Our cheapest offers for flights from Boston to Chicago

Here you can compare cheap flights from Boston (BOS) to Chicago (CHI) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Chicago. Prices and availability may change at any time.

	Outbound	Return	Airlines	Baggage	Price
Best option Boston Chicago	Outbound 09/23/25 direct B60811 02h 50min	Return 09/30/25 direct AA1485 02h 24min	JetBlue Airways	?	$93
Boston Chicago Pay attention to transfer at connecting flight	Outbound 10/18/25 3 Stopovers (FLL, PIT, PGD) NK2887, NK0228, G41110, G42478 25h 35min	Return 11/17/25 1 Stopover (TYS) G41432, G41397 16h 31min	Spirit Airlines, Allegiant Air		$264
Boston Chicago	Outbound 09/23/25 direct B60811 02h 50min	Return 09/30/25 direct B61012 02h 30min	JetBlue Airways	?	$99
Boston Chicago	Outbound 09/04/25 direct B60811 02h 50min	Return 09/28/25 direct AA3710 02h 24min	JetBlue Airways	?	$102
Boston Chicago	Outbound 09/23/25 direct B60811 02h 50min	Return 09/30/25 1 Stopover (FLL) NK0867, NK0616 08h 10min	JetBlue Airways	?	$105
Boston Chicago	Outbound 07/02/25 direct AA3324 02h 54min	Return 07/25/25 direct B61012 02h 35min	American Airlines	?	$106
Boston Chicago	Outbound 09/23/25 1 Stopover (FLL) NK2887, NK0003 09h 44min	Return 09/30/25 1 Stopover (FLL) NK0867, NK0616 08h 10min	Spirit Airlines		$109
Boston Chicago	Outbound 09/23/25 1 Stopover (FLL) NK0296, NK1026 12h 27min	Return 09/30/25 1 Stopover (FLL) NK0867, NK0616 08h 10min	Spirit Airlines		$111
Boston Chicago	Outbound 09/23/25 1 Stopover (FLL) NK0296, NK1026 12h 27min	Return 09/30/25 1 Stopover (FLL) NK0867, NK0616 08h 10min	Spirit Airlines		$121
Boston Chicago	Outbound 06/18/25 direct AA0598 02h 52min	Return 07/15/25 1 Stopover (JFK) B60406, B60418 04h 51min	American Airlines	?	$131

Tips and tricks to help you find cheap flights from Boston to Chicago

Important flight information

Flight information: Boston - Chicago

Roundtrip from	$92.34
Flight duration	min. 02:45 / max. 06:55
Return flight duration	min. 02:08/ max. 11:15
Distance	1371 km
Flights per week	162
Departure airport	Airport Boston Logan International Airport, MA (BOS)
Arrival airport	Airport Chicago-IL all Airports (ORD, MDW, RFD) (CHI)
Destination country	Flights to United States

Alternative routes to United States

Flight Boston - New York from $80
Flight Boston - Los Angeles from $181
Flight Boston - San Francisco from $203
Flight Boston - Miami from $133
Flight Boston - Orlando from $126
Flight Boston - Fort Myers from $182
Flight Boston - Washington-DC from $116
Flight Boston - Dallas from $122
Flight Boston - New York from $136
Flight Boston - Seattle-Tacoma from $178

Alternative flights to Chicago

Flight New York - Chicago from $93
Flight Los Angeles - Chicago from $103
Flight Las Vegas - Chicago from $143
Flight Washington-DC - Chicago from $187
Flight Atlanta - Chicago from $66
Flight Denver - Chicago from $102
Flight Fort Myers - Chicago from $141
Flight Tampa - Chicago from $124
Flight San Francisco - Chicago from $211
Flight Philadelphia - Chicago from $162

Flights from Boston to Chicago