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Midway

$64+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — MDW
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/105:09 am
DTW
-
MDW
1 stop8h 53m
Multiple Airlines
Tue 3/177:30 am
MDW
-
DTW
1 stop6h 54m
Multiple Airlines
Deal found 1/26$129
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 3/105:09 am
DTW
-
MDW
1 stop8h 53m
Multiple Airlines
Thu 3/127:30 am
MDW
-
DTW
1 stop6h 54m
Multiple Airlines
Deal found 1/25$141
This Expedia deal was found by Cheapflights users on 1/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:08 pm
DTW
-
MDW
1 stop6h 21m
Frontier
Mon 3/22:19 pm
MDW
-
DTW
1 stop5h 46m
Frontier
Deal found 1/26$148
This Frontier deal was found by Cheapflights users on 1/26. 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.
Thu 2/194:27 pm
DTW
-
MDW
1 stop7h 10m
Frontier
Mon 2/232:19 pm
MDW
-
DTW
1 stop5h 46m
Frontier
Deal found 1/26$154
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/32:35 pm
DTW
-
MDW
1 stop5h 32m
Multiple Airlines
Tue 3/107:30 am
MDW
-
DTW
1 stop8h 39m
Multiple Airlines
Deal found 1/26$159
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/32:35 pm
DTW
-
MDW
1 stop5h 32m
Multiple Airlines
Thu 3/127:30 am
MDW
-
DTW
1 stop6h 54m
Multiple Airlines
Deal found 1/26$160
This Lucky2Go deal was found by Cheapflights users on 1/27. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:24 pm
DTW
-
MDW
1 stop25h 23m
Frontier
Mon 3/166:05 am
MDW
-
DTW
1 stop25h 02m
Frontier
Deal found 1/27$161
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/232:35 pm
DTW
-
MDW
1 stop6h 12m
Multiple Airlines
Tue 2/246:10 am
MDW
-
DTW
1 stop6h 20m
Multiple Airlines
Deal found 1/27$162
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/25:08 pm
DTW
-
MDW
1 stop6h 21m
Multiple Airlines
Tue 3/107:30 am
MDW
-
DTW
1 stop8h 39m
Multiple Airlines
Deal found 1/26$165
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sat 3/72:35 pm
DTW
-
MDW
1 stop8h 49m
Multiple Airlines
Thu 3/127:30 am
MDW
-
DTW
1 stop6h 54m
Multiple Airlines
Deal found 1/26$166
This Frontier deal was found by Cheapflights users on 1/26. 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.
Mon 3/25:08 pm
DTW
-
MDW
1 stop6h 21m
Frontier
Wed 3/116:05 am
MDW
-
DTW
1 stop9h 07m
Frontier
Deal found 1/26$169

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$129
(Kiwi.com)

One-way from

$64
(Orbitz)

Popular in

December

Cheapest in

March

Average price

$200

Good round-trip deal

$301 or less

Good one-way deal

$209 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. 13% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 27, 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

Detroit

Fly to

Midway

Route

Depart

Return

Price

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 2/28

4:45 pm-5:05 pm

Nonstop1h 20m

Chicago Midway

Sat 2/28

8:30 pm-10:40 pm

Nonstop1h 10m

$178

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 4/22

7:10 pm-9:50 pm

1 stop3h 40m

Chicago Midway

Sat 4/25

7:50 am-10:00 am

Nonstop1h 10m

$185

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 3/11

12:15 pm-12:29 pm

Nonstop1h 14m

Chicago Midway

Wed 3/18

9:35 am-11:43 am

Nonstop1h 08m

$191

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 3/14

8:15 pm-8:30 pm

Nonstop1h 15m

Chicago Midway

Mon 3/16

5:25 am-12:15 pm

1 stop5h 50m

$197

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 3/2

5:15 pm-5:37 pm

Nonstop1h 22m

Chicago Midway

Tue 3/10

6:34 pm-8:45 pm

Nonstop1h 11m

$203

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 3/7

8:26 am-8:54 am

Nonstop1h 28m

Chicago Midway

Wed 3/11

1:10 pm-3:17 pm

Nonstop1h 07m

$203

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 3/14

12:15 pm-12:29 pm

Nonstop1h 14m

Chicago Midway

Mon 3/16

1:10 pm-3:17 pm

Nonstop1h 07m

$203

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 2/23

5:15 pm-5:37 pm

Nonstop1h 22m

Chicago Midway

Tue 3/24

9:35 am-11:43 am

Nonstop1h 08m

$203

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 3/3

5:15 pm-5:37 pm

Nonstop1h 22m

Chicago Midway

Wed 3/11

9:35 am-11:43 am

Nonstop1h 08m

$203

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 3/14

8:15 pm-8:30 pm

Nonstop1h 15m

$80

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 21 results
1
2
3

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 January.
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 $94). 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 January 27, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 28% 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 January 24, 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.

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 January 27, 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
4,268 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,119 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 10 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 and Delta can get you from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport in just under 1h 14m. Your travel time will be generally consistent. The distance between Detroit Metropolitan Wayne County Airport and Chicago Midway Airport is about 227 mi. Generally, flights for this route are nonstop.

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

    Delta, 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 Southwest. Delta is 62% 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 (77%), WestJet (64%) or Air France (60%) 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 $139. While the most popular route (Detroit Metropolitan Wayne County - Chicago Midway) can be booked for $129 on average, our data indicates $425 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 $94). 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$97Average$270FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$97Average$275FlexibilityNo cancel feeOn-time63%

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