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Midway

$59+ Cheap flights from Detroit Metropolitan Wayne County Airport (DTW) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — MDW
May 10 — May 171
Sun 5/10
Sun 5/17
1 adult, Economy
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Cheap flight deals from Detroit to Midway

Cheapest flights from Detroit to Midway
Explore the most affordable flight options available from Detroit to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 10, 2026.

This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:00 am
DTW
-
MDW
1 stop5h 35m
Southwest
Tue 5/51:55 pm
MDW
-
DTW
1 stop6h 20m
Southwest
Deal found 4/6$137
This Frontier deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:42 pm
DTW
-
MDW
1 stop5h 32m
Frontier
Tue 5/56:00 am
MDW
-
DTW
1 stop5h 36m
Frontier
Deal found 4/5$140
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/54:10 pm
DTW
-
MDW
1 stop7h 05m
Southwest
Tue 5/1210:10 am
MDW
-
DTW
2 stops7h 10m
Southwest
Deal found 4/7$142
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:10 am
DTW
-
MDW
2 stops10h 35m
Southwest
Wed 5/138:15 am
MDW
-
DTW
1 stop3h 45m
Southwest
Deal found 4/6$148
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:15 pm
DTW
-
MDW
1 stop17h 54m
Frontier
Wed 5/1312:04 pm
MDW
-
DTW
1 stop11h 35m
Frontier
Deal found 4/9$150
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2012:27 pm
DTW
-
MDW
Nonstop1h 15m
Delta
Thu 5/289:22 am
MDW
-
DTW
Nonstop1h 13m
Delta
Deal found 4/9$154
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:05 pm
DTW
-
MDW
1 stop18h 04m
Frontier
Thu 5/286:00 am
MDW
-
DTW
1 stop6h 04m
Frontier
Deal found 4/5$156
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:50 am
DTW
-
MDW
1 stop13h 41m
Multiple Airlines
Sat 4/257:34 pm
MDW
-
DTW
1 stop12h 31m
Multiple Airlines
Deal found 4/6$158
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:33 pm
DTW
-
MDW
1 stop7h 58m
Frontier
Wed 4/292:15 pm
MDW
-
DTW
1 stop17h 50m
Frontier
Deal found 4/9$159

Find flight deals from Detroit to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Detroit (DTW) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$137
(Southwest)

One-way from

$59
(Southwest)

Popular in

February

Cheapest in

January

Average price

$295

Good round-trip deal

$400 or less

Good one-way deal

$222 or less
Provider with most accurate pricing for Detroit Metropolitan Wayne County-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Detroit Metropolitan Wayne County-Chicago Midway flights.
Search Deals
From Detroit Metropolitan Wayne County to Chicago Midway
Search Deals
One-way flight from Detroit Metropolitan Wayne County to Chicago Midway
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Detroit Metropolitan Wayne County to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Detroit Metropolitan Wayne County to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Detroit to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 10, 2026.
Use the filters below to find and compare flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 5/5

7:00 am-11:35 am

1 stop5h 35m

Chicago Midway

Tue 5/5

1:55 pm-9:15 pm

1 stop6h 20m

$137

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 5/6

7:00 am-11:35 am

1 stop5h 35m

Chicago Midway

Wed 5/13

1:55 pm-9:15 pm

1 stop6h 20m

$137

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 5/6

6:10 am-3:45 pm

2 stops10h 35m

Chicago Midway

Wed 5/6

5:00 pm-10:30 pm

1 stop4h 30m

$148

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 4/30

5:40 pm-5:58 pm

Nonstop1h 18m

Chicago Midway

Mon 5/4

6:38 pm-8:53 pm

Nonstop1h 15m

$191

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 5/23

12:27 pm-12:42 pm

Nonstop1h 15m

Chicago Midway

Thu 5/28

9:22 am-11:35 am

Nonstop1h 13m

$191

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 5/23

5:05 pm-5:15 pm

Nonstop1h 10m

Chicago Midway

Sat 5/30

7:45 am-3:00 pm

1 stop6h 15m

$201

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 5/27

6:10 am-3:45 pm

2 stops10h 35m

Chicago Midway

Wed 5/27

5:00 pm-10:30 pm

1 stop4h 30m

$217

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 4/13

5:50 pm-10:19 pm

1 stop5h 29m

Chicago Midway

Thu 4/16

6:00 am-6:46 pm

1 stop11h 46m

$236
Quickest round-trip

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 5/16

6:19 pm-6:33 pm

Nonstop1h 14m

Chicago Midway

Sun 5/17

9:22 am-11:35 am

Nonstop1h 13m

$243

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 5/16

3:40 pm-8:05 pm

1 stop5h 25m

Chicago Midway

Sun 5/17

7:00 pm-9:05 pm

Nonstop1h 05m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/5

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

Compare providers for flights from Detroit to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Detroit to Midway in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Detroit Metropolitan Wayne County Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Detroit Metropolitan Wayne County Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Detroit Metropolitan Wayne County Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Detroit Metropolitan Wayne County Airport-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Detroit Metropolitan Wayne County Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Detroit to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Detroit with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport

What is the cheapest month to book a flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

Currently, August is the cheapest month in which you can book a flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport (average of $88). Flying from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport in December is currently the most expensive (average of $308). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DTW to MDW?

Find hourly flight availability from Detroit to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 10, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 25% on flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport by exploring options for tickets in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Detroit to Midway. Price data was last updated on April 4, 2026.

Travelers seeking maximum savings on their Detroit Metropolitan Wayne County Airport to Chicago Midway Airport flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

The best insider tips for Detroit Metropolitan Wayne County Airport to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Detroit Metropolitan Wayne County Airport to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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
Brandon Schultz

Brandon Schultz

Expert on DTW

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated April 10, 2026.
Read through reviews of airlines operating flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,334 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,334 reviews
Southwest
8.0
Very good
4,334 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,402 reviews
Southwest
8.0
Very good
4,334 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Detroit to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Detroit to Chicago Midway?

    If you book a flight to Chicago Midway from Detroit, you will be flying from Detroit Metropolitan Wayne County, which is the city’s only airport. Detroit Metropolitan Wayne County (DTW) is located 17.3 mi from the center of Detroit. There are 9 flights from Detroit Metropolitan Wayne County to Chicago Midway per day from 2 different airlines.

  • How long is the flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

    Southwest can get you from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport in just under 5h 35m. Your travel time can differ by up to . The distance between Detroit Metropolitan Wayne County Airport and Chicago Midway Airport is about 227 mi.

  • What are the cheapest airlines flying from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport round-trip?

    Southwest, at $97, was found to be the cheapest airline from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport. An alternate airline flying to your destination would be Delta. Southwest is 66% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the most reliable airlines from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

    No one likes to see their flight delayed. When booking a flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport consider choosing Southwest (71%), WestJet (67%) or Korean Air (64%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $118. While the most popular route (Detroit Metropolitan Wayne County - Chicago Midway) can be booked for $117 on average, our data indicates $397 when flying from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport.

  • Can I find deals for flights from Detroit to Midway that include hotel bookings?

    Yes. In addition to deals on Detroit to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Detroit to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Detroit to Midway.

  • Can I find deals for business class flights from Detroit to Midway?

    Yes. Cheapflights offers flight deals from Detroit to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, August is the cheapest month in which you can book a flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport (average of $88). Flying from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport in December is currently the most expensive (average of $308). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Detroit to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Detroit to O'Hare Intl flights

Top 2 airlines flying from Detroit to Midway

Discover the top 2 airlines that operate flights from Detroit to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$317FlexibilityNo cancel feeOn-time63%
DeltaCheapest$121Average$279FlexibilityNo cancel feeOn-timeN/A

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