Can I fly direct from Chicago to New York?

Yes, direct flights from Chicago to New York are available. Historically, approximately 41.6% of all flights on this route have been direct. For journeys that involve connecting flights, travelers typically experience a median of 2 stopovers. This means that while direct options are common, a notable portion of flights will include at least one stop.

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

A direct flight from Chicago to New York typically takes about 2 hours and 22 minutes. This is based on a median direct flight time of 142 minutes. For flights with one stop, the median duration is considerably longer, averaging 12 hours and 20 minutes, or 740 minutes. The air distance between the two cities is approximately 1145 kilometers.

How often do Chicago to New York flight prices drop?

Across the trailing 30 days, flight prices for the Chicago to New York route have historically shown frequent drops. This indicates that travelers may often find opportunities to secure more favorable fares. The route is characterized by its consistent price fluctuations, making it one of the more dynamic for deal availability.

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 7 days ago

483 airlines compared

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

Today’s best flight deals from Chicago to New York

Explore current cheapest deals departing from Chicago to New York

2027-01-12 – 2027-01-26
CHI - New York
38% AI deal score
$142
$183
Round trip
2027-01-13 – 2027-01-26
CHI - New York
38% AI deal score
$142
$186
Round trip
2027-02-03 – 2027-02-17
CHI - New York
40% AI deal score
$151
$186
Round trip
2027-01-13 – 2027-01-27
CHI - New York
38% AI deal score
$142
$187
Round trip
2027-01-13 – 2027-01-19
CHI - New York
38% AI deal score
$158
$187
Round trip
2027-01-13 – 2027-01-20
CHI - New York
38% AI deal score
$158
$187
Round trip
2027-01-12 – 2027-01-20
CHI - New York
38% AI deal score
$151
$187
Round trip
2027-01-12 – 2027-01-19
CHI - New York
38% AI deal score
$158
$187
Round trip
2027-02-03 – 2027-02-24
CHI - New York
39% AI deal score
$147
$187
Round trip
2026-12-15 – 2027-01-12
CHI - New York
48% AI deal score
$237
$187
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 1,145 kilometers, classifying this as a short-haul route. This means you can expect a relatively quick journey between these two major cities.

When looking for cheap flights from Chicago to New York, fares typically range from $327–$723, with a median price of $475. Right now, current fares are above the typical level for this route. New deals for this route appear almost daily, offering frequent opportunities to find better prices.

If you are wondering when is the cheapest time to fly from Chicago to New York, February stands out as the most affordable month, with a median fare of just $124. Other cost-effective options include April, with a median fare of $312, and June, where the median fare is $327.

For direct flights from Chicago to New York, a meaningful share of recent fares are non-stop, accounting for 41.6% of itineraries. For the remaining flights, most itineraries connect at least once, with a typical journey involving 2 stopovers.

A typical journey from Chicago to New York, including connections, takes approximately 2 hours and 22 minutes. While non-stop flights have a median duration of 2 hours and 22 minutes, connecting itineraries can extend the travel time significantly.

How much is a round trip from Chicago to New York

Regular price: $141 - $246

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

The regular price range for this route is $141 to $246. The current lowest deal is $177 with Frontier Airlines for travel from Feb 24-Mar 2.

now $177

Low $141

High $246

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 $124. The most expensive month is May, with a median price of $791. Prices are generally lower from February to December.

February

Cheapest

Flights from $124

May

Most Expensive

Flights from $791

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to New York

United Airlines

Last-minute flights going from Chicago to New York

Tue, Oct 27

⌛ Last-Minute

ORD - New York

Chicago (ORD) - New York (LGA)

Frontier Airlines

$388

$352

One-way

Wed, Oct 28

⌛ Last-Minute

ORD - New York

Chicago (ORD) - New York (EWR)

Frontier Airlines

$380

$352

One-way

Wed, Oct 28

⌛ Last-Minute

ORD - New York

Chicago (ORD) - New York (LGA)

Frontier Airlines

$384

$368

One-way

Thu, Oct 29

⌛ Last-Minute

ORD - New York

Chicago (ORD) - New York (LGA)

Frontier Airlines

$374

$351

One-way

Thu, Oct 29

⌛ Last-Minute

ORD - New York

Chicago (ORD) - New York (LGA)

Frontier Airlines

$374

$352

One-way

Sun, Nov 1

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (LGA)

Frontier Airlines

$368

$352

One-way

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

2 nights

Dec 7 - Dec 9

$311 → $199

36%

5 nights

Dec 7 - Dec 12

$303 → $199

34%

4 nights

Dec 5 - Dec 9

$311 → $211

32%

3 nights

Dec 2 - Dec 5

$312 → $214

31%

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 of $475.

📅 Best time to fly

February is historically cheapest at $124

Historically, February is the cheapest month to fly from Chicago to New York, with a median price of $124.

⏱️ Flight duration

Direct flights average 2h 22m

Direct flights from Chicago to New York typically average 2h 22m, while connecting flights average 22h 34m.

✈️ Airlines & availability

Direct flights available from United Airlines and JetBlue Airways

United Airlines and JetBlue Airways offer direct flights on this route, with 41.6% of recent flights being direct.

🏆 Airline highlight

Frontier Airlines offers a deal at $177

A recent deal from Frontier Airlines offers a flight for $177, departing February 24 and returning March 2.

🎯 Booking tip

Deals are frequent for this route

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

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers a wide selection of flights from Chicago to New York.

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

💸 Flights from ~$195

New York main airports to arrive at

Newark Liberty International (EWR)

Cheapest

Newark Liberty International Airport offers a convenient arrival option for flights from Chicago to New York.

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

💸 Flights from ~$168

Airports nearby New York used as alternative

Westchester County (HPN)

Westchester County (HPN) is a convenient regional airport for travelers in Manhattan, the Bronx, and Westchester suburbs.

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

💸 Flights from ~$290

Business & First Class Flight Deals to New York

84% AI deal score

$1,734

$497

Save $1,237

Frequently Asked Questions About Flights to New York

Historically, the optimal booking window for flights from Chicago to New York is typically between 28 and 59 days prior to departure. During this period, the average price for a ticket is around $543. Prices tend to increase significantly closer to the departure date, with tickets purchased 0-6 days out averaging $933. Even 7-13 days before departure, the average price is higher at $793, suggesting that planning ahead can lead to better value.

Across the trailing quarter, a good price for a flight from Chicago to New York is considered to be around $327. The median price for this route over the same period was $475. Prices can vary, with 75% of fares being $723 or less. Travelers aiming for a more economical trip should target prices at or below the $327 threshold.

Historically, February has been the cheapest month to fly from Chicago to New York, with a median price of $124. Other relatively inexpensive months include April, with a median price of $312, and June, with a median of $327. The annual median price for this route is $475, indicating that flights in February offer significant savings compared to the yearly average.

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

Flights from Chicago to New York cover 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.

How much is a round trip from Chicago to New York

Regular price: $141 - $246

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

The regular price range for this route is $141 to $246. The current lowest deal is $177 with Frontier Airlines for travel from Feb 24-Mar 2.

now $177

Low $141

High $246

The cheapest time to fly from Chicago to New York

February

Cheapest

Flights from $124

May

Most Expensive

Flights from $791

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec