Can I fly direct from New York to Chicago?

Yes, direct flights from New York to Chicago are available. Historically, direct flights have accounted for approximately 38.8% of all flight options on this route. For journeys that include connections, travelers typically experience a median of 2 stopovers. This indicates that while direct options exist, a significant portion of flights involve at least one stop.

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

Historically, flights from New York to Chicago are frequently discounted. This route is classified as one where deals appear often. Given the frequent availability of price reductions, setting a price alert could be beneficial for travelers seeking lower fares. This approach allows you to be notified when prices drop, potentially securing a more economical flight.

Flights From New York

To Chicago

Cheap Flights from New York to Chicago

Q: How long is the flight from New York to Chicago?

The direct flight from New York to Chicago typically takes 2 hours and 43 minutes, with a median duration of 163 minutes. For flights with one stop, the median travel time extends significantly to 12 hours and 51 minutes, or 771 minutes. The distance covered on this route is approximately 1141 kilometers. Travelers should account for these differences when planning their journeys.

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Deals from

New York

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

Prices updated 2 days ago

405 airlines compared

80%+ AI score for best value

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 New York to Chicago

Explore current cheapest deals departing from New York to Chicago

2026-10-21 – 2026-10-28
NYC - Chicago
43% AI deal score
$122
$197
Round trip
2026-10-20 – 2026-10-24
NYC - Chicago
44% AI deal score
$128
$197
Round trip
2026-10-17 – 2026-10-21
NYC - Chicago
44% AI deal score
$128
$197
Round trip
2026-10-26 – 2026-10-28
NYC - Chicago
43% AI deal score
$131
$198
Round trip
2026-10-20 – 2026-10-22
NYC - Chicago
43% AI deal score
$127
$201
Round trip
2026-10-03 – 2026-10-07
NYC - Chicago
43% AI deal score
$124
$202
Round trip
2026-08-21 – 2026-08-25
NYC - Chicago
47% AI deal score
$192
$203
Round trip
2026-09-08 – 2026-09-12
NYC - Chicago
43% AI deal score
$140
$203
Round trip
2026-08-12 – 2026-08-13
NYC - Chicago
47% AI deal score
$202
$204
Round trip
2026-08-19 – 2026-08-29
NYC - Chicago
45% AI deal score
$159
$204
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 two. This indicates that while direct flights from New York to Chicago are available, many travelers will experience at least one layover.

If you are looking for cheap flights from New York to Chicago, fares typically range from $207–$647, with a median of $407. Right now, current fares are below the typical level. However, the share of recent fares classified as a good price is 0%, suggesting that finding exceptionally low prices can be challenging. New deals appear almost daily, so setting up a price alert could be beneficial.

When is the cheapest time to fly from New York to Chicago? The data indicates that December is typically the most affordable month, with a median fare of just $94. January also offers competitive prices, with a median fare of $99, followed by March at $142. These months present the best opportunities for finding lower-cost travel.

How long is the flight from New York to Chicago? A typical journey from New York to Chicago takes about 2h 43m. This median duration includes both non-stop and connecting itineraries. For non-stop flights, the median time is also 2h 43m, while connecting flights have a significantly longer median duration of 16h 33m.

How much is a round trip from New York to Chicago

Regular price: $131 - $263

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 $131 and $263. The current lowest deal is $195 with JetBlue Airways, for travel from Aug 19-Aug 22.

now $195

Low $131

High $263

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

Sat, Jul 25

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (ORD)

Frontier Airlines

$324

$243

One-way

Sat, Aug 1

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (ORD)

Frontier Airlines

$467

$275

One-way

Sat, Aug 1

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (ORD)

Frontier Airlines

$426

$275

One-way

Sat, Aug 1

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (ORD)

Frontier Airlines

$362

$276

One-way

Sat, Aug 1

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (ORD)

Frontier Airlines

$552

$276

One-way

Sat, Aug 1

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (ORD)

Frontier Airlines

$556

$276

One-way

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

3 nights

Aug 1 - Aug 4

$556 → $276

50%

4 nights

Aug 1 - Aug 5

$552 → $276

50%

5 nights

Aug 1 - Aug 6

$492 → $299

39%

7 nights

Aug 1 - Aug 8

$467 → $275

41%

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 from New York to Chicago are below the typical level at $382.

📅 Best time to fly

January is historically the cheapest month to fly.

Historically, January is the cheapest month to fly from New York to Chicago, with a median price of $104.

⏱️ Flight duration

Direct flights take 2h 43m.

Direct flights from New York to Chicago typically take 2h 43m, connecting flights take 16h 33m.

✈️ Airlines & availability

Direct flights are offered by 2 airlines.

2 airlines offer direct flights on this route. Connecting flights are more common, making up 61.2% of recent deals.

🏆 Airline highlight

JetBlue Airways has a direct deal for $195.

JetBlue Airways has a direct deal from New York to Chicago for $195, from August 19 to August 22.

🎯 Booking tip

Deals appear frequently on this route.

Deals for flights from New York to Chicago appear frequently, with many deals within the last 30 days.

New York main airports to depart from

John F. Kennedy International (JFK)

Cheapest

John F. Kennedy International offers the cheapest flights to Chicago, making it a great value option.

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

💸 Flights from ~$126

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.

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

💸 Flights from ~$126

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers a major international airport with significant carrier presence and direct flight options.

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

💸 Flights from ~$175

Business & First Class Flight Deals to Chicago

85% AI deal score

$2,233

$529

Save $1,704

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 flights has been observed at approximately $323. Booking within 0-6 days of departure, however, tends to see average prices rise to around $582, while booking 7-13 days out shows an average of $495. This trend suggests that planning a few weeks in advance can lead to more favorable fares.

Across the trailing quarter, a good price for a flight from New York to Chicago is considered to be $207. This threshold represents the lowest 25% of fares observed over a 90-day period. The median price for this route during the same period was $407, while prices in the upper quartile reached $647. Travelers aiming for a budget-friendly trip should target fares at or below the $207 mark.

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 across the trailing 270 days was $407. These months typically offer more economical travel options for this route.

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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: $131 - $263

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 $131 and $263. The current lowest deal is $195 with JetBlue Airways, for travel from Aug 19-Aug 22.

now $195

Low $131

High $263

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