Cheap Flights From Detroit Metropolitan Wayne County (DTW) To Midway Intl. (MDW)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly

Cheapest Flights from Detroit (DTW) to Chicago (MDW)

The cheapest flights to Midway Intl. found within the past 7 days were CA $277 round trip and CA $83 one way. Prices and availability subject to change. Additional terms may apply.

Thu, Feb 26 - Sun, Mar 1
DTW
Detroit
MDW
Chicago
CA $277 Roundtrip, found 1 day ago
CA $277
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Feb 26 from Detroit to Chicago, returning Sun, Mar 1, priced at CA $277 found 1 day ago
Thu, Feb 26 - Sun, Mar 1
DTW
Detroit
MDW
Chicago
CA $320 Roundtrip, found 1 day ago
CA $320
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Feb 26 from Detroit to Chicago, returning Sun, Mar 1, priced at CA $320 found 1 day ago
Fri, Oct 31 - Sun, Nov 2
DTW
Detroit
MDW
Chicago
CA $353 Roundtrip, found 1 day ago
CA $353
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 31 from Detroit to Chicago, returning Sun, Nov 2, priced at CA $353 found 1 day ago
Thu, Feb 26 - Sun, Mar 1
DTW
Detroit
MDW
Chicago
CA $362 Roundtrip, found 1 day ago
CA $362
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Feb 26 from Detroit to Chicago, returning Sun, Mar 1, priced at CA $362 found 1 day ago
Fri, Oct 31 - Sun, Nov 2
DTW
Detroit
MDW
Chicago
CA $367 Roundtrip, found 1 day ago
CA $367
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 31 from Detroit to Chicago, returning Sun, Nov 2, priced at CA $367 found 1 day ago
Thu, Feb 26 - Sun, Mar 1
DTW
Detroit
MDW
Chicago
CA $404 Roundtrip, found 1 day ago
CA $404
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Feb 26 from Detroit to Chicago, returning Sun, Mar 1, priced at CA $404 found 1 day ago
Fri, Aug 7 - Mon, Aug 10
DTW
Detroit
MDW
Chicago
CA $414 Roundtrip, found 5 days ago
CA $414
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Aug 7 from Detroit to Chicago, returning Mon, Aug 10, priced at CA $414 found 5 days ago
Fri, Aug 7 - Mon, Aug 10
DTW
Detroit
MDW
Chicago
CA $428 Roundtrip, found 5 days ago
CA $428
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Aug 7 from Detroit to Chicago, returning Mon, Aug 10, priced at CA $428 found 5 days ago
Sat, Dec 20 - Sat, Dec 27
DTW
Detroit
MDW
Chicago
CA $430 Roundtrip, found 4 days ago
CA $430
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Dec 20 from Detroit to Chicago, returning Sat, Dec 27, priced at CA $430 found 4 days ago
Fri, Oct 31 - Sun, Nov 2
DTW
Detroit
MDW
Chicago
CA $438 Roundtrip, found 1 day ago
CA $438
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 31 from Detroit to Chicago, returning Sun, Nov 2, priced at CA $438 found 1 day ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
LA VILLA MOTEL

LA VILLA MOTEL

2 out of 5
Price was CA $537, price is now CA $525 per person
CA $525
per person
Dec 5 - Dec 7
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
The Inn on Sheridan

The Inn on Sheridan

3.5 out of 5
Price was CA $601, price is now CA $563 per person
CA $563
per person
Dec 5 - Dec 7
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Value Inn Kenosha I-94 - Exit 344

Value Inn Kenosha I-94 - Exit 344

2.5 out of 5
Price was CA $536, price is now CA $532 per person
CA $532
per person
Dec 5 - Dec 7
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (CHI)
Don't see what you're looking for?
See all available trips from Detroit Metropolitan Wayne County to Midway Intl.
View all trips

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.