Cheap Flights from Chicago - October 5 2

Cheap Flights from Chicago – October 5

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Cheap Flights From Chicago (October 5)

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

Destination Price Dates Airline
Vail, Colorado
Check Dates 		$465
Save 34% 		Dec 2026 – Aug 2027 United Airlines
Hilton Head, South Carolina
Check Dates 		$280
Save 35% 		Oct 2026 – Mar 2027 United Airlines
Madeira, Portugal
Check Dates 		$754
Save 53% 		Oct 2026 – Jun 2027 TAP Portugal
Aguadilla, Puerto Rico
Check Dates 		$224
Save 59% 		Oct 2026 – Mar 2027 United Airlines
Berlin, Germany
Check Dates 		$596
Save 43% 		Nov 2026 – Feb 2027 TAP Portugal
Florence, Italy
Check Dates 		$677
Save 37% 		Jan 2027 American Airlines

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

âš¡ 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.