S$ 38 Cheap Flights from New York to Chicago (NYC-CHI)

Cheap Flights from New York to Chicago

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Cheap Flights from New York to Chicago starting at CNY 38

We've found these cheap flights for you. You can book one-way or return flight tickets.

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Cheapest time to fly from New York to Chicago

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.

Cheapest Airlines flying from New York to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines

From S$ 71

Southwest Airlines

From S$ 86

Spirit Airlines

From S$ 96

Sun Country Airlines

From S$ 126

Jetblue Airways

From S$ 139

American Airlines

From S$ 139

Delta Air Lines

From S$ 153

Breeze Airways

From S$ 170

United Airlines

From S$ 179

Alaska Airlines

From S$ 479

ANA airlines

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Alternative Routes from New York to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from New York to Chicago.

Cheapest
LGA
08:35
2h 39m
Direct
ORD
10:14
New York LaGuardia Airport - O'Hare International Airport
Wed, May 15Spirit Airlines
S$ 44
EWR
11:31
7h 9m
1 transfer
ORD
17:40
Newark Liberty International Airport - O'Hare International Airport
Tue, May 21Spirit Airlines
S$ 67
LGA
12:29
8h 50m
1 transfer
MDW
20:19
New York LaGuardia Airport - Midway International Airport
Sat, May 4Frontier Airlines
S$ 104
LGA
12:29
8h 50m
1 transfer
MDW
20:19
New York LaGuardia Airport - Midway International Airport
Sat, May 4Frontier Airlines
S$ 104
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Frequently Asked Questions

When to buy flight tickets from New York (NYC) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from New York to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much is a flight from New York (NYC) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around S$ 283.
How long is a flight from New York (NYC) to Chicago (CHI)?
It takes about 2 hours 41 minutes to fly from New York (NYC) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
What time does the earliest flight from New York to Chicago depart?
The earliest flight departs from New York (LGA) at 06:00 and arrives in Chicago (ORD) at 07:42.
What time does the latest flight from New York to Chicago depart?
The latest flight departs from New York (EWR) at 21:59 and arrives in Chicago (ORD) at 23:37.
What are the most popular airlines that fly from New York (NYC) to Chicago (CHI)?
Airlines with flights from New York (NYC) to Chicago (CHI): KLM, Air New Zealand, Southwest Airlines, Royal Jordanian, American Airlines, Westjet, United Airlines, Air Canada, Spirit Airlines, Jetblue Airways and LATAM Airlines.
What's the most popular airline for direct flights from New York (NYC) to Chicago (CHI)?
Jetblue Airways operates 27 direct flights from New York (NYC) to Chicago (CHI).
How many airports in Chicago?
There are 5 airports near Chicago: O'Hare International Airport, Chicago Du Page County Airport, Midway International Airport, Chicago Palwaukee Airport and Chicago Rockford International Airport.

How to find a cheap flight from New York to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from New York to Chicago. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

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Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

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Find cheapest flight ticket from New York to Chicago

Cheapest direct flight price	S$ 38
Cheapest return ticket price	S$ 71
Cheapest month	March
Peak season for travel	October
Flight distance	1,145.24km
Average flight time	2 hours 41 minutes
Popular airline	American Airlines