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$63+ Cheap flights from Detroit (DTT) 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
DTT — MDW
juil. 8 — juil. 151
mar. 7/8
mar. 7/15
1 adult, Economy
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Cheap flight deals from Detroit to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Detroit (DTT) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated juillet 3, 2025.

Round-trip from

$122
(Southwest)

One-way from

$63
(Priceline)

Popular in

January

Cheapest in

November

Average price

$179

Good round-trip deal

$299 or less

Good one-way deal

$189 or less
From Detroit (DTT) to Chicago Midway
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One-way flight from Detroit (DTT) to Chicago Midway
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Highest demand for flights based on searches. 44% potential increase in price ($234 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Detroit (DTT) to Chicago Midway.
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Price to beat on a one-way flight from Detroit (DTT) to Chicago Midway.
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Find flight deals from Detroit to Midway

Cheapest flights from Detroit to Midway
Explore the most affordable flight options available from Detroit to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juillet 3, 2025.

This Southwest deal was found by Cheapflights users on 7/1. 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.
jeu. 8/145:40 amDTW - MDW
2 stops8h 50mSouthwest
lun. 8/185:10 amMDW - DTW
1 stop6h 40mSouthwest
Deal found 7/1$122
This Priceline deal was found by Cheapflights users on 7/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 8/294:08 pmDTW - MDW
1 stop8h 19mFrontier
dim. 8/316:15 amMDW - DTW
1 stop7h 57mFrontier
Deal found 7/2$123
This Delta deal was found by Cheapflights users on 7/1. 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.
mar. 8/1212:15 pmDTW - MDW
Nonstop1h 13mDelta
mar. 8/196:17 pmMDW - DTW
Nonstop1h 15mDelta
Deal found 7/1$134

Cheapflights Fare Finder

Customize your flight search to find flights from Detroit 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 juillet 3, 2025.
Use the filters below to find and compare flights from Detroit to Chicago Midway Airport that are best for you.

Fly from

Detroit

Fly to

Midway

Route

Depart

Return

Price

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

jeu. 8/14

5:40 am-1:30 pm

2 stops8h 50m

Chicago Midway

lun. 8/18

5:10 am-12:50 pm

1 stop6h 40m

$122

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

ven. 8/29

4:08 pm-11:27 pm

1 stop8h 19m

Chicago Midway

dim. 8/31

6:15 am-3:12 pm

1 stop7h 57m

$123

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

mar. 8/12

12:15 pm-12:28 pm

Nonstop1h 13m

Chicago Midway

mar. 8/19

6:17 pm-8:32 pm

Nonstop1h 15m

$134

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

dim. 8/10

9:36 am-1:47 pm

1 stop5h 11m

$63

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

jeu. 8/7

5:40 am-1:30 pm

2 stops8h 50m

$64

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

dim. 7/27

8:30 am-8:44 am

Nonstop1h 14m

$99

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

dim. 7/27

6:30 am-9:41 am

2 stops28h 11m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Best time to book a flight from Detroit to Midway

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

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

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

Find hourly flight availability from Detroit 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 juillet 3, 2025.

A simple way to save on the total cost of your ticket is to fly from Detroit to Chicago Midway Airport in the afternoon. If you’re flexible enough to do this you can expect to save up to 36% on your trip compared to booking a flight in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Detroit to Midway. Price data was last updated on June 29, 2025.

Travelers seeking maximum savings on their Detroit to Chicago Midway Airport flight should consider departing on Friday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Detroit to Chicago Midway Airport

Explore weekly flight availability from Detroit 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 juillet 3, 2025.

The most flights from DTT to MDW are scheduled on a Wednesday (12 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated juillet 3, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Frontier from Detroit to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

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

  • What airport do you fly from for flights from Detroit to Chicago Midway?

    Detroit All airports (DTT), located 0.6 mi from the city center, is the airport you fly out of when you book flights from Detroit to Chicago Midway. 2 airlines have flights from All airports to Chicago Midway on a regular basis. Booking flights from Detroit All airports to Chicago Midway should not be difficult; the airport handles an average of 7 outbound flights to Chicago Midway per day.

  • What are the cheapest airlines flying from Detroit to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Detroit to Chicago Midway Airport round-trip from $122. Other airlines that can offer you cheap pricing are Frontier, from $123, and Delta, from $134. You may be able to fly from Detroit to Chicago Midway Airport for 59% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Detroit to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $63. Southwest flights start at $64 while deals on Delta start at $76 one-way.

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

    Before booking your flight to Chicago Midway Airport from Detroit, check out the most reliable airlines to get you to your destination on time: Sun Country Air (100%), SkyWest Airlines (83%), Delta( 81%).

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

    Looking at all options, your cheapest flight can be booked for $137. While the most popular route (Detroit Metropolitan Wayne County - Chicago Midway) can be booked for $91 on average our data indicates $322 when flying from Detroit to Chicago Midway Airport.

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

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

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

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

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

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

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

Book flights to Detroit if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Detroit 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 Detroit to Midway

Discover the top 2 airlines that operate flights from Detroit 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 juillet 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$105Average$270FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$108Average$241FlexibilityNo cancel feeOn-time63%

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