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 $339 round trip and CA $127 one way. Prices and availability subject to change. Additional terms may apply.

Tue, Jun 9 - Mon, Jun 15
DTW
Detroit
MDW
Chicago
CA $339 Roundtrip, found 11 hours ago
CA $339
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Jun 9 from Detroit to Chicago, returning Mon, Jun 15, priced at CA $339 found 11 hours ago
Wed, May 27 - Fri, May 29
DTW
Detroit
MDW
Chicago
CA $358 Roundtrip, found 6 days ago
CA $358
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, May 27 from Detroit to Chicago, returning Fri, May 29, priced at CA $358 found 6 days ago
Tue, Jun 9 - Mon, Jun 15
DTW
Detroit
MDW
Chicago
CA $395 Roundtrip, found 11 hours ago
CA $395
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Jun 9 from Detroit to Chicago, returning Mon, Jun 15, priced at CA $395 found 11 hours ago
Wed, May 27 - Fri, May 29
DTW
Detroit
MDW
Chicago
CA $400 Roundtrip, found 6 days ago
CA $400
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, May 27 from Detroit to Chicago, returning Fri, May 29, priced at CA $400 found 6 days ago
Thu, Jul 9 - Sun, Jul 12
DTW
Detroit
MDW
Chicago
CA $405 Roundtrip, found 6 days ago
CA $405
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Jul 9 from Detroit to Chicago, returning Sun, Jul 12, priced at CA $405 found 6 days ago
Tue, Jun 9 - Mon, Jun 15
DTW
Detroit
MDW
Chicago
CA $410 Roundtrip, found 11 hours ago
CA $410
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Jun 9 from Detroit to Chicago, returning Mon, Jun 15, priced at CA $410 found 11 hours ago
Tue, Jun 9 - Mon, Jun 15
DTW
Detroit
MDW
Chicago
CA $437 Roundtrip, found 11 hours ago
CA $437
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Jun 9 from Detroit to Chicago, returning Mon, Jun 15, priced at CA $437 found 11 hours ago
Thu, Jul 9 - Sun, Jul 12
DTW
Detroit
MDW
Chicago
CA $446 Roundtrip, found 6 days ago
CA $446
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Jul 9 from Detroit to Chicago, returning Sun, Jul 12, priced at CA $446 found 6 days ago
Thu, Jul 9 - Sun, Jul 12
DTW
Detroit
MDW
Chicago
CA $447 Roundtrip, found 6 days ago
CA $447
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Jul 9 from Detroit to Chicago, returning Sun, Jul 12, priced at CA $447 found 6 days ago
Wed, May 27 - Fri, May 29
DTW
Detroit
MDW
Chicago
CA $456 Roundtrip, found 6 days ago
CA $456
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, May 27 from Detroit to Chicago, returning Fri, May 29, priced at CA $456 found 6 days 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
Price was CA $1,617, price is now CA $1,211 per person
CA $1,211
per person
Jun 9 - Jun 14
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was CA $2,256, price is now CA $1,519 per person
CA $1,519
per person
Jun 9 - Jun 14
found 23 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 $2,898, price is now CA $2,009 per person
CA $2,009
per person
Jun 9 - Jun 14
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was CA $2,130, price is now CA $1,568 per person
CA $1,568
per person
Jun 9 - Jun 14
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was CA $3,336, price is now CA $2,521 per person
CA $2,521
per person
Jun 9 - Jun 14
found 23 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.