NYC → ORD

Cheap Flights from New York to Chicago

Chicago, IL · 740 miles · nonstop from JFK, LaGuardia (LGA) and Newark (EWR)

2h 20m nonstop From $77 740 mi Cheapest in January

Lowest fare found via Travelpayouts for travel around Oct 7 · prices update daily.

$77

Lowest fare

live, one-way

$99

Average fare

one-way

2h 20m

Nonstop time

740 mi

Jan

Cheapest month

~$93

What cheap flights to Chicago actually cost

Across a full year, modelled one-way fares to Chicago range from about $93 in January to roughly $113 in September — a $20 swing, or about 20% around the $101 annual average. Peak demand months for this route are May, June, September, which is when both fares and hotel rates run highest. If your dates are flexible, moving a trip out of September and into January is worth more than almost any booking trick.

Month-by-month fares: New York to Chicago

$93

Jan

$97

Feb

$97

Mar

$100

Apr

$113

May

$113

Jun

$100

Jul

$97

Aug

$113

Sep

$100

Oct

$97

Nov

$97

Dec

* Modelled from this route's $99 historical average and its peak-demand months (May, Jun, Sep), scaled by haul length. Not a live quote — the search box above returns current fares.

About Chicago, IL

Chicago delivers world-class architecture along the lakefront plus deep-dish pizza and a legendary blues and comedy scene. The short 2-hour hop from NYC makes it an easy long-weekend city.

O'Hare is United's and American's shared fortress, which means brutal competition and cheap fares from all three NYC airports, often under two and a half hours in the air. LGA-ORD is the businessperson's shuttle, dozens of daily frequencies, so a missed flight rarely strands you. Watch ORD in winter, though: it's the country's worst hub for snow delays, so pad your connections. May, June and September are the sweet spots for both price and weather. Central time, one hour back. LGA tends cheapest for the quick turn; pick EWR if you're already on that side of the river.

Top things to do in Chicago:

•Millennium Park & 'The Bean'
•Architecture river cruise
•Art Institute of Chicago

Which NYC airport for Chicago?

At 740 miles, Chicago sits inside LaGuardia's 1,500-mile perimeter rule, so all three NYC-area airports can serve it nonstop. That gives you three separate fare markets to compare — JFK, LaGuardia and Newark rarely price the same route identically on the same day.

JFK guide LGA guide EWR guide

How to get the cheapest fare to Chicago

1Book roughly 3-6 weeks ahead — that is the window that fits a 740-mile short-haul route like Chicago, not the generic "book on a Tuesday" advice.
2Compare all three of JFK, LaGuardia and Newark — this route is short enough that all three fly it, and same-day fares between them commonly differ by $40-70.
3Target January (modelled around $93) and avoid September (around $113) if your dates can move.
4At 2h 20m this is a short sector — the first departure of the morning is both the cheapest bank and the least likely to be delayed by knock-on congestion.
5If you are comparing a $64 ultra-low-cost fare against a $99 mainline one, add the bag and seat fees first — on this route that gap usually closes to under $20.
6Set a price alert rather than watching manually. This route's modelled swing is $20 across the year, so the drops are worth catching.

Need a place to stay in Chicago?

Once your flight's sorted, it's worth comparing hotels and short stays early — the best-located rooms tend to book up first. Takes a minute to see what's available for your dates.

Search hotels for your trip

Sorted a ride in Chicago from the airport?

Booking an airport transfer ahead of time means a driver's waiting when you land — no taxi queue or surge pricing after a long flight. Worth comparing a fixed-price pickup for your arrival.

Compare airport transfers

Planning what to do in Chicago?

The popular museums, tours, and attractions often sell out on peak days — it's worth booking skip-the-line tickets before you go so your trip isn't spent waiting in queues.

Find things to do

FAQ: flights from NYC to Chicago

One-way fares to Chicago average about $99, with the cheapest tickets landing near $67 and round trips typically running $198-$248. Across the year our modelled fares move between $93 in January and $113 in September, averaging $101. That makes Chicago the 17th cheapest of the 50 US destinations we track from New York.

Aim for 3-6 weeks ahead. Chicago is 740 miles from New York, and booking windows scale with distance — short hops reward booking late, long hauls punish it. Booking inside two weeks on this route usually means paying close to the September peak of $113 regardless of when you actually travel.

January, at a modelled $93 one-way. The most expensive is September at around $113. Peak season for this route is May, June, September, so the shoulder weeks either side of those months are usually the sweet spot for fare and weather together.

A nonstop takes about 2h 20m covering 740 miles, and all three NYC airports can fly it. Connecting itineraries typically add two to four hours depending on the hub.

At an average of $99 one-way over 740 miles, Chicago works out to 13.4¢ per mile — a premium per mile compared with similar-length routes, cheaper per mile than 29% of the US destinations we track. By headline fare it is the 17th cheapest of our 50 US destinations. Fares above 10¢ per mile usually mean limited nonstop competition, so flexibility on dates matters more here than on a heavily-served route.

Chicago delivers world-class architecture along the lakefront plus deep-dish pizza and a legendary blues and comedy scene. The short 2-hour hop from NYC makes it an easy long-weekend city. Travellers from New York most often build a trip around Millennium Park & 'The Bean', Architecture river cruise, Art Institute of Chicago.