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 $235 round trip and CA $83 one way. Prices and availability subject to change. Additional terms may apply.

Tue, Sep 30 - Fri, Oct 3
DTW
Detroit
MDW
Chicago
CA $235 Roundtrip, found 5 days ago
CA $235
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Sep 30 from Detroit to Chicago, returning Fri, Oct 3, priced at CA $235 found 5 days ago
Fri, Oct 17 - Sun, Oct 19
DTW
Detroit
MDW
Chicago
CA $276 Roundtrip, found 1 day ago
CA $276
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 17 from Detroit to Chicago, returning Sun, Oct 19, priced at CA $276 found 1 day ago
Fri, Oct 3 - Sun, Oct 5
DTW
Detroit
MDW
Chicago
CA $299 Roundtrip, found 3 days ago
CA $299
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Oct 3 from Detroit to Chicago, returning Sun, Oct 5, priced at CA $299 found 3 days ago
Fri, Oct 24 - Sun, Oct 26
DTW
Detroit
MDW
Chicago
CA $304 Roundtrip, found 2 days ago
CA $304
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Oct 24 from Detroit to Chicago, returning Sun, Oct 26, priced at CA $304 found 2 days ago
Tue, Sep 30 - Fri, Oct 3
DTW
Detroit
MDW
Chicago
CA $320 Roundtrip, found 5 days ago
CA $320
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Sep 30 from Detroit to Chicago, returning Fri, Oct 3, priced at CA $320 found 5 days ago
Fri, Oct 17 - Sun, Oct 19
DTW
Detroit
MDW
Chicago
CA $361 Roundtrip, found 1 day ago
CA $361
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 17 from Detroit to Chicago, returning Sun, Oct 19, priced at CA $361 found 1 day ago
Thu, Sep 18 - Sun, Sep 28
DTW
Detroit
MDW
Chicago
CA $364 Roundtrip, found 6 days ago
CA $364
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Sep 18 from Detroit to Chicago, returning Sun, Sep 28, priced at CA $364 found 6 days ago
Fri, Oct 3 - Sun, Oct 5
DTW
Detroit
MDW
Chicago
CA $381 Roundtrip, found 3 days ago
CA $381
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Oct 3 from Detroit to Chicago, returning Sun, Oct 5, priced at CA $381 found 3 days ago
Fri, Oct 24 - Sun, Oct 26
DTW
Detroit
MDW
Chicago
CA $389 Roundtrip, found 2 days ago
CA $389
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Oct 24 from Detroit to Chicago, returning Sun, Oct 26, priced at CA $389 found 2 days ago
Fri, Oct 17 - Sun, Oct 19
DTW
Detroit
MDW
Chicago
CA $402 Roundtrip, found 1 day ago
CA $402
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 17 from Detroit to Chicago, returning Sun, Oct 19, priced at CA $402 found 1 day ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites, Lincolnshire by IHG

Staybridge Suites, Lincolnshire by IHG

3 out of 5
Price was CA $467, price is now CA $313 per person
CA $313
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Hilton Garden Inn Chicago OHare Airport

Hilton Garden Inn Chicago OHare Airport

3 out of 5
Price was CA $624, price is now CA $458 per person
CA $458
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
Price was CA $421, price is now CA $315 per person
CA $315
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Embassy Suites by Hilton Chicago O'Hare Rosemont

Embassy Suites by Hilton Chicago O'Hare Rosemont

4 out of 5
Price was CA $679, price is now CA $509 per person
CA $509
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Four Points by Sheraton Chicago O'Hare Airport

Four Points by Sheraton Chicago O'Hare Airport

3 out of 5
Price was CA $509, price is now CA $382 per person
CA $382
per person
Oct 11 - Oct 14
found 1 day 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.