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$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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
DTW — MDW
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$110
(Frontier)

One-way from

$49
(Southwest)

Popular in

June

Cheapest in

October

Average price

$240

Good round-trip deal

$265 or less

Good one-way deal

$159 or less
Provider with most accurate pricing for Detroit (DTT)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Detroit (DTT)-Chicago (CHI) flights.
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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 ($63 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 November 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 November 3, 2025.

This Frontier deal was found by Cheapflights users on 11/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:58 amDTW - MDW
1 stop11h 14mFrontier
Thu 12/117:23 pmMDW - DTW
1 stop12h 03mFrontier
Deal found 11/3$110
This Southwest deal was found by Cheapflights users on 11/1. 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 12/97:00 amDTW - MDW
Nonstop1h 25mSouthwest
Tue 12/168:30 pmMDW - DTW
Nonstop1h 10mSouthwest
Deal found 11/1$117
This Delta deal was found by Cheapflights users on 11/1. 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.
Mon 12/85:40 pmDTW - MDW
Nonstop1h 20mDelta
Wed 12/101:14 pmMDW - DTW
Nonstop1h 11mDelta
Deal found 11/1$144
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Thu 12/46:00 amDTW - MDW
1 stop8h 01mMultiple Airlines
Mon 12/88:42 pmMDW - DTW
1 stop10h 25mMultiple Airlines
Deal found 11/2$149
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/26:59 pmDTW - MDW
1 stop14h 47mMultiple Airlines
Tue 12/97:44 amMDW - DTW
1 stop6h 56mMultiple Airlines
Deal found 11/2$151
This Delta deal was found by Cheapflights users on 11/2. 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.
Thu 11/278:30 amDTW - MDW
Nonstop1h 24mDelta
Fri 11/289:34 amMDW - DTW
Nonstop1h 15mDelta
Deal found 11/2$157
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Sat 12/1311:24 amDTW - MDW
1 stop10h 58mMultiple Airlines
Mon 12/158:42 pmMDW - DTW
1 stop10h 25mMultiple Airlines
Deal found 11/1$161
This Delta deal was found by Cheapflights users on 11/2. 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.
Wed 12/171:59 pmGRR - MDW
1 stop5h 01mDelta
Wed 12/246:08 pmMDW - GRR
1 stop3h 13mDelta
Deal found 11/2$174
This Delta deal was found by Cheapflights users on 11/2. 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.
Fri 12/53:05 pmMBS - MDW
1 stop3h 55mDelta
Sun 12/76:40 pmMDW - MBS
1 stop2h 58mDelta
Deal found 11/2$199
This Delta deal was found by Cheapflights users on 11/3. 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 12/66:17 amTVC - MDW
1 stop3h 32mDelta
Mon 12/86:40 pmMDW - TVC
1 stop3h 28mDelta
Deal found 11/3$199
This Southwest deal was found by Cheapflights users on 10/31. 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 11/216:10 pmGRR - MDW
Nonstop1h 05mSouthwest
Mon 11/2410:10 pmMDW - GRR
Nonstop0h 55mSouthwest
Deal found 10/31$209
This Delta deal was found by Cheapflights users on 11/3. 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.
Thu 12/113:05 pmMBS - MDW
1 stop3h 55mDelta
Sun 12/149:34 amMDW - MBS
1 stop3h 51mDelta
Deal found 11/3$214

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 November 3, 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

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 12/9

7:00 pm-7:10 pm

Nonstop1h 10m

Chicago Midway

Tue 12/16

8:50 am-2:45 pm

1 stop4h 55m

$127

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 12/8

5:40 pm-6:00 pm

Nonstop1h 20m

Chicago Midway

Wed 12/10

1:14 pm-3:25 pm

Nonstop1h 11m

$144

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Tue 12/2

6:59 pm-8:46 am

1 stop14h 47m

Chicago Midway

Tue 12/9

7:44 am-3:40 pm

1 stop6h 56m

$151

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Tue 1/13

8:10 am-12:48 pm

1 stop5h 38m

Chicago Midway

Sat 1/17

9:34 am-3:17 pm

1 stop4h 43m

$157

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 11/27

8:30 am-8:54 am

Nonstop1h 24m

Chicago Midway

Fri 11/28

9:34 am-11:49 am

Nonstop1h 15m

$157

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 11/22

6:35 am-6:55 am

Nonstop1h 20m

Chicago Midway

Mon 11/24

9:35 pm-11:40 pm

Nonstop1h 05m

$164

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 12/4

8:30 am-8:54 am

Nonstop1h 24m

Chicago Midway

Thu 12/11

9:34 am-11:45 am

Nonstop1h 11m

$171

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 12/13

8:25 am-8:49 am

Nonstop1h 24m

Chicago Midway

Mon 12/15

1:14 pm-3:25 pm

Nonstop1h 11m

$171

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 12/4

8:30 am-8:54 am

Nonstop1h 24m

Chicago Midway

Mon 12/8

1:14 pm-3:25 pm

Nonstop1h 11m

$171

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 1/29

12:25 pm-12:48 pm

Nonstop1h 23m

Chicago Midway

Sat 1/31

9:34 am-11:45 am

Nonstop1h 11m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

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, August is the cheapest month in which you can book a flight from Michigan to Chicago Midway Airport (average of $94). Flying from Michigan to Chicago Midway Airport in July is currently the most expensive (average of $245). 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 November 3, 2025.

When flying from Michigan to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 5% versus a flight at noon.

What is the cheapest day to fly from Michigan to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Michigan to Midway. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Michigan to Chicago Midway Airport flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 3, 2025.

The most flights from USMI to MDW are scheduled on a Monday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 $127, Southwest can have you in Chicago Midway Airport from Michigan in 1h 10m. The distance from Michigan to Chicago Midway Airport is about 227 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, Flint Bishop - 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: Sun Country Air (100%), United Airlines (100%), Endeavor Airlines (95%).

  • 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 $297, our data indicates the cheapest price to be $58. The most popular route (Detroit Metropolitan Wayne County - Chicago Midway), is priced around $117.

  • 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, August is the cheapest month in which you can book a flight from Michigan to Chicago Midway Airport (average of $94). Flying from Michigan to Chicago Midway Airport in July is currently the most expensive (average of $245). 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
Porter
Benton Harbor

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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$251FlexibilityNo cancel feeOn-time63%
DeltaCheapest$98Average$350FlexibilityNo cancel feeOn-timeN/A

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