Can I fly direct from Chicago to New York?

Yes, direct flights are available from Chicago to New York. In the trailing 90 days, approximately 44.1% of all flights on this route were direct. For itineraries that included connecting flights, travelers typically experienced two stopovers.

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. This route covers a distance of 1145 kilometers. Flights with one stopover typically have a significantly longer median duration, averaging around 12 hours and 22 minutes.

How often do Chicago to New York flight prices drop?

Historically, flight prices for the Chicago to New York route have shown frequent drops. This indicates that travelers often have opportunities to find deals on this popular route. Prices tend to fluctuate, so monitoring fares can be beneficial.

Flights From Chicago

To New York

Cheap Flights from Chicago to New York

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

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

Prices updated 1 day ago

461 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Chicago to New York

Explore current cheapest deals departing from Chicago to New York

2026-10-06 – 2026-10-13
CHI - New York
46% AI deal score
$141
$174
Round trip
2026-10-20 – 2026-10-24
CHI - New York
46% AI deal score
$146
$174
Round trip
2026-10-21 – 2026-10-24
CHI - New York
46% AI deal score
$147
$174
Round trip
2026-10-27 – 2026-10-28
CHI - New York
48% AI deal score
$210
$174
Round trip
2026-10-27 – 2026-10-31
CHI - New York
48% AI deal score
$211
$174
Round trip
2026-11-07 – 2026-11-10
CHI - New York
47% AI deal score
$201
$174
Round trip
2026-11-10 – 2026-11-14
CHI - New York
71% AI deal score
$243
$174
Round trip
2026-10-28 – 2026-10-31
CHI - New York
73% AI deal score
$261
$177
Round trip
2026-11-04 – 2026-11-07
CHI - New York
66% AI deal score
$225
$178
Round trip
2026-10-27 – 2026-11-03
CHI - New York
68% AI deal score
$249
$178
Round trip

Chicago to New York: Overview

Insights for flights from Chicago to New York

Flights from Chicago to New York typically span a distance of 1,145 kilometers, classifying this as a short-haul route. This means you can expect a relatively quick journey between these two major cities.

For travelers seeking cheap flights from Chicago to New York, fares typically range from $234 to $634, with a median price 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, offering frequent opportunities to find better prices.

When considering the cheapest time to fly from Chicago to New York, February and January stand out as the most affordable months, both with a median fare of $99. April also offers competitive pricing, with a median fare of $164.

A meaningful share of itineraries between Chicago and New York are non-stop, while the rest typically involve two connections. This mixed availability means you have options for both direct and connecting services.

The typical journey time for flights from Chicago to New York is 2h 19m, including connections. This duration accounts for both direct flights and those with layovers, providing a realistic expectation for your travel time.

How much is a round trip from Chicago to New York

Regular price: $196 - $318

Prices are currently below the regular range.

Regular prices for flights from Chicago to New York typically range from $196 to $318. The current lowest deal is $179 on Kayak for travel from Oct 28-Oct 31.

now $179

Low $196

High $318

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 to fly 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

American Airlines

JetBlue Airways

Last-minute flights going from Chicago to New York

Tue, Sep 15

⌛ Last-Minute

ORD - New York

Chicago (ORD) - New York (JFK)

JetBlue Airways

$425

$295

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - New York

Chicago (ORD) - New York (JFK)

JetBlue Airways

$518

$299

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - New York

Chicago (ORD) - New York (EWR)

Frontier Airlines

$445

$301

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - New York

Chicago (ORD) - New York (JFK)

JetBlue Airways

$425

$301

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - New York

Chicago (ORD) - New York (JFK)

JetBlue Airways

$532

$301

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - New York

Chicago (ORD) - New York (LGA)

Deutsche Luft Hansa

$393

$335

One-way

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

1 night

Sep 14 - Sep 15

$643 → $325

49%

2 nights

Sep 14 - Sep 16

$640 → $325

49%

3 nights

Sep 14 - Sep 17

$631 → $345

45%

4 nights

Sep 14 - Sep 18

$627 → $345

45%

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 at $179.

📅 Best time to fly

Fly in February for prices below the typical level.

Historically, February and January offer the lowest median prices at $99.

⏱️ Flight duration

Direct flights average 2h 19m.

Direct flights from Chicago to New York typically take 2h 19m, while connecting flights take 20h 19m.

✈️ Airlines & availability

44.1% of flights are direct.

Historically, 44.1% of flights on this route are direct, with a mixed availability of airlines.

🏆 Airline highlight

American Airlines and JetBlue Airways offer direct flights.

American Airlines and JetBlue Airways provide direct flight options for this route.

🎯 Booking tip

Deals are frequent on this route.

Deals for flights from Chicago to New York are frequent, appearing often within 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers flights to New York, with prices from $200.

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

💸 Flights from ~$200

New York main airports to arrive at

Newark Liberty International (EWR)

Cheapest

Newark Liberty International Airport is a good choice for flights from Chicago to New York.

📍 ~14 km from New York city center (reachable by car)

💸 Flights from ~$200

Airports nearby New York used as alternative

Westchester County (HPN)

Westchester County is a useful alternative arrival airport, especially for travelers heading to Manhattan, the Bronx, and Westchester suburbs.

📍 ~45 km from New York (reachable by car)

💸 Flights from ~$316

Business & First Class Flight Deals to New York

83% AI deal score

$1,841

$532

Save $1,309

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 or more days before departure. Across the trailing quarter, prices for tickets bought within 6 days of departure averaged around $613. By comparison, fares purchased 60+ days out averaged $336. Planning ahead can lead to notable savings on this route.

Based on pricing across the trailing 90 days, a good price for a flight from Chicago to New York is considered to be $234 or less. The median price for this route was $420 during the same period. Fares exceeding $634 are typically in the higher price range.

Historically, January and February have been the cheapest months to fly from Chicago to New York, with median prices around $99. April also offered competitive fares, with a median price of $164. These months typically present better value compared to the annual median price of $420 for this route.

Related routes

More routes from Chicago

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Flights to New York from other cities

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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: $196 - $318

Prices are currently below the regular range.

Regular prices for flights from Chicago to New York typically range from $196 to $318. The current lowest deal is $179 on Kayak for travel from Oct 28-Oct 31.

now $179

Low $196

High $318

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