Cheap Flights From Chicago to USA

Active USA deals departing Chicago.

5 active deals

San Francisco

Chicago → San Francisco

$219 USDRoundtrip

✓ $211.96 USD−$7.04 · checked 20h ago

Oct 2026 – Feb 2027 · American Airlines · Nonstop

Found yesterdaySee deal

Honolulu

Chicago → Honolulu

$720 USDRoundtrip

✓ $659.89 USD−$60.11 · checked 20h ago

Sep – Nov 2026 · United Airlines · 1 stop

Found yesterdaySee deal

Miami

Chicago → Miami

$117 USDRoundtrip

$240.46 USD+$123.46 · checked 20h ago

Sep – Nov 2026 · United Airlines

Found yesterdaySee deal

Los Angeles

Chicago → Los Angeles

$189 USDRoundtrip

$273.40 USD+$84.40 · checked 20h ago

Jan – Feb 2027 · United Airlines · Nonstop

Found yesterdaySee deal

Key West

Chicago → Key West

$319 USDRoundtrip

$718.68 USD+$399.68 · checked 20h ago

Dec 2026 · Allegiant Air, American Airlines, JetBlue, United Airlines · Nonstop

Found yesterdaySee deal

Other regions from Chicago