Best time to go: what is the RIGHT price for a round-trip flight to Chicago (from: New York City)

The average price to go to Chicago from New York City airport is $ 229 (round trip). However, there are variations depending on the departure month. Thus, it is possible to pay for your plane ticket on average between $ 185 (in january) and $ 279 (in june), which is a saving of $ 45 or a surplus of $ 50 (compared to the average price) depending on the period you leave.

The analysis of all the prices reveals that the most frequent price is between $162 to $215 and that it is generally more economical to leave on a wednesday and return on a tuesday on a direct flight.

Be careful, the cheapest months may correspond to unfavorable weather periods . Check out our page best time to go to Chicago before booking your flight.

If you want to know when to book your flight at the best price, go straight to the second part of this page: When to buy your New York City-Chicago plane ticket.

How are these data calculated?

We have studied a sample of 60304 airfare prices from previous years for flights to Chicago from New York City and can thus establish precise and credible price variation trends based on different parameters. Of course, prices can vary from year to year, but the seasonal aspect of this data (recurrence of school holidays, events... from year to year) makes these statistics quite reliable.

Average price depending on the departure month

Data analysis:

By leaving in january, the price of the plane ticket will statistically be the cheapest ($ 185, saving $ 45 compared to the average price over the year which is $ 229). Conversely, june will be the most expensive ($ 279).

Flight New York City-Chicago: when is the best time to go for the best price?

Month Good price* Average price Our opinion
January$ 156 $ 185 very good price
February$ 156 $ 187 good price
March$ 186 $ 215 fair price
April$ 187 $ 225 fair price
May$ 186 $ 217 fair price
June$ 238 $ 279 very high price
July$ 211 $ 275 high price
August$ 203 $ 245 fair price
September$ 170 $ 207 good price
October$ 187 $ 235 fair price
November$ 185 $ 227 fair price
December$ 184 $ 244 fair price

*great price to buy your plane ticket: if you see this price or cheaper during your flight search, go for it and buy it!

Price breakdown to travel from New York City to Chicago

Data analysis:

The prices for flights from New York City to Chicago range from $54 to $484. 4% of tickets were purchased at the minimum price (from $54 to $108), 1% at the maximum price (from $430 to $484). The majority of plane tickets were purchased in the range of $162 to $215 (40% of tickets).

Cheapest airlines for the New York City->Chicago flight

There are 10 companies that serve New York City from Chicago airport: United, Delta, jetBlue, Spirit Airlines, American Airlines, Air New Zealand, Frontier Airlines, ANA, TAP and Alaska Airlines.

Data analysis:

Of the 60304 flights analyzed in previous years, United was the airline that offered the best fare most often in the flight ticket search results (21% of the time) on the New York City->Chicago route.

Direct flight or flight with layover?

Data analysis:

To get the best price for the New York City-Chicago flight, you should take a direct flight (saving an average of $ 11 compared to a flight with one or more layovers).

Which day of the week to leave?

Data analysis:

Statistically, New York City-Chicago flights departing on a wednesday are cheaper than on other days of the week. By choosing a wednesday as your departure date, you can save an average of $18. On the other hand, departing on a sunday may cost you an additional $31.

Which day of the week to come back?

Data analysis:

Statistically, return flights from Chicago to New York City departing on a tuesday are cheaper than on other days of the week. By choosing a tuesday for your return date, you will save an average of $25. Conversely, departing from Chicago on a sunday may cost you an additional $27.


Top prices New York City-Chicago

Round tripDatesPrice
New York City → Chicago04-06 to 12-06-2024$ 75 
New York City → Chicago06-09 to 13-09-2024$ 89 
New York City → Chicago10-09 to 14-09-2024$ 90 
New York City → Chicago12-09 to 18-09-2024$ 90 
New York City → Chicago13-09 to 17-09-2024$ 89 
New York City → Chicago15-09 to 22-09-2024$ 90 
New York City → Chicago20-09 to 24-09-2024$ 90 
New York City → Chicago01-10 to 05-10-2024$ 90 
New York City → Chicago18-10 to 22-10-2024$ 89 
New York City → Chicago25-10 to 30-10-2024$ 90 


When to book your flight New York City - Chicago to get the cheapest price?

Statistically, you will make the biggest savings by buying your plane ticket between 1 to 2 months in advance. However, you may end up paying a high price if you book between 11 to 12 months in advance.

Did you know: the price of plane tickets not only varies depending on how far in advance you book, but also on the day of the week you book! So, to maximize your chances of getting the best price for a New York City-Chicago flight, it is recommended to book your ticket on a friday.

How far in advance should I buy my flight?

Data analysis:

To get the cheapest flight ticket from New York City to Chicago, it is recommended to buy it 1 to 2 months before departure (it is then on average 181 $, which is a saving of 48 $ compared to the overall average price). On the other hand, if you buy your ticket 11 to 12 months in advance, you will pay the full price (737 $ more than the average price).

Depending on the departure month

The best time to buy your New York City to Chicago flight ticket may vary depending on your departure month. Therefore, we offer you statistics on when to book your flight month by month.

Departure on... How far in advance should I book?
January

Best time: 1 to 2 months before departure (average price: 151 $)

Other interesting period(s): 2 to 3 months ($ 165)

February

Best time: 1 to 2 months before departure (average price: 143 $)

Other interesting period(s): 2 to 3 months ($ 153), 3 to 4 months ($ 181)

March

Best time: 1 to 2 months before departure (average price: 175 $)

Other interesting period(s): 0 to 1 month ($ 203), 2 to 3 months ($ 183), 3 to 4 months ($ 199)

April

Best time: 1 to 2 months before departure (average price: 181 $)

Other interesting period(s): 0 to 1 month ($ 218), 2 to 3 months ($ 199), 3 to 4 months ($ 192), 4 to 5 months ($ 214)

May

Best time: 1 to 2 months before departure (average price: 164 $)

Other interesting period(s): 2 to 3 months ($ 177), 3 to 4 months ($ 187), 4 to 5 months ($ 188), 5 to 6 months ($ 204)

June

Best time: 2 to 3 months before departure (average price: 243 $)

Other interesting period(s): 1 to 2 months ($ 256), 3 to 4 months ($ 268), 4 to 5 months ($ 270), 5 to 6 months ($ 267), 6 to 7 months ($ 255)

July

Best time: 2 to 3 months before departure (average price: 244 $)

Other interesting period(s): 1 to 2 months ($ 267), 3 to 4 months ($ 246), 5 to 6 months ($ 258), 6 to 7 months ($ 265), 7 to 8 months ($ 257)

August

Best time: 3 to 4 months before departure (average price: 220 $)

Other interesting period(s): 2 to 3 months ($ 225), 4 to 5 months ($ 224), 5 to 6 months ($ 230), 6 to 7 months ($ 232), 7 to 8 months ($ 221), 8 to 9 months ($ 229)

September

Best time: 5 to 6 months before departure (average price: 172 $)

Other interesting period(s): 1 to 2 months ($ 186), 2 to 3 months ($ 191), 3 to 4 months ($ 192), 4 to 5 months ($ 182), 8 to 9 months ($ 200)

October

Best time: 1 to 2 months before departure (average price: 186 $)

Other interesting period(s): 0 to 1 month ($ 211), 2 to 3 months ($ 200), 4 to 5 months ($ 235), 5 to 6 months ($ 214), 6 to 7 months ($ 204)

November

Best time: 1 to 2 months before departure (average price: 174 $)

Other interesting period(s): 0 to 1 month ($ 220), 2 to 3 months ($ 206)

December

Best time: 1 to 2 months before departure (average price: 183 $)

Other interesting period(s): 2 to 3 months ($ 202)

What day of the week should I book my flight ticket?

Data analysis:

Statistically, friday is the day when plane tickets for New York City->Chicago are the cheapest. So, by buying your plane ticket on a friday, you will save $2. Conversely, by buying it on a sunday, you may end up paying $4 more.



New York City to Chicago: flight price when booking today

Information: this data is not statistics but comes from real prices collected less than 7 days ago. Some months may not be available as we do not have enough data for them.

Month Current price
May 2024$ 173
$76 to $371
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June 2024$ 185
$75 to $348
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July 2024$ 198
$119 to $306
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August 2024$ 207
$119 to $296
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September 2024$ 134
$89 to $289
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October 2024$ 165
$89 to $306
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November 2024$ 231
$90 to $477
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December 2024$ 347
$169 to $603
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January 2025$ 220
$169 to $279
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February 2025$ 195
$169 to $241
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Data analysis:

Compared to the average price, may, june, july, august, september and october are cheaper to travel to Chicago. So it may be interesting to book now to leave during these months!



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