New York to Chicago flights: the cheapest month to fly
$109one-way
Wed 3 Mar
Frontier Airlines, 1 stop, Newark Liberty International to O'Hare International, 6 h 47 min
Long connection: the journey takes at least twice the route's typical time.
See flights for Wed 3 Mar on Aviasales: New York to Chicago, Wed 3 Mar, 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: Wed 3 Mar, $109, Frontier Airlines, 1 stop from Newark Liberty International. Tap a month to see its days.
The cheapest one-way fare found from New York to Chicago is $109, a one-stop trip of 6 h 47 min, for a flight from Newark Liberty International in Mar 2027; the priciest month in the next ten, Jun 2027, shows $185. All are fares found in recent searches, not live quotes.
The cheapest fare with an ordinary journey time is $154 in Nov 2026 (American Airlines, direct). 5 of the 9 months with a fare are direct, usually about 2 h 48 min in the air. The median monthly fare is $154, so the cheapest month sits 29% below the usual; the priciest, Jun 2027, is 20% above it. Monthly lows come most often from American Airlines (4 months), Frontier Airlines (4) and Southwest Airlines (1); the $109 cheapest month is Frontier Airlines.
Every month
- November 2026Thu 19 Nov, American Airlines, direct, LaGuardia to O'Hare International, 2 h 48 min$154Search Thu 19 Nov on Aviasales: New York to Chicago, American Airlines, direct
- December 2026Wed 9 Dec, Frontier Airlines, 1 stop, Newark Liberty International to O'Hare International, 14 h 25 min; long connection$116Search Wed 9 Dec on Aviasales: New York to Chicago, Frontier Airlines, 1 stop
- January 2027Sun 10 Jan, Frontier Airlines, 1 stop, LaGuardia to Midway International, 8 h 21 min; long connection$121Search Sun 10 Jan on Aviasales: New York to Chicago, Frontier Airlines, 1 stop
- February 2027Wed 17 Feb, Frontier Airlines, 1 stop, Newark Liberty International to O'Hare International, 6 h 47 min; long connection$114Search Wed 17 Feb on Aviasales: New York to Chicago, Frontier Airlines, 1 stop
- March 2027Wed 3 Mar, Frontier Airlines, 1 stop, Newark Liberty International to O'Hare International, 6 h 47 min; long connection$109Search Wed 3 Mar on Aviasales: New York to Chicago, Frontier Airlines, 1 stop
- April 2027Sat 10 Apr, American Airlines, direct, LaGuardia to O'Hare International, 2 h 47 min$173Search Sat 10 Apr on Aviasales: New York to Chicago, American Airlines, direct
- May 2027Wed 5 May, American Airlines, direct, LaGuardia to O'Hare International, 2 h 50 min$180Search Wed 5 May on Aviasales: New York to Chicago, American Airlines, direct
- June 2027Wed 30 Jun, Southwest Airlines, direct, LaGuardia to Midway International, 2 h 25 min$185Search Wed 30 Jun on Aviasales: New York to Chicago, Southwest Airlines, direct
- July 2027Mon 19 Jul, American Airlines, direct, LaGuardia to O'Hare International, 2 h 53 min$170Search Mon 19 Jul on Aviasales: New York to Chicago, American Airlines, direct
- August 2027: no fare foundSearch August 2027 on Aviasales: New York to Chicago
For connecting trips the airline shown is the one the search returned as the main carrier; other legs may be with other airlines.