Can I fly direct from New York to Chicago?

Yes, direct flights are available from New York to Chicago. Historically, approximately 38.4% of all flights on this route have been direct. For journeys involving one or more stops, travelers typically experience a median of 2 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 direct flight from New York to Chicago typically takes approximately 2 hours and 45 minutes, covering a distance of 1141 kilometers. For flights with one stop, the median duration is considerably longer, averaging around 10 hours and 33 minutes. Travelers should account for this difference when planning their journey.

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 price changes, meaning opportunities for good deals arise regularly. An alert can help travelers capture a favorable price as soon as it becomes available, ensuring they don't miss out on potential savings.

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 6 days ago

483 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 27, 2026.)

Today’s best flight deals from New York to Chicago

Explore current cheapest deals departing from New York to Chicago

2027-02-03 – 2027-02-27
NYC - Chicago
30% AI deal score
$150
$182
Round trip
2027-01-09 – 2027-01-13
NYC - Chicago
41% AI deal score
$166
$189
Round trip
2027-01-05 – 2027-01-12
NYC - Chicago
30% AI deal score
$191
$189
Round trip
2026-12-08 – 2026-12-12
NYC - Chicago
50% AI deal score
$256
$189
Round trip
2026-12-08 – 2026-12-16
NYC - Chicago
47% AI deal score
$225
$189
Round trip
2027-01-20 – 2027-01-23
NYC - Chicago
40% AI deal score
$158
$189
Round trip
2027-01-06 – 2027-01-13
NYC - Chicago
42% AI deal score
$184
$189
Round trip
2027-01-05 – 2027-01-12
NYC - Chicago
28% AI deal score
$161
$191
Round trip
2027-01-12 – 2027-01-16
NYC - Chicago
40% AI deal score
$157
$192
Round trip
2027-01-06 – 2027-01-12
NYC - Chicago
42% AI deal score
$184
$192
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 38.4% of recent fares being non-stop. For connecting itineraries, the typical number of stopovers is 2. New deals for this route appear almost daily, indicating frequent opportunities for finding competitive prices.

When considering cheap flights from New York to Chicago, fares typically range from $356–$848, with a median of $550. Right now, current fares are above the typical level. However, February stands out as the cheapest month to fly, with a median fare of $247. Other affordable options include June, with a median fare of $266, and January, where the median fare is $300.

A typical journey from New York to Chicago takes about 2h 45m. This duration represents the median flight time for direct flights. For itineraries that include connections, the median journey time extends significantly to 21h 38m.

The distance between New York and Chicago is 1141 kilometers, classifying this as a short-haul route. This relatively short distance contributes to the overall travel time and the availability of various flight options.

How much is a round trip from New York to Chicago

Regular price: $126 - $239

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

The regular price range for this route is 126 USD to 239 USD. The current lowest deal is 186 USD with Frontier Airlines, for travel from Jan 30-Feb 27.

now $186

Low $126

High $239

The cheapest time to fly from New York to Chicago

The cheapest month to fly from NYC to CHI is February, with a median price of $247. The most expensive month is December, with a median price of $813. Prices are generally lower from January to November.

February

Cheapest

Flights from $247

December

Most Expensive

Flights from $813

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from New York to Chicago

United Airlines

Last-minute flights going from New York to Chicago

Tue, Oct 27

⌛ Last-Minute

EWR - Chicago

New York (EWR) - Chicago (MDW)

Frontier Airlines

$509

$348

One-way

Tue, Oct 27

⌛ Last-Minute

LGA - Chicago

New York (LGA) - Chicago (MDW)

Frontier Airlines

$474

$352

One-way

Tue, Oct 27

⌛ Last-Minute

JFK - Chicago

New York (JFK) - Chicago (ORD)

Deutsche Luft Hansa

$251

$496

One-way

Tue, Oct 27

⌛ Last-Minute

JFK - Chicago

New York (JFK) - Chicago (ORD)

American Airlines

$247

$496

One-way

Tue, Oct 27

⌛ Last-Minute

JFK - Chicago

New York (JFK) - Chicago (ORD)

Deutsche Luft Hansa

$252

$496

One-way

Wed, Oct 28

⌛ Last-Minute

LGA - Chicago

New York (LGA) - Chicago (MDW)

Frontier Airlines

$465

$352

One-way

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

3 nights

Oct 28 - Oct 31

$500 → $353

29%

2 nights

Oct 28 - Oct 30

$480 → $358

25%

2 nights

Oct 29 - Oct 31

$419 → $353

16%

1 night

Oct 28 - Oct 29

$413 → $350

15%

Popular Airports to fly from New York to Chicago

New York - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares from NYC to CHI are above the typical level, with a median price of $550.

📅 Best time to fly

February is historically the cheapest month to fly.

Historically, February is the cheapest month to fly from NYC to CHI, with a median price of $247.

⏱️ Flight duration

Direct flights take 2h 45m.

The median flight time for direct flights from NYC to CHI is 2h 45m.

✈️ Airlines & availability

38.4% of recent flights are direct.

38.4% of recent flights from NYC to CHI are direct, with connecting flights having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers a deal for $186.

Frontier Airlines has a deal for $186 from LGA to ORD, departing January 30 and returning February 27.

🎯 Booking tip

Deals are frequent on this route.

Deals on flights from NYC to CHI are frequent, appearing within a 30-day window.

New York main airports to depart from

Newark Liberty International (EWR)

Cheapest

Newark Liberty International offers flights to Chicago, with prices from $188, making it a budget-friendly option.

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

💸 Flights from ~$188

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 ~$159

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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

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

💸 Flights from ~$309

Business & First Class Flight Deals to Chicago

85% AI deal score

$1,872

$459

Save $1,413

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from New York to Chicago is typically between 28 and 59 days prior to departure. During this period, the average price observed was around $596. Booking within 0-6 days of departure typically sees prices rise significantly, averaging $957. Even booking 7-13 days out shows an average price of $901, indicating that planning ahead can lead to substantial savings.

Based on historical data across the trailing quarter, a good price for a flight from New York to Chicago is considered to be around $356 or less. The median price for this route was $550. Prices can go up to $848 or more, so finding a fare at or below the $356 threshold represents a notable saving for travelers.

Historically, the cheapest months to fly from New York to Chicago are February, with a median price of $247, and June, with a median price of $266. January also offers relatively lower prices, with a median of $300. These months typically present better value compared to the annual median price of $550 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: $126 - $239

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

The regular price range for this route is 126 USD to 239 USD. The current lowest deal is 186 USD with Frontier Airlines, for travel from Jan 30-Feb 27.

now $186

Low $126

High $239

The cheapest time to fly from New York to Chicago

February

Cheapest

Flights from $247

December

Most Expensive

Flights from $813

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec