NYC → ORD

Cheap Flights to Chicago

Find the cheapest flights from New York to Chicago, IL. Compare airlines from $99 one-way.

2h 20m direct flight
From $99 one-way
ORD Airport

$69

Lowest Fare

one-way

$99

Average Price

one-way

2h 20m

Flight Duration

direct

May

Best Month

to book

About Chicago, IL

Chicago is a popular destination for NYC travelers, offering a great mix of culture, cuisine, and attractions. The city is served by ORD airport, making it easy to reach from New York's three major airports.

The average flight price from NYC to Chicago is $99 one-way based on recent bookings. Prices are lowest in Mayand highest during holidays and summer peak travel.

Best airlines: JetBlue offers the best value with free carry-on bags. Delta and American Airlines have the most daily departures. Spirit and Frontier offer the cheapest base fares but charge extra for bags.

Best Time to Visit Chicago

🌸 Spring (Mar-May)

Mild weather, moderate prices. A great time to visit before summer crowds arrive.

Moderate

☀️ Summer (Jun-Aug)

Peak season with the highest prices. Book 3-4 months ahead if you must travel in summer.

Expensive

🍂 Fall (Sep-Nov)

Best value season with lower prices and comfortable weather. Highly recommended.

Affordable

❄️ Winter (Dec-Feb)

Prices vary — cheap in early January but expensive during the holidays.

Varies

Tips for Finding Cheap Flights to Chicago

1Book 3-5 weeks ahead for the best fares to Chicago
2Check flights from all three NYC airports (JFK, LGA, EWR) to find the lowest price
3Travel in shoulder season (May or Jun) for best value
4Pack light if flying Spirit or Frontier — carry-on fees can add $45+ each way
5Set a price alert to get notified when prices drop below your target
6Consider flying Tuesday/Wednesday for cheaper fares on this route

FAQ: Cheap Flights to Chicago

Cheap flights to Chicago from New York typically start from $69 one-way on budget carriers like Spirit or Frontier. The average round-trip price is $198–$277. Prices fluctuate based on season and booking timing.

Similar Destinations

Nashville

2h 30m

$99

Kansas City

2h 55m

$99

Omaha

3h 0m

$99

Jacksonville

2h 20m

$99

NYC Airports to Chicago

JFK

John F. Kennedy

$99+

LGA

LaGuardia

$104+

EWR

Newark Liberty

$94+

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