Cheap flights from Boston to Chicago
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Travel tip: Visit Chicago on your holidays!Check our current prices for flights from Boston to Chicago. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Boston to Chicago, you will need to run a search below.
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Cheap Chicago airfares from $285/RT are provided by Cheapoair.com. Outbound flight is leaving on 06/07/2022, 05:35 am from Boston Logan (BOS) airport and arrives at Chicago O`hare (ORD) at 07:01 pm. The flight time is 13 hours and 26 minutes. The Returning flight departes on 06/14/2022, 05:15 am (other return dates are also available). Date posted: 15 Apr 2022
Price evolution for flights From Boston To Chicago

Recent Deals on Flights from Boston to Chicago:Roundtrip / Oneway
- $285
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 06/07/2022 05:35 am Chicago, IL (ORD) Boston, MA (BOS) 06/14/2022 05:15 am - $351
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 06/17/2022 05:45 am Chicago, IL (ORD) Boston, MA (BOS) 06/21/2022 06:00 pm - $376
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 07/02/2022 11:13 am Chicago, IL (ORD) Boston, MA (BOS) 07/14/2022 11:05 am - $987
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 07/02/2022 11:13 am Chicago, IL (ORD) Boston, MA (BOS) 07/14/2022 09:25 pm - $125
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 06/22/2022 11:53 am - $140
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 05/28/2022 08:30 am - $148
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 05/20/2022 09:53 am - $192
Sun Country Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 05/20/2022 11:30 am - $305
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 05/28/2022 09:52 am
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Know what to do when flying to Chicago?
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