Chicago to New York flights: the cheapest month to fly
$103one-way
Tue 15 Dec
Frontier Airlines, 1 stop, O'Hare International to Newark Liberty International, 7 h 29 min
Long connection: the journey takes at least twice the route's typical time.
See flights for Tue 15 Dec on Aviasales: Chicago to New York, Tue 15 Dec, Frontier Airlines, 1 stopOpens the live search on Aviasales. A fare travellers found, not a live quote.
Each fold is a month; its height is the lowest one-way fare found. Coral is the cheapest; "none" means no fare was found.
Fare by month
tap a month; none = no fare foundCheapest found: Tue 15 Dec, $103, Frontier Airlines, 1 stop from O'Hare International. Tap a month to see its days.
The cheapest one-way fare found from Chicago to New York is $103, a one-stop trip of 7 h 29 min, for a flight from O'Hare International in Dec 2026; the priciest month in the next ten, Jan 2027, shows $180. All are fares found in recent searches, not live quotes.
The cheapest fare with an ordinary journey time is $113 in Nov 2026 (American Airlines, direct). 7 of the 10 months with a fare are direct, usually about 2 h 20 min in the air. The median monthly fare is $167, so the cheapest month sits 38% below the usual; the priciest, Jan 2027, is 8% above it. Monthly lows come most often from American Airlines (7 months) and Frontier Airlines (3); the $103 cheapest month is Frontier Airlines.
Every month
- November 2026Tue 17 Nov, American Airlines, direct, O'Hare International to John F. Kennedy International, 2 h 32 min$113Search Tue 17 Nov on Aviasales: Chicago to New York, American Airlines, direct
- December 2026Tue 15 Dec, Frontier Airlines, 1 stop, O'Hare International to Newark Liberty International, 7 h 29 min; long connection$103Search Tue 15 Dec on Aviasales: Chicago to New York, Frontier Airlines, 1 stop
- January 2027Fri 1 Jan, American Airlines, direct, O'Hare International to LaGuardia, 2 h 18 min$180Search Fri 1 Jan on Aviasales: Chicago to New York, American Airlines, direct
- February 2027Wed 3 Feb, Frontier Airlines, 1 stop, O'Hare International to LaGuardia, 9 h 27 min; long connection$108Search Wed 3 Feb on Aviasales: Chicago to New York, Frontier Airlines, 1 stop
- March 2027Wed 3 Mar, Frontier Airlines, 1 stop, O'Hare International to Newark Liberty International, 15 h 29 min; long connection$117Search Wed 3 Mar on Aviasales: Chicago to New York, Frontier Airlines, 1 stop
- April 2027Fri 9 Apr, American Airlines, direct, O'Hare International to LaGuardia, 2 h 11 min$167Search Fri 9 Apr on Aviasales: Chicago to New York, American Airlines, direct
- May 2027Sat 1 May, American Airlines, direct, O'Hare International to LaGuardia, 2 h 20 min$167Search Sat 1 May on Aviasales: Chicago to New York, American Airlines, direct
- June 2027Sun 20 Jun, American Airlines, direct, O'Hare International to LaGuardia, 2 h 17 min$178Search Sun 20 Jun on Aviasales: Chicago to New York, American Airlines, direct
- July 2027Mon 19 Jul, American Airlines, direct, O'Hare International to Newark Liberty International, 2 h 21 min$170Search Mon 19 Jul on Aviasales: Chicago to New York, American Airlines, direct
- August 2027Mon 2 Aug, American Airlines, direct, O'Hare International to John F. Kennedy International, 2 h 25 min$166Search Mon 2 Aug on Aviasales: Chicago to New York, American Airlines, direct
For connecting trips the airline shown is the one the search returned as the main carrier; other legs may be with other airlines.