Cheap Flights From Chicago (September 27)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Memphis, Tennessee Check Dates |
$117 Save 64% |
Oct 2026 – Mar 2027 | American Airlines |
|
Dallas, Texas Check Dates |
$223 Save 42% |
Oct 2026 – Nov 2026 | American Airlines |
|
Montego Bay, Jamaica Check Dates |
$451 Save 36% |
Feb 2027 – Mar 2027 | American Airlines |
|
Barcelona, Spain Check Dates |
$616 Save 37% |
Oct 2026 – Jun 2027 | TAP Portugal |
|
Marrakesh, Morocco Check Dates |
$597 Save 46% |
Jan 2027 | American Airlines |
|
Bangkok, Thailand Check Dates |
$875 Save 40% |
Oct 2026 – Nov 2026 | Ethiopian Airlines |
Note: Flight prices can change in the matter of minutes. On average we see these deals last 2-3 days.
âš¡ 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.