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Pizza, gangsters, and the Bulls are all synonymous with Chicago. But when visiting The Windy City, where does one start?
Do you stroll the Magnificent Mile or dive fork-first into a deep-dish slice? Take in skyline views from the Willis Tower, or trace the footsteps of legends like Al Capone and Michael Jordan? Whether you're here for the history, the eats, or the energy, Chicago has something for everybody, and we're highlighting some of Chicago's top spots!
Since 1932, Twin Anchors has been serving tender baby-back ribs and has become one of the city's oldest continuously operating restaurants. Its most iconic regular? Frank Sinatra. The legend himself made it a point to stop by every time he was in town—sometimes with equally famous friends in tow.
Gibsons Steakhouse isn't just a restaurant, it's a Chicago institution. With its glowing neon sign lighting up the Gold Coast, it's impossible to miss and even harder to forget once you've dined there. For decades, Gibsons has been serving USDA Certified Prime Beef, a distinction earned by only a small percentage of beef in the U.S. That commitment to quality has made it a go-to destination not just for locals and tourists but for celebrities, athletes, and politicians looking for a great steak in an atmosphere that's equal parts upscale and unapologetically Chicago.
You’ve probably heard the name Portillo’s—it’s practically part of Chicago’s DNA. Famous for its Chicago-style hot dogs and Italian beef sandwiches (dipped, of course), this iconic spot has been serving up classic street food since 1963. Wondering what makes a Chicago dog so iconic? It’s an all-beef hot dog “dragged through the garden” with mustard, onions, sweet pickle relish, tomato slices, a dill pickle spear, sport peppers, and a dash of celery salt all nestled in a poppy seed bun. (And nope, never ketchup!)
Ask any Chicagoan where to get the best Chicago-style pizza, and you’ll likely hear the same five names. Lou Malnati’s always makes the list. This isn’t your average slice—Chicago-style deep dish is meant to be savored with a fork and knife, giving you the full effect of the rich tomato sauce, gooey cheese, and signature buttery crust in every bite. Lou’s is all about quality, sourcing its mozzarella from the same small dairy farm for over 40 years and using a family-secret, flaky crust recipe passed down for generations.
Once named the Best Bourbon Bar in the U.S. and the coolest bar on Chicago's North Side, Delilah's is anything but modern, in the best way. On any given night, a DJ might be spinning rock, punk, or reggae, but the real draw? Its legendary bourbon and whiskey selection. And it's not just what's behind the bar that tells a story—the building dates back to 1894, with tales of its past life as a Prohibition-era speakeasy still lingering in the walls. A visit to Delilah's isn't just a night out—it's a step into Chicago history, served neat.
The Green Mill is one of the last great American gems—so old-school, it still only accepts cash. Originally opened in 1935, this legendary jazz club has deep roots in Chicago’s mob history. During Prohibition, it operated as a secret speakeasy, allegedly paying off the police to keep the doors open. One of its most infamous regulars? Al Capone. The mob boss reportedly had his own private booth, positioned so he could see both the front and back doors—just in case a quick exit was needed. Today, Green Mill remains a moody, musical time capsule—where live jazz and tales of the past still linger in the air.
Perhaps one of the most iconic hotels in Chicago, The Drake overlooks beautiful Lake Michigan from the north end of the Magnificent Mile. For over a century, it’s been a symbol of luxury and sophistication, welcoming legendary guests like Winston Churchill, Princess Diana, and Marilyn Monroe, to name a few. Stop in for afternoon tea in the Palm Court, sip a nightcap at the historic Coq d’Or, then retreat to the comfort of your luxury room just upstairs.
Virgin Hotels Chicago is the place to be if you love modern amenities and never travel without your four-legged sidekick. Just a short stroll from the Riverwalk, this pet-friendly hotel offers stunning skyline views, tech-savvy touches, and a seasonal rooftop deck that'll have you saying, 'Wait… this is the Midwest?!' It's city chic with a bold personality—perfect for travelers who want style, comfort, and a little bit of edge.
For an authentic Chicago experience that combines opulence with breathtaking views, look no further than The Langham. This 5-star hotel offers midcentury elegance, sweeping riverfront views, and a front-row seat to the city's iconic architecture. Guests can unwind in their tranquil spa, take advantage of complimentary fitness classes, or break a sweat in the state-of-the-art gym. Whether you're here to relax or explore, The Langham sets the stage for a stay that's nothing short of exceptional.
Looking for a unique place to stay in the vibrant neighborhoods of Wicker Park and Bucktown? The Robey is a boutique hotel that offers stunning 180-degree views of the city while giving you a glimpse of the charming tree-lined streets and historic Victorian homes nearby. With local restaurants, bars, and shops just steps away, you’ll never run out of things to explore.
The West Loop’s Fulton Market District has transformed from a historic meat-packing and warehouse hub into one of Chicago’s most exciting neighborhoods. Today, it’s home to buzzworthy dining, vibrant nightlife, one-of-a-kind boutiques, and standout art. The Emily Hotel offers a prime location with everything steps away.
If unique accommodations are more your style, The Neighborhood Hotel in Little Italy is just for you. This boutique stay transforms historic buildings into one-of-a-kind spaces that blend history, comfort, and modern charm. Each suite comes fully equipped with a kitchenette, perfect for stashing all your Chicago food finds.
Have you ever dreamed of living out your own scene from My Best Friend’s Wedding—cruising down the river, surrounded by stunning architecture and pure romance? You can! The Chicago Architecture Tour is an absolute must-do. In just one boat ride, you’ll experience the city’s skyline evolving from its historical roots to the modern-day wonders that define it today.
Chicago has some of the best museums in the country, and the Field Museum is a top pick for a family-friendly adventure. You’ve probably heard of its most famous resident, SUE, the T. rex, the largest and most complete adult T. rex skeleton ever discovered. The museum, which opened in 1894, houses over 4.6 billion years of natural history under one roof. Now that’s a trip through time!
If it’s your first time in the Windy City, visiting The Bean in Millennium Park is a must. This stunning outdoor space hosts concerts and festivals year-round with Lake Michigan as its backdrop. It’s also home to one of the most photographed sculptures in Chicago—a 110-ton masterpiece that reflects the city’s iconic skyline and the sky above. A true work of art!
Bill Murray, Dan Aykroyd, Tina Fey, and Jim and John Belushi—what do they all have in common? They started at the iconic Second City Chicago, where legendary comedy careers were born. This famous comedy club still hosts live shows and continues to discover the next generation of talent. If you’re up for a night of laughs—and maybe even spotting a future SNL star—be sure to catch a show!
Nothing says summer in the Midwest, like catching a Chicago Cubs game at Wrigley Field. While cheering from the stands is always a good time, why not experience the game from a different perspective—like a rooftop bar? The rooftops surrounding the ballpark offer a whole new way to experience America’s favorite pastime, and you can book your spot through Wrigley Rooftops.
One of Chicago’s most unique neighborhoods, historic Chinatown is always buzzing with energy. Don’t miss the vibrant Nine Dragon Wall—one of only three replicas outside of China. Hop on the seasonal water taxi from The Loop and take the scenic route to Chinatown via Ping Tom Park. Pro tip: visit hungry. The streets are packed with restaurants offering flavors from all across China, including dim sum.
From deep-dish pizza to stunning skyline views, Chicago sets the stage for stories worth sharing. Our team brings passion, creativity, and a deep understanding of what drives connection, crafting content and campaigns that truly resonate. Let’s tell your Chicago story together and make it as unforgettable as that first bite of Chicago-style pizza!
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