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$49+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
DTT — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$107
(Southwest)

One-way from

$49
(Southwest)

Popular in

January

Cheapest in

November

Average price

$268

Good round-trip deal

$296 or less

Good one-way deal

$160 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 June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. 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.
Mon 9/87:30 pmDTW - MDW
Nonstop1h 10mSouthwest
Wed 9/102:55 pmMDW - DTW
1 stop6h 20mSouthwest
Deal found 6/10$107
This Delta deal was found by Cheapflights users on 6/10. 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 9/2712:15 pmDTW - MDW
Nonstop1h 17mDelta
Mon 9/291:00 pmMDW - DTW
Nonstop1h 13mDelta
Deal found 6/10$124
This Frontier deal was found by Cheapflights users on 6/12. 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.
Sat 9/274:38 pmDTW - MDW
1 stop7h 31mFrontier
Mon 9/291:59 pmMDW - DTW
1 stop5h 56mFrontier
Deal found 6/12$224
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/178:38 amDTW - MDW
2 stops26h 03mMultiple Airlines
Mon 7/2110:31 amMDW - DTW
2 stops33h 40mMultiple Airlines
Deal found 6/11$344

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 June 12, 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

Mon 9/8

7:30 pm-7:40 pm

Nonstop1h 10m

Chicago Midway

Wed 9/10

2:55 pm-10:15 pm

1 stop6h 20m

$107

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sat 8/30

8:25 am-8:35 am

Nonstop1h 10m

Chicago Midway

Mon 9/1

9:30 am-11:43 am

Nonstop1h 13m

$174

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 6/16

12:18 pm-11:18 pm

1 stop12h 00m

Chicago Midway

Thu 6/19

9:12 pm-8:52 am

1 stop10h 40m

$228

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Thu 7/17

8:38 am-9:41 am

2 stops26h 03m

Chicago Midway

Mon 7/21

10:31 am-9:11 pm

2 stops33h 40m

$344

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 8/18

6:21 pm-6:37 pm

Nonstop1h 16m

$49

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 8/18

5:40 am-1:30 pm

2 stops8h 50m

$54

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Mon 9/1

4:08 pm-9:02 am

1 stop17h 54m

$143

DetroitChicago

DTW - MDW

DTWMDW

Detroit Metropolitan Wayne County

Sun 7/20

6:30 am-9:41 am

2 stops28h 11m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

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 June 12, 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 8, 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 June 12, 2025.

The most flights from DTT to MDW are scheduled on a Monday (13 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Read through reviews of airlines operating flights from Detroit to Chicago, such as Southwest, Delta and Frontier. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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 12 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 $107. Other airlines that can offer you cheap pricing are Delta, from $174, and Frontier, from $234. You may be able to fly from Detroit to Chicago Midway Airport for 64% 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 Southwest, which is currently one of the cheapest options available, starting at $49. Delta flights start at $76 while deals on Frontier start at $143 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%), Korean Air (85%), Virgin Atlantic( 84%).

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

    Looking at all options, your cheapest flight can be booked for $75. While the most popular route (Detroit Metropolitan Wayne County - Chicago Midway) can be booked for $97 on average our data indicates $313 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$108Average$237FlexibilityNo cancel feeOn-time63%
DeltaCheapest$112Average$270FlexibilityNo cancel feeOn-timeN/A

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