Cheap Flights From Chicago (September 11)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Maui, Hawaii Check Dates |
$476 Save 33% |
Oct 2026 – Nov 2026 | Southwest Airlines |
|
Honolulu, Hawaii Check Dates |
$476 Save 29% |
Oct 2026 – Nov 2026 | Southwest Airlines |
|
San Cristobal Island, Ecuador Check Dates |
$593 Save 56% |
Nov 2026 | Avianca |
|
Dubrovnik, Croatia Check Dates |
$621 Save 47% |
Oct 2026 | American Airlines |
|
Lisbon, Portugal Check Dates |
$572 Save 45% |
Jan 2027 – Mar 2027 | Delta |
|
Prague, Czech Republic Check Dates |
$606 Save 43% |
Nov 2026 – May 2027 | British Airways |
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.