Boston to Chicago Flights

BOS-CHI Flight Tickets Booking by Date

BOS-CHI Route

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 dateFlightAirlinesFind Ticket

19.02.2019

American Airlines (AA 1427)

142

01.03.2019

American Airlines (AA 1427)

198

22.04.2019

Southwest Airlines (WN 1929)

144

Round-trip Tickets from Boston to Chicago

Departure dateReturn dateFlightStopsFind Ticket

06.08.2019

13.08.2019

Southwest Airlines (WN 2224)

Direct

101

06.08.2019

13.08.2019

Southwest Airlines (WN 2224)

1 stop

109

16.09.2019

21.09.2019

American Airlines (AA 2387)

2 stops

230


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

Boston-Chicago Flight is Served by Airlines

  • American Airlines Flights
  • Alaska Airlines Flights
  • JetBlue Flights
  • Spirit Airlines Flights
  • United Airlines Flights
  • US Airways Flights
  • Southwest Airlines Flights

Departure Logan International Airport (Boston)

Weather:
  • 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:
  • 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.