Chicago to Boston Flights

Best Departing Flights from Chicago to Boston

Departure atTrip classStopsPriceDistanceFind tickets
27.02.2021EconomyDirect89 1367 ml89
27.02.2021Economy1 Stop102 1367 ml102
27.02.2021Economy2 Stops292 1367 ml292
28.02.2021EconomyDirect58 1367 ml58
28.02.2021Economy1 Stop77 1367 ml77
28.02.2021Economy2 Stops86 1367 ml86
01.03.2021EconomyDirect58 1367 ml58
01.03.2021Economy1 Stop75 1367 ml75
01.03.2021Economy2 Stops114 1367 ml114
02.03.2021EconomyDirect57 1367 ml57
02.03.2021Economy1 Stop76 1367 ml76
02.03.2021Economy2 Stops80 1367 ml80
05.03.2021EconomyDirect59 1367 ml59
05.03.2021Economy1 Stop77 1367 ml77
05.03.2021Economy2 Stops145 1367 ml145
06.03.2021EconomyDirect59 1367 ml59
06.03.2021Economy1 Stop56 1367 ml56
06.03.2021Economy2 Stops57 1367 ml57
07.03.2021EconomyDirect58 1367 ml58
07.03.2021Economy1 Stop57 1367 ml57
07.03.2021Economy2 Stops110 1367 ml110
08.03.2021EconomyDirect58 1367 ml58
08.03.2021Economy1 Stop57 1367 ml57
08.03.2021Economy2 Stops105 1367 ml105
23.03.2021EconomyDirect39 1367 ml39
23.03.2021Economy1 Stop31 1367 ml31
23.03.2021Economy2 Stops73 1367 ml73
27.03.2021EconomyDirect39 1367 ml39
27.03.2021Economy1 Stop82 1367 ml82
27.03.2021Economy2 Stops72 1367 ml72

CHI-BOS Flight Tickets Booking by Date


Book cheap flights to Boston from Chicago 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 Chicago to Boston

Departure atFlightAirlineFind tickets
28.02.2021 (ZZ 4888)117

Round-trip Tickets from Chicago to Boston

Departure atReturn atFlightStopsFind tickets
28.02.202102.03.2021 (ZZ 4888)Direct 117
01.03.202102.03.2021American Airlines (AA 668)1 Stop 137
01.03.202102.03.2021United Airlines (UA 5265)1 Stop 393
28.02.202104.03.2021Allegiant Air (G4 1903)1 Stop 469

CHI-BOS Compare Airline Prices

Departure atReturn atStopsPriceFlight numberAirlineFind tickets
28.02.202102.03.2021Direct117 4888117
01.03.202102.03.20211 Stop137 668137

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

Chicago-Boston Flight is Served by Airlines

  • American Airlines Flights
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  • Southwest Airlines Flights

Departure 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

Destination 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

*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.