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$49+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — MDW
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
1 adult, Economy
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Cheap 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 November 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$107
(Southwest)

One-way from

$49
(Southwest)

Popular in

November

Cheapest in

March

Average price

$423

Good round-trip deal

$265 or less

Good one-way deal

$169 or less
Provider with most accurate pricing for Detroit Metropolitan Wayne County-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Detroit Metropolitan Wayne County-Chicago Midway flights.
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From Detroit Metropolitan Wayne County to Chicago Midway
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One-way flight from Detroit Metropolitan Wayne County to Chicago Midway
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Highest demand for flights based on searches. 18% potential increase in price ($58 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Detroit Metropolitan Wayne County to Chicago Midway.
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Price to beat on a one-way flight from Detroit Metropolitan Wayne County to Chicago Midway.
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Find 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 November 12, 2025.

This Southwest deal was found by Cheapflights users on 11/10. 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 12/37:00 pmDTW - MDW
Nonstop1h 10mSouthwest
Wed 12/243:45 pmMDW - DTW
Nonstop1h 05mSouthwest
Deal found 11/10$107
This Frontier deal was found by Cheapflights users on 11/11. 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 12/411:58 amDTW - MDW
1 stop11h 14mFrontier
Thu 12/117:23 pmMDW - DTW
1 stop12h 03mFrontier
Deal found 11/11$110
This Delta deal was found by Cheapflights users on 11/11. 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.
Mon 11/245:47 pmDTW - MDW
Nonstop1h 21mDelta
Thu 11/279:34 amMDW - DTW
Nonstop1h 15mDelta
Deal found 11/11$117
This Southwest deal was found by Cheapflights users on 11/10. 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 12/106:10 amDTW - MDW
1 stop7h 35mSouthwest
Wed 12/178:30 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 11/10$127
This Delta deal was found by Cheapflights users on 11/11. 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.
Mon 12/88:30 amDTW - MDW
Nonstop1h 24mDelta
Wed 12/101:14 pmMDW - DTW
Nonstop1h 11mDelta
Deal found 11/11$144
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Thu 12/46:00 amDTW - MDW
1 stop8h 01mMultiple Airlines
Sat 12/66:00 amMDW - DTW
1 stop12h 52mMultiple Airlines
Deal found 11/12$151
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/811:19 amDTW - MDW
1 stop26h 42mMultiple Airlines
Mon 12/156:15 amMDW - DTW
1 stop12h 37mMultiple Airlines
Deal found 11/10$152
This Southwest deal was found by Cheapflights users on 11/10. 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 12/37:00 pmDTW - MDW
Nonstop1h 10mSouthwest
Thu 12/185:15 pmMDW - DTW
1 stop5h 50mSouthwest
Deal found 11/10$154

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 November 12, 2025.
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

Thu 12/25

5:07 pm-5:26 pm

Nonstop1h 19m

Chicago Midway

Thu 1/1

9:29 am-11:43 am

Nonstop1h 14m

$117

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 12/3

6:10 am-12:45 pm

1 stop7h 35m

Chicago Midway

Wed 12/24

3:45 pm-5:50 pm

Nonstop1h 05m

$117

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 3/10

12:15 pm-12:35 pm

Nonstop1h 20m

Chicago Midway

Wed 3/11

1:00 pm-3:14 pm

Nonstop1h 14m

$117

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 1/1

7:00 pm-7:10 pm

Nonstop1h 10m

Chicago Midway

Mon 1/5

9:40 am-11:50 am

Nonstop1h 10m

$134

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 12/8

5:40 pm-6:00 pm

Nonstop1h 20m

Chicago Midway

Wed 12/10

9:34 am-11:45 am

Nonstop1h 11m

$144

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 12/3

8:30 am-8:54 am

Nonstop1h 24m

Chicago Midway

Thu 12/18

9:34 am-11:45 am

Nonstop1h 11m

$144

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 12/11

8:30 am-8:54 am

Nonstop1h 24m

Chicago Midway

Wed 12/17

9:34 am-11:45 am

Nonstop1h 11m

$144

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 1/1

8:25 am-8:49 am

Nonstop1h 24m

Chicago Midway

Mon 1/5

1:28 pm-3:38 pm

Nonstop1h 10m

$145

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 12/10

5:40 am-1:00 pm

2 stops8h 20m

Chicago Midway

Wed 12/17

2:30 pm-10:35 pm

2 stops7h 05m

$147

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 12/25

6:10 am-6:40 am

Nonstop1h 30m

$49

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 18 results
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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Detroit Metropolitan Wayne County Airport-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $269). 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 November 12, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 24% 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 November 2, 2025.

Travelers seeking maximum savings on their Detroit Metropolitan Wayne County Airport to Chicago Midway Airport flight should consider departing on Saturday 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

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-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.
Cheapflights partnered with top experts to bring you the best recommendations for your Detroit Metropolitan Wayne County Airport to Chicago Midway Airport trip
Airports
DTW

Security lines at DTW are short, typically under 10 minutes at McNamara Terminal, even without TSA PreCheck.

Read more about DTWby Brandon Schultz
MDW

Use the Orange Line train for a quick, 30-minute ride from MDW to downtown Chicago.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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
Brandon Schultz

Brandon Schultz

Expert on DTW

Brandon Schultz

Brandon Schultz

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 November 12, 2025.
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
4,235 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,009 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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?

    Delta and Southwest can get you from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport in just under 1h 19m. Your travel time can differ by up to 6h 16m. The distance between Detroit Metropolitan Wayne County Airport and Chicago Midway Airport is about 227 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 63% 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 Sun Country Air (100%), United Airlines (100%) or Endeavor Airlines (95%) 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 $58. While the most popular route (Detroit Metropolitan Wayne County - Chicago Midway) can be booked for $107 on average, our data indicates $297 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 $269). 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
Hammond
Porter
Benton Harbor
Merrillville

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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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$275FlexibilityNo cancel feeOn-time63%
DeltaCheapest$98Average$267FlexibilityNo cancel feeOn-timeN/A

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