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CA $152 Cheap Flights from Detroit (DTW) to Chicago (MDW)

View CA $152 flight on Fri, Oct 30, 2026Opens in a new window

Popular airlines from Detroit Metropolitan Wayne County Airport (DTW) to Chicago Midway Airport (MDW)

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Cheap flights from Detroit (DTW) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $304 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Sep 5 - Fri, Sep 11
DTW
Detroit
MDW
Chicago
CA $304 Roundtrip, found 1 day ago
CA $304
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 5 from Detroit to Chicago, returning Fri, Sep 11, priced at CA $304 found 1 day ago
Delta
Sat, Sep 5 - Fri, Sep 11
DTW
Detroit
MDW
Chicago
CA $305 Roundtrip, found 1 day ago
CA $305
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 5 from Detroit to Chicago, returning Fri, Sep 11, priced at CA $305 found 1 day ago
Southwest Airlines
Sat, Sep 5 - Fri, Sep 11
DTW
Detroit
MDW
Chicago
CA $318 Roundtrip, found 1 day ago
CA $318
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Detroit to Chicago, returning Fri, Sep 11, priced at CA $318 found 1 day ago
Delta
Thu, Dec 17 - Fri, Dec 25
DTW
Detroit
MDW
Chicago
CA $326 Roundtrip, found 2 days ago
CA $326
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Dec 17 from Detroit to Chicago, returning Fri, Dec 25, priced at CA $326 found 2 days ago
Delta
Fri, Sep 11 - Sat, Sep 12
DTW
Detroit
MDW
Chicago
CA $328 Roundtrip, just found
CA $328
Roundtrip
just found
Select Delta flight, departing Fri, Sep 11 from Detroit to Chicago, returning Sat, Sep 12, priced at CA $328 just found
Delta
Mon, Aug 31 - Tue, Sep 8
DTW
Detroit
MDW
Chicago
CA $349 Roundtrip, found 1 day ago
CA $349
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Aug 31 from Detroit to Chicago, returning Tue, Sep 8, priced at CA $349 found 1 day ago
Delta
Tue, Sep 22 - Sat, Sep 26
DTW
Detroit
MDW
Chicago
CA $349 Roundtrip, found 23 hours ago
CA $349
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Sep 22 from Detroit to Chicago, returning Sat, Sep 26, priced at CA $349 found 23 hours ago
Delta
Tue, Sep 22 - Sat, Sep 26
DTW
Detroit
MDW
Chicago
CA $350 Roundtrip, found 23 hours ago
CA $350
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Sep 22 from Detroit to Chicago, returning Sat, Sep 26, priced at CA $350 found 23 hours ago
Delta
Tue, Dec 22 - Fri, Dec 25
DTW
Detroit
MDW
Chicago
CA $352 Roundtrip, found 2 days ago
CA $352
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Dec 22 from Detroit to Chicago, returning Fri, Dec 25, priced at CA $352 found 2 days ago
Delta
Fri, Dec 25 - Fri, Jan 1
DTW
Detroit
MDW
Chicago
CA $353 Roundtrip, found 2 days ago
CA $353
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Dec 25 from Detroit to Chicago, returning Fri, Jan 1, priced at CA $353 found 2 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $634
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $634

Frequently asked questions

How much does a flight from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from CA $152 and cheap return flights from CA $304 DTW to MDW with Expedia. Return flights often range between CA$393 and CA$1065. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when DTW to MDW ticket fares go up or down.
What is the cheapest month to fly from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
February is typically the cheapest month to fly from Detroit Metropolitan Wayne County (DTW) to Midway Intl. (MDW), with average return fares around CA$190. February often sees lower prices because it falls after the holiday travel rush, when demand drops and airlines compete for bookings. Other cheap months to fly from DTW to MDW include June and October.
Which airlines fly direct from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
There are 2 airlines offering direct flights from Detroit Metropolitan Wayne County (DTW) to Midway Intl. (MDW):
  • Delta operates 21 direct flights from DTW to MDW every week.
  • Southwest Airlines operates 20 direct flights from DTW to MDW every week.
What is the cheapest airline that flies from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
Delta is one of the cheapest airlines offering nonstop return flights from Detroit Metropolitan Wayne County (DTW) to Midway Intl. (MDW), with tickets starting from around CA$130 for flights that can be booked for departure within the next year. Frontier Airlines is one of the cheapest airlines offering connecting return flights on this route, with tickets starting from around CA$221. These prices are per adult for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.) will differ from traveler to traveler. If you like to fly early, Southwest Airlines offers early morning flights. If price is the most important factor, Southwest Airlines typically offers the lowest fares. Southwest Airlines offers the most daily flights from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from Detroit Metropolitan Wayne County (DTW) to Chicago Midway International (MDW) are typically February and June, with average return flights around CA$190. The most popular months for this route are January and September, meaning you'll find plenty of flight options during these times. While there isn't a single month that is both the cheapest and most popular, if you're looking for the best value, February and June offer lower fares, and if you prioritize flexibility and more flight choices, January and September are great options.
How many flights per day from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
You'll find approximately 6 nonstop flights per day from Detroit Metropolitan Wayne County (DTW) to Midway Intl. (MDW). For even more choices, look at flights that include layovers, as there are around 21 connecting flights per day. Some common connection points include Nashville Intl. (BNA), Baltimore Washington Intl. Thurgood Marshall (BWI), and Lambert-St. Louis Intl. (STL).
What is the earliest flight from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Detroit Metropolitan Wayne County (DTW) to Midway Intl. (MDW) typically departs around 5:00 AM local time, operated by Southwest Airlines. This is a seasonal service active in February. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Detroit Metropolitan Wayne County (DTW) to Chicago Midway Intl. (MDW) on a Thursday, with around 12 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Southwest Airlines, Delta, and Frontier Airlines. Flight schedules are fairly consistent throughout the week, so you'll have plenty of choices no matter when you plan to fly.
What are the most popular departure times for flights from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Detroit Metropolitan Wayne County (DTW) to Midway Intl. (MDW) are in the morning, from 6am to 9am. Many major carriers, including Delta, Southwest Airlines and Frontier Airlines, offer flights during this window. Many travellers prefer these early morning flights as they allow you to arrive at your destination with plenty of time for your day's activities.
How long does it take to fly from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
A nonstop flight from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.) typically takes about 1 hour 18 minutes. This route covers a distance of approximately 365 kilometres. If you opt for a flight with one stop, your travel time will be longer, usually around 5 hours 30 minutes. Flights with two or more stops generally take even longer, averaging about 9 hours 48 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic.
Can you fly business or first class from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
Yes, you can fly business class or first class between DTW and MDW. You can fly business class with Frontier Airlines and Delta.First class cabins are available on Delta.
How do I earn miles on a Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago, IL (MDW) from Detroit, MI (DTW)?
If you're planning to travel to Chicago from Detroit Metropolitan Wayne County (DTW), you can fly directly into Midway Intl. (MDW). Some flights may connect through major hubs like Cincinnati - Northern Kentucky Intl. (CVG), Baltimore Washington Intl. Thurgood Marshall (BWI), or Liberty Intl. (EWR) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

0
Origin airport
Detroit Metropolitan Wayne County
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
CA $303
Distance
363 km

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Detroit to Chicago Flights

The easy way to book your flights from Detroit to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Detroit whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Detroit to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Detroit Metropolitan Wayne County, DTW to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Detroit to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Detroit currently is just CA $304 rising to CA $353.  

Here are more money-saving tips: 

  • Fly in September when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Detroit 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Detroit to Chicago Flights

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