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

Save on Flight Bookings!

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save on select hotels after you book a flight*

  • Find the right fit

    We search billions of combinations of flights to help you find your next adventure

Frequently asked questions

Is it cheaper to buy a plane ticket from GYY to PWK last minute?
Booking your journey from GYY to Chicago Executive Airport (PWK) at the last minute could save you dollars if you get lucky and find an awesome deal. However, fares don't usually get cheaper as the departure date nears. If you take a wait-and-see approach, flights could also be booked up or the best seats taken (we hope you like the middle seat!). If you'd rather not take any chances, book well in advance of your departure date. Remember that some of the most awesome deals can be found up to a year in advance. If your favorite airline hasn't released its airfares yet, check back regularly as deals are updated on Expedia all the time.
What airports do you fly into for Chicago from Gary?
From Gary, you can journey to Chicago through Chicago Executive Airport (PWK), O'Hare Intl. Airport (ORD) and Midway Intl. Airport (MDW). Be sure to check which airport is the most convenient for you before making your decision. If you go with Chicago Executive Airport (PWK), it's roughly 32 kilometers northwest of the downtown area. Use the dollars you save when booking your seat with Expedia to experience the city's awesome sights, such as Wrigley Field and Millennium Park.
Can I change the date of my flight from GYY to Chicago Executive Airport?
We know life happens and plans change, so Expedia is here to help make amending your journey as easy as possible. To start, find your GYY to PWK itinerary through the Expedia Trips portal and check the fare conditions and rules about what sorts of changes are allowed. If you booked your airfare in the last 24 hours, some carriers allow you to cancel at no cost and book new flights. If you bought your fare more than 24 hours ago, get in touch with us via our Customer Service portal so we can help you further.

Travel information

Origin airport
Gary - Chicago Intl.
Destination airport
Chicago Executive
Distance
68 km

Book with confidence

Gary to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Gary to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Gary to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Gary to Chicago Flights