Planning a trip to the “Windy City” soon? Don’t miss out on these ten iconic venues and attractions while visiting Chicago. From comedy and dining to architecture and history, this list has something for every type of traveler.
Check Out a Show at “The Second City”
The Second City is the original improv comedy club. The likes of Tina Fey, Bill Murray, and Chris Farley have practiced their craft in this venue. Catch a show with original sketches, songs, and the improv that makes “The Second City” world-famous.
Eat in the West Loop
The West Loop used to be the city’s meatpacking district. On Randolph Street and Fulton Market, new restaurants pop up among beautiful boutique hotels and technology hubs.
Go Window Shopping on Michigan Avenue
Walk along Michigan Avenue and peek in the windows of the funky shops that line the street. Buy records, books, gourmet foods, luxury brands, vintage clothes, designer shoes, or just about anything else on Chicago’s “Magnificent Mile.”
Admire the 100-ton Bean Sculpture
Officially named “Cloud Gate,” this bean-shaped sculpture created by Indian-born British sculptor Anish Kapoor in Millennium Park is a must-see. Walk under its arch and check out the distorted reflections in the surface of the sculpture.
Grab a Drink at the “Old Town Ale House”
Known as “Le Première Dive Bar,” a visit to the Old Town Ale House for a drink should be on every visitor’s to-do list. This old bar has an interesting history, having seen multiple owners and being rebuilt after a fire.
Head up to the 95th Floor of the John Hancock Center
Take in the views of the city as you peruse the extensive wine list or enjoy the brunch buffet. No beachwear or athletic wear are permitted in this upscale lounge and don’t even think about wearing ripped or torn jeans.
Ride the Iconic Navy Pier Ferris Wheel
Head down to Navy Pier and ride in the enclosed gondolas of the Centennial Wheel. At nearly 200 feet, this Ferris wheel gives incredible 360-degree views of Chicago.
Visit Lake Michigan
Spend an afternoon soaking up the sun on one of the many beaches along Lake Michigan. With 26 free beaches and a bike path over 18 miles long, it’s not hard to find the perfect place to relax at the lake. North Avenue Beach is one of the most popular, though Montrose Beach is the largest and is a common spot to take dogs off-leash.
Try the Chicago Architectural Foundation Cruise
The world-famous cruise gives an overview of the architecture and history of Chicago, from the deck of an upscale boat complete with a full-service bar.
Fill up on Deep Dish Pizza at Giordano’s
Chicago’s famous deep-dish pizza is handmade at Giordano’s, constantly topping “Best Pizza” lists in many newspapers and magazines.