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 $355 round trip and CA $122 one way. Prices and availability subject to change. Additional terms may apply.

Tue, Dec 30 - Thu, Jan 1
DTW
Detroit
MDW
Chicago
CA $355 Roundtrip, found 6 days ago
CA $355
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Dec 30 from Detroit to Chicago, returning Thu, Jan 1, priced at CA $355 found 6 days ago
Tue, May 5 - Mon, May 11
DTW
Detroit
MDW
Chicago
CA $380 Roundtrip, found 5 days ago
CA $380
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, May 5 from Detroit to Chicago, returning Mon, May 11, priced at CA $380 found 5 days ago
Fri, Apr 17 - Sun, Apr 19
DTW
Detroit
MDW
Chicago
CA $420 Roundtrip, found 4 days ago
CA $420
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Apr 17 from Detroit to Chicago, returning Sun, Apr 19, priced at CA $420 found 4 days ago
Wed, Dec 24 - Sun, Dec 28
DTW
Detroit
MDW
Chicago
CA $424 Roundtrip, found 11 hours ago
CA $424
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Dec 24 from Detroit to Chicago, returning Sun, Dec 28, priced at CA $424 found 11 hours ago
Tue, Dec 30 - Thu, Jan 1
DTW
Detroit
MDW
Chicago
CA $441 Roundtrip, found 6 days ago
CA $441
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Dec 30 from Detroit to Chicago, returning Thu, Jan 1, priced at CA $441 found 6 days ago
Tue, May 5 - Mon, May 11
DTW
Detroit
MDW
Chicago
CA $463 Roundtrip, found 5 days ago
CA $463
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, May 5 from Detroit to Chicago, returning Mon, May 11, priced at CA $463 found 5 days ago
Fri, Apr 17 - Sun, Apr 19
DTW
Detroit
MDW
Chicago
CA $506 Roundtrip, found 4 days ago
CA $506
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Apr 17 from Detroit to Chicago, returning Sun, Apr 19, priced at CA $506 found 4 days ago
Wed, Dec 24 - Sun, Dec 28
DTW
Detroit
MDW
Chicago
CA $509 Roundtrip, found 11 hours ago
CA $509
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Dec 24 from Detroit to Chicago, returning Sun, Dec 28, priced at CA $509 found 11 hours ago
Tue, Dec 30 - Thu, Jan 1
DTW
Detroit
MDW
Chicago
CA $527 Roundtrip, found 6 days ago
CA $527
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Dec 30 from Detroit to Chicago, returning Thu, Jan 1, priced at CA $527 found 6 days ago
Tue, Dec 30 - Thu, Jan 1
DTW
Detroit
MDW
Chicago
CA $528 Roundtrip, found 6 days ago
CA $528
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Dec 30 from Detroit to Chicago, returning Thu, Jan 1, priced at CA $528 found 6 days ago

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.