Cheap Flights From Chicago (September 23)
👇 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 |
|
Denver, Colorado Check Dates |
$243 Save 35% |
Oct 2026 – Mar 2027 | American Airlines |
|
Malta Check Dates |
$698 Save 43% |
Oct 2026 – Feb 2027 | Turkish Airlines |
|
Florence, Italy Check Dates |
$624 Save 42% |
Nov 2026 – Feb 2027 | Iberia |
|
Zanzibar City, Tanzania Check Dates |
$1,087 Save 44% |
Oct 2026 – Nov 2026 | Royal Jordanian |
|
Chiang Mai, Thailand Check Dates |
$911 Save 40% |
Oct 2026 – Mar 2027 | Cathay Pacific |
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.