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 9/22. 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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Expert advice
Useful Info
Flights 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

Wed, Aug 6 - Thu, Aug 21
Southwest Logo
2:30 pm - 2:40 pmDTW-MDW
1h 10mnonstop
Southwest Logo
8:40 pm - 10:50 pmMDW-DTW
1h 10mnonstop
$97Southwest
Find Deal
Wed, Aug 6 - Thu, Aug 21
Southwest Logo
7:40 am - 12:40 pmDTW-MDW
6h 00m1 stop
Southwest Logo
9:35 am - 11:45 amMDW-DTW
1h 10mnonstop
$107Southwest
Find Deal
Thu, Aug 7 - Mon, Aug 11
Southwest Logo
5:40 am - 1:30 pmDTW-MDW
8h 50m2 stops
Southwest Logo
9:35 am - 11:45 amMDW-DTW
1h 10mnonstop
$112Southwest
Find Deal
Mon, Sep 8 - Wed, Sep 10
Southwest Logo
5:40 am - 1:30 pmDTW-MDW
8h 50m2 stops
Southwest Logo
8:35 am - 1:55 pmMDW-DTW
4h 20m1 stop
$122Southwest
Find Deal
Sat, Sep 27 - Mon, Sep 29
Delta Logo
12:15 pm - 12:32 pmDTW-MDW
1h 17mnonstop
Delta Logo
1:00 pm - 3:13 pmMDW-DTW
1h 13mnonstop
$124Delta
Find Deal
Sat, Sep 20 - Sat, Sep 27
Delta Logo
6:15 pm - 6:36 pmDTW-MDW
1h 21mnonstop
Delta Logo
5:59 pm - 8:13 pmMDW-DTW
1h 14mnonstop
$151Delta
Find Deal
Sat, Sep 27 - Mon, Sep 29
Frontier Logo
4:38 pm - 11:09 pmDTW-MDW
7h 31m1 stop
Frontier Logo
1:59 pm - 8:55 pmMDW-DTW
5h 56m1 stop
$224Frontier
Find Deal
Sat, Sep 6 - Sun, Sep 7
Frontier Logo
4:38 pm - 11:09 pmDTW-MDW
7h 31m1 stop
Frontier Logo
1:59 pm - 8:55 pmMDW-DTW
5h 56m1 stop
$234Frontier
Find Deal
Thu, Jul 17 - Mon, Jul 21
 Logo
8:38 am - 9:41 amDTW-MDW
26h 03m2 stops
 Logo
10:31 am - 9:11 pmMDW-DTW
33h 40m2 stops
Thu, Jul 17 - Mon, Jul 21
 Logo
8:38 am - 9:41 amDTW-MDW
26h 03m2 stops
 Logo
10:31 am - 12:28 amMDW-DTW
36h 57m3 stops
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
Useful Info

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.

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 Mondays 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 $367 and $336 respectively.

Good to know

Low seasonJanuary
High seasonSeptember
Cheapest flight$49
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 16% 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, Alaska Airlines, 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 Embraer 175 (Enhanced Winglets) 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 $270 and an overall rating of 8.0, Delta is the most popular choice. Southwest is also a great choice for the route, with an average price of $237 and an overall rating of 8.0.

  • 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 $160 or less one-way and $296 or less round-trip.

Prefer to fly direct from Detroit to Chicago Midway Airport?

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
See more direct flights

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 4287 reviews
7.1Food
8.2Boarding
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

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

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