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Cheap flights from Detroit Metropolitan Wayne County Airport to Chicago from $69

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Detroit Metropolitan Wayne County Airport to Chicago departing on 9/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Detroit Metropolitan Wayne County Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:43 pm - 11:12 am
DTW
-
MDW
18h 29m
1 stop
Frontier Logo
6:00 am - 12:39 am
MDW
-
DTW
17h 39m
1 stop
$155Frontier
Mon, May 25 - Mon, Jun 1
Southwest Logo
8:10 pm - 11:10 pm
DTW
-
MDW
4h 00m
1 stop
Southwest Logo
5:20 pm - 10:25 pm
MDW
-
DTW
4h 05m
1 stop
$157Southwest
Wed, Jun 17 - Wed, Jun 24
Delta Logo
6:19 pm - 6:33 pm
DTW
-
MDW
1h 14mnonstop
Delta Logo
1:22 pm - 3:35 pm
MDW
-
DTW
1h 13mnonstop
$164Delta
Tue, May 26 - Thu, May 28
Southwest Logo
8:15 am - 8:30 am
DTW
-
MDW
1h 15mnonstop
Southwest Logo
11:25 am - 5:55 pm
MDW
-
DTW
5h 30m
1 stop
$174Southwest
Tue, Jun 2 - Tue, Jun 9
Frontier Logo
6:50 am - 11:12 am
DTW
-
MDW
5h 22m
1 stop
Frontier Logo
12:04 pm - 12:39 am
MDW
-
DTW
11h 35m
1 stop
$180Frontier
Tue, Jun 2 - Wed, Jun 3
Southwest Logo
5:45 pm - 10:00 pm
DTW
-
MDW
5h 15m
1 stop
Southwest Logo
3:10 pm - 10:25 pm
MDW
-
DTW
6h 15m
1 stop
$184Southwest
Mon, Jun 8 - Tue, Jun 9
Frontier Logo
2:40 pm - 10:02 pm
DTW
-
MDW
8h 22m
1 stop
Frontier Logo
6:00 am - 1:42 pm
MDW
-
DTW
6h 42m
1 stop
$185Frontier
Sat, May 30 - Sat, Jun 6
Southwest Logo
8:15 pm - 10:45 pm
DTW
-
MDW
3h 30m
1 stop
Southwest Logo
10:10 am - 6:20 pm
MDW
-
DTW
7h 10m
2 stops
$189Southwest
Mon, Jun 1 - Tue, Jun 2
Frontier Logo
6:50 am - 11:12 am
DTW
-
MDW
5h 22m
1 stop
Frontier Logo
12:04 pm - 12:39 am
MDW
-
DTW
11h 35m
1 stop
$190Frontier
Tue, Jun 2 - Wed, Jun 3
Delta Logo
6:19 pm - 6:33 pm
DTW
-
MDW
1h 14mnonstop
Delta Logo
6:36 pm - 8:45 pm
MDW
-
DTW
1h 09mnonstop
$191Delta
Thu, May 28 - Mon, Jun 1

Southwest flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport

Our best Southwest deals on Detroit Metropolitan Wayne County Airport to Chicago Midway Airport flight tickets
Southwest
Jun 17
DTW8:10 pmDetroit Metropolitan Wayne County
4h 00m
1 stop
MDW11:10 pmChicago Midway
Jun 24
MDW5:20 pmChicago Midway
4h 05m
1 stop
DTW10:25 pmDetroit Metropolitan Wayne County
$157
Southwest
Jun 2
DTW8:15 amDetroit Metropolitan Wayne County
1h 15m
MDW8:30 amChicago Midway
Jun 9
MDW11:25 amChicago Midway
5h 30m
1 stop
DTW5:55 pmDetroit Metropolitan Wayne County
$174
Southwest
Jun 8
DTW5:45 pmDetroit Metropolitan Wayne County
5h 15m
1 stop
MDW10:00 pmChicago Midway
Jun 9
MDW3:10 pmChicago Midway
6h 15m
1 stop
DTW10:25 pmDetroit Metropolitan Wayne County
$184

Frontier flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport

Our best Frontier deals on Detroit Metropolitan Wayne County Airport to Chicago Midway Airport flight tickets
Frontier
May 25
DTW5:43 pmDetroit Metropolitan Wayne County
18h 29m
1 stop
MDW11:12 amChicago Midway
Jun 1
MDW6:00 amChicago Midway
17h 39m
1 stop
DTW12:39 amDetroit Metropolitan Wayne County
$155
Frontier
Jun 2
DTW6:50 amDetroit Metropolitan Wayne County
5h 22m
1 stop
MDW11:12 amChicago Midway
Jun 3
MDW12:04 pmChicago Midway
11h 35m
1 stop
DTW12:39 amDetroit Metropolitan Wayne County
$180
Frontier
May 30
DTW2:40 pmDetroit Metropolitan Wayne County
8h 22m
1 stop
MDW10:02 pmChicago Midway
Jun 6
MDW6:00 amChicago Midway
6h 42m
1 stop
DTW1:42 pmDetroit Metropolitan Wayne County
$185

momondo Fare Finder

 
Customize your flight search to find flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated May 6, 2026.
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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 5/25

5:43 pm-11:12 am

1 stop18h 29m

Chicago Midway

Mon 6/1

6:00 am-12:39 am

1 stop17h 39m

$155

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 6/17

8:10 pm-11:10 pm

1 stop4h 00m

Chicago Midway

Wed 6/24

5:20 pm-10:25 pm

1 stop4h 05m

$157

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 5/26

6:19 pm-6:33 pm

Nonstop1h 14m

Chicago Midway

Thu 5/28

1:22 pm-3:35 pm

Nonstop1h 13m

$164

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 6/2

8:15 am-8:30 am

Nonstop1h 15m

Chicago Midway

Tue 6/9

11:25 am-5:55 pm

1 stop5h 30m

$174

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 6/2

6:50 am-11:12 am

1 stop5h 22m

Chicago Midway

Wed 6/3

12:04 pm-12:39 am

1 stop11h 35m

$180

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 6/8

5:45 pm-10:00 pm

1 stop5h 15m

Chicago Midway

Tue 6/9

3:10 pm-10:25 pm

1 stop6h 15m

$184

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 5/30

2:40 pm-10:02 pm

1 stop8h 22m

Chicago Midway

Sat 6/6

6:00 am-1:42 pm

1 stop6h 42m

$185

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 6/1

8:15 pm-10:45 pm

1 stop3h 30m

Chicago Midway

Tue 6/2

10:10 am-6:20 pm

2 stops7h 10m

$189

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 6/2

6:50 am-11:12 am

1 stop5h 22m

Chicago Midway

Wed 6/3

12:04 pm-12:39 am

1 stop11h 35m

$190
Quickest round-trip

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 5/28

6:19 pm-6:33 pm

Nonstop1h 14m

Chicago Midway

Mon 6/1

6:36 pm-8:45 pm

Nonstop1h 09m

$191

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Detroit Metropolitan Wayne County Airport and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Detroit Metropolitan Wayne County Airport, with most prices found around $171. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Detroit Metropolitan Wayne County Airport during the month September is also very affordable. Most momondo users find prices during this month for around $197.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Detroit Metropolitan Wayne County Airport. The lowest ticket price found for a Saturday departure recently was $369. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Detroit Metropolitan Wayne County Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $468.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Detroit Metropolitan Wayne County Airport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $318 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $420. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Detroit Metropolitan Wayne County to Chicago Midway flight route?

Fly from Detroit Metropolitan Wayne County to Chicago Midway for the best Detroit Metropolitan Wayne County - Chicago Midway flight prices

How have Detroit Metropolitan Wayne County Airport to Chicago Midway Airport flight prices changed over time?

As of May 2026, prices for Detroit Metropolitan Wayne County Airport to Chicago Midway Airport flights are approximately 41% cheaper when compared to flights at the same time last year.

When to book flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Detroit Metropolitan Wayne County Airport to Chicago Midway Airport (DTW to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport

Best Price Found

$217

Fastest flight time

1h 10m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Detroit Metropolitan Wayne County Airport in the past 72 hours is $217. The best round-trip flight deal from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport found on momondo in the last 72 hours is $394.
The fastest flight from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport takes 1h 10m
Direct flights go from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport

  • How far is Detroit Metropolitan Wayne County to Chicago Midway by plane?

    A flight from Detroit Metropolitan Wayne County to Chicago Midway will travel around 227.4 mi. Flights usually cover this in 1h 10m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

    Prices for flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

  • What is the most popular airline from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport?

Best airlines flying from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $97Free CancellationRating
7.9
4,305 reviews
Search Southwest flights
DeltaPriceFrom $121Free CancellationRating
7.9
8,459 reviews
Search Delta flights

  • Southwest Flights From Detroit Metropolitan Wayne County Airport to Chicago Midway Airport

    Southwest is one of the most popular airlines flying from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport, operating 15 flights/week on average for this route. A good Southwest flight deal for Detroit Metropolitan Wayne County Airport to Chicago Midway Airport starts from $97 round-trip, up to an average price of $317. Our users have rated Southwest at 7.9/10.

  • Delta Flights From Detroit Metropolitan Wayne County Airport to Chicago Midway Airport

    Another popular option for Detroit Metropolitan Wayne County Airport to Chicago Midway Airport flights is Delta (7.9/10, 8,458 ratings). Delta flies from Detroit Metropolitan Wayne County Airport to Chicago Midway Airport around 7 times per week, with deals starting from $121 round-trip and rising to an average price of around $279.

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Why use momondo?

Why should I use momondo to find a flight deal from Detroit to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Detroit.

Can I find flights from Detroit to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Detroit which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Detroit to Chicago?

Once you have performed a search for Detroit to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Detroit to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Detroit and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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