Can I fly direct from Chicago to New York?

Yes, direct flights are available from Chicago to New York. Historically, approximately 44.1% of all flights on this route have been direct. For journeys involving connections, travelers typically encounter two stopovers. This indicates that while direct options are common, connecting flights are also a significant part of the route's offerings.

How many hours is the flight from Chicago to New York?

The median flight time for a direct flight from Chicago to New York is approximately 2 hours and 19 minutes, covering a distance of 1145 kilometers. For flights with one stop, the median duration is considerably longer, averaging 12 hours and 22 minutes. Travelers should account for these differences when planning their journeys. Direct flights offer a significantly shorter travel experience.

How often do Chicago to New York flight prices drop?

Historically, flight prices for the Chicago to New York route have shown frequent drops across the trailing 30 days. This indicates that it is a route where price fluctuations are common. Travelers may benefit from monitoring prices regularly to take advantage of these frequent changes. The consistent price movements suggest opportunities for finding better deals.

Flights From Chicago

To New York

Cheap Flights from Chicago to New York

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Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to New York

Prices updated 2 days ago

405 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Chicago to New York

Explore current cheapest deals departing from Chicago to New York

2026-08-22 – 2026-08-29
CHI - New York
49% AI deal score
$193
$193
Round trip
2026-08-15 – 2026-08-18
CHI - New York
66% AI deal score
$211
$193
Round trip
2026-09-02 – 2026-09-05
CHI - New York
47% AI deal score
$165
$193
Round trip
2026-08-15 – 2026-08-19
CHI - New York
65% AI deal score
$211
$197
Round trip
2026-10-27 – 2026-10-31
CHI - New York
43% AI deal score
$153
$197
Round trip
2026-08-26 – 2026-08-29
CHI - New York
50% AI deal score
$205
$198
Round trip
2026-09-26 – 2026-09-29
CHI - New York
46% AI deal score
$168
$199
Round trip
2026-08-18 – 2026-08-25
CHI - New York
48% AI deal score
$196
$204
Round trip
2026-08-19 – 2026-08-22
CHI - New York
49% AI deal score
$207
$204
Round trip
2026-08-22 – 2026-08-26
CHI - New York
49% AI deal score
$205
$204
Round trip

Chicago to New York: Overview

Insights for flights from Chicago to New York

Flights from Chicago to New York cover a distance of 1145 kilometers, classifying this as a short-haul route. For travelers seeking cheap flights from Chicago to New York, fares typically range from $234–$634, with a median of $420. Right now, current fares are above the typical level, and only 4% of recent fares were classified as a good price. New deals appear almost daily, suggesting frequent opportunities for savings.

When is the cheapest time to fly from Chicago to New York? The data indicates that February and January are the most affordable months, both with a median fare of $99. Following closely, April also presents a good option with a median fare of $164. Planning your trip during these months can lead to significant savings.

For direct flights from Chicago to New York, 44.1% of recent itineraries are non-stop. This means a meaningful share are non-stop, while the remaining itineraries typically involve 2 connections. Travelers should consider whether the convenience of a direct flight outweighs potential savings on connecting itineraries.

How long is the flight from Chicago to New York? A typical journey, including connections, takes approximately 2h 19m. While the non-stop flight time is also 2h 19m, the median connecting journey time extends to 20h 19m, reflecting the impact of layovers on overall travel duration.

How much is a round trip from Chicago to New York

Regular price: $135 - $247

Prices for flights from Chicago to New York are currently within the regular range.

The regular price range for flights from Chicago to New York is between $135 and $247. The current lowest deal is $193 with JetBlue Airways for travel from Aug 22-Aug 29.

now $193

Low $135

High $247

The cheapest time to fly from Chicago to New York

The cheapest month to fly from Chicago to New York is February, with a median price of $99. The most expensive month is May, with a median price of $470. Prices are generally lower from January to December.

February

Cheapest

Flights from $99

May

Most Expensive

Flights from $470

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to New York

JetBlue Airways

Southwest Airlines

United Airlines

Last-minute flights going from Chicago to New York

Tue, Jul 28

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (JFK)

$729

$355

One-way

Tue, Jul 28

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (JFK)

$713

$373

One-way

Wed, Jul 29

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (JFK)

$717

$366

One-way

Sat, Aug 1

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (EWR)

Frontier Airlines

$842

$252

One-way

Sat, Aug 1

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (EWR)

Frontier Airlines

$735

$253

One-way

Sat, Aug 1

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (EWR)

Frontier Airlines

$975

$277

One-way

Biggest price drops on these dates for flights from Chicago to New York

4 nights

Aug 1 - Aug 5

$975 → $277

72%

1 night

Aug 1 - Aug 2

$1,013 → $323

68%

6 nights

Aug 1 - Aug 7

$842 → $252

70%

1 night

Aug 4 - Aug 5

$777 → $248

68%

Popular Airports to fly from Chicago to New York

Chicago - New York route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Chicago to New York are above the typical level, with a median of $420.

📅 Best time to fly

Fly in February for prices as low as $99

Historically, February, January, and April offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights average 2h 19m

Direct flights typically take 2 hours and 19 minutes, while connecting flights average 20 hours 19 minutes.

✈️ Airlines & availability

44.1% of flights are direct

This route offers a mixed availability of direct and connecting flights, with 44.1% being direct.

🏆 Airline highlight

JetBlue Airways offers direct flights

JetBlue Airways is one of the airlines providing direct flight options for this route.

🎯 Booking tip

Deals are frequent for this route

Deals for flights from Chicago to New York are frequently available, appearing often.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub offering many flight options from Chicago to New York.

📍 ~25 km from Chicago city center (reachable by car or train)

💸 Flights from ~$126

New York main airports to arrive at

John F. Kennedy International (JFK)

Cheapest

John F. Kennedy International Airport is a good option for flights from Chicago to New York.

📍 ~21 km from New York city center (reachable by car, bus, train, and subway).

💸 Flights from ~$126

Airports nearby New York used as alternative

Westchester County (HPN)

Westchester County Airport is a convenient regional alternative for travelers in Manhattan, the Bronx, and Westchester suburbs.

📍 ~40 km from New York (reachable by car)

💸 Flights from ~$253

Business & First Class Flight Deals to New York

83% AI deal score

$2,357

$616

Save $1,741

Frequently Asked Questions About Flights to New York

Historically, the optimal time to purchase tickets for flights from Chicago to New York is typically 60+ days before departure. Across the trailing quarter, prices averaged around $336 for tickets booked in this window. In contrast, booking 0-6 days out saw average prices rise to $613, indicating a significant price increase for last-minute purchases. Planning ahead by at least two months can lead to more favorable fares.

Based on historical data from the trailing 90 days, a good price for a flight from Chicago to New York is considered to be around $234. The median price for this route across the trailing quarter was $420. Prices can vary, with 75% of fares being $634 or less. Aiming for a fare at or below $234 would typically secure a competitive deal.

Historically, January and February have been the cheapest months to fly from Chicago to New York, both showing a median price of $99. April also offered competitive fares, with a median price of $164. The annual median price for this route across the trailing 270 days was $420. Travelers looking for the lowest fares should consider planning their trips during these months.

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Chicago to New York: Overview

Insights for flights from Chicago to New York

How much is a round trip from Chicago to New York

Regular price: $135 - $247

Prices for flights from Chicago to New York are currently within the regular range.

The regular price range for flights from Chicago to New York is between $135 and $247. The current lowest deal is $193 with JetBlue Airways for travel from Aug 22-Aug 29.

now $193

Low $135

High $247

The cheapest time to fly from Chicago to New York

February

Cheapest

Flights from $99

May

Most Expensive

Flights from $470

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec