Route guide · 740 miles
Cheap Flights from New York to Chicago
JFK → ORD · Nonstop 2h 0m · Live round-trip fares
Looking for cheap flights from New York to Chicago? You're in the right place. Airfare Deal tracks live fares on this 740-mile route around the clock. As a rule of thumb, booking 2–4 weeks ahead lands the best prices — and a free fare alert means you never have to keep refreshing the page.
Live fares for JFK → ORD are updating. Use the search below for real-time prices.
Search live pricesNonstop flights from New York to Chicago
Want to skip the layover? Nonstops from New York to Chicago are flown by Delta Air Lines, Southwest Airlines, Alaska Airlines, getting you there in about 2h 0m. For the lowest fares, book around 2–4 weeks before departure — last-minute nonstops on this route rarely come cheap.
Booking insights: New York → Chicago
- Distance: 740 miles · nonstop flight time: 2h 0m.
- Cheapest upcoming week in the live data starts around Oct 15, with fares from $128.
- Of the months we're tracking right now, October 2026 has the lowest fares, starting at $128.
- Rule of thumb for this route: the sweet spot is usually 2–4 weeks before departure.
- Tuesday and Wednesday departures usually undercut Friday and Sunday fares on routes like this one.
- Set a free Airfare Deal alert instead of checking daily — the best fares can sell out in hours.
Price trend
Cheapest departure weeks ahead
Near-term departures around Oct 15 are currently the cheapest on this route. Based on recent fares found for this route; prices change quickly.
Cheapest month · New York → Chicago
October 2026
Every date's recent round-trip fare, at a glance.
Fares from
$128
Cheapest: Tue, Oct 20 — $128 · Priciest: Oct 18 — $250
Get this fare →Recent fares found for specific dates in October 2026. Blank days had no recent fare in our data — ask our team and we'll check them for you.
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New York to Chicago flight FAQs
How long is the flight from JFK to ORD?
Nonstop flights from New York to Chicago take about 2h 0m and cover roughly 740 miles. One-stop itineraries add 2–4 hours depending on the layover city.
Are there nonstop flights from New York to Chicago?
Yes — look for Delta Air Lines, Southwest Airlines, Alaska Airlines on this route. Nonstop seats are usually priced best 2–4 weeks before departure.
What is the cheapest month to fly from New York to Chicago?
Of the months we're tracking right now, October 2026 has the lowest fares from New York to Chicago, starting at $128. Fares update as new data comes in, so it's worth setting a free alert for your dates.
How much are last minute flights from JFK to ORD?
Last-minute flights from JFK to ORD (booked within 7 days of departure) typically cost noticeably more than fares booked 2–4 weeks out. Booking early is the smarter move.
What is a good round-trip deal from New York to Chicago?
A good deal is anything at or below the recent fares shown above. Set a free Airfare Deal alert and we'll ping you the moment fares drop.
Which airlines fly from New York to Chicago?
The main carriers on this route are Delta Air Lines, Southwest Airlines, Alaska Airlines. Comparing all of them on the live search below usually surfaces the lowest fare for your dates.
More cheap flights from New York
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