Cheap Flights from Chicago - September 26 2

Cheap Flights from Chicago – September 26

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Cheap Flights From Chicago (September 26)

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

Destination Price Dates Airline
New York
Check Dates 		$277
Save 27% 		Oct 2026 – Mar 2027 United Airlines
Memphis, Tennessee
Check Dates 		$117
Save 64% 		Oct 2026 – Mar 2027 Southwest Airlines
Stockholm, Sweden
Check Dates 		$507
Save 54% 		Apr 2027 Scandinavian Airlines (SAS)
Aguadilla, Puerto Rico
Check Dates 		$237
Save 57% 		Oct 2026 – Mar 2027 United Airlines
Madeira, Portugal
Check Dates 		$754
Save 53% 		Oct 2026 – Jun 2027 TAP Portugal
Berlin, Germany
Check Dates 		$597
Save 43% 		Oct 2026 – Dec 2026 TAP Portugal

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.