Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Best option Chicago Midway Boston | Outbound 07/01/25 direct WN3787 02h 10min | Return 07/06/25 1 Stopover (BNA) WN1148, WN4010 04h 55min | | ![]() | ? | $248 | |
Chicago Midway Boston | Outbound 07/01/25 2 Stopovers (ATL, EWR) F92144, UA1128, UA0577 26h 53min | Return 07/06/25 1 Stopover (TYS) G41426, G43027 26h 14min | | ![]() | ? | $377 |
Airline
- Frontier Airlines
- Southwest Airlines
Tips and tricks to help you find cheap flights from Chicago Midway to Boston
Favorite airline: Porter Airlines
Flight tickets on the route Chicago Midway – Boston are most frequently booked with Porter Airlines.

Porter Airlines
57 %

Delta
43 %
Favourite connection: via Toronto - City Centre
On this route, flights with a stopover in Toronto - City Centre are the most popular.
Route
bookings
1 stopover Toronto - City Centre Airport
09h 12min, from 498 $
57 %
1 stopover Hartsfield-Jackson Atlanta International Airport, GA
08h 11min, from 355 $
29 %
1 stopover Detroit Metropolitan Wayne County Airport, MI
05h 44min, from 735 $
14 %
Important flight information
Flight information: Chicago Midway - Boston
Roundtrip from | 247,67 $ |
---|---|
Flight duration | min. 02:10 / max. 11:15 |
Return flight duration | min. 02:45/ max. 06:55 |
Distance | 1383 km |
Flights per week | 23 |
Departure airport | Airport Chicago Midway International Airport, IL (MDW) |
Arrival airport | Airport Boston Logan International Airport, MA (BOS) |
Destination country | Flights to United States |
Alternative routes to United States
- Flight Chicago Midway - Atlanta from 67 $
- Flight Chicago Midway - Fort Lauderdale from 210 $
- Flight Chicago Midway - Los Angeles from 271 $
- Flight Chicago Midway - San Antonio from 254 $
- Flight Chicago Midway - Newark from 235 $
- Flight Chicago Midway - Las Vegas from 184 $
Alternative flights to Boston
- Flight New York - Boston from 95 $
- Flight Miami - Boston from 140 $
- Flight New York - Boston from 164 $
- Flight Chicago - Boston from 93 $
- Flight Tampa - Boston from 146 $
- Flight Washington-DC - Boston from 116 $
- Flight Orlando - Boston from 136 $
- Flight Los Angeles - Boston from 172 $
- Flight Buffalo - Boston from 140 $
- Flight San Francisco - Boston from 213 $
Flight destinations with a similar price
- Flight Boston - Istanbul from 429 $
- Flight Boston - Vienna from 428 $
- Flight Boston - Aruba from 353 $
- Flight Boston - London from 437 $
- Flight Boston - Bermuda from 287 $
- Flight Boston - Vancouver from 169 $
- Flight Boston - Toronto from 241 $
- Flight Boston - Toronto from 225 $
- Flight Boston - Toronto - City Centre from 225 $
- Flight Boston - Zurich from 415 $
Flight destinations with a similar price
- Flight Chicago Midway - Los Angeles from 271 $
- Flight Chicago Midway - San Antonio from 254 $
- Flight Chicago Midway - Newark from 235 $