Cheap Flights from Waukegan (UGN) to Chicago (PWK)

Popular airlines from Waukegan, IL (UGN-Waukegan Regional) to Chicago, IL (PWK-Chicago Executive)

Frequently asked questions

How much does a flight from Waukegan Regional Airport (UGN) to Chicago Executive Airport (PWK) cost?
Secure a cheap one-way flight or cheap return flight from Waukegan Regional Airport (UGN) to Chicago Executive Airport (PWK) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Waukegan Regional Airport (UGN) to Chicago Executive Airport (PWK)?
The cheapest month to fly from UGN to PWK is , when there's less demand. Off-peak months are often when airlines offer lower prices between these airports.
What is the cheapest airline that flies from Waukegan Regional Airport (UGN) to Chicago Executive Airport (PWK)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll take you from UGN to PWK. Then, sort your results by "Price (lowest to highest)" to snap up the best deal available.
How many flights per day from Waukegan Regional Airport (UGN) to Chicago Executive Airport (PWK)?
There aren't any daily nonstop flights from Waukegan Regional Airport (UGN) to Chicago Executive Airport (PWK). But you can opt for flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be cruising above the clouds before you know it.
What day of the week has the most flights from UGN to PWK?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Remember that flight schedules can vary depending on various factors, including the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Waukegan Regional Airport (UGN) to Chicago Executive Airport (PWK)?
To touch down at Chicago Executive Airport (PWK) on schedule, pick a flight that leaves Waukegan Regional Airport (UGN) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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.
Is it cheaper to buy a plane ticket from Waukegan Regional Airport (UGN) to Chicago Executive Airport (PWK) last-minute?
Booking your ticket from UGN to PWK just before your trip is typically more expensive. But if there's some wiggle room with your departure times and dates, you could grab a cheap last-minute fare.
Is it cheaper to book an UGN to PWK flight and hotel package?
Booking an UGN to PWK flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Choose from our extensive range of hotels and then add flights, car rentals and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Waukegan Regional Airport (UGN) to Chicago Executive Airport (PWK)?
Usually, it's possible to cancel or reschedule your UGN to PWK flight. However, for bookings made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Waukegan Regional
Destination airport
Chicago Executive
Distance
20 mi

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Waukegan to Chicago Flights

The cheapest times to fly from Waukegan 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 Waukegan to Chicago are during the month of . You can find some of the cheapest flights from Waukegan to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Waukegan to Chicago

Sunday is one of the best days to book for cheap flights from Waukegan 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 Waukegan 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 Waukegan 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 Waukegan 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 Waukegan 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.

 

Waukegan to Chicago Flights

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*Available to One Key members.