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 $165 round trip and CA $83 one way. Prices and availability subject to change. Additional terms may apply.

Mon, Sep. 29 - Tue, Sep. 30
DTW
Detroit
MDW
Chicago
CA $165 Roundtrip, found 2 days ago
CA $165
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Sep. 29 from Detroit to Chicago, returning Tue, Sep. 30, priced at CA $165 found 2 days ago
Mon, Sep. 29 - Tue, Sep. 30
DTW
Detroit
MDW
Chicago
CA $208 Roundtrip, found 2 days ago
CA $208
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Sep. 29 from Detroit to Chicago, returning Tue, Sep. 30, priced at CA $208 found 2 days ago
Tue, Sep. 30 - Fri, Oct. 3
DTW
Detroit
MDW
Chicago
CA $235 Roundtrip, found 1 day ago
CA $235
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep. 30 from Detroit to Chicago, returning Fri, Oct. 3, priced at CA $235 found 1 day ago
Mon, Sep. 29 - Tue, Sep. 30
DTW
Detroit
MDW
Chicago
CA $250 Roundtrip, found 2 days ago
CA $250
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Sep. 29 from Detroit to Chicago, returning Tue, Sep. 30, priced at CA $250 found 2 days ago
Mon, Sep. 29 - Tue, Sep. 30
DTW
Detroit
MDW
Chicago
CA $292 Roundtrip, found 2 days ago
CA $292
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Sep. 29 from Detroit to Chicago, returning Tue, Sep. 30, priced at CA $292 found 2 days ago
Tue, Sep. 30 - Fri, Oct. 3
DTW
Detroit
MDW
Chicago
CA $320 Roundtrip, found 1 day ago
CA $320
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep. 30 from Detroit to Chicago, returning Fri, Oct. 3, priced at CA $320 found 1 day ago
Mon, Sep. 29 - Tue, Sep. 30
DTW
Detroit
MDW
Chicago
CA $339 Roundtrip, found 2 days ago
CA $339
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Sep. 29 from Detroit to Chicago, returning Tue, Sep. 30, priced at CA $339 found 2 days ago
Thu, Sep. 18 - Sun, Sep. 28
DTW
Detroit
MDW
Chicago
CA $364 Roundtrip, found 1 day ago
CA $364
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Sep. 18 from Detroit to Chicago, returning Sun, Sep. 28, priced at CA $364 found 1 day ago
Fri, Sep. 26 - Tue, Sep. 30
DTW
Detroit
MDW
Chicago
CA $378 Roundtrip, found 3 days ago
CA $378
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep. 26 from Detroit to Chicago, returning Tue, Sep. 30, priced at CA $378 found 3 days ago
Mon, Sep. 29 - Tue, Sep. 30
DTW
Detroit
MDW
Chicago
CA $380 Roundtrip, found 2 days ago
CA $380
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Sep. 29 from Detroit to Chicago, returning Tue, Sep. 30, priced at CA $380 found 2 days ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Price was CA $920, price is now CA $575 per person
CA $575
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Detroit (DTT) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was CA $1,893, price is now CA $1,116 per person
CA $1,116
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Detroit (DTT) to Chicago (ORD)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Price was CA $1,386, price is now CA $872 per person
CA $872
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Detroit (DTT) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was CA $942, price is now CA $605 per person
CA $605
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Detroit (DTT) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Price was CA $968, price is now CA $643 per person
CA $643
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Detroit (DTT) 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.