Cheap Flights From Chicago (August 21)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
San Francisco, California Check Dates |
$237 Save 39% |
Sep 2026 – Mar 2027 | American Airlines |
|
Key West, Florida Check Dates |
$319 Save 32% |
Nov 2026 – Jul 2027 | American Airlines |
|
San Juan, Puerto Rico Check Dates |
$257 Save 54% |
Aug 2026 – Nov 2026 | American Airlines |
|
Oslo, Norway Check Dates |
$484 Save 52% |
Nov 2026 | Scandinavian Airlines (SAS) |
|
Nagoya, Japan Check Dates |
$841 Save 51% |
Sep 2026 – Oct 2026 | Air Canada |
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.