Cheap flights New York — Chicago
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Find tickets to Chicago
The cheapest ticket
Spirit
21:33 - 23:10
4 hr 37 min. on the way
28 May, 2025
Direct
New York (EWR) — Chicago (ORD)
-65%
63 $ The cheapest ticket from New York to Chicago, found by users in the last 48 hr. Flight ticket prices are dynamic and may vary.
Discounts and promotions on airline tickets New York - Chicago
The discount is calculated with respect to the average of the minimum prices for the last 3 months.
Buy tickets from New York to Chicago
Tripmydream will help you find and buy plane tickets from New York to Chicago at the cheapest price. With our service you can easily compare offers from different airlines, find the most convenient and favourable flights, and find out from which online seller it will be cheapest to buy the chosen ticket.
For the march, our users found direct and connecting flights from popular airlines such as:
Spirit
from 63$
Frontier Airlines
from 96$
American Airlines
from 152$
Jet Blue
from 152$
United Airlines
from 153$
Delta
from 162$
Southwest Airlines
from 176$
Round-trip airline tickets: New York - Chicago - New York
$63 - is the minimum round-trip ticket price, from New York to Chicago, found by our users recently.
$94 - lowest one-way ticket price.
You can find out exactly how much an air ticket for New York - Chicago costs by looking at the ticket price for specific dates and then going to the online seller's website. Prices in our airfare comparison platform are updated with a slight delay and may change in the meantime.
What is the best day to fly out?
According to the search statistics on tripmydream, the most affordable day of departure to Chicago — Monday.
Flight information
Airlines
Popular airlines operating flights New York - Chicago:
Direct flights
Direct flights from New York to Chicago operated by airlines United Airlines (Tuesday, Wednesday, Friday, Saturday), Jet Blue (Tuesday, Wednesday, Friday, Saturday), Delta (Tuesday, Wednesday, Friday, Saturday)
Delta Mon
Tue
Wed
Thu
Fri
Sat
Sun
Jet Blue Mon
Tue
Wed
Thu
Fri
Sat
Sun
United Airlines Mon
Tue
Wed
Thu
Fri
Sat
Sun
Airline Alliances
Flights from New York to Chicago are operated by airline alliances:
Change
Direct flights are the most convenient and fastest way to travel to anywhere. But if the cheapest ticket is important to you, we recommend you to look at flights from New York to Chicago with connections: in most cases, indirect flights take longer, but you can save a lot of money.
With connections
from 96 $
Direct
from 63 $
Aircraft types
Popular aircraft types on flights New York - Chicago:
Boeing 737
from 153 $
Airbus A330
from 176 $
Information about Chicago
Gangsters, mafia clans, gangsters and, of course, Al Capone. This is what Chicago is associated with thanks to famous Hollywood movies. But we hasten to reassure you: all this is in the distant past. Today Chicago (or just Chi, as locals call it) is a city of stunning architecture, green parks, great beaches and all kinds of museums. But for those who come here for the gangster romance, there's plenty to see, too.
Chicago: prices, weather and transport
What else you should know before flying from New York to Chicago
Weather in Chicago
FAQs about traveling to Chicago
Useful information, statistics and facts about the flight from New York to Chicago
How much is the cheapest ticket from New York to Chicago?
Cheapest flight ticket from New York to Chicago, found by our users in the last 48 hours, costs 63 USD for a round trip.
When is the best time to purchase an airplane ticketNew York – Chicago?
The cheapest air tickets New York - Chicago are to be bought days before departure.
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