Cheap Flights from New York (LGA) to Chicago (PWK)

Popular airlines from LaGuardia Airport (LGA) 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. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $154
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $154
Flights from New York (LGA) to Chicago (PWK)
Origin airport
LaGuardia
Destination airport
Chicago Executive
Distance
731 mi

New York to Chicago Flights

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

 

The best time to book a flight from New York to Chicago

Sunday is one of the best days to book for cheap flights from New York 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 New York 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 New York 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 New York 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 New York 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 LaGuardia Airport (LGA) to Chicago Executive Airport (PWK) cost?
Lock in a cheap one-way flight or cheap return flight from LaGuardia Airport (LGA) 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 LaGuardia Airport (LGA) to Chicago Executive Airport (PWK)?
The cheapest month to fly from LGA to PWK is , when there's less demand. Off-peak months are generally when better flight deals are available between these airports.
What is the cheapest airline that flies from LaGuardia Airport (LGA) to Chicago Executive Airport (PWK)?
To find the cheapest airline flying from LGA to PWK, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from LaGuardia Airport (LGA) to Chicago Executive Airport (PWK)?
You'll have to take a flight with a layover when traveling from LaGuardia Airport (LGA) 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 find an option that works for you.
What day of the week has the most flights from LGA to PWK?
Generally you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from LaGuardia Airport (LGA) to Chicago Executive Airport (PWK)?
Choose a flight from LaGuardia Airport (LGA) to Chicago Executive Airport (PWK) that takes off before 3 PM to reduce the risk of cancellations. Departures after this time are on average 22% more likely to be canceled.**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 LaGuardia Airport (LGA)?
Take a direct flight from LaGuardia Airport (LGA) to Chicago and arrive at O'Hare Intl. Airport (ORD). An alternative entry point into this destination is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from LaGuardia Airport (LGA) to Chicago Executive Airport (PWK) last-minute?
Booking your ticket from LGA to PWK just before your journey is usually more expensive. However, if you're flexible with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book a LGA to PWK flight and hotel package?
You'll generally save money by securing a LGA to PWK flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After choosing your ideal flights and accommodations, consider adding extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from LaGuardia Airport (LGA) to Chicago Executive Airport (PWK)?
If you booked your LGA 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 fare type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you want more information.

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*Available to One Key members.