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Midway

$49+ Cheap flights from Michigan 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Michigan to Midway

Keep the following information in mind while searching for Michigan to Midway flight deals. Data was last updated September 16, 2025.

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

June

Cheapest in

October

Average price

$174

Good round-trip deal

$230 or less

Good one-way deal

$144 or less
From Michigan to Chicago Midway
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One-way flight from Michigan to Chicago Midway
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Highest demand for flights based on searches. 22% potential increase in price ($65 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Michigan to Chicago Midway.
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Price to beat on a one-way flight from Michigan to Chicago Midway.
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Find flight deals from Michigan to Midway

Cheapest flights from Michigan to Midway
Explore the most affordable flight options available from Michigan to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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.
Thu 10/96:05 pmGRR - MDW
Nonstop1h 05mSouthwest
Mon 10/139:30 amMDW - GRR
Nonstop0h 55mSouthwest
Deal found 9/15$97
This Delta deal was found by Cheapflights users on 9/16. 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.
Sat 10/118:25 amDTW - MDW
Nonstop1h 15mDelta
Sat 10/116:23 pmMDW - DTW
Nonstop1h 12mDelta
Deal found 9/16$97
This Southwest deal was found by Cheapflights users on 9/15. 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.
Sat 10/113:30 pmDTW - MDW
Nonstop1h 10mSouthwest
Tue 10/145:35 amMDW - DTW
1 stop6h 30mSouthwest
Deal found 9/15$107
This Southwest deal was found by Cheapflights users on 9/15. 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.
Tue 10/71:30 pmDTW - MDW
2 stops6h 40mSouthwest
Wed 10/88:50 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 9/15$112
This Southwest deal was found by Cheapflights users on 9/15. 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.
Thu 10/306:25 pmDTW - MDW
1 stop5h 50mSouthwest
Mon 11/36:40 amMDW - DTW
1 stop4h 45mSouthwest
Deal found 9/15$117
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/141:30 pmDTW - MDW
2 stops6h 40mSouthwest
Tue 10/215:35 amMDW - DTW
1 stop6h 30mSouthwest
Deal found 9/14$122
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/281:30 pmDTW - MDW
2 stops6h 40mSouthwest
Thu 10/304:35 pmMDW - DTW
2 stops6h 30mSouthwest
Deal found 9/14$127
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/77:22 amDTW - MDW
1 stop7h 16mMultiple Airlines
Wed 10/88:05 amMDW - DTW
1 stop5h 42mMultiple Airlines
Deal found 9/15$131
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/63:42 pmDTW - MDW
1 stop8h 59mFrontier
Wed 10/88:05 amMDW - DTW
1 stop5h 42mFrontier
Deal found 9/15$133
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 11/78:25 pmDTW - MDW
Nonstop1h 10mSouthwest
Mon 11/105:40 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 9/15$134
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/179:05 pmDTW - MDW
1 stop26h 42mMultiple Airlines
Tue 10/218:05 amMDW - DTW
1 stop5h 29mMultiple Airlines
Deal found 9/15$139
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/297:22 amDTW - MDW
1 stop6h 19mMultiple Airlines
Wed 11/52:06 pmMDW - DTW
1 stop16h 54mMultiple Airlines
Deal found 9/14$140

Cheapflights Fare Finder

 
Customize your flight search to find flights from Michigan 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 September 16, 2025.
Use the filters below to find and compare flights from Michigan to Chicago Midway Airport that are best for you.

Fly from

Michigan

Fly to

Midway

Route

Depart

Return

Price

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Wed 10/22

5:00 pm-5:05 pm

Nonstop1h 05m

Chicago Midway

Sat 10/25

9:55 am-11:45 am

Nonstop0h 50m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 11/8

6:04 pm-6:25 pm

Nonstop1h 21m

Chicago Midway

Tue 11/11

9:32 am-11:45 am

Nonstop1h 13m

$97

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 10/9

6:05 pm-6:10 pm

Nonstop1h 05m

Chicago Midway

Mon 10/13

9:30 am-11:25 am

Nonstop0h 55m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 11/8

8:25 am-8:40 am

Nonstop1h 15m

Chicago Midway

Mon 11/10

6:48 pm-9:05 pm

Nonstop1h 17m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 10/30

8:25 am-8:40 am

Nonstop1h 15m

Chicago Midway

Thu 11/6

9:35 am-11:45 am

Nonstop1h 10m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 10/11

3:30 pm-3:40 pm

Nonstop1h 10m

Chicago Midway

Mon 10/13

9:25 pm-11:35 pm

Nonstop1h 10m

$97

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 11/3

7:00 pm-7:10 pm

Nonstop1h 10m

Chicago Midway

Wed 11/5

6:40 am-12:25 pm

1 stop4h 45m

$107

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 10/28

7:25 pm-10:05 pm

1 stop3h 40m

Chicago Midway

Thu 10/30

9:40 am-11:45 am

Nonstop1h 05m

$107

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 10/21

1:30 pm-6:30 pm

1 stop6h 00m

Chicago Midway

Tue 10/21

8:50 pm-11:00 pm

Nonstop1h 10m

$107

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Wed 10/8

7:25 pm-10:05 pm

1 stop3h 40m

Chicago Midway

Thu 10/9

9:40 am-11:45 am

Nonstop1h 05m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 60 results
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Best time to book a flight from Michigan to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Michigan 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 Michigan to Chicago Midway Airport

What is the cheapest month to book a flight from Michigan to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Michigan to Chicago Midway Airport (average of $160). Flying from Michigan 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 MI to MDW?

Find hourly flight availability from Michigan 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 September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Michigan to Chicago Midway Airport as you normally would.

Weekly flight availability from Michigan to Chicago Midway Airport

Explore weekly flight availability from Michigan 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 September 16, 2025.

The most flights from USMI to MDW are scheduled on a Monday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 on average).

Related info for your journey

Find useful and relevant information for your journey from Michigan to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Michigan to Chicago Midway Airport?

    For as low as $97, Southwest can have you in Chicago Midway Airport from Michigan in 1h 05m. The distance from Michigan to Chicago Midway Airport is about 136 mi. Most flights are nonstop.

  • What are the most popular routes from Michigan to Chicago Midway Airport?

    When deciding which route to take from Michigan to Chicago Midway Airport consider Detroit Metropolitan Wayne County - Chicago Midway, Traverse City Cherry Capital - Chicago Midway or Grand Rapids Gerald R. Ford Intl - Chicago Midway as they are the most popular.

  • What are the most reliable airlines from Michigan to Chicago Midway Airport?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Michigan to Chicago Midway Airport on time: Endeavor Airlines (80%), Korean Air (79%), Southwest (79%).

  • What are the cheapest flights from Michigan to Chicago Midway Airport?

    Looking for the cheapest flight from Michigan to Chicago Midway Airport? While on average our users pay $267, our data indicates the cheapest price to be $58. The most popular route (Detroit Metropolitan Wayne County - Chicago Midway), is priced around $97.

  • Can I find deals for flights from Michigan to Midway that include hotel bookings?

    Yes. In addition to deals on Michigan to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Michigan to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Michigan to Midway.

  • Can I find deals for business class flights from Michigan to Midway?

    Yes. Cheapflights offers flight deals from Michigan 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 Michigan to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Michigan to Chicago Midway Airport (average of $160). Flying from Michigan 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

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Alternative routes for Michigan to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Michigan to Midway

Discover the top 2 airlines that operate flights from Michigan 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$275FlexibilityNo cancel feeOn-time63%
DeltaCheapest$112Average$346FlexibilityNo cancel feeOn-timeN/A

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