Illinois
$249—Chicago 4-star getaway w/flights
Lindsay Benson
Deal Expert
See why "The Windy City" is always topping lists of must-see cities.
Why We Love This Deal
Whether it's your first or fiftieth trip, it's always a good time to visit Chicago. It earned a spot as one of our Best Bets of 2026, thanks to its consistent foodie reputation, 77 diverse neighborhoods and dozens of museums to wander, including the just-opened Obama Presidential Center. This deal covers your roundtrip flights and 3 nights in a 4-star hotel.
This package was negotiated exclusively for Travelzoo members. You won't find it anywhere else.
What's included:
- Roundtrip flights to Chicago
- 3 nights at the 4-star Le Meridien Essex Chicago in a Classic King Room
- All taxes and fees
- Options to extend your trip up to 6 nights
Per-person pricing:
- $249 ... Atlanta, Denver, Orlando
- $299 ... Fort Lauderdale, Houston, Los Angeles
- $349 ... Dallas; Washington, D.C.
- $399 ... Boston, Miami, Newark, New York (JFK)
Other departure cities are also available—call to book.
When to go: Depart on select dates in October–February. Other departures are available through March 2027. Dates vary by city—see our partner's website for more details.
Customize your trip: Call Yes Getaways' travel experts at 1-857-214-2664. They can help you upgrade your room, add nights or adjust your itinerary.
Book by Oct. 21.
This offer is booked through, and is therefore subject to, the travel or entertainment provider's terms and conditions, including but not limited to refund and cancellation policy. Become a member to see all offer details and learn how to book.