HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
DTT — MDW
ago. 18 — ago. 251
lun. 8/18
lun. 8/25
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Detroit to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 agosto 13, 2025.

Round-trip from

$92
(Delta)

One-way from

$49
(Southwest)

Popular in

January

Cheapest in

March

Average price

$238

Good round-trip deal

$239 or less

Good one-way deal

$156 or less
From Detroit (DTT) to Chicago Midway
Search Deals
One-way flight from Detroit (DTT) to Chicago Midway
Search Deals
Highest demand for flights based on searches. 42% potential increase in price ($228 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
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.
Search Deals

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 agosto 13, 2025.

This Delta deal was found by Cheapflights users on 8/13. 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.
jue. 9/46:21 pmDTW - MDW
Nonstop1h 16mDelta
lun. 9/86:17 pmMDW - DTW
Nonstop1h 15mDelta
Deal found 8/13$92
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/47:00 pmDTW - MDW
1 stop4h 50mSouthwest
lun. 9/85:10 amMDW - DTW
1 stop6h 40mSouthwest
Deal found 8/11$97
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/168:25 amDTW - MDW
Nonstop1h 15mDelta
sáb. 9/209:35 amMDW - DTW
Nonstop1h 10mDelta
Deal found 8/12$104
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/612:45 pmDTW - MDW
2 stops6h 45mSouthwest
lun. 9/83:25 pmMDW - DTW
2 stops6h 55mSouthwest
Deal found 8/11$107
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/106:15 amDTW - MDW
2 stops9h 45mSouthwest
mié. 9/104:30 pmMDW - DTW
1 stop3h 55mSouthwest
Deal found 8/12$108
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/1212:30 pmDTW - MDW
Nonstop1h 10mSouthwest
lun. 9/159:35 amMDW - DTW
Nonstop1h 10mSouthwest
Deal found 8/12$114
This Delta deal was found by Cheapflights users on 8/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/138:25 amDTW - MDW
Nonstop1h 15mDelta
sáb. 9/131:08 pmMDW - DTW
Nonstop1h 12mDelta
Deal found 8/10$117
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/46:21 pmDTW - MDW
Nonstop1h 16mDelta
sáb. 9/69:31 amMDW - DTW
Nonstop1h 13mDelta
Deal found 8/12$121
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/54:15 pmDTW - MDW
1 stop6h 20mSouthwest
sáb. 9/69:50 amMDW - DTW
Nonstop1h 10mSouthwest
Deal found 8/12$124
This Southwest deal was found by Cheapflights users on 8/10. 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.
lun. 10/208:15 pmDTW - MDW
Nonstop1h 15mSouthwest
lun. 10/279:40 amMDW - DTW
Nonstop1h 05mSouthwest
Deal found 8/10$127
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/303:55 pmDTW - MDW
Nonstop1h 10mSouthwest
mar. 9/28:20 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 8/12$128

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 agosto 13, 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

jue. 9/4

6:21 pm-6:37 pm

Nonstop1h 16m

Chicago Midway

lun. 9/8

6:17 pm-8:32 pm

Nonstop1h 15m

$92

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

mié. 9/24

1:05 pm-7:10 pm

2 stops7h 05m

Chicago Midway

mié. 10/1

4:15 pm-6:25 pm

Nonstop1h 10m

$92

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

mar. 12/9

5:40 am-10:10 am

1 stop5h 30m

Chicago Midway

mié. 1/7

1:50 pm-8:25 pm

1 stop5h 35m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

jue. 9/4

7:00 pm-10:50 pm

1 stop4h 50m

Chicago Midway

lun. 9/8

5:10 am-12:50 pm

1 stop6h 40m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

sáb. 9/13

12:45 pm-4:40 pm

1 stop4h 55m

Chicago Midway

lun. 9/15

7:15 am-12:50 pm

1 stop4h 35m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

mié. 1/28

4:05 pm-10:05 pm

1 stop7h 00m

Chicago Midway

lun. 2/2

6:50 am-12:45 pm

1 stop4h 55m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

jue. 10/16

5:40 pm-10:20 pm

1 stop5h 40m

Chicago Midway

lun. 10/20

5:50 am-12:30 pm

1 stop5h 40m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

sáb. 10/4

5:35 am-12:20 pm

2 stops7h 45m

Chicago Midway

sáb. 10/4

3:55 pm-8:50 pm

1 stop3h 55m

$102

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

sáb. 9/6

12:45 pm-6:30 pm

2 stops6h 45m

Chicago Midway

lun. 9/8

7:15 am-12:50 pm

1 stop4h 35m

$102

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

mié. 11/19

6:10 am-12:45 pm

1 stop7h 35m

$49

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

Showing 1-10 of 14 results
1
2

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 agosto 13, 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 32% 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 August 10, 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 agosto 13, 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 (7 on average).

How much does it cost to fly round-trip from Detroit to Chicago Midway Airport?

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 agosto 13, 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
4,246 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

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

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

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
7,979 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

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?

    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 11 outbound flights to Chicago Midway per day.

  • 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 $92. Another airline that can offer you cheap pricing is Southwest. You may be able to fly from Detroit to Chicago Midway Airport for 69% 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: Sun Country Air (100%), Southwest (87%), Endeavor Airlines( 79%).

  • What are the cheapest flights from Detroit 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 $282 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Detroit to Midway flights
Grand Rapids to O'Hare Intl flights
Flint to O'Hare Intl flights
Traverse City to O'Hare Intl flights
Bay City to O'Hare Intl flights
Traverse City to Midway flights
Grand Rapids to Midway flights
Bay City to Midway flights
Muskegon to O'Hare Intl flights
Pellston to O'Hare Intl flights
Lansing to O'Hare Intl flights
South Bend to O'Hare Intl flights
Marquette to O'Hare Intl flights
Kalamazoo to O'Hare Intl flights
Marquette to Midway flights
Lansing to Midway flights
Pellston to Midway flights
Kalamazoo to Midway flights
South Bend to Midway flights
Sault Ste. Marie to O'Hare Intl flights
Ironwood to O'Hare Intl flights
Escanaba to O'Hare Intl flights
Flint to Midway flights
Sault Ste. Marie to Midway 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 agosto 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$112Average$268FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$127Average$250FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.