Cheap Flights From Chicago (September 24)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Las Vegas, Nevada Check Dates |
$277 Save 29% |
Oct 2026 – Mar 2027 | Alaska Airlines |
|
Hilton Head, South Carolina Check Dates |
$309 Save 28% |
Oct 2026 – Mar 2027 | United Airlines |
|
Reykjavik, Iceland Check Dates |
$517 Save 57% |
Nov 2026 | United Airlines |
|
Copenhagen, Denmark Check Dates |
$489 Save 51% |
Nov 2026 – Dec 2026 | Scandinavian Airlines (SAS) |
|
Punta Cana, Dominican Republic Check Dates |
$345 Save 50% |
Jan 2027 – Mar 2027 | United Airlines |
|
San Cristobal Island, Ecuador Check Dates |
$671 Save 50% |
Nov 2026 – Aug 2027 | Avianca |
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.