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 $200/RT are provided by Cheapoair.com. Outbound flight is leaving on 03/21/2023, 06:00 am from Boston Logan (BOS) airport and arrives at Chicago O`hare (ORD) at 05:25 pm. The flight time is 11 hours and 25 minutes. The Returning flight departes on 04/05/2023, 05:00 am (other return dates are also available). Date posted: 01 Feb 2023
Price evolution for flights From Boston To Chicago

Recent Deals on Flights from Boston to Chicago:Roundtrip / Oneway
- $200
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 03/21/2023 06:00 am Chicago, IL (ORD) Boston, MA (BOS) 04/05/2023 05:00 am - $234
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 02/25/2023 03:20 pm Chicago, IL (ORD) Boston, MA (BOS) 03/06/2023 05:03 pm - $251
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 04/25/2023 11:08 am Chicago, IL (ORD) Boston, MA (BOS) 05/09/2023 10:00 pm - $276
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 04/18/2023 11:08 am Chicago, IL (ORD) Boston, MA (BOS) 05/03/2023 09:15 pm - $304
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 02/13/2023 08:00 am Chicago, IL (ORD) Boston, MA (BOS) 02/22/2023 10:00 am - $61
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 02/09/2023 01:20 pm - $67
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 02/13/2023 02:35 pm - $141
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 03/19/2023 01:05 pm - $365
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (MDW) 02/13/2023 09:15 am - $554
Alaska Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 03/19/2023 07:00 am
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Know what to do when flying to Chicago?
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