Cheap Flights from Tri-Cities (TRI) to Chicago (PWK)

Popular airlines from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (PWK-Chicago Executive)

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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. Average driving time to city center is 23 minutes. Flights from $295
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $295
Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $244
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $244

Frequently asked questions

How much does a flight from Tri-Cities Regional Airport (TRI) to Chicago Executive Airport (PWK) cost?
Get a cheap one-way flight or cheap return flight from Tri-Cities Regional Airport (TRI) 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 Tri-Cities Regional Airport (TRI) to Chicago Executive Airport (PWK)?
is the most affordable month to fly from TRI to PWK. Traveling during quieter months is often the key to finding better deals on flights.
What is the cheapest airline that flies from Tri-Cities Regional Airport (TRI) to Chicago Executive Airport (PWK)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest TRI to PWK flight.
How many flights per day from Tri-Cities Regional Airport (TRI) to Chicago Executive Airport (PWK)?
You'll need to hop on a flight with a layover if you're traveling from Tri-Cities Regional Airport (TRI) to Chicago Executive Airport (PWK). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to find an option that works for you.
What day of the week has the most flights from TRI to PWK?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change based on a number of 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 Tri-Cities Regional Airport (TRI) to Chicago Executive Airport (PWK)?
To reach Chicago Executive Airport (PWK) on schedule, pick a flight that leaves from Tri-Cities Regional Airport (TRI) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Tri-Cities Regional Airport (TRI) to Chicago Executive Airport (PWK) last-minute?
Booking your plane ticket from TRI to PWK right before your journey is usually more expensive. But if there's some wiggle room with your departure dates and times, you could land a cheap last-minute fare.
Is it cheaper to book a TRI to PWK flight and hotel package?
Opting for a TRI to PWK flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Pick from our impressive range of hotels and then add activities, flights and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Tri-Cities Regional Airport (TRI) to Chicago Executive Airport (PWK)?
If you booked your TRI to PWK flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Tri-Cities Regional
Destination airport
Chicago Executive
Distance
487 mi

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Tri-Cities to Chicago Flights

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

 

The best time to book a flight from Tri-Cities to Chicago

Sunday is one of the best days to book for cheap flights from Tri-Cities 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 Tri-Cities 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 Tri-Cities to Chicago in 2026. 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 Tri-Cities 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 Tri-Cities 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.

 

Tri-Cities to Chicago Flights

*Flight schedules are subject to change.

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