Cheap Flights From Chicago (September 4)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Los Angeles, California Check Dates |
$217 Save 43% |
Oct 2026 – Nov 2026 | American Airlines |
|
Kauai, Hawaii Check Dates |
$426 Save 40% |
Oct 2026 – Dec 2026 | Delta |
|
Reykjavik, Iceland Check Dates |
$530 Save 56% |
Sep 2026 – Dec 2026 | United Airlines |
|
Nassau, Bahamas Check Dates |
$375 Save 50% |
Sep 2026 – Oct 2026 | Air Canada |
|
Punta Cana, Dominican Republic Check Dates |
$395 Save 42% |
Oct 2026 – Feb 2027 | United Airlines |
|
Vienna, Austria Check Dates |
$700 Save 35% |
Oct 2026 – Feb 2027 | Turkish 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.