Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Best option Boston Chicago Midway | Outbound 07/02/25 direct WN1433 02h 40min | Return 07/25/25 direct WN1011 02h 15min | | ![]() | ? | $173 | |
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 06/07/25 direct WN1435 02h 35min | Return 06/23/25 direct WN1427 02h 15min | | ![]() | ? | $183 | |
Boston Chicago Midway | Outbound 06/08/25 1 Stopover (TPA) F91215, F93899 13h 36min | Return 06/12/25 1 Stopover (MCO) F93854, F93348 27h 00min | | ![]() | $240 | ||
Boston Chicago Midway | Outbound 06/08/25 1 Stopover (TPA) F91215, F93899 13h 36min | Return 06/12/25 1 Stopover (MCO) F93854, F93348 27h 00min | | ![]() | $250 | ||
Boston Chicago Midway | Outbound 06/08/25 1 Stopover (SAV) G41152, G41163 20h 44min | Return 06/12/25 1 Stopover (ATL) F92144, F93512 10h 58min | | ![]() | ? | $251 | |
Boston Chicago Midway | Outbound 07/02/25 1 Stopover (DCA, BWI) AA3240, F93087 11h 14min | Return 07/25/25 1 Stopover (VPS) G43081, G41443 25h 49min | | ![]() | ? | $317 | |
Boston Chicago Midway | Outbound 08/28/25 1 Stopover (DTW) DL1019, DL3858 04h 15min | Return 09/19/25 1 Stopover (MSP) DL3795, DL1502 07h 25min | | ![]() | ? | $318 | |
Boston Chicago Midway | Outbound 06/07/25 2 Stopovers (EWR, ATL) UA1308, UA2241, F92779 29h 09min | Return 06/23/25 1 Stopover (TYS) G43025, G41397 17h 24min | | ![]() | ? | $353 | |
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 |
Stops
- Direct flight
Airline
- Frontier Airlines
- Southwest Airlines
- United Airlines
- American 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 US$
37 %
1 stopover Philadelphia International Airport, PA
05h 45min, from 217 US$
32 %
1 stopover Toronto - City Centre Airport
10h 17min, from 550 US$
21 %
Important flight information
Flight information: Boston - Chicago Midway
Roundtrip from | 172,56 US$ |
---|---|
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 US$
- Flight Boston - Los Angeles from 181 US$
- Flight Boston - San Francisco from 203 US$
- Flight Boston - Miami from 133 US$
- Flight Boston - Chicago from 93 US$
- Flight Boston - Orlando from 126 US$
- Flight Boston - Fort Myers from 146 US$
- Flight Boston - Washington-DC from 116 US$
- Flight Boston - Dallas from 122 US$
- Flight Boston - New York from 136 US$
Alternative flights to Chicago Midway
- Flight San Francisco - Chicago Midway from 290 US$
- Flight Los Angeles - Chicago Midway from 263 US$
- Flight Orlando - Chicago Midway from 200 US$
- Flight Atlanta - Chicago Midway from 86 US$
- Flight Washington DC - Chicago Midway from 202 US$
- Flight Tampa - Chicago Midway from 243 US$
- Flight Newark - Chicago Midway from 244 US$
- Flight Minneapolis - Chicago Midway from 213 US$
Flight destinations with a similar price
- Flight Boston - Los Angeles from 181 US$
- Flight Boston - Seattle-Tacoma from 178 US$
- Flight Boston - Minneapolis from 174 US$
- Flight Boston - Washington DC from 159 US$
- Flight Boston - San Diego from 186 US$
- Flight Boston - Kansas City from 169 US$
- Flight Boston - St. Louis from 158 US$
- Flight Boston - Charlotte from 167 US$
- Flight Boston - Vancouver from 169 US$
- Flight Boston - San Juan (Puerto Rico) from 160 US$