Cheap Flights From Chicago (September 29)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Fort Lauderdale, Florida Check Dates |
$183 Save 53% |
Oct 2026 – Aug 2027 | American Airlines |
|
Boston Check Dates |
$222 Save 41% |
Oct 2026 – Nov 2026 | American Airlines |
|
San Juan, Puerto Rico Check Dates |
$237 Save 57% |
Oct 2026 – Dec 2026 | United Airlines |
|
Porto, Portugal Check Dates |
$583 Save 46% |
Oct 2026 – Dec 2026 | TAP Portugal |
|
Venice, Italy Check Dates |
$656 Save 43% |
Feb 2027 | British Airways |
|
Madrid, Spain Check Dates |
$591 Save 40% |
Nov 2026 – Jun 2027 | TAP Portugal |
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.