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., 1 Oct. - Tue., 8 Oct.
DTW
Detroit
MDW
Chicago
CA $145 Roundtrip, found 6 days ago
CA $145
Roundtrip
found 6 days ago
Tue., 1 Oct. - Tue., 8 Oct.
DTW
Detroit
MDW
Chicago
CA $162 Roundtrip, found 6 days ago
CA $162
Roundtrip
found 6 days ago
Tue., 1 Oct. - Tue., 8 Oct.
DTW
Detroit
MDW
Chicago
CA $208 Roundtrip, found 6 days ago
CA $208
Roundtrip
found 6 days ago
Tue., 1 Oct. - Tue., 8 Oct.
DTW
Detroit
MDW
Chicago
CA $226 Roundtrip, found 6 days ago
CA $226
Roundtrip
found 6 days ago
Tue., 1 Oct. - Tue., 8 Oct.
DTW
Detroit
MDW
Chicago
CA $228 Roundtrip, found 6 days ago
CA $228
Roundtrip
found 6 days ago
Tue., 1 Oct. - Tue., 8 Oct.
DTW
Detroit
MDW
Chicago
CA $245 Roundtrip, found 6 days ago
CA $245
Roundtrip
found 6 days ago
Tue., 3 Sep. - Sat., 7 Sep.
DTW
Detroit
MDW
Chicago
CA $263 Roundtrip, found 3 days ago
CA $263
Roundtrip
found 3 days ago
Tue., 1 Oct. - Tue., 8 Oct.
DTW
Detroit
MDW
Chicago
CA $291 Roundtrip, found 6 days ago
CA $291
Roundtrip
found 6 days ago
Tue., 1 Oct. - Tue., 8 Oct.
DTW
Detroit
MDW
Chicago
CA $308 Roundtrip, found 6 days ago
CA $308
Roundtrip
found 6 days ago
Fri., 9 Aug. - Tue., 13 Aug.
DTW
Detroit
MDW
Chicago
CA $320 Roundtrip, found 1 day ago
CA $320
Roundtrip
found 1 day ago
Best Midway Intl. Flight and Hotel Packages
Midway Intl. flight + hotel packages - economy flights
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Detroit Metropolitan Wayne County to Midway Intl.
View all tripsFrequently 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 Los Angeles
- Spirit Airlines Detroit to Miami
- Spirit Airlines Detroit to Fort Lauderdale
- Spirit Airlines Detroit to New York
- Air Canada Detroit to Delhi
- Spirit Airlines Detroit to Houston
- Spirit Airlines Detroit to New Orleans
- Spirit Airlines Detroit to Nashville
- Spirit Airlines Detroit to Dallas
Top Airlines Routes To MDW
Flights To MDW
- Spirit Airlines Detroit to Newark
- Spirit Airlines Detroit to Los Angeles
- Spirit Airlines Detroit to Miami
- Spirit Airlines Detroit to Fort Lauderdale
- Spirit Airlines Detroit to New York
- Air Canada Detroit to Delhi
- Spirit Airlines Detroit to Houston
- Spirit Airlines Detroit to New Orleans
- Spirit Airlines Detroit to Nashville
- Spirit Airlines Detroit to Dallas
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)