Can I fly direct from New York to Chicago?

Yes, direct flights from New York to Chicago are available. Historically, approximately 38.8% of all flights on this route have been direct. For journeys involving connections, travelers typically experienced two stopovers. This indicates that while direct options are common, connecting flights are also a significant portion of the available routes.

How long is the flight from New York to Chicago?

The median flight time for a direct flight from New York to Chicago is 2 hours and 43 minutes. For flights that include one stop, the median duration is considerably longer, at 12 hours and 51 minutes. The distance covered by this route is approximately 1141 kilometers.

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

Historically, deals for flights from New York to Chicago have been frequent. This route is classified as one where price fluctuations and discounts occur regularly. Setting a price alert can be beneficial to capture these opportunities as they arise.

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

457 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 7, 2026.)

Today’s best flight deals from New York to Chicago

Explore current cheapest deals departing from New York to Chicago

2026-09-26 – 2026-09-30
NYC - Chicago
44% AI deal score
$210
$198
Round trip
2026-09-19 – 2026-09-25
NYC - Chicago
42% AI deal score
$196
$200
Round trip
2026-10-01 – 2026-10-03
NYC - Chicago
46% AI deal score
$227
$201
Round trip
2026-09-23 – 2026-09-28
NYC - Chicago
45% AI deal score
$221
$204
Round trip
2026-09-19 – 2026-09-28
NYC - Chicago
41% AI deal score
$184
$204
Round trip
2026-09-23 – 2026-09-29
NYC - Chicago
42% AI deal score
$195
$204
Round trip
2026-09-22 – 2026-09-28
NYC - Chicago
44% AI deal score
$213
$204
Round trip
2026-09-15 – 2026-09-17
NYC - Chicago
47% AI deal score
$243
$206
Round trip
2026-09-22 – 2026-09-25
NYC - Chicago
46% AI deal score
$230
$206
Round trip
2026-09-23 – 2026-09-25
NYC - Chicago
46% AI deal score
$228
$206
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: $165 - $281

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 $165 and $281. The current lowest deal is $235 on Kayak for travel from Oct 17-Oct 20.

now $235

Low $165

High $281

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

Tue, Sep 1

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (MDW)

Frontier Airlines

$369

$266

One-way

Tue, Sep 1

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (MDW)

Frontier Airlines

$332

$268

One-way

Tue, Sep 1

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (ORD)

Frontier Airlines

$402

$268

One-way

Tue, Sep 1

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (ORD)

Frontier Airlines

$392

$271

One-way

Tue, Sep 1

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (MDW)

Frontier Airlines

$416

$293

One-way

Tue, Sep 1

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (ORD)

Frontier Airlines

$400

$293

One-way

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

3 nights

Sep 9 - Sep 12

$449 → $273

39%

1 night

Sep 8 - Sep 9

$476 → $305

36%

3 nights

Sep 8 - Sep 11

$416 → $246

41%

2 nights

Sep 8 - Sep 10

$474 → $305

36%

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 price of $407.

📅 Best time to fly

Fly in December for prices as low as $94

Historically, December, January, and March offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights average 2h 43m

Direct flights to Chicago typically take 2h 43m, while connecting flights average 16h 33m.

✈️ Airlines & availability

Connecting flights are more common

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

🏆 Airline highlight

JetBlue Airways and Southwest Airlines offer direct flights

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

🎯 Booking tip

Deals are frequent for 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

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

$2,330

$507

Save $1,823

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 observed was $323. Booking within 0-6 days of travel saw average prices rise to $582, while booking 7-13 days out had an average price of $495. Planning ahead by at least two weeks can lead to more favorable fares.

Across the trailing quarter, a good price for a flight from New York to Chicago was 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 include December, with a median price of $94, and January, with a median price of $99. March also presented a relatively low median price of $142. For comparison, the annual median price for this route was $407, indicating significant savings during these months.

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Flights to Chicago from other cities

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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: $165 - $281

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 $165 and $281. The current lowest deal is $235 on Kayak for travel from Oct 17-Oct 20.

now $235

Low $165

High $281

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