Cheapest weekends to fly Denver to Chicago nonstop

We price every nonstop weekend round-trip (2–4 nights, leaving Thu–Sat) on DEN → ORD and rank the weekends below by date. Right now the cheapest is Sep 26–29 at $149 round-trip — 47% below this route's typical short-trip price. Updated August 30, 2026.

Sat, Sep 5 → Tue, Sep 8 3 nights

F9 Frontier 9% below typical

$255 Check this weekend →

Fri, Sep 11 → Mon, Sep 14 3 nights

F9 Frontier

$263 Check this weekend →

Sat, Sep 19 → Tue, Sep 22 3 nights

UA United 24% below typical

$213 Check this weekend →

Cheapest weekend

Sat, Sep 26 → Tue, Sep 29 3 nights

F9 Frontier 47% below typical

$149 Check this weekend →

Fri, Oct 2 → Mon, Oct 5 3 nights

F9 Frontier 32% below typical

$190 Check this weekend →

Thu, Oct 8 → Sun, Oct 11 3 nights

F9 Frontier 24% below typical

$213 Check this weekend →

Sat, Oct 17 → Tue, Oct 20 3 nights

F9 Frontier 33% below typical

$188 Check this weekend →

Fri, Oct 23 → Mon, Oct 26 3 nights

F9 Frontier 33% below typical

$189 Check this weekend →

Thu, Oct 29 → Sun, Nov 1 3 nights

F9 Frontier 38% below typical

$174 Check this weekend →

Sat, Nov 7 → Tue, Nov 10 3 nights

F9 Frontier 47% below typical

$149 Check this weekend →

Fri, Nov 13 → Mon, Nov 16 3 nights

F9 Frontier 47% below typical

$149 Check this weekend →

Thu, Nov 19 → Sun, Nov 22 3 nights

F9 Frontier 42% below typical

$162 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.