Cheap Flights From Chicago (October 9)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Kauai, Hawaii Check Dates |
$424 Save 41% |
Oct 2026 – Aug 2027 | United Airlines |
|
Los Angeles, California Check Dates |
$217 Save 43% |
Dec 2026 – Mar 2027 | American Airlines |
|
Venice, Italy Check Dates |
$655 Save 43% |
Jan 2027 | American Airlines |
|
Dublin, Ireland Check Dates |
$624 Save 41% |
Jan 2027 – Mar 2027 | American Airlines |
|
Barcelona, Spain Check Dates |
$615 Save 37% |
Apr 2027 – Jun 2027 | TAP Portugal |
|
San Jose del Cabo, Mexico Check Dates |
$355 Save 41% |
Dec 2026 – Feb 2027 | Alaska 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
- Click the “Check Dates” button above.
- On Google Flights, click the Calendar icon to view the cheapest months.
- Select your specific dates and book directly with the airline.