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Cheap flights from Michigan 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 Michigan to Chicago departing on 5/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Michigan to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:04 pm - 7:31 pm
DTW
-
MDW
25h 27m
1 stop
Frontier Logo
6:00 am - 12:59 am
MDW
-
DTW
17h 59m
1 stop
$156Frontier
Tue, Apr 28 - Tue, May 5
Multiple Airlines Logo
8:30 pm - 1:00 pm
DTW
-
MDW
17h 30m
1 stop
Multiple Airlines Logo
6:00 am - 6:55 pm
MDW
-
DTW
11h 55m
1 stop
$158Multiple Airlines
Thu, Apr 23 - Thu, Apr 30
Frontier Logo
12:33 pm - 7:31 pm
DTW
-
MDW
7h 58m
1 stop
Frontier Logo
6:00 am - 4:14 pm
MDW
-
DTW
9h 14m
1 stop
$160Frontier
Wed, Apr 29 - Sat, May 2
Multiple Airlines Logo
5:09 pm - 10:14 pm
DTW
-
MDW
6h 05m
1 stop
Multiple Airlines Logo
7:30 am - 8:02 am
MDW
-
DTW
23h 32m
1 stop
$162Multiple Airlines
Sat, Apr 18 - Mon, Apr 20
Southwest Logo
6:45 am - 6:45 am
GRR
-
MDW
1h 00mnonstop
Southwest Logo
10:10 am - 12:05 pm
MDW
-
GRR
0h 55mnonstop
$191Southwest
Sat, Apr 25 - Sat, Apr 25
Southwest Logo
6:45 am - 6:45 am
GRR
-
MDW
1h 00mnonstop
Southwest Logo
9:05 am - 2:30 pm
MDW
-
GRR
4h 25m
1 stop
$201Southwest
Sat, Apr 25 - Sat, Apr 25
Delta Logo
3:50 pm - 5:58 pm
GRR
-
MDW
3h 08m
1 stop
Delta Logo
6:38 pm - 11:57 pm
MDW
-
GRR
4h 19m
1 stop
$223Delta
Sat, Apr 18 - Mon, Apr 20
Delta Logo
5:30 am - 8:43 am
AZO
-
MDW
4h 13m
1 stop
Delta Logo
6:36 pm - 11:47 pm
MDW
-
AZO
4h 11m
1 stop
$248Delta
Mon, May 18 - Tue, May 26
Allegiant Air Logo
10:10 am - 8:31 am
SBN
-
MDW
23h 21m
1 stop
Allegiant Air Logo
9:11 am - 5:18 pm
MDW
-
SBN
7h 07m
1 stop
$398Allegiant Air
Sat, Jun 13 - Sun, Jun 28
Allegiant Air Logo
10:10 am - 8:31 am
SBN
-
MDW
23h 21m
1 stop
Allegiant Air Logo
9:11 am - 5:18 pm
MDW
-
SBN
7h 07m
1 stop
$432Allegiant Air
Sat, Jun 20 - Sun, Jun 28

Frontier flights from Michigan to Chicago Midway Airport

Our best Frontier deals on Michigan to Chicago Midway Airport flight tickets
Frontier
Apr 28
DTW7:04 pmDetroit Metropolitan Wayne County
25h 27m
1 stop
MDW7:31 pmChicago Midway
May 5
MDW6:00 amChicago Midway
17h 59m
1 stop
DTW12:59 amDetroit Metropolitan Wayne County
$156
Frontier
Apr 29
DTW12:33 pmDetroit Metropolitan Wayne County
7h 58m
1 stop
MDW7:31 pmChicago Midway
May 2
MDW6:00 amChicago Midway
9h 14m
1 stop
DTW4:14 pmDetroit Metropolitan Wayne County
$160
Frontier
May 27
DTW6:20 amDetroit Metropolitan Wayne County
5h 49m
1 stop
MDW11:09 amChicago Midway
May 31
MDW6:00 amChicago Midway
6h 04m
1 stop
DTW1:04 pmDetroit Metropolitan Wayne County
$171

Delta flights from Michigan to Chicago Midway Airport

Our best Delta deals on Michigan to Chicago Midway Airport flight tickets
Delta
Apr 27
DTW5:40 pmDetroit Metropolitan Wayne County
1h 18m
MDW5:58 pmChicago Midway
Apr 29
MDW9:27 amChicago Midway
1h 12m
DTW11:39 amDetroit Metropolitan Wayne County
$154
Delta
May 12
DTW12:27 pmDetroit Metropolitan Wayne County
1h 15m
MDW12:42 pmChicago Midway
May 16
MDW6:36 pmChicago Midway
1h 09m
DTW8:45 pmDetroit Metropolitan Wayne County
$178
Delta
Apr 28
DTW8:25 amDetroit Metropolitan Wayne County
1h 22m
MDW8:47 amChicago Midway
May 2
MDW1:24 pmChicago Midway
1h 15m
DTW3:39 pmDetroit Metropolitan Wayne County
$196

momondo Fare Finder

 
Customize your flight search to find flights from Michigan 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 March 31, 2026.
Use the filters below to find and compare flights from Michigan 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

Tue 4/28

7:04 pm-7:31 pm

1 stop25h 27m

Chicago Midway

Tue 5/5

6:00 am-12:59 am

1 stop17h 59m

$156

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 4/23

8:30 pm-1:00 pm

1 stop17h 30m

Chicago Midway

Thu 4/30

6:00 am-6:55 pm

1 stop11h 55m

$158

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 4/29

12:33 pm-7:31 pm

1 stop7h 58m

Chicago Midway

Sat 5/2

6:00 am-4:14 pm

1 stop9h 14m

$160

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 4/18

5:09 pm-10:14 pm

1 stop6h 05m

Chicago Midway

Mon 4/20

7:30 am-8:02 am

1 stop23h 32m

$162
Quickest round-trip

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 4/25

6:45 am-6:45 am

Nonstop1h 00m

Chicago Midway

Sat 4/25

10:10 am-12:05 pm

Nonstop0h 55m

$191

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 4/25

6:45 am-6:45 am

Nonstop1h 00m

Chicago Midway

Sat 4/25

9:05 am-2:30 pm

1 stop4h 25m

$201

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 4/18

3:50 pm-5:58 pm

1 stop3h 08m

Chicago Midway

Mon 4/20

6:38 pm-11:57 pm

1 stop4h 19m

$223

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Mon 5/18

5:30 am-8:43 am

1 stop4h 13m

Chicago Midway

Tue 5/26

6:36 pm-11:47 pm

1 stop4h 11m

$248

South BendChicago

SBN - MDW

SBNMDW

South Bend/Michiana

Sat 6/13

10:10 am-8:31 am

1 stop23h 21m

Chicago Midway

Sun 6/28

9:11 am-5:18 pm

1 stop7h 07m

$398

South BendChicago

SBN - MDW

SBNMDW

South Bend/Michiana

Sat 6/20

10:10 am-8:31 am

1 stop23h 21m

Chicago Midway

Sun 6/28

9:11 am-5:18 pm

1 stop7h 07m

$432

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 Michigan 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 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 Michigan. The lowest ticket price found for a Wednesday departure recently was $359. 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 Michigan because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $461.

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

Flying to Chicago Midway Airport from Michigan in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $307 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $414. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Michigan to Chicago Midway flight route?

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

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

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

Can stopping save me money on Michigan to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Michigan to Chicago Midway Airport.

Cheap Michigan to Chicago Midway Airport flight deals and tips

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

Best Price Found

$198

Fastest flight time

1h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Michigan in the past 72 hours is $198. The best round-trip flight deal from Michigan to Chicago Midway Airport found on momondo in the last 72 hours is $389.
The fastest flight from Michigan to Chicago Midway Airport takes 1h 00m
Direct flights go from Michigan to Chicago Midway Airport every day.
Search flight deals

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

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

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

  • How old do you have to be to fly from Michigan 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 Michigan to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

Best airlines flying from Michigan to Chicago Midway Airport

Compare and see reviews for airlines that fly from Michigan to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $97Free CancellationRating
8.0
4,332 reviews
Search Southwest flights
DeltaPriceFrom $121Free CancellationRating
7.9
8,368 reviews
Search Delta flights

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
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Michigan 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 Michigan.

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

Yes. momondo allows you to filter the results for Michigan to Chicago flights to just show those with flexible booking policies.

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

momondo helps you find the best flight between Michigan and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes. momondo can track prices for Michigan 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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