Cheap Flights from Gary (GYY) to Chicago (PWK)

Popular airlines from Gary, IN (GYY-Gary - Chicago Intl.) to Chicago, IL (PWK-Chicago Executive)

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Frequently asked questions

How much does a flight from Gary, IN (GYY-Gary - Chicago Intl.) to Chicago Executive Airport (PWK) cost?
Secure a cheap one-way flight or cheap return flight from Gary, IN (GYY-Gary - Chicago Intl.) 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 Gary, IN (GYY-Gary - Chicago Intl.) to Chicago Executive Airport (PWK)?
The cheapest month to fly from GYY to PWK is , when there's less demand. Off-peak months are typically when you'll find lower airfares between these airports.
What is the cheapest airline that flies from Gary, IN (GYY-Gary - Chicago Intl.) to Chicago Executive Airport (PWK)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest GYY to PWK flight.
How many flights per day from Gary, IN (GYY-Gary - Chicago Intl.) to Chicago Executive Airport (PWK)?
You'll need to catch a flight with a layover when traveling from Gary, IN (GYY-Gary - Chicago Intl.) to Chicago Executive Airport (PWK). There are no daily direct flights on this route. However, just filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from GYY to PWK?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can vary depending on a range of factors, such as 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 Gary, IN (GYY-Gary - Chicago Intl.) to Chicago Executive Airport (PWK)?
To land at Chicago Executive Airport (PWK) without delays, choose a flight that leaves from Gary, IN (GYY-Gary - Chicago Intl.) before 3 PM. The chance 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 Gary, IN (GYY-Gary - Chicago Intl.) to Chicago Executive Airport (PWK) last-minute?
Waiting until right before your break to book a ticket from GYY to PWK often results in higher prices. While it's possible to find some last-minute deals, they aren't always guaranteed. Keep your travel plans flexible to maximize your chances of getting a bargain.
Is it cheaper to book a GYY to PWK flight and hotel package?
Booking a GYY to PWK flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Pick from our extensive range of stays and then add flights, car rentals and activities 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 Gary, IN (GYY-Gary - Chicago Intl.) to Chicago Executive Airport (PWK)?
Typically, you can reschedule or cancel your GYY to PWK flight. However, additional fees may apply, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's guidelines and fees on flight changes, or if you want further information, head to our Customer Service portal.

Travel information

Origin airport
Gary - Chicago Intl.
Destination airport
Chicago Executive
Distance
42 mi

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Gary to Chicago Flights

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

 

The best time to book a flight from Gary to Chicago

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

 

Gary to Chicago Flights

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*Available to One Key members.