Cheap Flights From Chicago (June 20)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Destin, Florida Check Dates |
$215 Save 51% |
Aug 2026 | Delta |
|
Fort Lauderdale, Florida Check Dates |
$171 Save 50% |
Aug 2026 – Dec 2026 | American Airlines |
|
Miami, Florida Check Dates |
$171 Save 58% |
Aug 2026 – Dec 2026 | American Airlines |
|
Orlando, Florida Check Dates |
$217 Save 48% |
Aug 2026 – Dec 2026 | American Airlines |
|
San Juan, Puerto Rico Check Dates |
$237 Save 53% |
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.