DTW - MDW

$112 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 10/30. 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

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Everything you should know

Cheapest round-trip
$200
Typical prices: $197-$309
Frontier
Tue 9/8Sat 9/12
DTW - MDW • 1 stop
Cheapest non-stop
$217
Typical prices: $168-$326
Southwest
Wed 10/28Sat 10/31
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 $200 (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 12m
Direct flights
Direct flights
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Direct flights
Direct flights
+1
When to travel
Cheapest • 47% 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

Tue, Sep 8 - Sat, Sep 12
Frontier Logo
6:00 am - 10:55 am
DTW
-
MDW
5h 55m
1 stop
Frontier Logo
1:02 pm - 8:46 pm
MDW
-
DTW
6h 44m
1 stop
$200Frontier
Wed, Oct 28 - Sat, Oct 31
Frontier Logo
3:34 pm - 9:53 pm
DTW
-
MDW
7h 19m
1 stop
Frontier Logo
12:03 pm - 12:42 am
MDW
-
DTW
11h 39m
1 stop
$200Frontier
Wed, Aug 12 - Sat, Aug 15
Frontier Logo
5:13 pm - 10:03 pm
DTW
-
MDW
5h 50m
1 stop
Frontier Logo
6:05 am - 1:44 pm
MDW
-
DTW
6h 39m
1 stop
$200Frontier
Tue, Sep 29 - Sat, Oct 3
Frontier Logo
3:34 pm - 9:58 pm
DTW
-
MDW
7h 24m
1 stop
Frontier Logo
7:25 am - 2:39 pm
MDW
-
DTW
6h 14m
1 stop
$200Frontier
Sat, Aug 22 - Sat, Aug 22
Delta Logo
8:54 am - 9:17 am
DTW
-
MDW
1h 23mnonstop
Delta Logo
1:25 pm - 3:42 pm
MDW
-
DTW
1h 17mnonstop
$217Delta
Sat, Aug 15 - Mon, Aug 17
Delta Logo
8:54 am - 9:17 am
DTW
-
MDW
1h 23mnonstop
Delta Logo
1:25 pm - 3:42 pm
MDW
-
DTW
1h 17mnonstop
$217Delta
Wed, Oct 28 - Sat, Oct 31
Southwest Logo
7:30 pm - 7:40 pm
DTW
-
MDW
1h 10mnonstop
Southwest Logo
8:50 am - 11:00 am
MDW
-
DTW
1h 10mnonstop
$217Southwest
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
1:20 pm - 1:30 pm
DTW
-
MDW
1h 10mnonstop
Southwest Logo
6:40 pm - 8:50 pm
MDW
-
DTW
1h 10mnonstop
$217Southwest
Sat, Aug 22 - Mon, Aug 24
Delta Logo
6:15 pm - 6:33 pm
DTW
-
MDW
1h 18mnonstop
Delta Logo
6:42 pm - 9:00 pm
MDW
-
DTW
1h 18mnonstop
$217Delta
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
8:55 am - 9:15 am
DTW
-
MDW
1h 20mnonstop
Southwest Logo
8:15 am - 10:30 am
MDW
-
DTW
1h 15mnonstop
$217Southwest
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 October.

Flight prices are typical for this route right now.

Flights to Chicago Midway Airport from Detroit Metropolitan Wayne County Airport usually cost between $121 and $382 in October.
The lowest price found in the past 5 days was $200 on Frontier (Oct 28-Oct 31).

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 June, where the average cost of round-trip tickets is $503 and $397 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 $349 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 season

January

Cheapest flight

$112
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly and prices are also 18% 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 $112 for a one-way ticket and $200 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 Aeromexico 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, 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 $313 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 $323 and an overall rating of 7.8.

  • 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 $206 or less one-way and $358 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 4228 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

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

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

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

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.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Chaotic boarding at these gates, multiple gates squeezed in at the very end of a concourse, behind a restaurant. Agents gave up on boarding by individual zones. Flight itself was uneventful, which is all we hope for any more.

Weather in Atlanta necessitated an hour's hold on the tarmac before we could leave Detroit. The plane was packed, and I expected some surliness. But no! The crew was fantastic (jovial even!), responsive to people's needs, and kept us informed. Consequently, the passengers took the delay in stride, and what could have been an ugly situation turned out to be no more than a minor inconvenience. The crew were the stars here.

The flight was mostly smooth and direct (although it was 2 hours late). The glow of the flight attendant’s phone was annoying as I tried to sleep on this midnight flight.

Everything about this flight was good except for the very end when I reached my destination. Everyone from the tune to the wheelchair escorts were great with the case were great but I miss you with people at the check in this at the very end. I need help from the chicken desk because I forgot my pillow on the plane The female worker at the chicken desk said that they found my pillow and she was going to retrieve it for me. She left a 30 minutes without any update and her so she saw me walking back and forth waiting for her and they didn't even bother calling her or radioing her for any updates. They were busy because they were behind schedule and they were overwhelmed but thanks because at least glanced me and try to give me an update just a quick radio check or phone call. I don't care about the pillow but if you tell me to wait, I waited for at least half an hour before I said something and I just left because they wouldn't bother talking to me so I could, so everything's going in the review. I took pictures of the two men that were left working at the check-in counter. The totally ignored me despite the signals I've been giving them. I don't see any offers in the kayak review to add pictures or screenshots so I'm going to post another review I don't know their name but I'm pretty sure Delta will find other names when they see the review. Google with pictures. There was another guy at the chicken counter bring an orange workers vest who finally left after telling me that the girl that was retrieving my pillow is working the gates now. That would have been if they just told me that's what happened. But I had no update. Make me wait for nothing. Thank you Delta airlines!

Crew was real good, flight was smooth and came in early.

Should never have had to go to Detroit from Orlando back to Tennessee!

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

Cramped seating for me. Luckily it wasn’t a long flight

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

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

Information on your arrival and departure airports