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Chicago's First-time Visitor’s Guide

Updated: Jan 24, 2023

First time in Chicago? Here's your guide to the city's must-see attractions, vibrant food scene, and only-in-Chicago experiences that you shouldn't miss.

There are a lot of iconic things to see and do at Millennium Park Campus, which is a classic Chicago attraction. The Frank Gehry-designed Jay Pritzker Pavilion, Jaume Plens' interactive Crown Fountain, Gustafson Guthrie Nichol Ltd's contemporary Lurie Garden, and Anish Kapoor's massively popular Cloud Gate sculpture are just a few of the highlights of the park. Millennium Park is home to the Millennium Parking Garages and a railroad yard, making it one of the world's largest green roofs.

Navy Pier is a family-friendly destination with picturesque boat excursions, summer fireworks displays, local culinary outposts, the county's largest rooftop bar, and carnival rides. One of Navy Pier's most iconic views is the Centennial Wheel at Pier Park. This approximately 200-foot ride boasts its climate-controlled gondolas and opened at the Chicago World Fair in 1893.

The Skydeck of Willis Tower encourages guests to practically step out onto The Ledge, a glass box that extends 4 feet from the skyscraper's face, nearly 1,300 feet above ground level. Moreover, from 1,000 feet up, TILT at 360 CHICAGO leans you over The Magnificent Mile, providing views of the city and Lake Michigan.

Three Beaux-Arts-inspired buildings sit on the shores of Lake Michigan, providing the perfect setting for Museum Campus. Also, Field Museum, Shedd Aquarium, and Adler Planetarium exist side by side amid lush parks and gardens, attracting lovers of ancient civilizations, aquatic realms, and astounding galaxies.

Don't miss out on Uno Pizzeria & Grill's deep-dish pizza that features a generous amount of sausage, pepperoni, onions, peppers, mushrooms, and chunky tomato sauce, topped with mozzarella and romano.

Savor the dense and chewy Bertha's Famous Brownie from Palmer House. This brownie was originally created for the Chicago World's Fair in 1893. Both Potter's and Lockwood Restaurant serve brownies.

Cool craft beer bars can be found in Chicago's hippest neighborhoods. Learn about an urban farm, play cornhole at the local hangout or visit Illinois' largest independent craft brewery. You can even order a deep dish pizza and have it delivered to a bring-your-own-food taproom. The possibilities are endless! It's all centered on or near Milwaukee Avenue.

The charm and proximity of Lincoln Park and Lakeview to the scenic lakeshore make these residential enclaves popular. They know that these neighborhoods are also home to a variety of local breweries, pubs, and restaurants, all nestled among tree-lined streets and charming boutiques. Take a look at them all together!

Experience classic Chicago by watching a Cubs game from the rooftops, listening to native jazz, and laughing out loud in The Second City.

The skyline of Chicago, with architectural marvels like the Wrigley Building, Willis Tower, and Tribune Building, is one of the city's greatest triumphs. One of the greatest ways to view all of the modern and historic marvels is to take a tour. A cruise along the Chicago River or out on Lake Michigan to see the architecture. After that, visit the Chicago Architecture Center to see intriguing exhibitions on the history of skyscrapers, the Great Chicago Fire, and more.

But it's not all about buildings. Visit Oak Park, a suburb of Chicago about 10 miles from the Loop, to view more examples of Frank Lloyd Wright's work than anywhere else on the planet. Alternatively, explore some of Wright's Chicago masterpieces, such as the light court within The Rookery and the restored Robie House in Hyde Park, which is a UNESCO World Heritage Site.

Why stay in a mundane motel when you can stay in a historic Chicago gem? You'll feel like you've gone back in time when you enter the lobbies of any of these historic hotels. From historic to contemporary, elegant to homey, Chicago's large list of fascinating hotels and hostels has a personality fit for just about everyone. You can check them out here. (link not yet available)

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