Cheap Flights From Detroit Metropolitan Wayne County (DTW) To Midway Intl. (MDW)

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Cheapest Flights from Detroit (DTW) to Chicago (MDW)

The cheapest flights to Midway Intl. found within the past 7 days were CA $322 round trip and CA $159 one way. Prices and availability subject to change. Additional terms may apply.

Fri., Jun. 27 - Mon., Jun. 30
DTW
Detroit
MDW
Chicago
CA $322 Roundtrip, found 11 hours ago
CA $322
Roundtrip
found 11 hours ago
Select Delta flight, departing Fri., Jun. 27 from Detroit to Chicago, returning Mon., Jun. 30, priced at CA $322 found 11 hours ago
Fri., Oct. 3 - Wed., Oct. 8
DTW
Detroit
MDW
Chicago
CA $334 Roundtrip, found 5 days ago
CA $334
Roundtrip
found 5 days ago
Select Delta flight, departing Fri., Oct. 3 from Detroit to Chicago, returning Wed., Oct. 8, priced at CA $334 found 5 days ago
Wed., Sep. 24 - Sun., Sep. 28
DTW
Detroit
MDW
Chicago
CA $343 Roundtrip, found 1 day ago
CA $343
Roundtrip
found 1 day ago
Select Delta flight, departing Wed., Sep. 24 from Detroit to Chicago, returning Sun., Sep. 28, priced at CA $343 found 1 day ago
Mon., Jul. 7 - Wed., Jul. 9
DTW
Detroit
MDW
Chicago
CA $352 Roundtrip, just found
CA $352
Roundtrip
just found
Select Delta flight, departing Mon., Jul. 7 from Detroit to Chicago, returning Wed., Jul. 9, priced at CA $352 just found
Sat., Aug. 2 - Sat., Aug. 30
DTW
Detroit
MDW
Chicago
CA $357 Roundtrip, found 3 days ago
CA $357
Roundtrip
found 3 days ago
Select Delta flight, departing Sat., Aug. 2 from Detroit to Chicago, returning Sat., Aug. 30, priced at CA $357 found 3 days ago
Fri., Oct. 3 - Wed., Oct. 8
DTW
Detroit
MDW
Chicago
CA $365 Roundtrip, found 5 days ago
CA $365
Roundtrip
found 5 days ago
Select Delta flight, departing Fri., Oct. 3 from Detroit to Chicago, returning Wed., Oct. 8, priced at CA $365 found 5 days ago
Thu., Oct. 2 - Thu., Oct. 23
DTW
Detroit
MDW
Chicago
CA $375 Roundtrip, found 3 days ago
CA $375
Roundtrip
found 3 days ago
Select Delta flight, departing Thu., Oct. 2 from Detroit to Chicago, returning Thu., Oct. 23, priced at CA $375 found 3 days ago
Wed., Sep. 24 - Sun., Sep. 28
DTW
Detroit
MDW
Chicago
CA $379 Roundtrip, found 1 day ago
CA $379
Roundtrip
found 1 day ago
Select Delta flight, departing Wed., Sep. 24 from Detroit to Chicago, returning Sun., Sep. 28, priced at CA $379 found 1 day ago
Sat., Jun. 7 - Wed., Jun. 11
DTW
Detroit
MDW
Chicago
CA $390 Roundtrip, found 5 days ago
CA $390
Roundtrip
found 5 days ago
Select Delta flight, departing Sat., Jun. 7 from Detroit to Chicago, returning Wed., Jun. 11, priced at CA $390 found 5 days ago
Wed., Jun. 11 - Thu., Jun. 12
DTW
Detroit
MDW
Chicago
CA $390 Roundtrip, found 23 hours ago
CA $390
Roundtrip
found 23 hours ago
Select Delta flight, departing Wed., Jun. 11 from Detroit to Chicago, returning Thu., Jun. 12, priced at CA $390 found 23 hours ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 6
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 6
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
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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!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.