$49 Cheap Flights from Detroit (DTW) to Chicago (MDW)

View $49 flight on Wed, Feb 18, 2026Opens in a new window

Popular airlines from Detroit Metropolitan Wayne County Airport (DTW) to Chicago Midway Airport (MDW)

Cheap Flights from Detroit to Chicago (DTW-MDW)

Prices were available within the past 7 days and start at $49 for one-way flights and $97 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Feb 18 - Fri, Feb 20
DTW
Detroit
MDW
Chicago
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Feb 18 from Detroit to Chicago, returning Fri, Feb 20, priced at $97 found 1 day ago
Southwest Airlines
Sun, Feb 15 - Wed, Feb 18
DTW
Detroit
MDW
Chicago
$101 Roundtrip, found 6 days ago
$101
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Feb 15 from Detroit to Chicago, returning Wed, Feb 18, priced at $101 found 6 days ago
Southwest Airlines
Wed, Feb 18 - Fri, Feb 20
DTW
Detroit
MDW
Chicago
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Feb 18 from Detroit to Chicago, returning Fri, Feb 20, priced at $107 found 1 day ago
Frontier Airlines
Thu, Jan 15 - Wed, Jan 21
DTW
Detroit
MDW
Chicago
$109 Roundtrip, found 2 days ago
$109
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Jan 15 from Detroit to Chicago, returning Wed, Jan 21, priced at $109 found 2 days ago
Southwest Airlines
Sun, Feb 15 - Wed, Feb 18
DTW
Detroit
MDW
Chicago
$111 Roundtrip, found 6 days ago
$111
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Feb 15 from Detroit to Chicago, returning Wed, Feb 18, priced at $111 found 6 days ago
Frontier Airlines
Thu, Dec 4 - Mon, Dec 8
DTW
Detroit
MDW
Chicago
$115 Roundtrip, found 2 days ago
$115
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Dec 4 from Detroit to Chicago, returning Mon, Dec 8, priced at $115 found 2 days ago
Southwest Airlines
Wed, Dec 31 - Wed, Jan 7
DTW
Detroit
MDW
Chicago
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Dec 31 from Detroit to Chicago, returning Wed, Jan 7, priced at $117 found 1 day ago
Southwest Airlines
Wed, Dec 31 - Wed, Jan 7
DTW
Detroit
MDW
Chicago
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Dec 31 from Detroit to Chicago, returning Wed, Jan 7, priced at $127 found 1 day ago
Southwest Airlines
Tue, Dec 16 - Wed, Dec 17
DTW
Detroit
MDW
Chicago
$127 Roundtrip, found 12 hours ago
$127
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Detroit to Chicago, returning Wed, Dec 17, priced at $127 found 12 hours ago
Frontier Airlines
Thu, Jan 15 - Wed, Jan 21
DTW
Detroit
MDW
Chicago
$129 Roundtrip, found 2 days ago
$129
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Jan 15 from Detroit to Chicago, returning Wed, Jan 21, priced at $129 found 2 days ago

Find the cheapest month to fly from Detroit (DTW) to Chicago (MDW)

August is typically the cheapest month to fly

From $76 - $275 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $270
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $270
0
Flights from Detroit (DTW) to Chicago (MDW)
Origin airport
Detroit Metropolitan Wayne County
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$97
Distance
227 mi

Detroit to Chicago Flights

The cheapest times to fly from Detroit to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Detroit to Chicago are during the month of February. You can find some of the cheapest flights from Detroit to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Detroit to Chicago

Sunday is one of the best days to book for cheap flights from Detroit to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Detroit to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Detroit to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $49 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Detroit to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Detroit to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $49 or cheap return flight from $97 from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW)?
Traveling in February is a good way to save, as it's the cheapest month for flights between DTW and MDW. You'll usually find the lowest fares during off-peak months.
Which airlines fly direct from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW)?
You can fly straight from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW) on a Delta Air Lines flight.
What is the cheapest airline that flies from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW)?
While prices can vary depending on when you travel, low-cost airlines like WestJet and Southwest Airlines are generally the cheapest options for flights between Detroit Metropolitan Wayne County Airport (DTW) and Midway Intl. Airport (MDW). Use Expedia's search tool to compare carriers and find the one that offers the best deal for your DTW to MDW flight.
How many flights per day from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW)?
Daily, an average of 5 nonstop flights operate from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW). Choose the departure date that works for you.
What are the most popular departure times for flights from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW)?
Flights between DTW and MDW tend to be busiest at 12 PM. For a quieter trip and possibly cheaper tickets, choose a time when demand is lower.
What day of the week has the most flights from DTW to MDW?
Wednesday has the most flights from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW). Consider taking off on this day and you'll have a greater chance of finding a schedule that works for you.
What is the earliest flight from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW)?
Catch the earliest flight at around 7:00AM UTC-5, departing from Detroit Metropolitan Wayne County Airport (DTW). You'll be in the air for approximately 1h 30m, landing at Midway Intl. Airport (MDW) at approximately 7:30AM UTC-6.
How long does it take to fly from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW)?
The average flight duration from DTW to MDW is 1 hour and 20 minutes, covering a total distance of 230 mi.
What airline has the least delays from DTW to MDW?
Aeromexico has the strongest track record for on-time direct flights from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW), with an on-time rating of 100%. Use the Expedia App to check your flight schedule before you leave and get immediate updates about any trip changes.
What is the best time to fly from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW) route, travel before 3 PM. Departures after this hour are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Detroit Metropolitan Wayne County Airport (DTW)?
Catch a direct flight from Detroit Metropolitan Wayne County Airport (DTW) to Chicago and land at O'Hare Intl. Airport (ORD). Another convenient point of entry into this destination is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from DTW to MDW are usually more expensive. To lock in the cheapest rates, start searching for flights early. That said, if your travel plans are flexible, it's possible to find a cheap ticket right before your journey.
Is it cheaper to book a DTW to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a DTW to MDW flight and hotel package with Expedia could result in significant savings. Better still, having everything in one convenient place takes the hassle out of travel planning. Just pick your flights and select from our extensive range of stays, then personalize your trip with extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Detroit Metropolitan Wayne County Airport (DTW) to Midway Intl. Airport (MDW)?
In most instances, you can cancel or reschedule your DTW to MDW flight. However, additional fees may apply, especially if you made your booking more than 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you need more details, go to our Customer Service portal.

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*Available to One Key members.