Cheap Flights From Chicago (July 29)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Boston Check Dates |
$217 Save 42% |
Sep 2026 – Nov 2026 | American Airlines |
|
Nassau, Bahamas Check Dates |
$379 Save 49% |
Nov 2026 | Air Canada |
|
Paris, France Check Dates |
$586 Save 43% |
Sep 2026 – Dec 2026 | TAP Portugal |
|
Punta Cana, Dominican Republic Check Dates |
$375 Save 45% |
Oct 2026 – Dec 2026 | United Airlines |
|
San Diego, California Check Dates |
$237 Save 36% |
Aug 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.