When to buy flight tickets from New York (NYC) to Chicago (CHI) the cheapest?

Airlines adjust prices for flights from New York⇒Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest 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$309.

How long is a flight from New York (NYC) to Chicago (CHI)?

It takes about 2 hours 44 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 07:53.

What time does the latest flight from New York to Chicago depart?

The latest flight departs from New York (LGA) at 21:35 and arrives in Chicago (MDW) at 22:55.

What's the most popular airline for non-stop flights from New York (NYC) to Chicago (CHI)?

Delta Air Lines operates 69 non-stop flights from New York (NYC) to Chicago (CHI).

What are some travel guidelines for Chicago during the COVID19 pandemic?

Entry restrictions and flight schedule changes and cancellations are frequently updated and subject to change. If you plan to travel to Chicago, please obtain the most updated information from the airline you plan to book your travels with. You can also refer to COVID19 Country/Region Entry Restrictions for more information.

Which airlines offer free date changes for flights to this city during the COVID19 pandemic?

There are no airlines with flights to this city that provide this service. Please use this information as a reference only and confirm with the airline prior to booking.

✈️Cheap Flights from New York(NYC) to Chicago(CHI)

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Cheap Flights from New York to Chicago

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

Flight Price Trends for the Coming 12 Weeks

New York (NYC) to Chicago (CHI)

814
1521
2228
Sep
294
511
1218
1925
Oct
262
39
1016
1723
2430

Flight Information from New York to Chicago

Cheapest return ticket price	S$208
Cheapest direct flight price	S$71
Peak season for travel	November
Off-season for travel	March

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⇒Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest 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$309.
How long is a flight from New York (NYC) to Chicago (CHI)?
It takes about 2 hours 44 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 07:53.
What time does the latest flight from New York to Chicago depart?
The latest flight departs from New York (LGA) at 21:35 and arrives in Chicago (MDW) at 22:55.
What's the most popular airline for non-stop flights from New York (NYC) to Chicago (CHI)?
Delta Air Lines operates 69 non-stop flights from New York (NYC) to Chicago (CHI).
What are some travel guidelines for Chicago during the COVID19 pandemic?
Entry restrictions and flight schedule changes and cancellations are frequently updated and subject to change. If you plan to travel to Chicago, please obtain the most updated information from the airline you plan to book your travels with. You can also refer to COVID19 Country/Region Entry Restrictions for more information.
Which airlines offer free date changes for flights to this city during the COVID19 pandemic?
There are no airlines with flights to this city that provide this service. Please use this information as a reference only and confirm with the airline prior to booking.

Plan Your Trip from New York to Chicago
Chicago attracts thousands of visitors every year for both business and pleasure. Whether you’re taking a last-minute break or a much needed getaway, flights from New York to Chicago on Trip.com can help you get there with ease. With Trip.com, you can browse popular airlines with flights to Chicago, check the best season to visit, and preview Chicago attractions before you arrive. With flight deals and exciting attractions waiting for you to explore in Chicago, the best time to book flights from New York to Chicago is now! Planning a trip from New York to Chicago is easy when you use Trip.com to help you make travel arrangements. Whether you are flying one-way, non-stop, or round-trip, you will find just the flight you need with us. If you want to lock in a great deal for your flights, go for a round-trip flight, if you need flexibility with your itinerary, book a one-way flight to Chicago. With Trip.com, you can search for available flights and hotel rooms, and then make your booking quickly and easily online and on the go. Pack your travel accessories, make a must-see bucket list, and book your flight to Chicago on Trip.com today!
A Trip to Remember (NYC—CHI)
Make your journey from New York (NYC) to Chicago (CHI) a trip to remember by using Trip.com to view Chicago attractions before you arrive. Once you know what to do in Chicago, you can reserve and book in advance for the best travel experience possible. Planning ahead is the most effective way to ensure your whole travel experience goes smoothly. Whether you need help choosing the perfect restaurant, discovering the best places to try local flavors, or finding the most stunning views in town, Trip.com is with you every step of the way for your trip to Chicago.

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