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 $375 round trip and CA $177 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Jul 15 - Sat, Jul 18
DTW
Detroit
MDW
Chicago
CA $375 Roundtrip, found 1 day ago
CA $375
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jul 15 from Detroit to Chicago, returning Sat, Jul 18, priced at CA $375 found 1 day ago
Fri, Jun 19 - Sat, Jun 20
DTW
Detroit
MDW
Chicago
CA $402 Roundtrip, found 1 day ago
CA $402
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jun 19 from Detroit to Chicago, returning Sat, Jun 20, priced at CA $402 found 1 day ago
Thu, Jun 25 - Mon, Jun 29
DTW
Detroit
MDW
Chicago
CA $430 Roundtrip, found 3 days ago
CA $430
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Jun 25 from Detroit to Chicago, returning Mon, Jun 29, priced at CA $430 found 3 days ago
Thu, Apr 2 - Sun, Apr 5
DTW
Detroit
MDW
Chicago
CA $432 Roundtrip, found 2 days ago
CA $432
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Apr 2 from Detroit to Chicago, returning Sun, Apr 5, priced at CA $432 found 2 days ago
Wed, Jul 15 - Sat, Jul 18
DTW
Detroit
MDW
Chicago
CA $457 Roundtrip, found 1 day ago
CA $457
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jul 15 from Detroit to Chicago, returning Sat, Jul 18, priced at CA $457 found 1 day ago
Thu, Apr 2 - Sun, Apr 5
DTW
Detroit
MDW
Chicago
CA $473 Roundtrip, found 2 days ago
CA $473
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Apr 2 from Detroit to Chicago, returning Sun, Apr 5, priced at CA $473 found 2 days ago
Fri, Jun 19 - Sat, Jun 20
DTW
Detroit
MDW
Chicago
CA $474 Roundtrip, found 1 day ago
CA $474
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jun 19 from Detroit to Chicago, returning Sat, Jun 20, priced at CA $474 found 1 day ago
Fri, Jun 19 - Sat, Jun 20
DTW
Detroit
MDW
Chicago
CA $484 Roundtrip, found 1 day ago
CA $484
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jun 19 from Detroit to Chicago, returning Sat, Jun 20, priced at CA $484 found 1 day ago
Thu, Jun 25 - Mon, Jun 29
DTW
Detroit
MDW
Chicago
CA $511 Roundtrip, found 3 days ago
CA $511
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Jun 25 from Detroit to Chicago, returning Mon, Jun 29, priced at CA $511 found 3 days ago
Thu, Apr 2 - Sun, Apr 5
DTW
Detroit
MDW
Chicago
CA $515 Roundtrip, found 2 days ago
CA $515
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Apr 2 from Detroit to Chicago, returning Sun, Apr 5, priced at CA $515 found 2 days ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Price was CA $739, price is now CA $582 per person
CA $582
per person
Apr 26 - Apr 29
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was CA $925, price is now CA $695 per person
CA $695
per person
Apr 26 - Apr 29
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Price was CA $1,788, price is now CA $1,349 per person
CA $1,349
per person
Apr 26 - Apr 29
found 4 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
Price was CA $976, price is now CA $748 per person
CA $748
per person
Apr 26 - Apr 29
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Price was CA $907, price is now CA $708 per person
CA $708
per person
Apr 26 - Apr 29
found 4 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.

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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.