Cheap Flights from Detroit (DTW) to Chicago (PWK)

Popular airlines from Detroit Metropolitan Wayne County Airport (DTW) to Chicago, IL (PWK-Chicago Executive)

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 center is 23 minutes. Flights from $154
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $154
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $197
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $197
Flights from Detroit (DTW) to Chicago (PWK)
Origin airport
Detroit Metropolitan Wayne County
Destination airport
Chicago Executive
Distance
233 mi

Detroit to Chicago Flights

The cheapest times to fly from Detroit to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Detroit to Chicago are during the month of . You can find some of the cheapest flights from Detroit to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Detroit to Chicago

Sunday is one of the best days to book for cheap flights from Detroit to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Detroit to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Detroit to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Detroit to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Detroit to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Detroit Metropolitan Wayne County Airport (DTW) to Chicago Executive Airport (PWK) cost?
Get a cheap one-way flight or cheap return flight from Detroit Metropolitan Wayne County Airport (DTW) to Chicago Executive Airport (PWK) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Detroit Metropolitan Wayne County Airport (DTW) to Chicago Executive Airport (PWK)?
Planning your getaway for is a good way to save, as it's the cheapest month for flights between DTW and PWK. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from Detroit Metropolitan Wayne County Airport (DTW) to Chicago Executive Airport (PWK)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll take you from DTW to PWK. Then, sort your results by "Price (lowest to highest)" to snag a good deal.
How many flights per day from Detroit Metropolitan Wayne County Airport (DTW) to Chicago Executive Airport (PWK)?
There are no daily nonstop flights departing from Detroit Metropolitan Wayne County Airport (DTW) to Chicago Executive Airport (PWK). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be on your way before you know it.
What day of the week has the most flights from DTW to PWK?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Detroit Metropolitan Wayne County Airport (DTW) to Chicago Executive Airport (PWK)?
To avoid possible delays on the Detroit Metropolitan Wayne County Airport (DTW) to Chicago Executive Airport (PWK) route, aim to travel before 3 PM. Later flights have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Detroit Metropolitan Wayne County Airport (DTW)?
If you're leaving on a direct flight from Detroit Metropolitan Wayne County Airport (DTW) to Chicago, you can arrive at either O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Detroit Metropolitan Wayne County Airport (DTW) to Chicago Executive Airport (PWK) last-minute?
Last-minute bookings from DTW to PWK are typically more expensive. To lock in the best rates, start searching for flights as soon as possible. That being said, if your travel plans are flexible, you may find a cheap ticket right before your trip.
Is it cheaper to book a DTW to PWK flight and hotel package?
Compared with arranging flights and hotels separately, booking a DTW to PWK flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one easy place will take the stress out of planning your trip. Simply pick your flights and choose from our wide range of hotels, then personalize your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Detroit Metropolitan Wayne County Airport (DTW) to Chicago Executive Airport (PWK)?
Typically, it's possible to reschedule or cancel your DTW to PWK flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more information on our Customer Service portal.

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*Available to One Key members.