Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
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 | ||
Best option Boston Chicago Midway | Outbound 04/21/25 1 Stopover (TPA) F91215, F91185 10h 21min | Return 05/19/25 1 Stopover (MCO) F93854, F93348 10h 25min | | ![]() | $303 | ||
Boston Chicago Midway | Outbound 04/12/25 1 Stopover (ATL) F93511, F92779 17h 16min | Return 04/27/25 1 Stopover (ATL) F92292, F93512 18h 13min | | ![]() | ? | $247 | |
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 04/21/25 2 Stopovers (MIA, ATL) AA1397, AA0659, F92143 16h 43min | Return 05/19/25 2 Stopovers (ATL, MCO) F92292, F93976, F93348 29h 08min | | ![]() | ? | $303 | |
Boston Chicago Midway | Outbound 04/21/25 1 Stopover (TPA) F91215, F91185 10h 21min | Return 05/19/25 1 Stopover (MCO) F93854, F93348 10h 25min | | ![]() | $313 | ||
Boston Chicago Midway | Outbound 04/21/25 1 Stopover (TPA) F91215, F91185 10h 21min | Return 05/19/25 1 Stopover (MCO) F93854, F93348 10h 25min | | ![]() | ? | $314 | |
Boston Chicago Midway | Outbound 06/20/25 1 Stopover (ATL) F93511, F92779 18h 55min | Return 07/19/25 2 Stopovers (ATL, MSP) F92292, SY0356, SY0253 27h 59min | | ![]() | ? | $427 | |
Boston Chicago Midway | Outbound 06/10/25 1 Stopover (ATL) F93511, F92779 18h 55min | Return 06/29/25 1 Stopover (ATL) F92144, F93512 10h 58min | | ![]() | ? | $500 |
Airline
- Frontier Airlines
- American Airlines
- Allegiant Air
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 USD
37 %
1 stopover Philadelphia International Airport, PA
05h 45min, from 217 USD
32 %
1 stopover Toronto - City Centre Airport
10h 17min, from 550 USD
21 %
Important flight information
Flight information: Boston - Chicago Midway
Roundtrip from | 239,95 USD |
---|---|
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 77 USD
- Flight Boston - Los Angeles from 181 USD
- Flight Boston - San Francisco from 235 USD
- Flight Boston - Miami from 138 USD
- Flight Boston - Chicago from 120 USD
- Flight Boston - Fort Myers from 176 USD
- Flight Boston - Orlando from 130 USD
- Flight Boston - Washington-DC from 116 USD
- Flight Boston - Dallas from 156 USD
- Flight Boston - New York from 136 USD
Alternative flights to Chicago Midway
- Flight San Francisco - Chicago Midway from 220 USD
- Flight Minneapolis - Chicago Midway from 229 USD
- Flight Los Angeles - Chicago Midway from 210 USD
- Flight Tampa - Chicago Midway from 134 USD
- Flight Atlanta - Chicago Midway from 75 USD
- Flight Orlando - Chicago Midway from 204 USD
- Flight Washington DC - Chicago Midway from 222 USD
- Flight Newark - Chicago Midway from 112 USD
Flight destinations with a similar price
- Flight Boston - San Francisco from 235 USD
- Flight Boston - Las Vegas from 217 USD
- Flight Boston - San Diego from 256 USD
- Flight Boston - Phoenix - Sky Harbor from 219 USD
- Flight Boston - Toronto from 241 USD
- Flight Boston - Toronto from 240 USD
- Flight Boston - Toronto - City Centre from 240 USD