Cheap Flights From Chicago to USA

Active USA deals departing Chicago.

2 active deals

Key West

Chicago → Key West

$319 USDRoundtrip

✓ $306 USD−$13 · checked 16 days ago

Dec 1 – Dec 8, 2026 · Allegiant Air, American Airlines, JetBlue, United Airlines · Nonstop

Found 1 month agoSee deal

Kona

Chicago → Kona

$470 USDRoundtrip

$581.79 USD+$111.79 · checked 18 days ago

Oct 22 – Oct 29, 2026 · Alaska Airlines

Found 25 days agoSee deal

Other regions from Chicago