Wander Wisely with exceptional service, 24/7 support
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
Find The Best Dates To Fly
Cheapest Flights from Detroit (DTW) to Chicago (MDW)
The cheapest flights to Midway Intl. found within the past 7 days were CA $145 round trip and CA $72 one way. Prices and availability subject to change. Additional terms may apply.
Tue., 6 Aug. - Sat., 10 Aug.
DTW
Detroit
MDW
Chicago
CA $145 Roundtrip, found 6 days ago
CA $145
Roundtrip
found 6 days ago
Tue., 24 Sep. - Thu., 26 Sep.
DTW
Detroit
MDW
Chicago
CA $179 Roundtrip, found 2 days ago
CA $179
Roundtrip
found 2 days ago
Tue., 24 Sep. - Thu., 26 Sep.
DTW
Detroit
MDW
Chicago
CA $221 Roundtrip, found 2 days ago
CA $221
Roundtrip
found 2 days ago
Fri., 8 Nov. - Mon., 11 Nov.
DTW
Detroit
MDW
Chicago
CA $222 Roundtrip, found 3 days ago
CA $222
Roundtrip
found 3 days ago
Tue., 6 Aug. - Sat., 10 Aug.
DTW
Detroit
MDW
Chicago
CA $227 Roundtrip, found 6 days ago
CA $227
Roundtrip
found 6 days ago
Thu., 15 Aug. - Sun., 18 Aug.
DTW
Detroit
MDW
Chicago
CA $232 Roundtrip, found 3 days ago
CA $232
Roundtrip
found 3 days ago
Tue., 24 Sep. - Thu., 26 Sep.
DTW
Detroit
MDW
Chicago
CA $257 Roundtrip, found 2 days ago
CA $257
Roundtrip
found 2 days ago
Fri., 8 Nov. - Mon., 11 Nov.
DTW
Detroit
MDW
Chicago
CA $258 Roundtrip, found 3 days ago
CA $258
Roundtrip
found 3 days ago
Tue., 24 Sep. - Thu., 26 Sep.
DTW
Detroit
MDW
Chicago
CA $262 Roundtrip, found 2 days ago
CA $262
Roundtrip
found 2 days ago
Thu., 15 Aug. - Sun., 18 Aug.
DTW
Detroit
MDW
Chicago
CA $267 Roundtrip, found 3 days ago
CA $267
Roundtrip
found 3 days ago
Frequently asked questions
Popular Flight Routes from Detroit (DTW)
Travelers at DTW love to visit these top cities. Roam to the top destinations from Detroit (DTW) today with the cheap prices from Travelocity!
Popular Flight Routes from Chicago (MDW)
Travelers at MDW love to visit these top cities. Roam to the top destinations from Chicago(MDW) today with the cheap prices from Travelocity!
Top Airlines Routes From DTW
- Spirit Airlines Detroit to Newark
- Spirit Airlines Detroit to Phoenix
- Spirit Airlines Detroit to Fort Lauderdale
- Spirit Airlines Detroit to New York
- Air Canada Detroit to Delhi
- Spirit Airlines Detroit to Dallas
- Spirit Airlines Detroit to Nashville
- Qatar Airways Detroit to Ahmedabad
- Spirit Airlines Detroit to Atlanta
- Aeromexico Detroit to Cancun
Top Airlines Routes To MDW
Flights To MDW
Most Popular
Flights
Delta Kincheloe (CIU) to Fort Lauderdale (FLL) flightsDelta Kincheloe (CIU) to Detroit (DTW) flightsDelta Toronto (YYZ) to Traverse City (TVC) flightsDelta Kincheloe (CIU) to Las Vegas (LAS) flightsKalamazoo to Greenville (AZO - GLH)American Airlines Toronto (YYZ) to Chicago (ORD) flightsSault Ste. Marie to Orlando (CIU - MCO)Montreal to Chicago (YUL - ORD)Delta Kincheloe (CIU) to Minneapolis - St. Paul (MSP) flightsUnited Toronto (YYZ) to Chicago (ORD) flightsToronto to Champaign (YYZ - CMI)Delta Kincheloe (CIU) to Tampa (TPA) flightsSeattle to Chicago (SEA - ORD)Air Canada Vancouver (YVR) to Chicago (ORD) flightsSault Ste. Marie to Minneapolis (CIU - MSP)Calgary to Chicago (YYC - ORD)Toronto to Chicago (YYZ - ORD)Edmonton to Chicago (YEG - ORD)Air Canada Montreal (YUL) to Chicago (ORD) flightsDelta Detroit (DTW) to Chicago (ORD) flightsKitchener to Chicago (YKF - ORD)Vancouver to Chicago (YVR - ORD)Air Canada Toronto (YYZ) to Chicago (ORD) flightsHamilton to Chicago (YHM - ORD)Delta Detroit (DTW) to Kincheloe (CIU) flightsDetroit to Chicago (DTW - ORD)Buffalo to Chicago (BUF - ORD)