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Cheap flights from Detroit to Chicago from $59

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 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 to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
4:45 pm - 4:55 pm
DTW
-
MDW
1h 10mnonstop
Southwest Logo
8:35 am - 10:55 am
MDW
-
DTW
1h 20mnonstop
$164Southwest
Sat, Sep 26 - Tue, Sep 29
Southwest Logo
5:35 am - 11:00 am
DTW
-
MDW
6h 25m
1 stop
Southwest Logo
5:30 pm - 10:50 pm
MDW
-
DTW
4h 20m
1 stop
$172Southwest
Wed, Jun 10 - Wed, Jun 10
Southwest Logo
11:05 am - 5:00 pm
DTW
-
MDW
6h 55m
1 stop
Southwest Logo
4:10 pm - 10:50 pm
MDW
-
DTW
5h 40m
1 stop
$174Southwest
Sat, Jun 6 - Tue, Jun 9
Southwest Logo
4:45 pm - 4:55 pm
DTW
-
MDW
1h 10mnonstop
Southwest Logo
12:45 pm - 9:15 pm
MDW
-
DTW
7h 30m
2 stops
$179Southwest
Sat, Sep 26 - Tue, Sep 29
Delta Logo
6:07 pm - 6:31 pm
DTW
-
MDW
1h 24mnonstop
Delta Logo
9:17 am - 11:35 am
MDW
-
DTW
1h 18mnonstop
$187Delta
Mon, Jun 22 - Tue, Jun 23
Frontier Logo
2:02 pm - 10:11 pm
DTW
-
MDW
9h 09m
1 stop
Frontier Logo
6:00 am - 4:40 pm
MDW
-
DTW
9h 40m
1 stop
$190Frontier
Tue, Sep 1 - Wed, Sep 2
Delta Logo
12:27 pm - 12:42 pm
DTW
-
MDW
1h 15mnonstop
Delta Logo
1:26 pm - 3:44 pm
MDW
-
DTW
1h 18mnonstop
$191Delta
Thu, Jun 4 - Mon, Jun 8
Delta Logo
8:25 am - 8:43 am
DTW
-
MDW
1h 18mnonstop
Delta Logo
1:22 pm - 3:35 pm
MDW
-
DTW
1h 13mnonstop
$192Delta
Wed, Jun 3 - Wed, Jun 3
Southwest Logo
7:40 pm - 7:50 pm
DTW
-
MDW
1h 10mnonstop
Southwest Logo
3:10 pm - 10:25 pm
MDW
-
DTW
6h 15m
1 stop
$196Southwest
Wed, Jun 3 - Tue, Jun 30
Southwest Logo
1:25 pm - 1:35 pm
DTW
-
MDW
1h 10mnonstop
Southwest Logo
11:25 am - 5:55 pm
MDW
-
DTW
5h 30m
1 stop
$197Southwest
Tue, Jul 21 - Tue, Jul 28

Southwest flights from Detroit to Chicago Midway Airport

Our best Southwest deals on Detroit to Chicago Midway Airport flight tickets
Southwest
Sep 26
DTW4:45 pmDetroit Metropolitan Wayne County
1h 10m
MDW4:55 pmChicago Midway
Sep 29
MDW8:35 amChicago Midway
1h 20m
DTW10:55 amDetroit Metropolitan Wayne County
$164
Southwest
Jun 10
DTW5:35 amDetroit Metropolitan Wayne County
6h 25m
1 stop
MDW11:00 amChicago Midway
Jun 10
MDW5:30 pmChicago Midway
4h 20m
1 stop
DTW10:50 pmDetroit Metropolitan Wayne County
$172
Southwest
Sep 26
DTW8:30 amDetroit Metropolitan Wayne County
1h 15m
MDW8:45 amChicago Midway
Sep 29
MDW7:40 amChicago Midway
4h 15m
1 stop
DTW12:55 pmDetroit Metropolitan Wayne County
$174

Frontier flights from Detroit to Chicago Midway Airport

Our best Frontier deals on Detroit to Chicago Midway Airport flight tickets
Frontier
Sep 1
DTW2:02 pmDetroit Metropolitan Wayne County
9h 09m
1 stop
MDW10:11 pmChicago Midway
Sep 2
MDW6:00 amChicago Midway
9h 40m
1 stop
DTW4:40 pmDetroit Metropolitan Wayne County
$190
Frontier
Jun 29
DTW5:38 pmDetroit Metropolitan Wayne County
18h 34m
1 stop
MDW11:12 amChicago Midway
Jul 6
MDW6:00 amChicago Midway
17h 40m
1 stop
DTW12:40 amDetroit Metropolitan Wayne County
$200
Frontier
Jun 8
DTW6:20 amDetroit Metropolitan Wayne County
5h 49m
1 stop
MDW11:09 amChicago Midway
Jun 11
MDW12:27 pmChicago Midway
11h 17m
1 stop
DTW12:44 amDetroit Metropolitan Wayne County
$210

momondo Fare Finder

 
Customize your flight search to find flights from Detroit 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 16, 2026.
Use the filters below to find and compare flights from Detroit to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 9/26

4:45 pm-4:55 pm

Nonstop1h 10m

Chicago Midway

Tue 9/29

8:35 am-10:55 am

Nonstop1h 20m

$164

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 6/10

5:35 am-11:00 am

1 stop6h 25m

Chicago Midway

Wed 6/10

5:30 pm-10:50 pm

1 stop4h 20m

$172

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 6/6

11:05 am-5:00 pm

1 stop6h 55m

Chicago Midway

Tue 6/9

4:10 pm-10:50 pm

1 stop5h 40m

$174

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 9/26

4:45 pm-4:55 pm

Nonstop1h 10m

Chicago Midway

Tue 9/29

12:45 pm-9:15 pm

2 stops7h 30m

$179

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 6/22

6:07 pm-6:31 pm

Nonstop1h 24m

Chicago Midway

Tue 6/23

9:17 am-11:35 am

Nonstop1h 18m

$187

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 9/1

2:02 pm-10:11 pm

1 stop9h 09m

Chicago Midway

Wed 9/2

6:00 am-4:40 pm

1 stop9h 40m

$190

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 6/4

12:27 pm-12:42 pm

Nonstop1h 15m

Chicago Midway

Mon 6/8

1:26 pm-3:44 pm

Nonstop1h 18m

$191

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 6/3

8:25 am-8:43 am

Nonstop1h 18m

Chicago Midway

Wed 6/3

1:22 pm-3:35 pm

Nonstop1h 13m

$192

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 6/3

7:40 pm-7:50 pm

Nonstop1h 10m

Chicago Midway

Tue 6/30

3:10 pm-10:25 pm

1 stop6h 15m

$196

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 7/21

1:25 pm-1:35 pm

Nonstop1h 10m

Chicago Midway

Tue 7/28

11:25 am-5:55 pm

1 stop5h 30m

$197

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 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 and Chicago Midway Airport?

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

The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from Detroit, with most prices found around $67. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Detroit during the month November is also very affordable. Most momondo users find prices during this month for around $68.

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. The lowest ticket price found for a Saturday departure recently was $371. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $466.

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

Flying to Chicago Midway Airport from Detroit 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 at noon because they tend to be around $422. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Detroit to Chicago Midway flight route?

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

When to book flights from Detroit to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Detroit 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 to Chicago Midway Airport (DTT to MDW) flight deals and tips

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

Best Price Found

$218

Fastest flight time

1h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Detroit in the past 72 hours is $218. The best round-trip flight deal from Detroit to Chicago Midway Airport found on momondo in the last 72 hours is $386.
The fastest flight from Detroit to Chicago Midway Airport takes 1h 05m
Direct flights go from Detroit to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Detroit to Chicago Midway Airport

  • How far is Detroit to Chicago Midway by plane?

    The distance between Detroit and Chicago Midway is about 243.6 mi. Flights usually cover this in 1h 05m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Detroit to Chicago Midway Airport are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Detroit to Chicago Midway Airport.

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

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

Best airlines flying from Detroit to Chicago Midway Airport

Compare and see reviews for airlines that fly from Detroit to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $97Free CancellationRating
8.0
4,299 reviews
Search Southwest flights
DeltaPriceFrom $121Free CancellationRating
7.9
8,453 reviews
Search Delta flights

  • Southwest Flights From Detroit to Chicago Midway Airport

    Southwest flies from Detroit to Chicago Midway Airport around 11 times per week, with 4,298 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Detroit to Chicago Midway Airport in the last 72 hours was $97 (round-trip), much lower than the average airfare cost of $313 for Southwest flights on this route.

  • Delta Flights From Detroit to Chicago Midway Airport

    The best Delta deal for Detroit to Chicago Midway Airport flight tickets found on momondo in the last 72 hours was $121, round-trip. It should be noted that an average Delta flight deal for this route in this time was higher, at $287 round-trip. Delta operates 21 flights out of Detroit into Chicago Midway Airport in an average week, so prices vary by time and availability. 8,455 Delta reviews by users on momondo have scored the airline at 7.9/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

Finding the right flight to Chicago from Detroit is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

All flight searches from Detroit to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Detroit to Chicago.

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

Yes. momondo can track prices for Detroit to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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