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Cheap flights from Detroit to Chicago from $49

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 11/13. 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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Cheap round-trip flights

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Southwest Logo
6:10 am - 9:55 amDTW-MDW
4h 45m1 stop
Southwest Logo
9:35 pm - 11:40 pmMDW-DTW
1h 05mnonstop
$104Southwest
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Thu, Nov 20 - Mon, Nov 24
Southwest Logo
12:25 pm - 12:35 pmDTW-MDW
1h 10mnonstop
Southwest Logo
6:40 am - 12:25 pmMDW-DTW
4h 45m1 stop
$107Southwest
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Thu, Nov 13 - Thu, Nov 20
Southwest Logo
7:00 am - 7:25 amDTW-MDW
1h 25mnonstop
Southwest Logo
2:30 pm - 10:35 pmMDW-DTW
7h 05m2 stops
$112Southwest
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Wed, Nov 12 - Wed, Nov 12
Southwest Logo
5:30 pm - 11:00 pmDTW-MDW
6h 30m1 stop
Southwest Logo
6:40 am - 12:25 pmMDW-DTW
4h 45m1 stop
$117Southwest
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Thu, Nov 13 - Mon, Nov 17
Multiple Airlines Logo
7:00 am - 12:41 pmDTW-MDW
6h 41m1 stop
Multiple Airlines Logo
1:37 pm - 5:26 pmMDW-DTW
26h 49m1 stop
$124Multiple Airlines
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Wed, Nov 12 - Fri, Nov 14
Delta Logo
12:15 pm - 12:34 pmDTW-MDW
1h 19mnonstop
Delta Logo
9:34 am - 11:49 amMDW-DTW
1h 15mnonstop
$127Delta
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Wed, Nov 12 - Wed, Nov 19
Multiple Airlines Logo
7:00 am - 12:41 pmDTW-MDW
6h 41m1 stop
Multiple Airlines Logo
6:30 am - 5:16 pmMDW-DTW
9h 46m1 stop
$129Multiple Airlines
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Wed, Nov 12 - Thu, Nov 13
Delta Logo
6:04 pm - 6:25 pmDTW-MDW
1h 21mnonstop
Delta Logo
1:15 pm - 3:30 pmMDW-DTW
1h 15mnonstop
$134Delta
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Sat, Nov 8 - Mon, Nov 10
Frontier Logo
1:49 pm - 11:20 pmDTW-MDW
10h 31m1 stop
Frontier Logo
6:20 am - 5:12 pmMDW-DTW
9h 52m1 stop
$150Frontier
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Mon, Oct 27 - Thu, Oct 30
Frontier Logo
7:28 pm - 8:31 pmDTW-MDW
26h 03m1 stop
Frontier Logo
5:40 am - 12:49 pmMDW-DTW
6h 09m1 stop
$152Frontier
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Thu, Nov 13 - Sun, Nov 16

Frontier flights from Detroit to Chicago Midway Airport

Our best Frontier deals on Detroit to Chicago Midway Airport flight tickets
Frontier
Oct 27
DTW1:49 pmDetroit Metropolitan Wayne County
10h 31m
1 stop
MDW11:20 pmChicago Midway
Oct 30
MDW6:20 amChicago Midway
9h 52m
1 stop
DTW5:12 pmDetroit Metropolitan Wayne County
$150
Find similar
Frontier
Nov 13
DTW7:28 pmDetroit Metropolitan Wayne County
26h 03m
1 stop
MDW8:31 pmChicago Midway
Nov 16
MDW5:40 amChicago Midway
6h 09m
1 stop
DTW12:49 pmDetroit Metropolitan Wayne County
$152
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Frontier
Oct 30
DTW1:44 pmDetroit Metropolitan Wayne County
7h 59m
1 stop
MDW8:43 pmChicago Midway
Nov 3
MDW6:20 amChicago Midway
9h 56m
1 stop
DTW5:16 pmDetroit Metropolitan Wayne County
$156
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Delta flights from Detroit to Chicago Midway Airport

Our best Delta deals on Detroit to Chicago Midway Airport flight tickets
Delta
Nov 12
DTW12:15 pmDetroit Metropolitan Wayne County
1h 19m
MDW12:34 pmChicago Midway
Nov 19
MDW9:34 amChicago Midway
1h 15m
DTW11:49 amDetroit Metropolitan Wayne County
$127
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Delta
Nov 8
DTW6:04 pmDetroit Metropolitan Wayne County
1h 21m
MDW6:25 pmChicago Midway
Nov 10
MDW1:15 pmChicago Midway
1h 15m
DTW3:30 pmDetroit Metropolitan Wayne County
$134
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Delta
Nov 6
DTW8:25 amDetroit Metropolitan Wayne County
1h 15m
MDW8:40 amChicago Midway
Nov 9
MDW9:34 amChicago Midway
1h 15m
DTW11:49 amDetroit Metropolitan Wayne County
$147
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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 October 16, 2025.
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

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 11/20

6:10 am-9:55 am

1 stop4h 45m

Chicago Midway

Mon 11/24

9:35 pm-11:40 pm

Nonstop1h 05m

$104

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 11/13

12:25 pm-12:35 pm

Nonstop1h 10m

Chicago Midway

Thu 11/20

6:40 am-12:25 pm

1 stop4h 45m

$107

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 11/12

7:00 am-7:25 am

Nonstop1h 25m

Chicago Midway

Wed 11/12

2:30 pm-10:35 pm

2 stops7h 05m

$112

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 11/13

5:30 pm-11:00 pm

1 stop6h 30m

Chicago Midway

Mon 11/17

6:40 am-12:25 pm

1 stop4h 45m

$117

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 11/12

7:00 am-12:41 pm

1 stop6h 41m

Chicago Midway

Fri 11/14

1:37 pm-5:26 pm

1 stop26h 49m

$124

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 11/12

12:15 pm-12:34 pm

Nonstop1h 19m

Chicago Midway

Wed 11/19

9:34 am-11:49 am

Nonstop1h 15m

$127

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 11/12

7:00 am-12:41 pm

1 stop6h 41m

Chicago Midway

Thu 11/13

6:30 am-5:16 pm

1 stop9h 46m

$129

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 11/8

6:04 pm-6:25 pm

Nonstop1h 21m

Chicago Midway

Mon 11/10

1:15 pm-3:30 pm

Nonstop1h 15m

$134

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 10/27

1:49 pm-11:20 pm

1 stop10h 31m

Chicago Midway

Thu 10/30

6:20 am-5:12 pm

1 stop9h 52m

$150

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 11/13

7:28 pm-8:31 pm

1 stop26h 03m

Chicago Midway

Sun 11/16

5:40 am-12:49 pm

1 stop6h 09m

$152

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 cheapest month to fly to Chicago Midway Airport?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from Detroit, with most prices found around $137. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Detroit during the month November is also very affordable. Most momondo users find prices during this month for around $147.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Detroit. The lowest ticket price found for a Wednesday 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $442.

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 $308 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $427. 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

What cabin class options are available on Detroit to Chicago Midway flights?

There are 4 cabin classes available to choose from on Detroit to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

$169

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 $169. The best round-trip flight deal from Detroit to Chicago Midway Airport found on momondo in the last 72 hours is $280.
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

  • 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 10m, 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
4,241 reviews
Search Southwest flights
DeltaPriceFrom $112Free CancellationRating
7.9
7,984 reviews
Search Delta flights

  • Southwest Flights From Detroit to Chicago Midway Airport

    Southwest flies from Detroit to Chicago Midway Airport around 15 times per week, with 4,241 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 $277 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 $112, round-trip. It should be noted that an average Delta flight deal for this route in this time was higher, at $266 round-trip. Delta operates 20 flights out of Detroit into Chicago Midway Airport in an average week, so prices vary by time and availability. 7,984 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
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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