Chicago Loop: What to See & Do + Where to Eat, Drink & Stay

Heading to the Windy City for a vacation? Make a beeline for the bustling and vibrant Chicago Loop neighborhood. This central area, also known as Downtown Chicago, is the heart of the city and has loads to offer both locals and visitors alike.

The Chicago Loop is home to some of the world’s finest architecture. The skyline is nothing less than spectacular, with towering skyscrapers like the Willis Tower (formerly known as the Sears Tower) and the John Hancock Center dominating the landscape.

Aside from the stunning architecture, the Chicago Loop has an abundance of shopping, dining, and entertainment options. If you’re looking for high-end shopping, head north of the Chicago River to the Magnificent Mile, which features luxury brands like Gucci, Prada, and Louis Vuitton.

Entertainment-wise, the Chicago Loop has you covered, too. The famous Chicago Theatre hosts a variety of shows and concerts throughout the year, while the Art Institute of Chicago is a must-visit for art lovers. And if you’re a sports fan, you can catch a game at the United Center, home of the Bulls and the Blackhawks.

Ready to begin your Windy City adventure? Check out the city’s most exciting neighborhood with this complete Chicago Loop guide, including what to see & do, where to eat & drink, and where to stay.

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What to see & do in The Loop

The Art Institute of Chicago

The first stop on your adventures in the Chicago Loop should be the incredible Art Institute of Chicago. This exceptional museum features an extensive world-renowned art collection from classic to contemporary works.

There’s no shortage of awe-inspiring art here, from the iconic American Gothic painting by Grant Wood to the captivating sculptures by Auguste Rodin. You’ll find everything at the Art Institute of Chicago, from ancient Egyptian artifacts to contemporary African art, reflecting the rich tapestry of human history and creativity.

The Art Institute of Chicago

If you’re a fan of impressionist art, you’re in for a real treat! The Art Institute of Chicago is home to some of the world’s most beautiful impressionist paintings, including Monet, Renoir, and Degas.

Beyond simply admiring art, the museum offers a range of educational programs and events such as lectures, workshops, and guided tours.

Millennium Park

Millennium Park is the beating heart of the Chicago Loop neighborhood and is packed with amazing sights, sounds, and experiences you won’t want to miss. Built to celebrate the new millennium, it’s open year-round and offers an incredible range of public art, from architecture and sculptures to exhibitions, concerts, and family activities.

One of the most iconic features of Millennium Park is the Cloud Gate sculpture, affectionately known as “The Bean” by locals. This massive, reflective sculpture is a perfect spot for a photo op, and a lively crowd of visitors always surrounds it.

Millennium Park

If you’re in the mood for live entertainment, head to the Jay Pritzker Pavilion. This outdoor concert venue hosts an impressive lineup of performers throughout the year, including concerts by the Chicago Symphony Orchestra and other world-class musicians.

For a more tranquil experience, check out the Lurie Garden, a beautiful garden filled with native plants and flowers. It’s one of the most popular places to visit in Chicago to relax and take in the city’s natural beauty.

If you’re traveling with kids, stop by the Crown Fountain. This interactive sculpture features two 50-foot towers that project images of faces, which then spout water from their mouths. It’s a playful and interactive way to cool off on a hot day.

Willis Tower

Standing sentry in the heart of The Loop, the Willis Tower is one of the most iconic buildings in Chicago. Make your way to the top of the 110-story skyscraper, formerly known as the Sears Tower, for spectacular panoramic city views.

As you step into the massive lobby, marvel at the soaring ceilings and the sheer size of the tower. You’ll understand why Willis Tower earns its place as the third-tallest building in the Western Hemisphere!

Willis Tower

Hop on the fastest elevators in the world, which will whisk you up to the Skydeck. Located on the 103rd floor, this observation deck gives you a 360-degree view of Chicago and the surrounding areas. You’ll be able to see for miles and miles, taking in the city’s stunning architecture and natural beauty.

If you’re feeling brave on your Chicago itinerary, step out onto The Ledge, a glass box extending four feet outside the building; it’s a heart-stopping experience and one you’ll never forget!

Grant Park

Escape the hustle and bustle of the city and head to Grant Park for an afternoon of relaxation. Fondly known as “Chicago’s Front Yard,” Grant Park is home to beautiful green spaces, spectacular lakefront views, and iconic monuments.

Like New York’s Central Park, this expansive park is a city centerpiece and a must-see destination for locals and visitors alike. Grant Park is home to some of Chicago’s most famous museums, like the Field Museum of Natural History and the popular Art Institute of Chicago.

Grant Park

One of the highlights of Grant Park is Buckingham Fountain, a massive fountain featured in movies, TV shows, and countless postcards. The kids will love Maggie Daley Park’s climbing walls, slides, and skating ribbon.

Grant Park sits right on the shore of Lake Michigan, boasting gorgeous views of the water and the city skyline. It’s the perfect place to walk, ride a bike, or sit and relax.

Chicago Riverwalk

Another incredible spot to soak up the buzz of the city is the Chicago Riverwalk. Stretching for 1.25 miles along the south bank of the Chicago River, the award-winning, pedestrian-friendly is the place to be on a glorious summer’s day!

As you stroll along the Riverwalk, you’ll find charming cafés, bars and wineries, museums and monuments, quiet spots for relaxing, and loads of water-based activities. Take in beautiful views of the city skyline and the river and enjoy an array of rotating public art exhibitions.

Chicago Riverwalk

Rent a kayak or take a water taxi and explore the river from the water. Hop on a guided boat tour and get a unique perspective of the city. Visit the Mies van Der Rohe-designed Chicago Architecture Center at One Illinois Center and the McCormick Bridgehouse & Chicago River Museum.

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Finish your meander at one of the bars and restaurants along the Riverwalk, where you can enjoy a delicious meal and a drink against a backdrop of spectacular city and river views.

Skydeck Chicago

For heart-stopping views of the city, make your way to the Skydeck Chicago at the top of the Willis Tower (formerly the Sears Tower) on S. Wacker Drive. Head to the 103rd floor on the world’s fastest elevators, where you’ll step out on the Skydeck.

Skydeck Chicago

The Skydeck boasts breathtaking 360-degree views of Chicago. You can spot famous landmarks like Navy Pier, the Chicago River, and Millennium Park from high above. On a cloudless day, you can see four different states from the observation deck!

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If you’re feeling brave, step onto The Ledge, a glass balcony that extends four feet outside the building, and look straight down for a thrilling experience you won’t forget!

Cadillac Palace Theatre

Catch a show at the historic Cadillac Palace Theatre. Built in 1926, the theater was designed to emulate the magnificent Versailles Palace in France. Breathtaking interiors with rose-marbled walls, crystal chandeliers, and gilt mirrors transport you back to the golden age of theater.

Cadillac Palace Theatre

The 2,300-seat theater hosts various performances throughout the year, from Broadway musicals to ballets to concerts.

The Cadillac Palace Theatre is next to the Hotel Allegro in the heart of the newly revived Randolph Street theater district. Surrounded by many fantastic restaurants and bars, it’s ideally located for a fun night out on the town.

Maggie Daley Park

If you’re looking for a fun-filled day outdoors in the Windy City, head to Maggie Daley Park. Nestled in the midst of the city, the 20-acre is a fantastic spot to escape the city for a while.

The crowning jewel of Maggie Daley Park is the Play Garden. Designed to resemble a whimsical village with a lighthouse, bridges, and water features, the Play Garden is an oasis of fun for kids of all ages where they can climb, slide, and explore to their heart’s content.

Maggie Daley Park

Maggie Daley Park also boasts a skating ribbon, an ice-skating path that winds through the park’s scenic landscape. The ribbon transforms into a walking and rollerblading path in the summer, so you can enjoy the beautiful surroundings no matter what time of year you visit.

There are also plenty of opportunities to get your heart pumping: Maggie Daley Park has multiple sports fields, including baseball and softball diamonds, a climbing wall, and a mini-golf course.

Where to eat & drink

When it comes to wining and dining in The Loop, you’ll find a plethora of restaurants, ranging from casual spots to upscale dining destinations.

Stylish, contemporary, and oh-so-chic, The Dearborn is perfect for a special night out. Anchoring the southeast corner of Dearborn and Randolph Streets, this sleek American tavern serves market-driven fare and signature cocktails with a laid-back, cosmopolitan vibe.

If you’ve got a hankering for traditional German schnitzel and sauerkraut, The Berghoff Restaurant is the only place to be! This iconic family-owned restaurant has been around for 125 years and oozes a warm and welcoming charm. Settle into a cozy booth and tuck into steaming dishes of bratwurst, knockwurst, and smoked Thüringer.

The Berghoff Restaurant in Chicago Loop

Book a table at The Village for classic Italian fare in a bustling, vibrant atmosphere. Chicago’s oldest Italian restaurant brings the sun-kissed hills of Tuscany to the heart of The Loop. Warm, hand-painted interiors welcome you, and steaming plates of homemade pasta and wood-fired pizza transport your taste buds to the Mediterranean.

Remington’s is your go-to for a great steak! Set on North Michigan Avenue, the classic steakhouse won’t disappoint with a stylish setting, cozy booths, and a mouthwatering menu. Start with Oysters Rockefeller followed by filet mignon or a perfectly seared ribeye. And then, toast the Windy City with an Old Fashioned!

Boasting a nostalgic atmosphere with dark wood, stained glass, and vintage oil paintings, Miller’s Pub is a great place to grab a coffee during the day or a cocktail in the evening. Hide away in a cozy booth, and people watch for Broadway actors, musicians, and local politicians.

Italian Village, Chicago Loop

For something more casual, head to the 2Twenty2 Tavern. Sip cold draft beer, signature handcrafted cocktails, or aged whiskey from the tap at the long bar. Challenge your friends to shuffleboard or video games in a laid-back, friendly atmosphere.

Looking for a fun, lighthearted night of karaoke? Brando’s Speakeasy is a must! Chicago’s best-kept secret, this vintage tavern is the go-to spot to sing your heart out while you sip cocktails. If you prefer cocktails without a sing-along, kick back in the 1920s-style cocktail lounge.

Watch the sunset over the city from the sophisticated Cindy’s Rooftop on the 13th floor of the historic Chicago Athletic Association. With sweeping views of Millennium Park and Lake Michigan, Cindy’s promises an unforgettable evening. Tuck into platters of fresh seafood, handcrafted cocktails, and fine wines in one of Chicago’s most beautiful bars.

Where to stay

As it’s the beating heart of the city, The Loop is the top choice for where to stay in Chicago. The accommodation scene is varied, with a wide selection of the city’s top hotels. With its central location, you should expect to pay higher prices here.

For alternatives, set your sights on areas a little further removed from downtown. These include neighborhoods in the Near North Side like the Magnificent Mile, Streeterville, and River North, or areas to the west like West Loop Gate, Fulton Market, and the West Loop.

The Buckingham Hotel

The Buckingham Hotel

Located on the 40th floor of a high-rise tower, just a 12-minute walk from the Art Institute of Chicago, the Buckingham Hotel has an intimate and elegant atmosphere. You’ll feel right at home with stylish rooms featuring panoramic city views, free Wi-Fi, minibars, and soaking tubs. You can enjoy complimentary continental breakfast, concierge services, and access to a massive athletic club.

citizenM Downtown

citizenM Chicago Downtown

Situated in a prime spot on 300 North Michigan Avenue between the Riverwalk and Millennium Park, citizenM Chicago Downtown boasts tech-controlled bedrooms and an art-filled living room. Enjoy easy access to shopping on the ground floor and relax in stylishly decorated rooms. Unlimited barista-made coffee, lovely tea, and hot chocolate are free all day.

Hotel Blake, an Ascend Hotel Collection Member

Hotel Blake, an Ascend Hotel Collection Member

Housed in a stately 19th-century building in the charming Printer’s Row neighborhood, the Hotel Blake, an Ascend Hotel Collection Member, is a luxurious retreat. A short stroll from the iconic Willis Tower, the hotel offers airy rooms with flat-screen TVs and free Wi-Fi. Indulge at the contemporary cafe/bar and 24-hour gym.

Pendry Chicago

Pendry Chicago

Nestled within the historic Carbide & Carbon Building, the Pendry Chicago is a beautiful high-end hotel close to the Chicago River. Sophisticated rooms offer Wi-Fi, smart TVs, and sitting areas. Sip cocktails on the seasonal rooftop terrace and enjoy a fine dining experience in the posh French restaurant.

LondonHouse Chicago

LondonHouse Chicago, Curio Collection by Hilton

Set in a historic 1920s high-rise building with stunning views of the Chicago River, the LondonHouse Chicago, Curio Collection by Hilton is perfectly located for exploring the Magnificent Mile. The polished rooms are the epitome of comfort, with free Wi-Fi, flat-screen TVs, minifridges, and Nespresso machines. Impressive amenities include a lobby bar and a chic rooftop restaurant/bar with a terrace offering stunning river views.


Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.

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