Cheap Flights From Chicago (June 22)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Boston Check Dates |
$149 Save 58% |
Aug 2026 – Sep 2026 | American Airlines |
|
Gibraltar Check Dates |
$824 Save 51% |
Sep 2026 – May 2027 | American Airlines |
|
La Romana, Dominican Republic Check Dates |
$355 Save 43% |
Jul 2026 – Aug 2026 | American Airlines |
|
Nassau, Bahamas Check Dates |
$401 Save 46% |
Sep 2026 | Air Canada |
|
San Cristobal Island, Ecuador Check Dates |
$758 Save 44% |
Sep 2026 | Avianca |
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.