Cheapest weekends to fly Chicago to New York nonstop

We price every nonstop weekend round-trip (2–4 nights, leaving Thu–Sat) on ORD → JFK and rank the weekends below by date. Right now the cheapest is Oct 10–13 at $247 round-trip — 1% below this route's typical short-trip price. Updated August 30, 2026.

Fri, Sep 4 → Mon, Sep 7 3 nights

AA American

$464 Check this weekend →

Thu, Sep 10 → Sun, Sep 13 3 nights

AA American

$362 Check this weekend →

Thu, Oct 1 → Sun, Oct 4 3 nights

AA American

$322 Check this weekend →

Cheapest weekend

Sat, Oct 10 → Tue, Oct 13 3 nights

B6 JetBlue Airways

$247 Check this weekend →

Fri, Oct 16 → Mon, Oct 19 3 nights

DL Delta

$267 Check this weekend →

Thu, Oct 22 → Sun, Oct 25 3 nights

AA American

$362 Check this weekend →

Fri, Nov 6 → Mon, Nov 9 3 nights

AA American

$247 Check this weekend →

Prices are the cheapest nonstop round-trip we found for each weekend, checked within the last 14 days. Fares move — "Check this weekend" re-prices the exact dates live.