Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Best option Boston Chicago Midway | Outbound 10/09/25 1 Stopover (MIA) F91435, F92109 10h 43min | Return 11/01/25 1 Stopover (MIA) F92110, F91436 18h 31min | | ![]() | $249 | ||
Boston Chicago Midway | Outbound 10/18/25 3 Stopovers (FLL, PIT, PGD) NK2887, NK0228, G41110, G42478 25h 35min | Return 11/17/25 1 Stopover (TYS) G41432, G41397 16h 31min | | ![]() | $264 | ||
Boston Chicago Midway | Outbound 09/04/25 1 Stopover (TPA) F91215, F93899 26h 54min | Return 09/28/25 1 Stopover (MCO) F93854, F93348 22h 59min | | ![]() | $250 | ||
Boston Chicago Midway | Outbound 10/09/25 1 Stopover (MIA) F91435, F92109 10h 43min | Return 11/01/25 1 Stopover (MIA) F92110, F91436 18h 31min | | ![]() | $260 | ||
Boston Chicago Midway | Outbound 09/04/25 1 Stopover (TPA) F91215, F93899 26h 54min | Return 09/28/25 1 Stopover (MCO) F93854, F93348 22h 59min | | ![]() | $261 | ||
Boston Chicago Midway | Outbound 10/18/25 2 Stopovers (MSP, VPS) SY0254, SY1811, G43078 28h 47min | Return 11/17/25 1 Stopover (TYS) G41432, G41397 16h 31min | | ![]() | ? | $449 | |
Boston Chicago Midway | Outbound 10/18/25 2 Stopovers (MSP, VPS) SY0254, SY1811, G43078 28h 47min | Return 10/24/25 1 Stopover (TYS) G41440, G43026 18h 26min | | ![]() | ? | $493 |
Airline
- Frontier Airlines
- Sun Country Airlines
- Spirit Airlines
Tips and tricks to help you find cheap flights from Boston to Chicago Midway
Favorite airline: Frontier Airlines
The most popular airline for flights from Boston to Chicago Midway is Frontier Airlines.

Frontier Airlines
52 %

Delta
24 %

Porter Airlines
16 %
Cheapest weekday: Thursday
The cheapest days to fly on this route are Thursday.
Favourite connection: via Orlando
37 % of booked tickets on this route are for flights with a transfer in Orlando.
Route
bookings
1 stopover Orlando International Airport, FL
25h 34min, from 396 $
37 %
1 stopover Philadelphia International Airport, PA
05h 45min, from 217 $
32 %
1 stopover Toronto - City Centre Airport
10h 17min, from 550 $
21 %
Important flight information
Flight information: Boston - Chicago Midway
Roundtrip from | 248,27 $ |
---|---|
Flight duration | min. 02:45 / max. 06:55 |
Return flight duration | min. 02:10/ max. 11:15 |
Distance | 1383 km |
Flights per week | 23 |
Departure airport | Airport Boston Logan International Airport, MA (BOS) |
Arrival airport | Airport Chicago Midway International Airport, IL (MDW) |
Destination country | Flights to United States |
Alternative routes to United States
- Flight Boston - New York from 80 $
- Flight Boston - Los Angeles from 181 $
- Flight Boston - San Francisco from 203 $
- Flight Boston - Miami from 147 $
- Flight Boston - Chicago from 93 $
- Flight Boston - Orlando from 126 $
- Flight Boston - Fort Myers from 146 $
- Flight Boston - Washington-DC from 130 $
- Flight Boston - Dallas from 158 $
- Flight Boston - New York from 159 $
Alternative flights to Chicago Midway
- Flight San Francisco - Chicago Midway from 290 $
- Flight Los Angeles - Chicago Midway from 279 $
- Flight Orlando - Chicago Midway from 200 $
- Flight Atlanta - Chicago Midway from 131 $
- Flight Tampa - Chicago Midway from 243 $
- Flight Minneapolis - Chicago Midway from 213 $
Flight destinations with a similar price
- Flight Boston - St. Louis from 254 $
- Flight Boston - Cancun from 273 $
- Flight Boston - Portland-Oregon from 228 $
- Flight Boston - San Jose from 243 $
- Flight Boston - Toronto from 264 $
- Flight Boston - Burbank from 258 $
- Flight Boston - Toronto from 243 $
- Flight Boston - Toronto - City Centre from 243 $