DTW - MDW

$49 Find Cheap Flights from Detroit to Chicago Midway Airport

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 11/15. 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

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
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Booking Insights
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

Tue, Sep 23 - Tue, Sep 30
Delta Logo
6:20 pm - 6:35 pmDTW-MDW
1h 15mnonstop
Delta Logo
1:08 pm - 3:20 pmMDW-DTW
1h 12mnonstop
$97Delta
Find Deal
Sat, Sep 20 - Mon, Sep 22
Southwest Logo
12:45 pm - 4:40 pmDTW-MDW
4h 55m1 stop
Southwest Logo
9:35 am - 11:45 amMDW-DTW
1h 10mnonstop
$107Southwest
Find Deal
Tue, Sep 23 - Tue, Sep 30
Southwest Logo
6:15 am - 10:45 amDTW-MDW
5h 30m1 stop
Southwest Logo
6:25 am - 1:55 pmMDW-DTW
6h 30m1 stop
$117Southwest
Find Deal
Tue, Sep 23 - Tue, Sep 30
Southwest Logo
7:20 pm - 10:25 pmDTW-MDW
4h 05m1 stop
Southwest Logo
1:00 pm - 10:15 pmMDW-DTW
8h 15m2 stops
$122Southwest
Find Deal
Wed, Sep 24 - Sat, Sep 27
Southwest Logo
1:05 pm - 7:10 pmDTW-MDW
7h 05m2 stops
Southwest Logo
2:20 pm - 10:15 pmMDW-DTW
6h 55m2 stops
$127Southwest
Find Deal
Tue, Sep 23 - Tue, Sep 30
Southwest Logo
6:15 am - 3:00 pmDTW-MDW
9h 45m2 stops
Southwest Logo
1:00 pm - 10:15 pmMDW-DTW
8h 15m2 stops
$133Southwest
Find Deal
Wed, Sep 17 - Wed, Sep 24
 Logo
7:20 am - 3:58 pmDTW-MDW
9h 38m1 stop
 Logo
9:00 am - 6:12 pmMDW-DTW
8h 12m1 stop
Thu, Sep 25 - Sat, Sep 27
Delta Logo
8:25 am - 8:40 amDTW-MDW
1h 15mnonstop
Delta Logo
6:15 pm - 8:33 pmMDW-DTW
1h 18mnonstop
$137Delta
Find Deal
Mon, Sep 8 - Thu, Sep 11
Frontier Logo
3:42 pm - 11:20 pmDTW-MDW
8h 38m1 stop
Frontier Logo
6:20 am - 2:46 pmMDW-DTW
7h 26m1 stop
$142Frontier
Find Deal
Fri, Sep 26 - Fri, Oct 3
Frontier Logo
10:32 am - 6:43 pmDTW-MDW
9h 11m1 stop
Frontier Logo
6:20 am - 2:46 pmMDW-DTW
7h 26m1 stop
$143Frontier
Find Deal
Expert advice

Expert advice for your flight from Detroit to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Delta

Delta offers free Wi-Fi for SkyMiles members on domestic flights, enhancing productivity and connectivity.


Delta's Sky Priority check-in speeds up the process for elite status and premium cabin travelers.

Read more about Deltaby Stefanie Waldek
Southwest

Southwest allows two free checked bags, saving costs for travelers with more luggage.


Set an alarm for 24-hour check-in to secure a better boarding position on Southwest.

Read more about Southwestby Blane Bachelor
Airports
DTW

For early departures, consider staying at an airport hotel. Many offer cheaper parking and a shuttle service to DTW.

Read more about DTWby Ramsey Qubein
MDW

Take the CTA Orange Line from MDW to downtown Chicago. It's a quick 25-30 minute ride, avoiding traffic delays.

Read more about MDWby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Delta and MDW

Stefanie Waldek

Stefanie Waldek

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.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

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.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on DTW

Ramsey Qubein

Ramsey Qubein

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.

Read more
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?

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 Wednesday 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 March, where tickets cost $132 (return) on average. On the other hand, the most expensive months are July and February, where the average cost of round-trip tickets is $340 and $336 respectively.

Good to know

Low seasonJanuary
Cheapest flight$49
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 19% 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 3 days, the lowest price for a flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport was $49 for a one-way ticket and $97 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, Aeromexico, 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 Boeing 737 MAX 8 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, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Detroit to Chicago are Southwest and Delta. With an average price for the route of $275 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $267 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 $138 or less one-way and $239 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

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

Tuesday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

Wednesday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

Thursday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

Friday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

Saturday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

Sunday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

See more direct flights

Direct returns

Chicago Midway to Detroit Metropolitan Wayne County

Monday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

Tuesday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

Wednesday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

Thursday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

Friday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

Saturday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

Sunday

Air France, Delta, KLM, +4 more

Air France, Delta, +5 more

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.
8.0
SouthwestOverall score based on 4242 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

2.0 MediocreMike, Aug 2025AUS - BWI
Read more Southwest reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

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

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