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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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — MDW
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$92
(Southwest)

One-way from

$49
(Southwest)

Popular in

July

Cheapest in

March

Average price

$221

Good round-trip deal

$244 or less

Good one-way deal

$152 or less
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. 8% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 18, 2025.

This Southwest deal was found by Cheapflights users on 8/16. 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 9/91:05 pmDTW - MDW
2 stops7h 05mSouthwest
Wed 9/104:15 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 8/16$92
This Southwest deal was found by Cheapflights users on 8/15. 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.
Sat 9/137:10 amDTW - MDW
Nonstop1h 10mSouthwest
Tue 9/238:20 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 8/15$97
This Delta deal was found by Cheapflights users on 8/18. 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 9/108:25 amDTW - MDW
Nonstop1h 10mDelta
Sat 9/201:08 pmMDW - DTW
Nonstop1h 12mDelta
Deal found 8/18$104
This Southwest deal was found by Cheapflights users on 8/17. 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 9/91:05 pmDTW - MDW
2 stops7h 05mSouthwest
Thu 9/188:40 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 8/17$112
This Delta deal was found by Cheapflights users on 8/17. 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.
Thu 9/118:25 amDTW - MDW
Nonstop1h 15mDelta
Mon 9/156:15 pmMDW - DTW
Nonstop1h 18mDelta
Deal found 8/17$117
This Southwest deal was found by Cheapflights users on 8/17. 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 9/161:05 pmDTW - MDW
2 stops7h 05mSouthwest
Sat 9/2011:40 amMDW - DTW
1 stop4h 25mSouthwest
Deal found 8/17$122
This Southwest deal was found by Cheapflights users on 8/17. 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.
Thu 9/116:30 amDTW - MDW
Nonstop1h 05mSouthwest
Mon 9/157:15 amMDW - DTW
1 stop4h 35mSouthwest
Deal found 8/17$127
This Southwest deal was found by Cheapflights users on 8/17. 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.
Thu 10/91:15 pmDTW - MDW
Nonstop1h 05mSouthwest
Sat 10/183:25 pmMDW - DTW
2 stops5h 50mSouthwest
Deal found 8/17$132

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 August 18, 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

Tue 9/9

1:05 pm-7:10 pm

2 stops7h 05m

Chicago Midway

Wed 9/10

8:20 pm-10:30 pm

Nonstop1h 10m

$92

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 9/16

1:05 pm-7:10 pm

2 stops7h 05m

Chicago Midway

Tue 9/23

8:20 pm-10:30 pm

Nonstop1h 10m

$92

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 10/1

7:10 am-7:20 am

Nonstop1h 10m

Chicago Midway

Tue 10/7

1:25 pm-10:45 pm

2 stops8h 20m

$92

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 10/7

1:30 pm-7:10 pm

2 stops6h 40m

Chicago Midway

Wed 10/8

10:00 am-12:05 pm

Nonstop1h 05m

$92

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 1/20

5:25 am-9:05 am

1 stop4h 40m

Chicago Midway

Wed 1/21

10:05 am-3:05 pm

1 stop4h 00m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 9/13

7:10 am-7:20 am

Nonstop1h 10m

Chicago Midway

Tue 9/23

8:20 pm-10:30 pm

Nonstop1h 10m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 12/15

12:55 pm-1:05 pm

Nonstop1h 10m

Chicago Midway

Wed 12/17

8:30 pm-10:40 pm

Nonstop1h 10m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 9/16

2:30 pm-2:40 pm

Nonstop1h 10m

Chicago Midway

Sat 9/20

7:35 pm-9:45 pm

Nonstop1h 10m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 9/23

7:20 pm-10:25 pm

1 stop4h 05m

$49

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 12/10

6:10 am-9:55 am

1 stop4h 45m

$49

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 12 results
1
2

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

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, April is the cheapest month in which you can book a flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport (average of $160). Flying from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 August 18, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 32% 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 August 17, 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.

Weekly flight availability from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport

Explore weekly flight availability from Detroit to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 18, 2025.

The most flights from DTW to MDW are scheduled on a Monday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 on average).

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 August 18, 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
4,246 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 12 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 7h 05m. 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?

    Delta, at $112, 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 56% 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%), Endeavor Airlines (74%) or WestJet (71%) 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 $75. While the most popular route (Detroit Metropolitan Wayne County - Chicago Midway) can be booked for $77 on average our data indicates $288 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, April is the cheapest month in which you can book a flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport (average of $160). Flying from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$112Average$269FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$127Average$268FlexibilityNo cancel feeOn-time63%

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