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First-Time Chicago Visitor Guide

Posted  4 years ago  in  Loop List  by  Ammanuel M. Ayalew

Welcome to Chicago, a city that rolls out the welcome mat and keeps you engaged throughout your stay. There is so much to see and do, and that can be overwhelming. To help you make the most out of your stay, we’ve rounded up the perfect things to do for first-timers so that you can cherry-pick what excites you.

Catch a Show

From family-friendly blockbusters to soul-rejuvenating musicals and magical illusions, the Loop’s glitzy Theatre District boasts Tony Award-winning performances. It’s a significant aspect of Chicago’s arts and culture, attracting millions of people to the pinnacle of entertainment every year. Stay tuned to HotTix for half-price tickets to an array of shows.

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Cloud Gate A.K.A. The Bean at Millennium Park

Visit Millennium Park

What once began as a railroad and parking lot is now one of the most iconic places in the city of Chicago. At Millennium Park, you will find a new kind of town square—a lively, spectacular gathering spot. Discover a state-of-the-art collection of architecture, landscape design and art that provide the backdrop for hundreds of free cultural programs.

While you’re at it, splash around Crown Fountain, which consists of two 50-foot glass block towers at each end of a shallow reflecting pool. The towers project video images from a broad social spectrum of Chicagoans spouting at you. Or go to the rock climbing wall and skating ribbon at Maggie Daley Park.

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Get a Taste of Chicago

At the heart of the 2017's Restaurant City of the Year, the Chicago Loop is home to a myriad of cuisines that can satisfy all your cravings. With a growing number of trendy restaurants emerging on the scene, the Loop offers a great way to indulge in your visit and immerse yourself in the city's culinary culture.

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AceBounce Food
Shoreline Sightseeing Boat Tour

Hop Aboard for a Boat Tour

Chicago’s best attractions look even grander from the river or lake. Learn about the city’s history as you glide through its world-famous architecture. Shoreline Sightseeing’s Chicago River Architecture Tour (ranked seventh by TripAdvisor’s Traveler’s Choice Award), Chicago Architecture Foundation and Wendella’s boat tours are lined up to give you a spectacular tour of the city on its waterways.

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Shop on State Street—"that great street"—and beyond with plenty of retail options. From designer brands to specialty shops you won't find anywhere else, the Loop has what you're looking for. For a variety of options under one roof, visit Macy’s on State Street, the second largest department store in the world recognized as a National Historic Landmark, and Block Thirty Seven, a trendy urban shopping, dining and entertainment center.

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Macy's on State Street
Art Institute of Chicago

See a Museum

Experience the breeze of the world within the Windy City thanks to the Loop’s world-class museums. See exquisite pieces of art from around the globe. Whether you are visiting Chicago for a couple of days or a local wondering how to spend your weekend, these institutions are must-see destinations.

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Libate on a Rooftop Bar

Take your Chicago visit to a whole new level (literally) at the Loop’s elegant rooftop bars. These skyscraping patios boast perfectly crafted cocktails, award-winning dining and some of the best views of the city. They are Chicago’s sky-high oases.

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Cindy's Rooftop
Skydeck at Willis Tower

Soar High at Skydeck

Step outside the tallest building in the Western Hemisphere. At 1,353 feet in the air, the Ledge’s glass boxes extend out 4.3 feet from the Skydeck. Offering spectacular views spanning up to four states, a one-stop Chicago experience full of interactive exhibits--and The Ledge, a glass balcony extending four feet outside the 103rd floor of Willis Tower.

The Skydeck is open 365 days a year including Thanksgiving Day, Christmas Eve, Christmas Day, New Year’s Eve and New Year’s Day. Its entrance is located on Franklin Street (east side of the building).

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Relax on the Riverwalk

Stroll down the Chicago Riverwalk and enjoy the best view of Chicago’s breathtaking architecture. You can also dine al fresco at City Winery, or get a taste of the islands at Island Party Hut while enjoying bocce ball, bag games, Jenga, Bimini Island Ring game and live music on weekends. During the winter, you can reserve one of City Winery's heated domes.

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City Winterys Riverwalk River Domes Photo by Dan Conroe
Big Buss Tours

Big Bus Tours

Besides the breathtaking boat tours, hop on a bus tour for extensive sightseeing. Take in the panoramic views of the city’s iconic architecture and cultural landmarks while listening to an entertaining and educational commentary by the tour guides.

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If you’re going to be driving, download iParkit for discounted parking at any of InterPark's 18 city-wide locations. It will give you quick access to the city's best attractions. Millennium Garages also offers multiple convenient parking garages. You can purchase your spot ahead of time from its website. If you are going to be drinking, we recommend you take a Lyft or the CTA for a safe ride back home.