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 $248 round trip and CA $107 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Dec 31 - Thu, Jan 1
DTW
Detroit
MDW
Chicago
CA $248 Roundtrip, found 4 hours ago
CA $248
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Dec 31 from Detroit to Chicago, returning Thu, Jan 1, priced at CA $248 found 4 hours ago
Wed, Dec 31 - Thu, Jan 1
DTW
Detroit
MDW
Chicago
CA $333 Roundtrip, found 4 hours ago
CA $333
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Dec 31 from Detroit to Chicago, returning Thu, Jan 1, priced at CA $333 found 4 hours ago
Tue, Jan 6 - Wed, Jan 7
DTW
Detroit
MDW
Chicago
CA $408 Roundtrip, found 4 hours ago
CA $408
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Jan 6 from Detroit to Chicago, returning Wed, Jan 7, priced at CA $408 found 4 hours ago
Fri, Apr 17 - Sun, Apr 19
DTW
Detroit
MDW
Chicago
CA $420 Roundtrip, found 6 days ago
CA $420
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Apr 17 from Detroit to Chicago, returning Sun, Apr 19, priced at CA $420 found 6 days ago
Wed, Dec 31 - Thu, Jan 1
DTW
Detroit
MDW
Chicago
CA $424 Roundtrip, found 4 hours ago
CA $424
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Dec 31 from Detroit to Chicago, returning Thu, Jan 1, priced at CA $424 found 4 hours ago
Fri, Jun 19 - Sun, Jun 21
DTW
Detroit
MDW
Chicago
CA $452 Roundtrip, found 1 day ago
CA $452
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jun 19 from Detroit to Chicago, returning Sun, Jun 21, priced at CA $452 found 1 day ago
Tue, Dec 30 - Wed, Dec 31
DTW
Detroit
MDW
Chicago
CA $467 Roundtrip, found 1 day ago
CA $467
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Dec 30 from Detroit to Chicago, returning Wed, Dec 31, priced at CA $467 found 1 day ago
Fri, Jun 19 - Sun, Jun 21
DTW
Detroit
MDW
Chicago
CA $492 Roundtrip, found 1 day ago
CA $492
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jun 19 from Detroit to Chicago, returning Sun, Jun 21, priced at CA $492 found 1 day ago
Tue, Jan 6 - Wed, Jan 7
DTW
Detroit
MDW
Chicago
CA $492 Roundtrip, found 4 hours ago
CA $492
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Jan 6 from Detroit to Chicago, returning Wed, Jan 7, priced at CA $492 found 4 hours ago
Fri, Apr 17 - Sun, Apr 19
DTW
Detroit
MDW
Chicago
CA $506 Roundtrip, found 6 days ago
CA $506
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Apr 17 from Detroit to Chicago, returning Sun, Apr 19, priced at CA $506 found 6 days ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Chicago/ Schaumburg

Hyatt Place Chicago/ Schaumburg

3 out of 5
Price was CA $591, price is now CA $392 per person
CA $392
per person
Feb 11 - Feb 14
found 11 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Price was CA $937, price is now CA $604 per person
CA $604
per person
Feb 11 - Feb 14
found 11 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 $1,392, price is now CA $920 per person
CA $920
per person
Feb 11 - Feb 14
found 11 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was CA $708, price is now CA $515 per person
CA $515
per person
Feb 11 - Feb 14
found 11 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Price was CA $638, price is now CA $468 per person
CA $468
per person
Feb 11 - Feb 14
found 11 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.