Featured Destination: Chicago

  • Love it? Share it!

  • Email a friend
  • Share on Facebook
  • Share on Twitter
 
 

Savings in the Second City

No matter what the season, there are new reasons to fall in love with -- or rekindle love for -- Chicago. Skyscraper views, free events and a flourishing culinary scene are just the beginning for those who time a trip this spring or summer.

Travelzoo Deal Experts have sourced hotel, entertainment and local deals that can save more than 50% on regular prices.

Discover why Chicago has a legacy of churning out some of America's most colorful characters, from the influential (President Barack Obama) to the iconic (Michael Jordan) to the infamous (Al Capone). Before you know it, Chicago will be your kind of town, too.

 
 
 
Hotel Deals
Additional savings through spring.
More »
Show Deals
Book your tickets in advance.
More »
Spa & Dining Deals
Make those reservations.
More »
Travelzoo Facebook
Join our 1 million+ fans.
More »
Travelzoo App
Deals at your fingertips.
More »
 

Top Deals Handpicked by Travelzoo

 
Weekends in May; +$20 Weekends in April
Hilton Chicago O'Hare
 
 
Redeem by May 10, 2014
deca Restaurant + Bar at the Ritz-Carlton Chicago
 
 
 
 
Redeem by Sept. 14, 2014
Chicago Sailboat Charters
 
Use by June 13, 2014
Balance Spa & Fitness at Palmer House a Hilton Hotel
 
 
Use by July 28, 2014
Sun Aero Helicopters Inc.
 
 
 

From: To: Travelers:
Depart: Return: One-way
Round-trip   
Enter city: Guests:
Check-in: Check-out: Rooms:
From: To: Travelers:
Depart: Return: Rooms:
Enter city: Pick-up Time:
Pick-up Date: Return Date: Return Time: