Cheap Flights From Chicago (September 5)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Berlin, Germany Check Dates |
$649 Save 38% |
Nov 2026 – Dec 2026 | TAP Portugal |
|
Dubai, United Arab Emirates Check Dates |
$723 Save 39% |
Oct 2026 – Mar 2027 | Delta |
|
Las Vegas, Nevada Check Dates |
$271 Save 31% |
Oct 2026 – Mar 2027 | Alaska Airlines |
|
Milan, Italy Check Dates |
$629 Save 42% |
Oct 2026 – Nov 2026 | TAP Portugal |
|
Montreal, Canada Check Dates |
$315 Save 39% |
Sep 2026 – Oct 2026 | American Airlines |
|
Seattle, Washington Check Dates |
$197 Save 43% |
Oct 2026 – Mar 2027 | American 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.