Can I fly direct from New York to Chicago?

Yes, direct flights from New York to Chicago are available. Historically, approximately 38.8% of flights on this route have been direct. For those flights that include connections, the median number of stopovers is typically 2. Travelers have options for both direct and connecting services.

How long is the flight from New York to Chicago?

The typical direct flight from New York to Chicago has a median duration of 2 hours and 43 minutes. For flights with one stop, the median duration is considerably longer, averaging 12 hours and 51 minutes. The distance covered on this route is approximately 1141 kilometers.

Should I set a price alert for New York to Chicago flights?

Yes, setting a price alert for flights from New York to Chicago is advisable. This route is classified as one with frequent deal activity. Historically, price fluctuations and attractive offers occur regularly, making price alerts a useful tool for travelers seeking good value.

Flights From New York

To Chicago

Cheap Flights from New York to Chicago

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

Deals from

New York

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

Prices updated today

462 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 15, 2026.)

Today’s best flight deals from New York to Chicago

Explore current cheapest deals departing from New York to Chicago

2026-10-10 – 2026-10-14
NYC - Chicago
45% AI deal score
$121
$174
Round trip
2026-10-06 – 2026-10-07
NYC - Chicago
45% AI deal score
$121
$174
Round trip
2026-10-17 – 2026-10-24
NYC - Chicago
45% AI deal score
$112
$175
Round trip
2026-10-17 – 2026-10-20
NYC - Chicago
45% AI deal score
$119
$175
Round trip
2026-10-20 – 2026-10-27
NYC - Chicago
48% AI deal score
$202
$179
Round trip
2026-10-20 – 2026-10-28
NYC - Chicago
46% AI deal score
$191
$179
Round trip
2026-10-20 – 2026-10-31
NYC - Chicago
43% AI deal score
$178
$179
Round trip
2026-10-17 – 2026-10-19
NYC - Chicago
45% AI deal score
$119
$180
Round trip
2026-10-07 – 2026-10-27
NYC - Chicago
48% AI deal score
$202
$180
Round trip
2026-10-14 – 2026-10-21
NYC - Chicago
47% AI deal score
$202
$180
Round trip

New York to Chicago: Overview

Insights for flights from New York to Chicago

Most itineraries for flights from New York to Chicago connect at least once, with only 38.8% of recent fares being non-stop. For connecting itineraries, the typical number of stopovers is 2. New deals appear almost daily for this route, offering frequent opportunities to find competitive prices.

When considering cheap flights from New York to Chicago, fares typically range from $207 to $647, with a median of $407. Right now, current fares are below the typical level. However, 0% of recent fares were classified as a good price, indicating that finding exceptional value may require careful timing.

To find the cheapest time to fly from New York to Chicago, you should consider traveling in December, which has a median fare of $94. January also offers lower prices, with a median fare of $99. Another month with more affordable options is March, where the median fare is $142.

A typical journey from New York to Chicago takes about 2h 43m. This duration includes both direct flights and those with connections, as most itineraries on this route involve at least one stop. For non-stop flights, the median duration is 2h 43m, while connecting flights have a significantly longer median journey time of 16h 33m.

How much is a round trip from New York to Chicago

Regular price: $91 - $267

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

The regular price range for flights from New York to Chicago is between $91 and $267. The current lowest deal is $166 with JetBlue Airways for travel from Oct 7-Oct 10.

now $166

Low $91

High $267

The cheapest time to fly from New York to Chicago

The cheapest month to fly from NYC to CHI is January, with a median price of $104. The most expensive month is July, with a median price of $485. Prices are generally lower from January to December.

January

Cheapest

Flights from $104

July

Most Expensive

Flights from $485

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from New York to Chicago

JetBlue Airways

Southwest Airlines

Last-minute flights going from New York to Chicago

Mon, Sep 14

⌛ Last-Minute

JFK - Chicago

New York (JFK) - Chicago (ORD)

JetBlue Airways

$465

$302

One-way

Tue, Sep 15

⌛ Last-Minute

JFK - Chicago

New York (JFK) - Chicago (ORD)

JetBlue Airways

$476

$294

One-way

Tue, Sep 15

⌛ Last-Minute

JFK - Chicago

New York (JFK) - Chicago (ORD)

JetBlue Airways

$468

$295

One-way

Tue, Sep 15

⌛ Last-Minute

JFK - Chicago

New York (JFK) - Chicago (ORD)

JetBlue Airways

$372

$297

One-way

Tue, Sep 15

⌛ Last-Minute

JFK - Chicago

New York (JFK) - Chicago (ORD)

$465

$305

One-way

Tue, Sep 15

⌛ Last-Minute

JFK - Chicago

New York (JFK) - Chicago (ORD)

$474

$318

One-way

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

1 night

Sep 15 - Sep 16

$476 → $294

38%

3 nights

Sep 15 - Sep 18

$468 → $295

37%

4 nights

Sep 14 - Sep 18

$465 → $302

35%

4 nights

Sep 15 - Sep 19

$465 → $305

34%

Popular Airports to fly from New York to Chicago

New York - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares for New York to Chicago are below the typical level, with a median of $407.

📅 Best time to fly

Fly in December for the best prices

Historically, December offers the lowest median price at $94 for flights from New York to Chicago.

⏱️ Flight duration

Direct flights average 2h 43m

The typical direct flight from New York to Chicago takes 2 hours and 43 minutes.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights make up 61.2% of recent routes, with a median of 2 stopovers.

🏆 Airline highlight

JetBlue Airways has direct deals

JetBlue Airways offers direct flights on this route, with recent deals found for $166.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from New York to Chicago are frequent, appearing within a 30-day window.

New York main airports to depart from

Newark Liberty International (EWR)

Cheapest

Newark Liberty International Airport offers the cheapest flights from New York to Chicago.

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

💸 Flights from ~$202

John F. Kennedy International (JFK)

John F. Kennedy International Airport is a major hub for flights from New York to Chicago.

📍 ~21 km from New York city center (reachable by car or train)

💸 Flights from ~$244

LaGuardia (LGA)

LaGuardia Airport provides a convenient option for flights from New York to Chicago.

📍 ~13 km from New York city center (reachable by car or train)

💸 Flights from ~$221

New York Stewart International Airport (SWF)

New York Stewart International Airport is an alternative for flights from New York to Chicago.

📍 ~88 km from New York city center (reachable by car)

💸 Flights from ~$226

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago, offering many connections from New York.

📍 ~25 km from Chicago city center (reachable by car, train, and bus).

💸 Flights from ~$231

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$240

Business & First Class Flight Deals to Chicago

85% AI deal score

$2,188

$570

Save $1,618

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from New York to Chicago is typically 14-27 days before departure. During this period, the average price for a ticket is around $323. Booking within 0-6 days of departure sees the average price increase to $582, while booking 7-13 days out averages $495. Prices tend to be higher outside this sweet spot, with flights booked 28-59 days in advance averaging $511 and those booked 60+ days out averaging $413.

Across the trailing quarter, a good price for a flight from New York to Chicago is considered to be $207 or less. This threshold represents the lowest 25% of fares observed. The median price for this route over the same period was $407, with 75% of fares being $647 or less.

Historically, the cheapest months to fly from New York to Chicago are December, with a median price of $94, and January, with a median price of $99. March also offers relatively low prices, with a median of $142. The annual median price for this route is $407, indicating significant savings are possible during these months.

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New York to Chicago: Overview

Insights for flights from New York to Chicago

How much is a round trip from New York to Chicago

Regular price: $91 - $267

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

The regular price range for flights from New York to Chicago is between $91 and $267. The current lowest deal is $166 with JetBlue Airways for travel from Oct 7-Oct 10.

now $166

Low $91

High $267

The cheapest time to fly from New York to Chicago

The cheapest month to fly from NYC to CHI is January, with a median price of $104. The most expensive month is July, with a median price of $485. Prices are generally lower from January to December.

January

Cheapest

Flights from $104

July

Most Expensive

Flights from $485

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec