Cheap Flights From Chicago (September 18)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Miami, Florida Check Dates |
$121 Save 70% |
Oct 2026 – Mar 2027 | American Airlines |
|
New Orleans, Louisiana Check Dates |
$185 Save 51% |
Oct 2026 – Mar 2027 | United Airlines |
|
Montego Bay, Jamaica Check Dates |
$360 Save 49% |
Nov 2026 – Dec 2026 | American Airlines |
|
Paris, France Check Dates |
$584 Save 43% |
Oct 2026 – Dec 2026 | TAP Portugal |
|
Rome, Italy Check Dates |
$626 Save 43% |
Nov 2026 – Jun 2027 | TAP Portugal |
|
Puerto Vallarta, Mexico Check Dates |
$362 Save 45% |
Jan 2027 – Feb 2027 | Alaska 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.