Cheap Flights From Chicago (August 9)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Bermuda Check Dates |
$402 Save 45% |
Sep 2026 – Nov 2026 | Air Canada |
|
Charleston, South Carolina Check Dates |
$237 Save 41% |
Sep 2026 – Dec 2026 | American Airlines |
|
Punta Cana, Dominican Republic Check Dates |
$375 Save 45% |
Oct 2026 – Dec 2026 | United Airlines |
|
Seville, Spain Check Dates |
$648 Save 44% |
Oct 2026 – Dec 2026 | TAP Portugal |
|
Tampa, Florida Check Dates |
$225 Save 42% |
Sep 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.
⚡ 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.