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 - Las Vegas from $ 184
- Flight Chicago Midway - Los Angeles from $ 322
- Flight Chicago Midway - San Antonio from $ 304
- Flight Chicago Midway - Newark from $ 235
Alternative flights to Boston
- Flight New York - Boston from $ 111
- Flight Miami - Boston from $ 155
- Flight New York - Boston from $ 164
- Flight Chicago - Boston from $ 120
- Flight Tampa - Boston from $ 154
- Flight Washington-DC - Boston from $ 116
- Flight Orlando - Boston from $ 136
- Flight Buffalo - Boston from $ 155
- Flight Los Angeles - Boston from $ 172
- Flight San Francisco - Boston from $ 244
Flight destinations with a similar price
- Flight Boston - Istanbul from $ 567
- Flight Boston - Vienna from $ 495
- Flight Boston - London Heathrow from $ 456
- Flight Boston - Aruba from $ 353
- Flight Boston - Sydney from $ 740
- Flight Boston - London from $ 456
- Flight Boston - Bermuda from $ 287
- Flight Boston - Vancouver from $ 174
- Flight Boston - Toronto from $ 241
- Flight Boston - Toronto from $ 225
Flight destinations with a similar price
- Flight Chicago Midway - Newark from $ 235