Cheap Flights From Boston To Chicago From ₺9.623 | BOS - CHI

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Estimated lowest fares found within 7 days

The cheapest airline(s) flying from Boston to Chicago is JetBlue Airways

₺ 6.303

₺ 12.607

₺ 18.910

₺ 9.623

₺ 12.942

₺ 18.910

The cheapest airline(s) flying from Boston to Chicago is JetBlue Airways

₺ 6.303

₺ 12.607

₺ 18.910

₺ 9.623

₺ 12.942

₺ 18.910

Flight Schedules From Boston to Chicago

Last Update: Wed, 02 Sep 2026

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Time Earliest	Depart Earliest	Arrive	Duration	Stopover All	Airline All Airlines	Aircraft All Aircrafts	Availability
06:00BOS 08:10ORD	3 Hrs,10m Direct	American AirlinesAA 3324·A321 M T W T F S S	BOS 06:00 - ORD 08:10 3h 10m·Direct	BOS 06:00	ORD 08:10	3h 10m	Direct	American AirlinesAA 3324	A321	M T W T F S S
06:00BOS 07:59ORD	2 Hrs,59m Direct	United AirlinesUA 1414·B7M9 M T W T F S -	BOS 06:00 - ORD 07:59 2h 59m·Direct	BOS 06:00	ORD 07:59	2h 59m	Direct	United AirlinesUA 1414	B7M9	M T W T F S -
06:00BOS 07:59ORD	2 Hrs,59m Direct	United AirlinesUA 1414·B738 - - - - - - S	BOS 06:00 - ORD 07:59 2h 59m·Direct	BOS 06:00	ORD 07:59	2h 59m	Direct	United AirlinesUA 1414	B738	- - - - - - S
07:00BOS 08:48ORD	2 Hrs,48m Direct	JetBlue AirwaysB6 111·A223 M T W T F S S	BOS 07:00 - ORD 08:48 2h 48m·Direct	BOS 07:00	ORD 08:48	2h 48m	Direct	JetBlue AirwaysB6 111	A223	M T W T F S S
07:00BOS 09:06ORD	3 Hrs,6m Direct	American AirlinesAA 1509·A321 M T W T F S S	BOS 07:00 - ORD 09:06 3h 6m·Direct	BOS 07:00	ORD 09:06	3h 6m	Direct	American AirlinesAA 1509	A321	M T W T F S S
07:05BOS 09:03ORD	2 Hrs,58m Direct	United AirlinesUA 2631·B7M8 - T W - - S -	BOS 07:05 - ORD 09:03 2h 58m·Direct	BOS 07:05	ORD 09:03	2h 58m	Direct	United AirlinesUA 2631	B7M8	- T W - - S -
07:05BOS 08:40MDW	2 Hrs,35m Direct	Southwest AirlinesWN 744·B7M8 - - - - - S -	BOS 07:05 - MDW 08:40 2h 35m·Direct	BOS 07:05	MDW 08:40	2h 35m	Direct	Southwest AirlinesWN 744	B7M8	- - - - - S -
07:05BOS 09:03ORD	2 Hrs,58m Direct	United AirlinesUA 2631·B739 M - - T F - S	BOS 07:05 - ORD 09:03 2h 58m·Direct	BOS 07:05	ORD 09:03	2h 58m	Direct	United AirlinesUA 2631	B739	M - - T F - S
07:20BOS 12:20MDW	6 Hrs,0m Direct	Southwest AirlinesWN 280·B7M8 - - - T - - -	BOS 07:20 - MDW 12:20 6h 0m·Direct	BOS 07:20	MDW 12:20	6h 0m	Direct	Southwest AirlinesWN 280	B7M8	- - - T - - -
07:30BOS 09:05MDW	2 Hrs,35m Direct	Southwest AirlinesWN 744·B7M8 M T W T - - S	BOS 07:30 - MDW 09:05 2h 35m·Direct	BOS 07:30	MDW 09:05	2h 35m	Direct	Southwest AirlinesWN 744	B7M8	M T W T - - S
07:40BOS 12:20MDW	5 Hrs,40m Direct	Southwest AirlinesWN 280·7S7 M - - - F - -	BOS 07:40 - MDW 12:20 5h 40m·Direct	BOS 07:40	MDW 12:20	5h 40m	Direct	Southwest AirlinesWN 280	7S7	M - - - F - -
07:46BOS 09:45ORD	2 Hrs,59m Direct	United AirlinesUA 717·B738 M T W T F S S	BOS 07:46 - ORD 09:45 2h 59m·Direct	BOS 07:46	ORD 09:45	2h 59m	Direct	United AirlinesUA 717	B738	M T W T F S S
08:33BOS 10:35ORD	3 Hrs,2m Direct	American AirlinesAA 1239·B738 M T W T F S S	BOS 08:33 - ORD 10:35 3h 2m·Direct	BOS 08:33	ORD 10:35	3h 2m	Direct	American AirlinesAA 1239	B738	M T W T F S S
08:40BOS 10:15MDW	2 Hrs,35m Direct	Southwest AirlinesWN 175·B7M8 - - - - - S -	BOS 08:40 - MDW 10:15 2h 35m·Direct	BOS 08:40	MDW 10:15	2h 35m	Direct	Southwest AirlinesWN 175	B7M8	- - - - - S -
09:00BOS 10:59ORD	2 Hrs,59m Direct	United AirlinesUA 1349·A32Q M T W T F S S	BOS 09:00 - ORD 10:59 2h 59m·Direct	BOS 09:00	ORD 10:59	2h 59m	Direct	United AirlinesUA 1349	A32Q	M T W T F S S

06:00BOS

08:10ORD

3 Hrs,10m

Direct

American Airlines·AA 3324·A321

06:00BOS

07:59ORD

2 Hrs,59m

Direct

United Airlines·UA 1414·B7M9

06:00BOS

07:59ORD

2 Hrs,59m

Direct

United Airlines·UA 1414·B738

07:00BOS

08:48ORD

2 Hrs,48m

Direct

JetBlue Airways·B6 111·A223

07:00BOS

09:06ORD

3 Hrs,6m

Direct

American Airlines·AA 1509·A321

07:05BOS

09:03ORD

2 Hrs,58m

Direct

United Airlines·UA 2631·B7M8

07:05BOS

08:40MDW

2 Hrs,35m

Direct

Southwest Airlines·WN 744·B7M8

07:05BOS

09:03ORD

2 Hrs,58m

Direct

United Airlines·UA 2631·B739

07:20BOS

12:20MDW

6 Hrs,0m

Direct

Southwest Airlines·WN 280·B7M8

07:30BOS

09:05MDW

2 Hrs,35m

Direct

Southwest Airlines·WN 744·B7M8

07:40BOS

12:20MDW

5 Hrs,40m

Direct

Southwest Airlines·WN 280·7S7

07:46BOS

09:45ORD

2 Hrs,59m

Direct

United Airlines·UA 717·B738

08:33BOS

10:35ORD

3 Hrs,2m

Direct

American Airlines·AA 1239·B738

08:40BOS

10:15MDW

2 Hrs,35m

Direct

Southwest Airlines·WN 175·B7M8

09:00BOS

10:59ORD

2 Hrs,59m

Direct

United Airlines·UA 1349·A32Q

The fastest flight time for direct flights from Boston to Chicago is 2 hours 30 minutes. Check latest flight schedules & prices on Wego.

The most popular airline flying from Boston to Chicago is American Airlines. Find the latest flight deals on Wego.

The flight distance between Boston and Chicago is 1366km. Check all available flights on Wego.

The earliest flight of the day departs at 06:00. The last flight of the day departs at 21:05. See the full list of flight times on Wego.

There are 4 airlines that offer direct flights from Boston to Chicago. Find out the list of airlines on Wego.