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$64+ Cheap flights from Detroit (DTT) 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.
DTT — MDW
Feb 1 — Feb 81
Sun 2/1
Sun 2/8
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 2, 2026.

This Delta deal was found by Cheapflights users on 12/31. 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 12/315:07 pmDTW - MDW
Nonstop1h 19mDelta
Thu 1/19:29 amMDW - DTW
Nonstop1h 14mDelta
Deal found 12/31$723
This Southwest deal was found by Cheapflights users on 12/30. 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 12/317:00 pmDTW - MDW
Nonstop1h 10mSouthwest
Sat 1/35:25 amMDW - DTW
1 stop5h 50mSouthwest
Deal found 12/30$733
This Southwest deal was found by Cheapflights users on 12/30. 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 12/315:40 amDTW - MDW
2 stops8h 20mSouthwest
Thu 1/13:45 pmMDW - DTW
Nonstop1h 05mSouthwest
Deal found 12/30$738

Find flight deals from Detroit to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Detroit (DTT) 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 2, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$153
(Delta)

One-way from

$64
(Expedia)

Popular in

October

Cheapest in

March

Average price

$673

Good round-trip deal

$305 or less

Good one-way deal

$176 or less
Provider with most accurate pricing for Detroit (DTT)-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Detroit (DTT)-Chicago Midway flights.
Search Deals
From Detroit (DTT) to Chicago Midway
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One-way flight from Detroit (DTT) to Chicago Midway
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($32 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 (DTT) to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Detroit (DTT) to Chicago Midway.
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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 2, 2026.
Use the filters below to find and compare flights from Detroit 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

Wed 2/4

8:25 am-8:52 am

Nonstop1h 27m

Chicago Midway

Thu 2/5

9:33 am-11:44 am

Nonstop1h 11m

$162

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 2/14

8:26 am-8:54 am

Nonstop1h 28m

Chicago Midway

Wed 2/18

1:28 pm-3:38 pm

Nonstop1h 10m

$162

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 2/23

5:15 pm-5:37 pm

Nonstop1h 22m

Chicago Midway

Tue 2/24

6:20 pm-8:37 pm

Nonstop1h 17m

$162

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 1/28

12:25 pm-12:46 pm

Nonstop1h 21m

Chicago Midway

Sat 1/31

1:26 pm-3:33 pm

Nonstop1h 07m

$162

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 1/22

5:05 am-11:45 am

1 stop7h 40m

Chicago Midway

Mon 1/26

1:00 pm-10:54 am

1 stop20h 54m

$163

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 1/22

1:40 pm-1:55 pm

Nonstop1h 15m

Chicago Midway

Mon 1/26

1:25 pm-3:30 pm

Nonstop1h 05m

$171

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 1/31

12:25 pm-12:46 pm

Nonstop1h 21m

Chicago Midway

Sat 2/7

1:26 pm-3:33 pm

Nonstop1h 07m

$171

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 2/7

8:25 am-8:52 am

Nonstop1h 27m

Chicago Midway

Mon 2/9

9:33 am-11:44 am

Nonstop1h 11m

$171

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 1/22

12:25 pm-12:46 pm

Nonstop1h 21m

Chicago Midway

Mon 1/26

1:26 pm-3:33 pm

Nonstop1h 07m

$171

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 1/29

5:31 pm-5:55 pm

Nonstop1h 24m

Chicago Midway

Sat 1/31

1:26 pm-3:33 pm

Nonstop1h 07m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/29

Showing 1-10 of 22 results
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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 Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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-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-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Detroit-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Detroit-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-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 to Chicago Midway Airport

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

Currently, August is the cheapest month in which you can book a flight from Detroit to Chicago Midway Airport (average of $94). Flying from Detroit to Chicago Midway Airport in December is currently the most expensive (average of $281). 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 DTT 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 2, 2026.

A simple way to save on the total cost of your ticket is to fly from Detroit to Chicago Midway Airport in the afternoon. If you’re flexible enough to do this you can expect to save up to 30% on your trip compared to booking a flight in the evening.

What is the cheapest day to fly from Detroit 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 December 27, 2025.

Travelers seeking maximum savings on their Detroit 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.

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 2, 2026.
Read reviews from past customers who have flown Southwest and Delta from Detroit to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

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
8,021 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

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?

    Detroit All airports (DTT), located 0.6 mi from the city center, is the airport you fly out of when you book flights from Detroit to Chicago Midway. 2 airlines have flights from All airports to Chicago Midway on a regular basis. Booking flights from Detroit All airports to Chicago Midway should not be difficult; the airport handles an average of 5 outbound flights to Chicago Midway per day.

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

    A quick flight from Detroit to Chicago Midway Airport can take about 1h 25m. Delta provides one of the quickest options available for as low as $171. The distance between Detroit and Chicago Midway Airport is about 227 mi. This flight may include one or multiple stops.

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

    Cheapflights users have booked flights from Detroit to Chicago Midway Airport round-trip from $97. Another airline that can offer you cheap pricing is Southwest. You may be able to fly from Detroit to Chicago Midway Airport for 73% less than the average price by searching for these airlines.

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

    Before booking your flight to Chicago Midway Airport from Detroit, check out the most reliable airlines to get you to your destination on time: Air France (93%), Virgin Atlantic (90%), Southwest( 86%).

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

    Looking at all options, your cheapest flight can be booked for $87. While the most popular route (Detroit Metropolitan Wayne County - Chicago Midway) can be booked for $162 on average, our data indicates $328 when flying from Detroit 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 to Chicago Midway Airport?

    Currently, August is the cheapest month in which you can book a flight from Detroit to Chicago Midway Airport (average of $94). Flying from Detroit to Chicago Midway Airport in December is currently the most expensive (average of $281). 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.
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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 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$97Average$266FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$97Average$275FlexibilityNo cancel feeOn-time63%

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