CA $93 Cheap Flights from Detroit (DTW) to Chicago (MDW)

View CA $93 flight on Wed, Aug 12, 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 $93 for one-way flights and CA $186 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Aug 12 - Tue, Sep 1
DTW
Detroit
MDW
Chicago
CA $186 Roundtrip, found 7 hours ago
CA $186
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Aug 12 from Detroit to Chicago, returning Tue, Sep 1, priced at CA $186 found 7 hours ago
Delta
Tue, Jun 2 - Tue, Jun 9
DTW
Detroit
MDW
Chicago
CA $187 Roundtrip, found 22 hours ago
CA $187
Roundtrip
found 22 hours ago
Select Delta flight, departing Tue, Jun 2 from Detroit to Chicago, returning Tue, Jun 9, priced at CA $187 found 22 hours ago
Delta
Sat, Aug 22 - Tue, Sep 8
DTW
Detroit
MDW
Chicago
CA $223 Roundtrip, found 2 hours ago
CA $223
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Aug 22 from Detroit to Chicago, returning Tue, Sep 8, priced at CA $223 found 2 hours ago
Delta
Tue, Jun 2 - Sat, Jun 6
DTW
Detroit
MDW
Chicago
CA $224 Roundtrip, found 22 hours ago
CA $224
Roundtrip
found 22 hours ago
Select Delta flight, departing Tue, Jun 2 from Detroit to Chicago, returning Sat, Jun 6, priced at CA $224 found 22 hours ago
Delta
Wed, Aug 12 - Tue, Sep 1
DTW
Detroit
MDW
Chicago
CA $234 Roundtrip, found 7 hours ago
CA $234
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Aug 12 from Detroit to Chicago, returning Tue, Sep 1, priced at CA $234 found 7 hours ago
Delta
Tue, Jun 2 - Tue, Jun 9
DTW
Detroit
MDW
Chicago
CA $235 Roundtrip, found 2 days ago
CA $235
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jun 2 from Detroit to Chicago, returning Tue, Jun 9, priced at CA $235 found 2 days ago
Delta
Wed, Aug 12 - Tue, Sep 1
DTW
Detroit
MDW
Chicago
CA $241 Roundtrip, found 7 hours ago
CA $241
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Aug 12 from Detroit to Chicago, returning Tue, Sep 1, priced at CA $241 found 7 hours ago
Delta
Wed, Aug 12 - Tue, Sep 1
DTW
Detroit
MDW
Chicago
CA $254 Roundtrip, found 7 hours ago
CA $254
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Aug 12 from Detroit to Chicago, returning Tue, Sep 1, priced at CA $254 found 7 hours ago
Delta
Sat, Aug 22 - Sat, Sep 12
DTW
Detroit
MDW
Chicago
CA $259 Roundtrip, found 2 hours ago
CA $259
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Aug 22 from Detroit to Chicago, returning Sat, Sep 12, priced at CA $259 found 2 hours ago
Delta
Mon, Jun 1 - Sat, Jun 6
DTW
Detroit
MDW
Chicago
CA $260 Roundtrip, found 22 hours ago
CA $260
Roundtrip
found 22 hours ago
Select Delta flight, departing Mon, Jun 1 from Detroit to Chicago, returning Sat, Jun 6, priced at CA $260 found 22 hours 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 $395
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $395

Frequently asked questions

How much does a flight from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.) cost?
One-way flights typically cost between $458 and $1,621 and return flights often range between $458 and $1,621. 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 Anaa (AAA) to Toronto, ON (YYZ-Pearson Intl.) 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 round-trip fares around 332 CAD. This is about 29% lower than the average price throughout the year. February often sees lower prices because it's outside of peak holiday seasons, leading to less demand for flights. Other cheap months to fly from Detroit Metropolitan Wayne County (DTW) to Midway Intl. (MDW) include June and October.
Which airlines fly direct from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
Enter DTW to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
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, WN offers early morning flights. If price is the most important factor, WN typically offers the lowest fares. WN 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 best time to fly from Detroit Metropolitan Wayne County (DTW) to Chicago Midway International Airport (MDW) is typically June. This month offers a great balance, as it's both one of the cheapest and most popular times to travel. You can expect round-trip flights to be around 332 CAD, and with its popularity, you'll find plenty of flight options to fit your schedule. This information is based on booking data from the past year.
How many flights per day from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 6 nonstop flights per day from Detroit Metropolitan Wayne County (DTW) to Midway Intl. (MDW). For even more choice, look at flights that include layovers, as there are around 24 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 at approximately 5:00 AM local time, operated by Southwest Airlines. This is a seasonal service active in February. An early departure like this can help maximize 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 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 Air Lines, and Frontier Airlines.
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. About 32% of passengers prefer this time. Many major carriers, including Delta and Southwest Airlines, offer flights during this window. This timing works well because it allows you to get an early start on your day in Chicago.
How long does it take to fly from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
Flying nonstop from DTW to MDW takes around 1 hour 20 minutes, with the route covering approximately 227 miles. Flights with a layover typically take 4 hours 10 minutes longer than direct options. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Chicago, IL (MDW-Midway Intl.)?
Select the "Business class" and "First class" filters when looking for DTW to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
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 from Detroit Metropolitan Wayne County (DTW)?
When traveling from Detroit Metropolitan Wayne County (DTW) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Cincinnati - Northern Kentucky Intl. (CVG), Ronald Reagan Washington National (DCA), Charlotte-Douglas Intl. (CLT) 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
Roundtrip price
CA $186
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 $186 rising to CA $260.  

Here are more money-saving tips: 

  • Fly in August 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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