Cheap flights from New York to Chicago from $42

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Cheap New York - Chicago flight offers

Find cheap flight tickets and last-minute flight deals from New York to Chicago

DELTA
Tue, 07/21 (NYC) New York City -> (CHI) Chicago
Direct
DELTA
Thu, 08/06 (CHI) Chicago -> (NYC) New York City
Direct

Price found 5 days ago
from $55
United
Sat, 09/19 (NYC) New York City -> (CHI) Chicago
Direct
United
Tue, 09/22 (CHI) Chicago -> (NYC) New York City
Direct

Price found 9 days ago
from $59
Southwest Airlines
Tue, 08/11 (NYC) New York City -> (CHI) Chicago
Direct
Southwest Airlines
Fri, 08/14 (CHI) Chicago -> (NYC) New York City
Direct

Price found 3 days ago
from $66
United
Sun, 09/13 (NYC) New York City -> (CHI) Chicago
Direct
United
Wed, 09/16 (CHI) Chicago -> (NYC) New York City
Direct

Price found 10 days ago
from $86
Southwest Airlines
Wed, 07/29 (NYC) New York City -> (CHI) Chicago
Direct
Southwest Airlines
Sat, 08/01 (CHI) Chicago -> (NYC) New York City
Direct

Price found 12 days ago
from $88
Southwest Airlines
Thu, 08/20 (NYC) New York City -> (CHI) Chicago
Direct
Southwest Airlines
Sat, 08/22 (CHI) Chicago -> (NYC) New York City
Direct

Price found 2 days ago
from $90
American Airlines
Fri, 07/10 (NYC) New York City -> (CHI) Chicago
Direct
American Airlines
Sun, 07/12 (CHI) Chicago -> (NYC) New York City
Direct

Price found 8 days ago
from $97
Southwest Airlines
Fri, 07/24 (NYC) New York City -> (CHI) Chicago
Direct
Southwest Airlines
Sun, 07/26 (CHI) Chicago -> (NYC) New York City
Direct

Price found 13 days ago
from $98
DELTA
Thu, 10/01 (NYC) New York City -> (CHI) Chicago
Direct

Price found 8 days ago
from $39
JetBlue Airways
Tue, 07/07 (NYC) New York City -> (CHI) Chicago
Direct

Price found 9 days ago
from $42
Frontier Airlines
Wed, 07/29 (NYC) New York City -> (CHI) Chicago
Direct

Price found 8 days ago
from $44
DELTA
Sat, 06/27 (NYC) New York City -> (CHI) Chicago
Direct

Price found Yesterday
from $54
American Airlines
Sun, 06/28 (NYC) New York City -> (CHI) Chicago
Direct

Price found 13 days ago
from $57
DELTA
Fri, 08/28 (NYC) New York City -> (CHI) Chicago
Direct

Price found 11 days ago
from $76
Southwest Airlines
Tue, 06/30 (NYC) New York City -> (CHI) Chicago
Direct

Price found 6 days ago
from $80
JetBlue Airways
Thu, 07/02 (NYC) New York City -> (CHI) Chicago
Direct

Price found 2 days ago
from $91
DELTA
Tue, 07/21 (NYC) New York City -> (CHI) Chicago
Direct
DELTA
Thu, 08/06 (CHI) Chicago -> (NYC) New York City
Direct

Price found 5 days ago
from $55
United
Sat, 09/19 (NYC) New York City -> (CHI) Chicago
Direct
United
Tue, 09/22 (CHI) Chicago -> (NYC) New York City
Direct

Price found 9 days ago
from $59
Southwest Airlines
Tue, 08/11 (NYC) New York City -> (CHI) Chicago
Direct
Southwest Airlines
Fri, 08/14 (CHI) Chicago -> (NYC) New York City
Direct

Price found 3 days ago
from $66
United
Sun, 09/13 (NYC) New York City -> (CHI) Chicago
Direct
United
Wed, 09/16 (CHI) Chicago -> (NYC) New York City
Direct

Price found 10 days ago
from $86
Southwest Airlines
Wed, 07/29 (NYC) New York City -> (CHI) Chicago
Direct
Southwest Airlines
Sat, 08/01 (CHI) Chicago -> (NYC) New York City
Direct

Price found 12 days ago
from $88
Southwest Airlines
Thu, 08/20 (NYC) New York City -> (CHI) Chicago
Direct
Southwest Airlines
Sat, 08/22 (CHI) Chicago -> (NYC) New York City
Direct

Price found 2 days ago
from $90
American Airlines
Fri, 07/10 (NYC) New York City -> (CHI) Chicago
Direct
American Airlines
Sun, 07/12 (CHI) Chicago -> (NYC) New York City
Direct

Price found 8 days ago
from $97
Southwest Airlines
Fri, 07/24 (NYC) New York City -> (CHI) Chicago
Direct
Southwest Airlines
Sun, 07/26 (CHI) Chicago -> (NYC) New York City
Direct

Price found 13 days ago
from $98

Info about flights from New York to Chicago

Some useful info about flights from New York to Chicago to help you plan your next trip

Best price last 15 days $42
Average flight duration 2h 22m
Cheapest month February
Average number of flights per week 126
First flight time 00:15
Last flight time 23:05

When is it best to fly from New York to Chicago

Find out what is the best time of year to fly from New York to Chicago

Jun $112
Jul $97
Aug $78
Sep $92
Oct $98
Nov $335
Dec $88
Jan $69
Feb $56
Mar $83
Apr $84
May $89
Most expensive month November
Average price $335
Cheapest month February
Average price $56
How do we get the info you see here? Please note that we offer an online comparison service and that all information and prices regarding services and/or products available on our website are provided by our third-party partners. We do our best to show you up-to-date information, but please note that we are not responsible for the completeness or accuracy of the information published, so please check all conditions carefully on the website of the partner before making a booking. Please check our Terms and Conditions for more details. Read more

Top airlines on the route New York - Chicago

Airlines providing flights to Chicago from New York

Find cheap flights from New York to Chicago in a few seconds with Jetcost

At only two hours and ten minutes flying time, these are cities that are ideal for a week end break for Culture, or just to eat some wonderful food, shop and relax. However, try this selection of ideas in Chicago to make the most of your stay and your cheap flights from New York to Chicago:

  • 'Millennium Park' is a great place to check out modern architecture and lovely flowers.
  • 'The Adler' planetarium is a great way to learn about the solar system.
  • 'The Museum of Contemporary Art' houses some of the USA 's finest works.
  • 'Michigan Avenue and the Magnificent Mile' is stylish, great for luxury shopping.
  • The view from the top of the 'Willis 110 floor tower' is spectacular.
Some of Chicago''s appeal has to be that it's set on a lake, so water activities feature but also this is a city that has some truly dazzling skyscrapers so just strolling around is a good time. Flights to ChicagoThere's also some very up market luxury hotels and for good packages take a look at hotels in Chicago and you will definitely find a good deal. There's also some wonderful events and theatres to enjoy, so perhaps book some tickets ahead, along with your New York to Chicago flights, to make the most of your stay!

All flights from New York to Chicago arrive into either O Hare International Airport, or Midway Airport. Many easy transport options are available, but why not consider car hire? Take a look at car rental in Chicago for good deals on all kinds of cars, so you can enjoy this city at your own pace.

Frequently Asked Questions

Frequently asked questions about flights from New York to Chicago.

How much does an airline ticket from New York to Chicago cost?

The lowest price recorded in the last 15 days for a flight from New York to Chicago is $42.

How far is New York City from Chicago?

New York City is about 714 mi from Chicago.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the airports in New York City?

New York City has 3 airports: John F. Kennedy, La Guardia, Newark.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Atlanta, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from New York City to Chicago?

The best time to book a flight from New York City to Chicago is 3 months in advance, while the worst time is 1 week in advance.

What is the cheapest month to fly from New York City to Chicago?

The cheapest month to fly from New York City to Chicago is February.

What is the most expensive month to fly from New York City to Chicago?

The most expensive month to fly from New York City to Chicago is November.

What is the best day of the week to fly from New York City to Chicago?

For flights from New York City to Chicago Tuesday is on average the cheapest day to fly, while Saturday is the most expensive day to fly.