Boston to Chicago Flights

Best Departing Flights from Boston to Chicago

Departure dateFlight classStopsPriceDistanceFind Ticket

20.10.2019

Economy

Direct

150

849.41 m

150

20.10.2019

Economy

1 stop

157

849.41 m

157

20.10.2019

Economy

2 stops

385

849.41 m

385

22.10.2019

Economy

Direct

44

849.41 m

44

22.10.2019

Economy

1 stop

62

849.41 m

62

22.10.2019

Economy

2 stops

380

849.41 m

380

03.11.2019

Economy

Direct

72

849.41 m

72

03.11.2019

Economy

1 stop

72

849.41 m

72

03.11.2019

Economy

2 stops

134

849.41 m

134

13.11.2019

Economy

Direct

34

849.41 m

34

13.11.2019

Economy

1 stop

43

849.41 m

43

13.11.2019

Economy

2 stops

114

849.41 m

114

21.11.2019

Economy

Direct

52

849.41 m

52

21.11.2019

Economy

1 stop

67

849.41 m

67

21.11.2019

Economy

2 stops

84

849.41 m

84

26.11.2019

Economy

Direct

141

849.41 m

141

26.11.2019

Economy

1 stop

99

849.41 m

99

26.11.2019

Economy

2 stops

156

849.41 m

156

27.11.2019

Economy

Direct

230

849.41 m

230

27.11.2019

Economy

1 stop

157

849.41 m

157

27.11.2019

Economy

2 stops

196

849.41 m

196

28.11.2019

Economy

Direct

124

849.41 m

124

28.11.2019

Economy

1 stop

119

849.41 m

119

28.11.2019

Economy

2 stops

155

849.41 m

155

29.11.2019

Economy

Direct

142

849.41 m

142

29.11.2019

Economy

1 stop

119

849.41 m

119

29.11.2019

Economy

2 stops

137

849.41 m

137

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

06.11.2019

Southwest Airlines (WN 1744)

71

Round-trip Tickets from Boston to Chicago

Departure dateReturn dateFlightStopsFind Ticket

06.11.2019

09.11.2019

Southwest Airlines (WN 1744)

Direct

71

06.11.2019

09.11.2019

Frontier Airlines (F9 1683)

1 stop

89

24.11.2019

03.12.2019

Spirit Airlines (NK 615)

2 stops

179

BOS-CHI Compare Airline Prices

Departure dateReturn dateStopsPriceFlight numberAirlinesFind Ticket

20.10.2019

22.10.2019

Direct

197

AA 2265

197

22.10.2019

25.10.2019

Direct

114

WN 1349

114

24.10.2019

07.11.2019

Direct

107

AA 2265

107


* 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.