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$49+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
DTT — MDW
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
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 (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 September 19, 2025.

Round-trip from

$97
(Delta)

One-way from

$49
(Southwest)

Popular in

January

Cheapest in

March

Average price

$197

Good round-trip deal

$230 or less

Good one-way deal

$144 or less
From Detroit (DTT) to Chicago Midway
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One-way flight from Detroit (DTT) to Chicago Midway
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Highest demand for flights based on searches. 42% potential increase in price ($226 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($34 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 (DTT) to Chicago Midway.
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Price to beat on a one-way flight from Detroit (DTT) 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 19, 2025.

This Southwest deal was found by Cheapflights users on 9/16. 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.
Sat 10/113:30 pmDTW - MDW
Nonstop1h 10mSouthwest
Mon 10/139:25 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 9/16$97
This Southwest deal was found by Cheapflights users on 9/16. 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.
Thu 10/165:40 pmDTW - MDW
1 stop5h 40mSouthwest
Thu 10/239:25 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 9/16$107
This Southwest deal was found by Cheapflights users on 9/16. 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 10/141:30 pmDTW - MDW
2 stops6h 40mSouthwest
Tue 10/2110:00 amMDW - DTW
Nonstop1h 05mSouthwest
Deal found 9/16$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 9/18. 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 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 10/205:50 amMDW - DTW
1 stop5h 40mSouthwest
Deal found 9/18$117
This Southwest deal was found by Cheapflights users on 9/16. 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 10/71:30 pmDTW - MDW
2 stops6h 40mSouthwest
Tue 10/1412:40 pmMDW - DTW
1 stop6h 20mSouthwest
Deal found 9/16$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 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.
Fri 10/108:15 pmDTW - MDW
Nonstop1h 15mSouthwest
Tue 10/1410:00 amMDW - DTW
Nonstop1h 05mSouthwest
Deal found 9/17$134
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.
Wed 10/157:22 amDTW - MDW
1 stop7h 16mMultiple Airlines
Wed 10/228:05 amMDW - DTW
1 stop8h 45mMultiple Airlines
Deal found 9/17$138
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.
Fri 10/179:05 pmDTW - MDW
1 stop26h 42mMultiple Airlines
Tue 10/218:05 amMDW - DTW
1 stop5h 29mMultiple Airlines
Deal found 9/15$139

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 19, 2025.
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

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 10/11

8:25 am-8:40 am

Nonstop1h 15m

Chicago Midway

Sat 10/11

1:06 pm-3:15 pm

Nonstop1h 09m

$97

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

Tue 11/11

5:40 am-1:00 pm

2 stops8h 20m

Chicago Midway

Tue 11/11

3:45 pm-5:50 pm

Nonstop1h 05m

$112

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 10/18

1:05 pm-6:25 pm

2 stops6h 20m

Chicago Midway

Tue 10/21

8:50 pm-11:00 pm

Nonstop1h 10m

$112

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 10/16

5:40 pm-10:20 pm

1 stop5h 40m

Chicago Midway

Mon 10/20

5:50 am-12:30 pm

1 stop5h 40m

$117

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Fri 10/17

6:04 pm-6:25 pm

Nonstop1h 21m

Chicago Midway

Mon 10/20

6:23 pm-8:35 pm

Nonstop1h 12m

$134

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Fri 10/10

8:15 pm-8:30 pm

Nonstop1h 15m

Chicago Midway

Tue 10/14

10:00 am-12:05 pm

Nonstop1h 05m

$134

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Fri 11/7

8:25 am-8:40 am

Nonstop1h 15m

Chicago Midway

Mon 11/10

1:14 pm-3:29 pm

Nonstop1h 15m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 22 results
1
2
3

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, April is the cheapest month in which you can book a flight from Detroit to Chicago Midway Airport (average of $160). Flying from Detroit 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 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 September 19, 2025.

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 31% 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 September 14, 2025.

Travelers seeking maximum savings on their Detroit 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 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 September 19, 2025.

The most flights from DTT to MDW are scheduled on a Monday (13 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 September 19, 2025.
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
4,242 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
7,964 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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?

    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 12 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 21m. Delta provides one of the quickest options available for as low as $97. 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 Delta. You may be able to fly from Detroit to Chicago Midway Airport for 68% 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: Endeavor Airlines (80%), Korean Air (79%), Southwest( 79%).

  • What are the cheapest flights from Detroit 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 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, April is the cheapest month in which you can book a flight from Detroit to Chicago Midway Airport (average of $160). Flying from Detroit 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.
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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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$275FlexibilityNo cancel feeOn-time63%
DeltaCheapest$112Average$258FlexibilityNo cancel feeOn-timeN/A

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