 85 € · max: 175 €

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175 €

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143 €

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103 €

18

Good deal

92 €

19

Good deal

88 €

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143 €

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125 €

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85 €

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154 €

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156 €

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119 €

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124 €

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Cheap flights Chicago to Boston

Jetblue Airways

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

Price from

€84

United Airlines

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

Price from

€88

Southwest Airlines

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

Price from

€89

Frontier Airlines

Wed, Thu, Fri, Sat

Price from

€120

American Airlines

Wed, Thu, Sat, Sun

Price from

€125

Popular destinations from Chicago

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Popular destinations to Boston

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ORL

Orlando — Boston

United States → United States

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from

€23

FLL

Fort Lauderdale — Boston

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from

€38

WAS

Washington — Boston

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from

€39

NYC

New York — Boston

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from

€52

MIA

Miami — Boston

United States → United States

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from

€59

ATL

Atlanta — Boston

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from

€64

BUF

Buffalo — Boston

United States → United States

BOS

from

€66

LAX

Los Angeles — Boston

United States → United States

BOS

from

€68

Cheap flights Chicago to Boston

Interesting facts about the route

Flight time

2h 33min

Distance

1 389 km

Average price

€120

Most frequent flight

B6 1012

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

change

3 GB

data

30

days

€8

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2 GB

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15

days

€11

change

5 GB

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30

days

€12

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3 GB

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30

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€14

change

5 GB

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30

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€19

Frequently Asked Questions

The average ticket price Chicago Boston is €120. The cheapest ticket costs €92, 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.