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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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$97
(Delta)

One-way from

$49
(Delta)

Popular in

July

Cheapest in

March

Average price

$210

Good round-trip deal

$230 or less

Good one-way deal

$144 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. 7% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:04 pmDTW - MDW
Nonstop1h 21mDelta
Tue 10/141:08 pmMDW - DTW
Nonstop1h 11mDelta
Deal found 9/15$97
This Southwest deal was found by Cheapflights users on 9/15. 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.
Thu 10/165:40 pmDTW - MDW
1 stop5h 40mSouthwest
Mon 10/209:25 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 9/15$107
This Southwest deal was found by Cheapflights users on 9/15. 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.
Tue 10/71:30 pmDTW - MDW
2 stops6h 40mSouthwest
Wed 10/88:50 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 9/15$112
This Southwest deal was found by Cheapflights users on 9/17. 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.
Wed 10/86:15 amDTW - MDW
1 stop10h 40mSouthwest
Wed 10/88:50 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 9/17$113
This Southwest deal was found by Cheapflights users on 9/14. 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 10/141:30 pmDTW - MDW
2 stops6h 40mSouthwest
Tue 10/215:35 amMDW - DTW
1 stop6h 30mSouthwest
Deal found 9/14$122
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/17:22 amDTW - MDW
1 stop12h 17mMultiple Airlines
Sat 11/81:37 pmMDW - DTW
1 stop5h 32mMultiple Airlines
Deal found 9/17$125
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/77:22 amDTW - MDW
1 stop7h 16mMultiple Airlines
Wed 10/88:05 amMDW - DTW
1 stop5h 42mMultiple Airlines
Deal found 9/15$131
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/63:42 pmDTW - MDW
1 stop8h 59mFrontier
Wed 10/88:05 amMDW - DTW
1 stop5h 42mFrontier
Deal found 9/15$133
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:25 amDTW - MDW
Nonstop1h 15mDelta
Mon 10/276:23 pmMDW - DTW
Nonstop1h 12mDelta
Deal found 9/15$134

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 September 17, 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

Sat 10/18

8:25 am-8:40 am

Nonstop1h 15m

Chicago Midway

Tue 10/21

1:08 pm-3:19 pm

Nonstop1h 11m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 10/11

3:30 pm-3:40 pm

Nonstop1h 10m

Chicago Midway

Mon 10/13

9:25 pm-11:35 pm

Nonstop1h 10m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 11/8

8:25 am-8:40 am

Nonstop1h 15m

Chicago Midway

Mon 11/10

6:48 pm-9:05 pm

Nonstop1h 17m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 10/30

12:15 pm-12:28 pm

Nonstop1h 13m

Chicago Midway

Thu 11/6

9:35 am-11:45 am

Nonstop1h 10m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 10/7

6:04 pm-6:25 pm

Nonstop1h 21m

Chicago Midway

Thu 10/9

9:35 am-11:45 am

Nonstop1h 10m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 11/1

12:15 pm-12:31 pm

Nonstop1h 16m

Chicago Midway

Sat 11/8

1:06 pm-3:10 pm

Nonstop1h 04m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 10/18

3:30 pm-3:40 pm

Nonstop1h 10m

Chicago Midway

Tue 10/21

5:35 am-1:05 pm

1 stop6h 30m

$107

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 10/8

7:25 pm-10:05 pm

1 stop3h 40m

Chicago Midway

Thu 10/9

9:40 am-11:45 am

Nonstop1h 05m

$107

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 10/22

1:30 pm-6:30 pm

1 stop6h 00m

Chicago Midway

Wed 10/22

8:50 pm-11:00 pm

Nonstop1h 10m

$107

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 10/30

6:15 am-9:05 am

1 stop3h 50m

Chicago Midway

Mon 11/3

8:30 pm-10:40 pm

Nonstop1h 10m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 20 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 September 17, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 31% 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 September 14, 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.

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 September 17, 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
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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 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?

    Delta can get you from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport in just under 1h 15m. 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?

    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 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 Endeavor Airlines (80%), Korean Air (79%) or Southwest (79%) 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 $97 on average, our data indicates $267 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$275FlexibilityNo cancel feeOn-time63%
DeltaCheapest$112Average$258FlexibilityNo cancel feeOn-timeN/A

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