Cheap Flights From Chicago (June 8)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Chengdu, China Check Dates |
$1,078 Save 38% |
Sep 2026 – Dec 2026 | Cathay Pacific |
|
Kauai, Hawaii Check Dates |
$284 Save 59% |
Dec 2026 | American Airlines |
|
Madeira, Portugal Check Dates |
$670 Save 58% |
Nov 2026 – Dec 2026 | Scandinavian Airlines (SAS) |
|
New York Check Dates |
$163 Save 51% |
Aug 2026 – Dec 2026 | United Airlines |
|
Providenciales, Turks and Caicos Check Dates |
$458 Save 38% |
Oct 2026 – Nov 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.