DTW - MDW

$59 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 5/6. 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
$136
Typical prices: $349-$242
Frontier
ma 5/11wo 5/13
DTW - MDW • 1 stop
Cheapest non-stop
$154
Typical prices: $349-$247
Delta
wo 5/20za 5/30
DTW - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest offers two free checked bags, reducing costs.
Use the CTA Orange Line from MDW for quick downtown access.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $136 (round-trip)
Best reviews • 8.0 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 15m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
Cheapest • 42% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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KAYAK searches 100s of sites at once to find you the best travel deals.
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

ma, mei. 11 - wo, mei. 13
Frontier Logo
6:05 pm - 11:09 am
DTW
-
MDW
18h 04m
1 stop
Frontier Logo
6:00 am - 5:20 pm
MDW
-
DTW
10h 20m
1 stop
$136Frontier
di, mei. 5 - di, mei. 5
Southwest Logo
7:00 am - 11:35 am
DTW
-
MDW
5h 35m
1 stop
Southwest Logo
1:55 pm - 9:15 pm
MDW
-
DTW
6h 20m
1 stop
$137Southwest
za, mei. 2 - di, mei. 5
Frontier Logo
5:42 pm - 10:14 pm
DTW
-
MDW
5h 32m
1 stop
Frontier Logo
6:00 am - 12:36 pm
MDW
-
DTW
5h 36m
1 stop
$140Frontier
za, mei. 2 - di, mei. 5
Frontier Logo
5:42 pm - 10:14 pm
DTW
-
MDW
5h 32m
1 stop
Frontier Logo
6:00 am - 12:36 pm
MDW
-
DTW
5h 36m
1 stop
$141Frontier
di, mei. 5 - di, mei. 12
Southwest Logo
4:10 pm - 10:15 pm
DTW
-
MDW
7h 05m
1 stop
Southwest Logo
10:10 am - 6:20 pm
MDW
-
DTW
7h 10m
2 stops
$142Southwest
di, mei. 5 - di, mei. 12
Southwest Logo
1:20 pm - 7:25 pm
DTW
-
MDW
7h 05m
2 stops
Southwest Logo
10:10 am - 6:20 pm
MDW
-
DTW
7h 10m
2 stops
$147Southwest
wo, mei. 6 - wo, mei. 13
Southwest Logo
6:10 am - 3:45 pm
DTW
-
MDW
10h 35m
2 stops
Southwest Logo
8:15 am - 1:00 pm
MDW
-
DTW
3h 45m
1 stop
$148Southwest
ma, mei. 4 - wo, mei. 13
Frontier Logo
6:15 pm - 11:09 am
DTW
-
MDW
17h 54m
1 stop
Frontier Logo
12:04 pm - 12:39 am
MDW
-
DTW
11h 35m
1 stop
$150Frontier
wo, mei. 6 - wo, mei. 13
Southwest Logo
6:10 am - 3:45 pm
DTW
-
MDW
10h 35m
2 stops
Southwest Logo
10:10 am - 6:20 pm
MDW
-
DTW
7h 10m
2 stops
$153Southwest
wo, mei. 20 - do, mei. 28
Delta Logo
12:27 pm - 12:42 pm
DTW
-
MDW
1h 15mnonstop
Delta Logo
9:22 am - 11:35 am
MDW
-
DTW
1h 13mnonstop
$154Delta
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 May.

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 Saturdays and the most expensive ones on Mondays.

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.

No, with an average price for the route of $330, prices are generally cheapest when you fly direct.

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$59
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly and prices are also 17% 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 $59 for a one-way ticket and $136 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, JetBlue, and Air Canada 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 Airbus A320-100/200 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 $317 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 $281 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 $222 or less one-way and $400 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.
8.0
SouthwestOverall score based on 4334 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

It was as expected and I was grateful for the wheel chair help and ease of use.

10.0 ExcellentAnonymous, Apr 2026
LAS - PDX
Read more Southwest reviews

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Okay considering we had weather delays which the Pilot notified us of immediately!

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

2+hrs delay without any reason provided and a cramped flight

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

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

Information on your arrival and departure airports