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 $213 round trip and CA $120 one way. Prices and availability subject to change. Additional terms may apply.

Tue, Mar 24 - Tue, Apr 7
DTW
Detroit
MDW
Chicago
CA $213 Roundtrip, found 6 days ago
CA $213
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Mar 24 from Detroit to Chicago, returning Tue, Apr 7, priced at CA $213 found 6 days ago
Tue, Mar 10 - Tue, Mar 24
DTW
Detroit
MDW
Chicago
CA $218 Roundtrip, found 6 days ago
CA $218
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Mar 10 from Detroit to Chicago, returning Tue, Mar 24, priced at CA $218 found 6 days ago
Wed, Feb 4 - Mon, Feb 16
DTW
Detroit
MDW
Chicago
CA $220 Roundtrip, found 6 days ago
CA $220
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Feb 4 from Detroit to Chicago, returning Mon, Feb 16, priced at CA $220 found 6 days ago
Mon, Feb 16 - Tue, Mar 3
DTW
Detroit
MDW
Chicago
CA $225 Roundtrip, found 6 days ago
CA $225
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Feb 16 from Detroit to Chicago, returning Tue, Mar 3, priced at CA $225 found 6 days ago
Thu, Mar 12 - Tue, Mar 24
DTW
Detroit
MDW
Chicago
CA $230 Roundtrip, found 6 days ago
CA $230
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Mar 12 from Detroit to Chicago, returning Tue, Mar 24, priced at CA $230 found 6 days ago
Thu, Feb 5 - Mon, Feb 16
DTW
Detroit
MDW
Chicago
CA $232 Roundtrip, found 6 days ago
CA $232
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Feb 5 from Detroit to Chicago, returning Mon, Feb 16, priced at CA $232 found 6 days ago
Thu, Feb 19 - Thu, Feb 19
DTW
Detroit
MDW
Chicago
CA $238 Roundtrip, found 5 days ago
CA $238
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Feb 19 from Detroit to Chicago, returning Thu, Feb 19, priced at CA $238 found 5 days ago
Mon, Feb 16 - Mon, Mar 2
DTW
Detroit
MDW
Chicago
CA $238 Roundtrip, found 6 days ago
CA $238
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Feb 16 from Detroit to Chicago, returning Mon, Mar 2, priced at CA $238 found 6 days ago
Thu, Feb 12 - Thu, Feb 12
DTW
Detroit
MDW
Chicago
CA $244 Roundtrip, found 4 days ago
CA $244
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Feb 12 from Detroit to Chicago, returning Thu, Feb 12, priced at CA $244 found 4 days ago
Wed, Feb 25 - Sat, Mar 14
DTW
Detroit
MDW
Chicago
CA $245 Roundtrip, found 6 days ago
CA $245
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Feb 25 from Detroit to Chicago, returning Sat, Mar 14, priced at CA $245 found 6 days ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was CA $845, price is now CA $579 per person
CA $579
per person
Mar 17 - Mar 20
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was CA $977, price is now CA $749 per person
CA $749
per person
Mar 17 - Mar 20
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was CA $919, price is now CA $720 per person
CA $720
per person
Mar 17 - Mar 20
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North

3.5 out of 5
Price was CA $754, price is now CA $599 per person
CA $599
per person
Mar 17 - Mar 20
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was CA $813, price is now CA $649 per person
CA $649
per person
Mar 17 - Mar 20
found 21 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.