Cheap Flights From Chicago (October 4)
👇 Click “Check Dates” to book directly with the airline
| Destination | Price | Dates | Airline |
|---|---|---|---|
|
Reykjavik, Iceland Check Dates |
$478 Save 61% |
Nov 2026 – Dec 2026 | United Airlines |
|
Punta Cana, Dominican Republic Check Dates |
$350 Save 49% |
Oct 2026 – Mar 2027 | United Airlines |
|
Rio de Janeiro, Brazil Check Dates |
$488 Save 49% |
Feb 2027 – Aug 2027 | Avianca |
|
Copenhagen, Denmark Check Dates |
$506 Save 50% |
Nov 2026 – Feb 2027 | TAP Portugal |
|
Las Vegas, Nevada Check Dates |
$291 Save 26% |
Nov 2026 – Mar 2027 | Alaska Airlines |
|
Denver, Colorado Check Dates |
$277 Save 26% |
Dec 2026 – Jan 2027 | Southwest Airlines |
Note: Flight prices can change in the matter of minutes. On average we see these deals last 2-3 days.
âš¡ 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.