Cheap Flights From Chicago (July 31)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Kauai, Hawaii Check Dates |
$438 Save 39% |
Aug 2026 – Sep 2026 | American Airlines |
|
Orlando, Florida Check Dates |
$257 Save 38% |
Aug 2026 – Feb 2027 | American Airlines |
|
Reykjavik, Iceland Check Dates |
$516 Save 58% |
Oct 2026 – Dec 2026 | United Airlines |
|
Madeira, Portugal Check Dates |
$726 Save 55% |
Jan 2027 | Scandinavian Airlines (SAS) |
|
Gibraltar Check Dates |
$706 Save 51% |
Nov 2026 – Dec 2026 | 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
- 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.