Cheap Flights From Chicago (June 15)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Aspen, Colorado Check Dates |
$343 Save 43% |
Aug 2026 – Apr 2027 | United Airlines |
|
Bridgetown, Barbados Check Dates |
$448 Save 43% |
Oct 2026 – Nov 2026 | Air Canada |
|
Miami, Florida Check Dates |
$187 Save 54% |
Sep 2026 – Dec 2026 | American Airlines |
|
San Juan, Puerto Rico Check Dates |
$227 Save 55% |
Aug 2026 – Sep 2026 | American Airlines |
|
Vail, Colorado Check Dates |
$374 Save 42% |
Aug 2026 | American 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.