Cheap Flights from Chicago - September 8 2

Cheap Flights from Chicago – September 8

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Cheap Flights From Chicago (September 8)

👇 Click “Check Dates” to book directly with the airline

Destination Price Dates Airline
Aspen, Colorado
Check Dates 		$393
Save 35% 		Oct 2026 – Apr 2027 American Airlines
Hilton Head, South Carolina
Check Dates 		$299
Save 30% 		Dec 2026 American Airlines
Kelowna, Canada
Check Dates 		$282
Save 48% 		Sep 2026 – Mar 2027 Air Canada
Madeira, Portugal
Check Dates 		$679
Save 58% 		Oct 2026 – Nov 2026 TAP Portugal
Madrid, Spain
Check Dates 		$549
Save 45% 		Oct 2026 – Nov 2026 TAP Portugal
Rome, Italy
Check Dates 		$571
Save 48% 		Nov 2026 – Apr 2027 British Airways

Note: Flight prices can change in the matter of minutes. On average we see these deals last 2-3 days.

⚡ How to Book

  1. Click the “Check Dates” button above.
  2. On Google Flights, click the Calendar icon to view the cheapest months.
  3. Select your specific dates and book directly with the airline.