Boston to Chicago Flights

Best Departing Flights from Boston to Chicago

Departure atTrip classStopsPriceDistanceFind tickets
08.03.2021EconomyDirect53 1367 ml53
08.03.2021Economy1 Stop56 1367 ml56
08.03.2021Economy2 Stops66 1367 ml66
13.03.2021EconomyDirect51 1367 ml51
13.03.2021Economy1 Stop51 1367 ml51
13.03.2021Economy2 Stops84 1367 ml84
24.03.2021EconomyDirect38 1367 ml38
24.03.2021Economy1 Stop50 1367 ml50
24.03.2021Economy2 Stops92 1367 ml92

BOS-CHI Flight Tickets Booking by Date


Book cheap flights to Chicago from Boston today with using OutTrippin’s ticket finder. We help you compare flights, carriers and seating classes all year round. Be sure to find the right flight to match your budget, plans and travel preferences.

Direct Flights from Boston to Chicago

Departure atFlightAirlineFind tickets
15.03.2021United Airlines (UA 772)98
16.04.2021Spirit Airlines (NK 1051)83

Round-trip Tickets from Boston to Chicago

Departure atReturn atFlightStopsFind tickets
21.05.202124.05.2021Spirit Airlines (NK 1051)Direct 51
21.05.202124.05.2021Spirit Airlines (NK 609)2 Stops 71
11.05.202116.05.2021Spirit Airlines (NK 1051)3 106
21.05.202125.05.2021Spirit Airlines (NK 1051)4 144
11.03.202116.03.2021Spirit Airlines (NK 609)5 342

BOS-CHI Compare Airline Prices

Departure atReturn atStopsPriceFlight numberAirlineFind tickets
11.03.202114.03.2021Direct110 772110
15.03.202125.03.2021Direct98 371098
18.03.202121.03.20211 Stop132 4888132
19.03.202121.03.20211 Stop132 4888132
16.04.202118.04.2021Direct83 105183
11.05.202114.05.2021Direct58 105158
21.05.202124.05.2021Direct51 105151
28.07.202102.08.20211 Stop134 5730134
05.08.202109.08.2021Direct137 345137

* Total price includes taxes + fees for 1 adult. Additional bag fees and other fees may apply.

Boston-Chicago Flight is Served by Airlines

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  • Southwest Airlines Flights

Departure Logan International Airport (Boston)

Weather: [simple-weather location=”Boston, United States” days=”2″]
  • Airport Name: Logan International Airport
  • Country Code: US
  • City Code: BOS
  • Airport Code: BOS
  • Flightable: Active
  • Time Zone: America/New_York
  • Latitude: 42.36646
  • Longitude: -71.02018

Destination Chicago Midway International Airport (Chicago)

Weather: [simple-weather location=”Chicago, United States” days=”2″]
  • Airport Name: Chicago Midway International Airport
  • Country Code: US
  • City Code: CHI
  • Airport Code: MDW
  • Flightable: Active
  • Time Zone: America/Chicago
  • Latitude: 41.788136
  • Longitude: -87.74087

*Flight prices are indicative, based on passenger numbers and may vary dependent on your individual flight dates. Complete a new search to view live pricing.

* Checked baggage is not included but may be added for a fee. Carry-on baggage limits, including size restrictions, will be strictly applied. Passengers with more than the applicable carry-on baggage allowance will need to check in baggage, and charges will apply.