Boston to Chicago Flights

Best Departing Flights from Boston to Chicago

Departure dateFlight classStopsPriceDistanceFind Ticket

20.04.2019

Economy

Direct

148

849.41 m

148

20.04.2019

Economy

1 stop

164

849.41 m

164

20.04.2019

Economy

2 stops

304

849.41 m

304

21.04.2019

Economy

Direct

77

849.41 m

77

21.04.2019

Economy

1 stop

149

849.41 m

149

21.04.2019

Economy

2 stops

380

849.41 m

380

22.04.2019

Economy

Direct

139

849.41 m

139

22.04.2019

Economy

1 stop

165

849.41 m

165

22.04.2019

Economy

2 stops

279

849.41 m

279

25.04.2019

Economy

Direct

76

849.41 m

76

25.04.2019

Economy

1 stop

83

849.41 m

83

25.04.2019

Economy

2 stops

88

849.41 m

88

26.04.2019

Economy

Direct

71

849.41 m

71

26.04.2019

Economy

1 stop

162

849.41 m

162

26.04.2019

Economy

2 stops

249

849.41 m

249

28.04.2019

Economy

Direct

75

849.41 m

75

28.04.2019

Economy

1 stop

179

849.41 m

179

28.04.2019

Economy

2 stops

365

849.41 m

365

04.05.2019

Economy

Direct

57

849.41 m

57

04.05.2019

Economy

1 stop

94

849.41 m

94

04.05.2019

Economy

2 stops

166

849.41 m

166

05.05.2019

Economy

Direct

70

849.41 m

70

05.05.2019

Economy

1 stop

140

849.41 m

140

05.05.2019

Economy

2 stops

206

849.41 m

206

15.05.2019

Economy

Direct

50

849.41 m

50

15.05.2019

Economy

1 stop

94

849.41 m

94

15.05.2019

Economy

2 stops

125

849.41 m

125

24.05.2019

Economy

Direct

68

849.41 m

68

24.05.2019

Economy

1 stop

123

849.41 m

123

24.05.2019

Economy

2 stops

209

849.41 m

209

27.05.2019

Economy

Direct

112

849.41 m

112

27.05.2019

Economy

1 stop

133

849.41 m

133

27.05.2019

Economy

2 stops

190

849.41 m

190

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

27.04.2019

United Airlines (UA 439)

169

22.05.2019

Spirit Airlines (NK 773)

119

Round-trip Tickets from Boston to Chicago

Departure dateReturn dateFlightStopsFind Ticket

22.05.2019

30.05.2019

Spirit Airlines (NK 773)

Direct

119

11.05.2019

13.05.2019

Spirit Airlines (NK 773)

1 stop

129

16.05.2019

19.05.2019

Southwest Airlines (WN 746)

2 stops

202

BOS-CHI Compare Airline Prices

Departure dateReturn dateStopsPriceFlight numberAirlinesFind Ticket

25.04.2019

25.04.2019

Direct

179

AA 1427

179

26.04.2019

29.04.2019

1 stop

176

UA 449

176

27.04.2019

29.04.2019

Direct

169

UA 789

169

28.04.2019

29.04.2019

2 stops

400

AA 2387

400


* 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.