Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Best option Boston Chicago Midway | Outbound 07/08/25 direct WN1435 02h 35min | Return 08/07/25 direct WN3544 02h 20min | | ![]() | ? | $157 | |
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 07/02/25 direct WN1433 02h 40min | Return 07/25/25 direct WN1011 02h 15min | | ![]() | ? | $173 | |
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 10/09/25 1 Stopover (MIA) F91435, F92109 10h 43min | Return 11/01/25 1 Stopover (MIA) F92110, F91436 18h 31min | | ![]() | $260 | ||
Boston Chicago Midway | Outbound 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 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 07/08/25 1 Stopover (DCA, BWI) B61955, F93087 26h 26min | Return 08/07/25 3 Stopovers (ATL, LHR, LGW, JFK) VS2618, VS4044, AA6938, AA4659 35h 28min | | ![]() | ? | $1,339 |
Stops
- Direct flight
Airline
- Frontier Airlines
- Southwest Airlines
- Spirit Airlines
- American Airlines
- Delta Air Lines
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 | $ 156,95 |
---|---|
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 $ 133
- 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 $ 122
- 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 $ 86
- Flight Washington DC - Chicago Midway from $ 202
- Flight Tampa - Chicago Midway from $ 243
- Flight Newark - Chicago Midway from $ 212
- Flight Minneapolis - Chicago Midway from $ 213
Flight destinations with a similar price
- Flight Boston - Fort Myers from $ 146
- Flight Boston - New York from $ 159
- Flight Boston - Washington DC from $ 159
- Flight Boston - New Orleans from $ 153
- Flight Boston - New York from $ 146
- Flight Boston - Kansas City from $ 169
- Flight Boston - St. Louis from $ 158
- Flight Boston - Charlotte from $ 167
- Flight Boston - Houston - George Bush from $ 143
- Flight Boston - Jacksonville, Florida from $ 155