Cheap Flights From Chicago (June 23)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Aspen, Colorado Check Dates |
$343 Save 43% |
Aug 2026 – Sep 2026 | American Airlines |
|
Chania, Greece Check Dates |
$659 Save 56% |
Aug 2026 | Scandinavian Airlines (SAS) |
|
Kauai, Hawaii Check Dates |
$424 Save 38% |
Oct 2026 – Dec 2026 | American Airlines |
|
Madeira, Portugal Check Dates |
$582 Save 64% |
Nov 2026 – Dec 2026 | Scandinavian Airlines (SAS) |
|
Reykjavik, Iceland Check Dates |
$420 Save 60% |
Sep 2026 – Oct 2026 | Delta |
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.