Cheap Flights From Chicago (June 29)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Gibraltar Check Dates |
$866 Save 49% |
Sep 2026 – May 2027 | American Airlines |
|
Mykonos, Greece Check Dates |
$662 Save 50% |
Aug 2026 – Sep 2026 | American Airlines |
|
New York Check Dates |
$171 Save 49% |
Sep 2026 – Dec 2026 | American Airlines |
|
Vail, Colorado Check Dates |
$340 Save 48% |
Aug 2026 – Sep 2026 | United Airlines |
Note: Flight prices can change in the matter of minutes. On average we see these deals last 2-3 days.
⚡ 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.