Open interactive map →Cheap flights from New York to Chicago
Cheap flights from New York to Chicago, United States recently found from €91. Tracked fares on this route include at least one stop. Browse the month-by-month price calendar below, then click through to book.
SkyHopp's cheapest tracked fare from New York to Chicago is €91. Tracked fares on this route include at least one stop. The calendar above lists the months with data; more months are needed before naming a cheapest month.
One-way fares
From €91
Cheapest tracked fare
Return fares
From €167
Tracked return fares (out 23 Nov 2026, back 2 Dec 2026)
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Cheapest month to fly
- November 2026€911 stopCheapest
SkyHopp has tracked fares for this route in November at around €91. That is the only month with data so far, so it is too early to name a cheapest month.
Cheapest fare last seen 26 October 2026.
Entry requirements for United States
EU passportESTA required (visa-waiver)
US passportN/A (domestic)
Requirements vary by nationality and change without notice. Check requirements for your nationality →
About Chicago
Chicago is the great American city that the coasts overlook - a dense, architecturally extraordinary lakefront city with world-class museums, deep-dish pizza, and jazz and blues venues that trace the music's northern migration. O'Hare (ORD) and Midway (MDW) together give the city one of the world's widest airport choices.
Alternative routes
Other ways to reach Chicago
Frequently asked questions
How much does a flight from New York to Chicago cost?
The cheapest tracked fare from New York to Chicago is €91. The month-by-month price calendar on this page lists the months SkyHopp has fares for. A tracked return fare on this pair is currently from €167. Fares are refreshed as our flight partners publish new availability.
Are there direct flights from New York to Chicago?
SkyHopp has not observed a non-stop fare from New York to Chicago in the current dataset. Tracked fares on this pair include at least one stop. Schedules change - check the booking site for a full breakdown by stop count on your dates.
When is the cheapest time to fly from New York to Chicago?
SkyHopp does not yet have enough months of fares on this route to name a cheapest month. The calendar above lists the months that already have data. Set a price alert on this page to watch the fare.