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 $310 round trip and CA $136 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Nov. 26 - Thu, Nov. 27
DTW
Detroit
MDW
Chicago
CA $310 Roundtrip, found 4 days ago
CA $310
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Nov. 26 from Detroit to Chicago, returning Thu, Nov. 27, priced at CA $310 found 4 days ago
Wed, Jul. 30 - Mon, Aug. 4
DTW
Detroit
MDW
Chicago
CA $406 Roundtrip, found 4 days ago
CA $406
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jul. 30 from Detroit to Chicago, returning Mon, Aug. 4, priced at CA $406 found 4 days ago
Fri, Oct. 10 - Tue, Oct. 14
DTW
Detroit
MDW
Chicago
CA $417 Roundtrip, found 5 days ago
CA $417
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Oct. 10 from Detroit to Chicago, returning Tue, Oct. 14, priced at CA $417 found 5 days ago
Thu, Oct. 9 - Mon, Oct. 13
DTW
Detroit
MDW
Chicago
CA $426 Roundtrip, found 15 hours ago
CA $426
Roundtrip
found 15 hours ago
Select Delta flight, departing Thu, Oct. 9 from Detroit to Chicago, returning Mon, Oct. 13, priced at CA $426 found 15 hours ago
Wed, Nov. 26 - Thu, Nov. 27
DTW
Detroit
MDW
Chicago
CA $429 Roundtrip, found 4 days ago
CA $429
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Nov. 26 from Detroit to Chicago, returning Thu, Nov. 27, priced at CA $429 found 4 days ago
Thu, Oct. 9 - Mon, Oct. 13
DTW
Detroit
MDW
Chicago
CA $476 Roundtrip, found 15 hours ago
CA $476
Roundtrip
found 15 hours ago
Select Delta flight, departing Thu, Oct. 9 from Detroit to Chicago, returning Mon, Oct. 13, priced at CA $476 found 15 hours ago
Tue, Jul. 22 - Thu, Jul. 31
DTW
Detroit
MDW
Chicago
CA $483 Roundtrip, found 1 day ago
CA $483
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul. 22 from Detroit to Chicago, returning Thu, Jul. 31, priced at CA $483 found 1 day ago
Tue, Jul. 22 - Thu, Jul. 31
DTW
Detroit
MDW
Chicago
CA $517 Roundtrip, found 1 day ago
CA $517
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul. 22 from Detroit to Chicago, returning Thu, Jul. 31, priced at CA $517 found 1 day ago
Thu, Oct. 9 - Mon, Oct. 13
DTW
Detroit
MDW
Chicago
CA $536 Roundtrip, found 15 hours ago
CA $536
Roundtrip
found 15 hours ago
Select Delta flight, departing Thu, Oct. 9 from Detroit to Chicago, returning Mon, Oct. 13, priced at CA $536 found 15 hours ago
Tue, Jul. 22 - Thu, Jul. 31
DTW
Detroit
MDW
Chicago
CA $552 Roundtrip, found 1 day ago
CA $552
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul. 22 from Detroit to Chicago, returning Thu, Jul. 31, priced at CA $552 found 1 day ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Sep 3 - Sep 6
found 9 hours 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
Sep 3 - Sep 6
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
per person
Sep 3 - Sep 6
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Sep 3 - Sep 6
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
Sep 3 - Sep 6
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
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Frequently asked questions

Are there direct flights from Metro Airport to Midway Intl. Airport (MDW)?
Sometimes, travel is all about the journey; other times, it's all about the destination. If you're itching to get to Chicago fast, multiple airlines offer direct flights from DTW to Midway Intl. Airport (MDW), including Southwest Airlines and Delta.
What airlines fly from Metro Airport to Midway Intl. Airport (MDW)?
There are a few airlines that have direct flights between Detroit and Chicago. Southwest Airlines (WN) is one of the most popular. This air carrier operates about 86 flights every month. Another possibility is Delta (DL), which has 86 flights every month. The more airlines you look into, the more likely you are to snag a terrific deal.
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

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.