Boston to Chicago Flights

Best Departing Flights from Boston to Chicago

Departure dateFlight classStopsPriceDistanceFind Ticket

08.12.2019

Economy

Direct

85

849.41 m

85

08.12.2019

Economy

1 stop

98

849.41 m

98

08.12.2019

Economy

2 stops

215

849.41 m

215

19.12.2019

Economy

Direct

94

849.41 m

94

19.12.2019

Economy

1 stop

98

849.41 m

98

19.12.2019

Economy

2 stops

242

849.41 m

242

20.12.2019

Economy

Direct

143

849.41 m

143

20.12.2019

Economy

1 stop

170

849.41 m

170

20.12.2019

Economy

2 stops

235

849.41 m

235

21.12.2019

Economy

Direct

224

849.41 m

224

21.12.2019

Economy

1 stop

128

849.41 m

128

21.12.2019

Economy

2 stops

201

849.41 m

201

23.12.2019

Economy

Direct

98

849.41 m

98

23.12.2019

Economy

1 stop

123

849.41 m

123

23.12.2019

Economy

2 stops

231

849.41 m

231

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

14.12.2019

JetBlue Airways (B6 1011)

158

10.01.2020

American Airlines (AA 408)

156

Round-trip Tickets from Boston to Chicago

Departure dateReturn dateFlightStopsFind Ticket

12.01.2020

26.01.2020

American Airlines (AA 1509)

Direct

157

12.01.2020

26.01.2020

American Airlines (AA 1509)

1 stop

164

13.12.2019

16.12.2019

JetBlue Airways (B6 1011)

2 stops

215

BOS-CHI Compare Airline Prices

Departure dateReturn dateStopsPriceFlight numberAirlinesFind Ticket

04.12.2019

18.12.2019

Direct

208

AA 2265

208

05.12.2019

07.12.2019

Direct

302

AA 2265

302

12.12.2019

14.12.2019

Direct

162

B6 311

162

13.12.2019

16.12.2019

Direct

161

AA 1239

161

14.12.2019

17.12.2019

Direct

158

B6 1011

158

15.12.2019

17.12.2019

Direct

161

B6 1011

161

18.12.2019

01.01.2020

1 stop

217

AA 130

217

19.12.2019

03.01.2020

1 stop

212

WN 591

212

24.12.2019

28.12.2019

Direct

248

B6 211

248

27.12.2019

30.12.2019

Direct

295

UA 203

295


* 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.