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 $365 round trip and CA $177 one way. Prices and availability subject to change. Additional terms may apply.

Mon, May 4 - Tue, May 5
DTW
Detroit
MDW
Chicago
CA $365 Roundtrip, found 1 day ago
CA $365
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, May 4 from Detroit to Chicago, returning Tue, May 5, priced at CA $365 found 1 day ago
Wed, Jul 15 - Sat, Jul 18
DTW
Detroit
MDW
Chicago
CA $375 Roundtrip, found 6 days ago
CA $375
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jul 15 from Detroit to Chicago, returning Sat, Jul 18, priced at CA $375 found 6 days ago
Mon, May 4 - Tue, May 5
DTW
Detroit
MDW
Chicago
CA $395 Roundtrip, found 1 day ago
CA $395
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, May 4 from Detroit to Chicago, returning Tue, May 5, priced at CA $395 found 1 day ago
Mon, Jul 13 - Thu, Aug 6
DTW
Detroit
MDW
Chicago
CA $403 Roundtrip, found 2 days ago
CA $403
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jul 13 from Detroit to Chicago, returning Thu, Aug 6, priced at CA $403 found 2 days ago
Thu, Jul 30 - Sun, Aug 2
DTW
Detroit
MDW
Chicago
CA $404 Roundtrip, just found
CA $404
Roundtrip
just found
Select Delta flight, departing Thu, Jul 30 from Detroit to Chicago, returning Sun, Aug 2, priced at CA $404 just found
Mon, Jul 13 - Thu, Aug 6
DTW
Detroit
MDW
Chicago
CA $421 Roundtrip, found 2 days ago
CA $421
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jul 13 from Detroit to Chicago, returning Thu, Aug 6, priced at CA $421 found 2 days ago
Thu, Jul 30 - Sun, Aug 2
DTW
Detroit
MDW
Chicago
CA $436 Roundtrip, just found
CA $436
Roundtrip
just found
Select Delta flight, departing Thu, Jul 30 from Detroit to Chicago, returning Sun, Aug 2, priced at CA $436 just found
Mon, May 4 - Tue, May 5
DTW
Detroit
MDW
Chicago
CA $448 Roundtrip, found 1 day ago
CA $448
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, May 4 from Detroit to Chicago, returning Tue, May 5, priced at CA $448 found 1 day ago
Wed, Jul 15 - Sat, Jul 18
DTW
Detroit
MDW
Chicago
CA $457 Roundtrip, found 6 days ago
CA $457
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jul 15 from Detroit to Chicago, returning Sat, Jul 18, priced at CA $457 found 6 days ago
Mon, May 4 - Tue, May 5
DTW
Detroit
MDW
Chicago
CA $461 Roundtrip, found 1 day ago
CA $461
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, May 4 from Detroit to Chicago, returning Tue, May 5, priced at CA $461 found 1 day 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.

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*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.