Cheap Flights From Chicago (August 16)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Kauai, Hawaii Check Dates |
$438 Save 39% |
Aug 2026 – Jun 2027 | American Airlines |
|
Savannah, Georgia Check Dates |
$237 Save 41% |
Jan 2027 – Mar 2027 | American Airlines |
|
Reykjavik, Iceland Check Dates |
$516 Save 58% |
Oct 2026 – Dec 2026 | United Airlines |
|
Stockholm, Sweden Check Dates |
$603 Save 45% |
Feb 2027 | Scandinavian Airlines (SAS) |
|
San Jose, Costa Rica Check Dates |
$364 Save 33% |
Oct 2026 – Dec 2026 | United 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.