DTW - MDW

$79 Find Cheap Flights from Detroit to Chicago Midway Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Detroit to Midway departing on 7/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Detroit to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Detroit to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$167
Typical prices: $437-$317
Southwest
ter 7/14ter 7/21
DTW - MDW • 1 stop
Cheapest non-stop
$177
Typical prices: $382-$144
Delta
qua 8/12qua 8/19
DTW - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Delta offers free Wi-Fi on domestic flights; Southwest includes a free carry-on.
Southwest's cancellation policy is flexible; checked bags now add fees.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $167 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Delta and Southwest. Average duration is 1h 14m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
Cheapest • 43% price drop
Most popular
Good to know
Good to know
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Good to know
Good to know
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We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Detroit to Midway (DTW-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Detroit to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Detroit to Midway

ter, jul 14 - ter, jul 21
Southwest Logo
10:40 am - 2:30 pm
DTW
-
MDW
4h 50m
1 stop
Southwest Logo
6:10 pm - 8:25 pm
MDW
-
DTW
1h 15mnonstop
$167Southwest
qua, jul 8 - qua, jul 15
Southwest Logo
6:40 am - 11:00 am
DTW
-
MDW
5h 20m
1 stop
Southwest Logo
5:20 pm - 10:30 pm
MDW
-
DTW
4h 10m
1 stop
$177Southwest
qua, ago 12 - qua, ago 19
Southwest Logo
7:05 pm - 7:15 pm
DTW
-
MDW
1h 10mnonstop
Southwest Logo
8:35 am - 10:55 am
MDW
-
DTW
1h 20mnonstop
$178Southwest
qua, ago 12 - qua, ago 19
Southwest Logo
7:05 pm - 7:15 pm
DTW
-
MDW
1h 10mnonstop
Southwest Logo
3:05 pm - 9:15 pm
MDW
-
DTW
5h 10m
1 stop
$187Southwest
qua, ago 12 - qua, ago 19
Southwest Logo
3:35 pm - 8:10 pm
DTW
-
MDW
5h 35m
2 stops
Southwest Logo
8:35 am - 10:55 am
MDW
-
DTW
1h 20mnonstop
$193Southwest
ter, ago 4 - qui, ago 6
Southwest Logo
7:05 pm - 7:15 pm
DTW
-
MDW
1h 10mnonstop
Southwest Logo
6:40 pm - 8:50 pm
MDW
-
DTW
1h 10mnonstop
$196Southwest
qua, ago 12 - qua, ago 19
Southwest Logo
3:35 pm - 10:20 pm
DTW
-
MDW
7h 45m
2 stops
Southwest Logo
3:05 pm - 9:15 pm
MDW
-
DTW
5h 10m
1 stop
$203Southwest
ter, ago 4 - qui, ago 6
Southwest Logo
7:10 pm - 10:20 pm
DTW
-
MDW
4h 10m
1 stop
Southwest Logo
8:15 am - 10:30 am
MDW
-
DTW
1h 15mnonstop
$206Southwest
ter, ago 25 - qua, ago 26
Frontier Logo
6:45 am - 11:12 am
DTW
-
MDW
5h 27m
1 stop
Frontier Logo
6:00 am - 4:40 pm
MDW
-
DTW
9h 40m
1 stop
$210Frontier
seg, ago 17 - ter, ago 18
Southwest Logo
7:30 pm - 7:40 pm
DTW
-
MDW
1h 10mnonstop
Southwest Logo
12:45 pm - 9:15 pm
MDW
-
DTW
7h 30m
2 stops
$211Southwest
Booking Insights

KAYAK's insights & trends for Detroit to Midway flights

Get data-powered insights and trends into flights from Detroit to Midway to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport departing in July.

What’s the cheapest day of the week to fly from Detroit to Chicago Midway Airport?

The average price of all round-trip flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

When flying from Detroit to Chicago Midway Airport, you should consider leaving on a Saturday and avoid Sundays if you are looking for the best rates. For your return to Detroit, you’ll find the best rates on Fridays and the most expensive ones on Sundays.

What is the cheapest month to fly from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport is January, where tickets cost $171 (return) on average. On the other hand, the most expensive months are February and December, where the average cost of round-trip tickets is $469 and $384 respectively.

Can I save money by flying with a layover from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $293 on average.

Expert advice

Expert advice for your flight from Detroit to Midway

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Delta and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Ramsey Qubein

Ramsey Qubein

Expert on DTW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Good to know

Low seasonJanuary
Cheapest flight$79
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Detroit to Chicago Midway Airport

When to book flights from Detroit to Midway

Are your dates flexible? Find out the best times to travel from Detroit to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Detroit to Chicago Midway Airport flights

  • What is the cheapest flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

    In the last 5 days, the lowest price for a flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport was $79 for a one-way ticket and $167 for a round-trip.

  • Do I need a passport to fly between Detroit and Chicago Midway Airport?

    A passport is not required to fly from Detroit to Chicago Midway Airport.

  • Which airports will I be using when flying from Detroit to Chicago Midway Airport?

    Detroit airport is called Detroit Metropolitan Wayne County and the only airport in Chicago Midway Airport is Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Detroit to Chicago Midway Airport?

    Delta, American Airlines, and JetBlue offer inflight Wi-Fi service on the Detroit to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Detroit to Chicago Midway Airport?

    The Canadair (Bombardier) Regional Jet 700 is the aircraft model that flies most regularly on the Detroit to Chicago Midway Airport flight route.

  • Which airline alliances offer flights from Detroit to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Detroit and Chicago Midway Airport.

  • On which days can I fly direct from Detroit to Chicago Midway Airport?

    There are nonstop flights from Detroit to Chicago Midway Airport on a daily basis.

  • Which is the best airline for flights from Detroit to Chicago, Delta or Southwest?

    The two airlines most popular with KAYAK users for flights from Detroit to Chicago are Delta and Southwest. With an average price for the route of $306 and an overall rating of 7.9, Delta is the most popular choice. Southwest is also a great choice for the route, with an average price of $290 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Detroit to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Detroit to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Detroit to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Detroit is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Detroit to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Detroit with another airline. Booking your flights between Detroit and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Detroit to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Detroit up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $225 or less one-way and $320 or less round-trip.

Prefer to fly direct from Detroit to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Detroit Metropolitan Wayne County to Chicago Midway.
Find which airlines fly direct from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Detroit Metropolitan Wayne County to Chicago Midway

Monday

Delta,Southwest

Delta,Southwest

Tuesday

Delta,Southwest

Delta,Southwest

Wednesday

Delta,Southwest

Delta,Southwest

Thursday

Delta,Southwest

Delta,Southwest

Friday

Delta,Southwest

Delta,Southwest

Saturday

Delta,Southwest

Delta,Southwest

Sunday

Delta,Southwest

Delta,Southwest

See more direct flights

Direct returns

Chicago Midway to Detroit Metropolitan Wayne County

Monday

Delta,Southwest

Delta,Southwest

Tuesday

Delta,Southwest

Delta,Southwest

Wednesday

Delta,Southwest

Delta,Southwest

Thursday

Delta,Southwest

Delta,Southwest

Friday

Delta,Southwest

Delta,Southwest

Saturday

Delta,Southwest

Delta,Southwest

Sunday

Delta,Southwest

Delta,Southwest

See more direct flights

Reviews of the top airlines flying from Detroit to Midway

 
See real verified KAYAK customer reviews for airlines flying from Detroit to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Detroit to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4235 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Everything you need to know for your flight from Detroit to Midway

Information on your arrival and departure airports