Cheap flights New York — Chicago
The cheapest ticket
Frontier Airlines
06:05 - 16:07
11 hr 2 min. on the way
03 Dec, 2026
With connections
New York (EWR) — Chicago (MDW)
The cheapest ticket from New York to Chicago, found by users in the last 48 hr. Flight ticket prices are dynamic and may vary.
Ticket prices by month for 2026-2027
How much do airline tickets cost New York - Chicago depending on the month of departure.
month
one-way
price
round-trip
price
January
19 Jan, Tue
18 Jan, Mon - 01 Feb, Mon
February
-
March
-
11 Mar, Thu - 16 Mar, Tue
April
-
May
-
June
-
July
-
August
-
September
-
October
-
November
-
20 Nov, Fri - 23 Nov, Mon
December
19 Dec, Sat
03 Dec, Thu - 09 Dec, Wed
Airfare prices found by users in the last 48 hours. Flight ticket prices are dynamic and may vary.
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 november, our users found direct and connecting flights from popular airlines such as:
Round-trip airline tickets: New York - Chicago - New York
$226 - is the minimum round-trip ticket price, from New York to Chicago, found by our users recently.
$158 - 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's the best time to buy a flight ticket?
The best time to buy a flight ticket New York – Chicago — is 1 day before departure. And the most expensive time to buy a ticket is 8 days before departure.
Plan your trip well and start tracking ticket prices in advance. This way, you will have a better chance of finding the best flight from New York to Chicago.
What is the best day to fly out?
According to the search statistics on tripmydream, the most affordable day of departure to Chicago — Wednesday.
What time of day is the cheapest flight?
The cheapest flights to Chicago depart in the night.
Flight information
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 226 $
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
| Month | Day | Night |
|---|---|---|
| January | 7° | -15° |
| February | 9° | -14° |
| March | 14° | -8° |
| April | 20° | -2° |
| May | 26° | 5° |
| June | 32° | 10° |
| July | 35° | 13° |
| August | 34° | 12° |
| September | 30° | 8° |
| October | 23° | 1° |
| November | 16° | -6° |
| December | 11° | -11° |
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 226 USD for a round trip.
When is the best time to purchase an airplane ticket New York – Chicago?
The cheapest air tickets New York - Chicago are to be bought 22 days before departure.
When airplane tickets New York – Chicago are the cheapest?
January, February, March – months when airplane tickets from New York to Chicago will be cheapest. The most favorable day of departure is Wednesday, and the cheapest time is night.
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