To New York

Cheap Flights from Chicago to New York

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Chicago

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

Prices updated 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Chicago to New York

Explore current cheapest deals departing from Chicago to New York

Round trip

Sort by: Cheapest

August 11 - August 18

Cheapest

Best

Earliest

ORD - New York

$188

$120

Round trip

August 18 - August 25

Cheapest

Best

ORD - New York

$190

$120

Round trip

August 12 - August 17

ORD - New York

$196

$131

Round trip

August 13 - August 18

ORD - New York

$195

$131

Round trip

September 17 - September 23

ORD - New York

$169

$131

Round trip

September 17 - September 29

ORD - New York

$150

$133

Round trip

August 18 - August 19

ORD - New York

$198

$134

Round trip

September 15 - September 22

ORD - New York

$169

$135

Round trip

October 20 - October 27

ORD - New York

$175

$135

Round trip

August 12 - August 19

ORD - New York

$190

$136

Round trip

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Route Intelligence — 486,190 Searches this Week

Insights for flights from Chicago to New York

For cheap flights from Chicago to New York, fares typically range from $107–$539, with a median of $290 over the last 90 days. Right now, current fares are above the typical level. Only about 2% of recent fares were classified as a good price, indicating that finding deals may require some flexibility.

When is the cheapest time to fly from Chicago to New York? Historically, the most affordable months to fly are February and January, both with a median fare of $99. April also offers competitive pricing, with a median fare of $164. Planning your trip during these months could lead to significant savings.

A meaningful share of itineraries between Chicago and New York are non-stop, with 55.7% of recent fares being direct flights from Chicago to New York. For itineraries that include connections, the typical number of stopovers is 2.

How long is the flight from Chicago to New York? A typical journey, including connections, takes approximately 5h 9m. This duration accounts for the median travel time across all observed itineraries, reflecting both direct and connecting flights.

How much is a round trip from Chicago to New York

Regular price: $131 - $227

Prices are currently below the regular range.

The regular price range for flights from Chicago to New York is $131 to $227. The current lowest deal is $120 with JetBlue Airways, for travel from Aug 11-Aug 18.

now $120

Low $131

High $227

The cheapest time to fly from Chicago to New York

The cheapest month to fly from Chicago to New York is January, with a median price of $99. The most expensive month is May, with a median price of $415. Prices are generally lower from January to December.

January

Cheapest

Flights from $99

May

Most Expensive

Flights from $415

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to New York

JetBlue Airways

Southwest Airlines

United Airlines

Last-minute flights going from Chicago to New York

Fri, Jun 19

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (JFK)

$670

$361

One-way

Sat, Jun 20

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (JFK)

$659

$327

One-way

Sat, Jun 20

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (JFK)

$655

$344

One-way

Sat, Jun 20

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (JFK)

$670

$361

One-way

Tue, Jun 30

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (JFK)

$403

$212

One-way

Tue, Jun 30

⌛ Last-Minute

MDW - New York

Chicago (MDW) - New York (JFK)

$513

$227

One-way

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

2 nights

Aug 10 - Aug 12

$599 → $195

67%

3 nights

Jun 20 - Jun 23

$659 → $327

50%

13 nights

Aug 12 - Aug 25

$504 → $177

65%

4 nights

Jun 20 - Jun 24

$655 → $344

47%

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 for the past 90 days.

📅 Best time to fly

Fly in February or January for cheapest fares

Historically, the cheapest flights from Chicago to New York are in February and January, at around $99.

⏱️ Flight duration

Direct flights take 5h 9m

The median flight duration for this route is 5h 9m. 55.7% of recent deals are for direct flights.

✈️ Airlines & availability

Deals are frequent for this route

Deals for flights from Chicago to New York are frequent, with over 1 deals per day historically.

🏆 Airline highlight

JetBlue Airways offers direct flights

JetBlue Airways has offered direct flights on the Chicago to New York route recently.

🎯 Booking tip

Good prices are rare for this route

Historically, only 2% of recent fares from Chicago to New York were considered good prices.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport is a good option for flights from Chicago to New York.

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

💸 Flights from ~$120

Chicago Midway International (MDW)

Chicago Midway International Airport offers another choice for your trip to New York.

📍 ~15 km from Chicago city center (reachable by car or train)

💸 Flights from ~$137

Chicago Rockford International (RFD)

Chicago Rockford International Airport provides an alternative departure point for New York flights.

📍 ~120 km from Chicago city center (reachable by car)

💸 Flights from ~$247

New York main airports to arrive at

John F. Kennedy International (JFK)

Cheapest

John F. Kennedy International is a primary arrival airport for flights from Chicago to New York.

📍 ~20 km from New York city center (reachable by car)

💸 Flights from ~$120

LaGuardia (LGA)

LaGuardia is a convenient arrival airport for travelers flying from Chicago to New York.

📍 ~10 km from New York city center (reachable by car)

💸 Flights from ~$137

New York Stewart International Airport (SWF)

New York Stewart International Airport offers an alternative arrival option for flights to the New York area.

📍 ~90 km from New York city center (reachable by car)

💸 Flights from ~$211

Newark Liberty International (EWR)

Newark Liberty International is a major arrival airport for those traveling from Chicago to New York.

📍 ~15 km from New York city center (reachable by car)

💸 Flights from ~$137

Airports nearby New York used as alternative

Westchester County (HPN)

Westchester County Airport is a useful alternative for travelers located in the Bronx, Upper Manhattan, or Westchester.

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

💸 Flights from ~$291

Philadelphia International (PHL)

Cheapest

Philadelphia International Airport is a major international hub offering competitive pricing and a vast network of destinations.

📍 ~130 km from New York (reachable by rail)

💸 Flights from ~$135

Long Island MacArthur (ISP)

Long Island MacArthur Airport is an excellent alternative for residents of Queens, Brooklyn, and Long Island.

📍 ~80 km from New York (reachable by rail)

💸 Flights from ~$260

Bradley International (BDL)

Bradley International Airport is a reliable regional option when NYC airports experience severe delays or price spikes.

📍 ~160 km from New York (reachable by car)

💸 Flights from ~$209

Trenton–Mercer (TTN)

Trenton–Mercer Airport is a viable ultra-low-cost option with quick curb-to-gate times due to its small terminal.

📍 ~85 km from New York (reachable by car)

💸 Flights from ~$191

Business & First Class Flight Deals to New York

48% AI deal score

$516

From ORD

Elite

Oct 24

New York, United States

47% AI deal score

$586

From ORD

Elite

Oct 24

New York, United States

47% AI deal score

$586

From ORD

Elite

Aug 11

New York, United States

47% AI deal score

Elite

Aug 08

New York, United States

45% AI deal score

$2,083

From ORD

Elite

Sep 12

New York, United States

45% AI deal score

$587

From MDW

Elite

Jul 16

New York, United States

45% AI deal score

$1,761

$1,743

Save $18

From ORD

Elite

Aug 05

New York, United States

44% AI deal score

$2,083

From ORD

Elite

Aug 12

New York, United States

44% AI deal score

$2,103

From ORD

Elite

Jul 31

New York, United States

44% AI deal score

$2,172

From MDW

Elite

Jun 16

New York, United States

44% AI deal score

New York, United States

41% AI deal score

$5,482

From ORD

Elite

Nov 21

New York, United States

40% AI deal score

$832

Frequently Asked Questions About Flights to New York

Historically, the optimal time to purchase tickets for flights from Chicago to New York is 60+ days prior to departure. Across the trailing quarter, prices averaged around $336 for tickets bought in this window. In contrast, tickets purchased within 0-6 days of departure typically cost significantly more, with an average price of $613. Planning ahead by at least two months can lead to considerable savings on this route.

Based on data from the trailing 90 days, a good price for a flight from Chicago to New York is considered to be $107 or less. The median price for this route across the trailing quarter was $290. For travelers seeking more budget-friendly options, aiming for fares at or below the $107 threshold is advisable.

Historically, January and February are the cheapest months to fly from Chicago to New York, with a median price of $99 for both. April also offers a relatively low median price of $164. The annual median price for this route is $290, indicating that these months offer significant savings compared to the yearly average.

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