Cheap flights from New York to Chicago

Compare New York to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from New York to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from New York to Chicago? Find the lowest prices on one-way and round-trip tickets right here.

Chicago.C$85 per passenger.Departing Tue, May 6, returning Tue, May 20.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from New York LaGuardia on Tue, May 6, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departing from Chicago O'Hare International on Tue, May 20, arriving in New York LaGuardia.Price includes taxes and charges.From C$85, select.

Chicago.C$87 per passenger.Departing Tue, Apr 22, returning Mon, May 5.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from New York LaGuardia on Tue, Apr 22, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departing from Chicago O'Hare International on Mon, May 5, arriving in New York LaGuardia.Price includes taxes and charges.From C$87, select.

Chicago.C$88 per passenger.Departing Tue, Apr 22, returning Tue, Apr 29.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from New York LaGuardia on Tue, Apr 22, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departing from Chicago O'Hare International on Tue, Apr 29, arriving in New York LaGuardia.Price includes taxes and charges.From C$88, select.

Chicago.C$116 per passenger.Departing Tue, May 20, returning Wed, Jun 4.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from New York LaGuardia on Tue, May 20, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Wed, Jun 4, arriving in New York LaGuardia.Price includes taxes and charges.From C$116, select.

Chicago.C$135 per passenger.Departing Sat, May 31, returning Wed, Jun 4.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from New York Newark on Sat, May 31, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departing from Chicago O'Hare International on Wed, Jun 4, arriving in New York LaGuardia.Price includes taxes and charges.From C$135, select.

Chicago.C$155 per passenger.Departing Sun, May 25, returning Sat, Sep 20.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from New York Newark on Sun, May 25, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departing from Chicago O'Hare International on Sat, Sep 20, arriving in New York Newark.Price includes taxes and charges.From C$155, select.

Chicago.C$155 per passenger.Departing Thu, Jun 5, returning Tue, Jun 17.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from New York Newark on Thu, Jun 5, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departing from Chicago O'Hare International on Tue, Jun 17, arriving in New York Newark.Price includes taxes and charges.From C$155, select.

Chicago.C$155 per passenger.Departing Tue, Nov 11, returning Thu, Nov 13.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from New York Newark on Tue, Nov 11, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departing from Chicago O'Hare International on Thu, Nov 13, arriving in New York Newark.Price includes taxes and charges.From C$155, select.

Find the cheapest month to fly from New York to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like New York to Chicago flights are currently cheapest in May.

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Direct flights from New York to Chicago

Alternative New York to Chicago routes

Looking for the cheapest, fastest or easiest route from New York to Chicago? You could fly into the following airports instead.

New York to Chicago: Flight information

The things to know before you go.

Cheapest flight found	C$85
Cheapest month to fly	May
Average flight time	2 hrs, 43 mins
Most popular airline	American Airlines
Average flights per week	1,738

Finding cheap flights from New York to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are round-trip flights from New York to Chicago?

The best price we found for a round-trip flight from New York to Chicago is C$85. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from New York to Chicago?

2 hours and 43 minutes is the average flight time from New York to Chicago.

Which airlines fly direct from New York to Chicago?

American Airlines, Alaska Airlines and United fly direct from New York to Chicago.

How many flights are there a week from New York to Chicago?

There are 1,738 flights per week flying from New York to Chicago, as of March 2025.

When is the cheapest time to fly from New York to Chicago?

The cheapest month to fly from New York to Chicago is usually March 2025.

What's the cheapest airport to fly to in Chicago?

If you're flying from New York, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the center of Chicago. We've found flights to this airport from C$85.

Which upcoming date is cheapest to fly from New York to Chicago on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from New York to Chicago on Tuesday, May 6, 2025.

Can I get a direct flight from New York to Chicago?

Yes – the average flight time is 2 hours and 43 minutes.

How can I get the best flight deal from New York to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly with from New York to Chicago?

The cheapest airline that flies to Chicago is Spirit Airlines.

Ready for that fun filled vacation from New York to Chicago? Let Skyscanner help you find the best route and the cheapest airfare between these two mega cities. New York has three airports to depart from and Chicago has two to welcome you. With all these routes, it makes sense to get a little online help. Check out hotel and car rental deals while you're at it.

Best time to Book a Flight to Chicago

Chicago is busiest between April and August. You can usually save money, even during the summer, by flying Tuesdays through Thursdays. Skyscanner's Whole Month Search program comes in handy. Pull up an entire month's airfares to see which dates have the cheapest rates. Find a great rate? Book it, the earlier the better. Being flexible on your travel dates can save you money.

Airlines that Fly from New York to Chicago

Spirit Airlines tends to have the cheapest fares, leaving from La Guardia and arriving into Chicago O'Hare. American Airlines also flies this route. Both carriers offer non-stop service. JetBlue and Delta Airlines are competitively priced out of Kennedy Airport, Both airlines sell code share tickets, where you purchase a fare from one carrier and fly at least one flight on a partner carrier. JetBlue, for example, code shares with Spirit Airlines so you could fly to Chicago out of La Guardia and back into Kennedy. This route is not only a code share, but an open jaw, flying out of one airport and back into another. Non-stops are still the norm. Southwest Airlines, also offering non-stops, tends to fly into Chicago Midway from either New York airport.

Departure Airports in New York

La Guardia International (LGA) is 26 kilometres from Manhattan, about an hour's drive. Taxis can run upwards of $70.00 CAD, while the Airport Shuttles are roughly half that if you book them round trip. Domestic flights leave from both the North and South Terminals.

John F. Kennedy International (JFK) is 29 kilometres from downtown and roughly a $90.00 CAD taxi ride. Shuttle rates are a bit more than from La Guardia. JFK has six operating terminals. Your flight could leave from any of them except Terminal 4, which is dedicated to international flights.

Newark International (EWR) is technically in New Jersey. It's about 25 kilometres from Manhattan, about a $70.00 CAD taxi ride. Shuttle rates are similar to those at La Guardia. Flights to Chicago may leave from any of its three terminals.

All three airports offer free Wi-Fi, a selection of name-brand and local shops, restaurants, fast food outlets and plenty of ATMs.

Arrival Airports in Chicago

Passengers arriving at Chicago Midway will find themselves about 13 kilometres from downtown Chicago, which is about a 30-minute drive. A taxi ride to downtown runs about $40.00 CAD, while the CTA "L" Train Orange Line can get you there for about $5.00 CAD. Midway has one Main Terminal with three concourses. Depending on your airline, you could end up at any one of them.

Chicago O'Hare International is much larger and about 29 kilometres from downtown. Domestic flights use three out of the four terminals. A taxi ride costs about $55.00 CAD into downtown, depending on the distance. The CTA Blue Line connects all three domestic terminals and gets you downtown for about $5.00 CAD.

Both airports have their share of restaurants, delis, fast food outlets, boutique shops and sundry stores. O'Hare has a much larger selection. ATMs are found throughout both airports. Wi-Fi is free.

What to See and Do in Chicago

Deep dish Chicago pizza. Fully loaded all-beef hot dogs in steamed poppy-seed buns. Both are not-to-be-missed delights. Chicago is a city of both fun and sophistication. Millenium Park is a perfect blend of both. This open green space is filled with shops, art displays and has its own theatre and ice rink. Navy Pier, a 1,200-metre long structure jutting out from the Chicago shoreline, features restaurants, carnival rides, shops and regular fireworks shows.

Downtown you'll find The Art Institute of Chicago, home to works by Monet, Gauguin, Picasso and more. A few blocks away is the Chicago Tribune building. Embedded along its outer walls are bits of history, including a piece of the Berlin Wall, a chunk of the Taj Mahal and relics from each of the 50 States.

Interested in dinosaurs? The Field Museum of Natural History has the largest skeleton of a T-Rex ever found. Next door, the Shedd Aquarium features creatures from around the globe, displayed in recreated natural habitats. For a bird's eye view of Chicago and beyond, head for the Hancock Building. The observation deck sits more than 320 metres above the city streets below.