Chicago is a vibrant metropolis known for its stunning architecture, diverse cultural scene and iconic skyline. As such, the Windy City is a blend of modern innovation and rich history, offering something for everyone. From the bustling Magnificent Mile to the tranquil, lakefront paths, Chicago is a place where every corner has a story to tell. So, to help you navigate this dynamic city, we’ve gathered insights from local experts on the best things to do in Chicago. Here’s what they recommend:
Explore Diverse Neighborhoods
Chloe Streif, a professional organizer with Mission 2 Organize, highlighted the ethnic and cultural diversity that makes Chicago a captivating destination.
“Narrowing down the top activities in Chicago proves challenging due to its rich tapestry of ethnic and cultural diversity,” she said. “However, that’s what makes Chicago such a captivating destination!”
Streif emphasized the importance of exploring the city’s diverse neighborhoods by hopping on the CTA trains or buses.
“One of the best ways to experience Chicago’s culture and cuisine is by sampling authentic fare from places like Pilsen, Little India, Chinatown or Greektown,” she specified.
Meanwhile, for those visiting during the warmer months, Streif suggested taking a kayak or boat tour to learn about the city’s history and architecture.
“Other warm-weather activities include biking the miles of lakefront path,” she added. “For such a large city, Chicago has a plethora of green space!”
No matter the weather, Streif encourages visitors to take a break from the hustle and bustle of city life and enjoy Chicago’s outdoor spaces.
“Millennium Park offers stunning skyline views and a chance to see the iconic Cloud Gate sculpture up close,” she shared. “Lincoln Park is home to a free zoo and botanical garden, providing a peaceful retreat from urban life.”
She also invites everyone to experience Chicago’s unique charm: “Whatever you choose to do, Chicago promises a fun and memorable experience for all of its visitors! Come and see all that the ‘second city’ has to offer.”
Start Your Day with Brunch
Lydia Reynolds, marketing and public relations manager at Pendry Chicago, shared her ideal day in the Windy City, which would begin with a delightful brunch on the Magnificent Mile.
“The best days in Chicago start with brunch at my favorite Parisian-inspired cafe, Venteux,” she said.
After brunch, Reynolds recommends taking a leisurely stroll to Millennium Park to see the Lake Michigan shoreline and visit the Museum of Science and Industry.
“‘The 007 Science: Inventing the World of James Bond’ exhibit is a must,” she added.
For a unique perspective on the city, Lydia suggests taking an architecture river tour with Chicago’s First Lady, where Pendry Chicago’s own Carbide & Carbon Building is a featured highlight. She also encourages visitors to attend some of the city’s incredible food and music festivals.
“Lollapalooza in August and Taste of Chicago in September are not to be missed,” Reynolds reported.
To wrap up the day, Reynolds enjoys cocktails and small bites from Chicago’s renowned rooftop scene at Chateau Carbide.
“And, my favorite day ever always ends with a game at Wrigley Field. Go Cubs!”
Enjoy Music Festivals & Local Markets
Matt Eskew, head of digital marketing at J. Blanton Plumbing, believes that tourists should immerse themselves in Chicago’s vibrant music festivals and local events.
“Chicago has a lot to offer and there’s plenty of things to see here, but I think the thing a lot of tourists will want to be a part of are our music festivals that happen all over Chicago and its surrounding suburbs,” he explained.
These festivals, organized by both government entities and non-profits, showcase a diverse range of musicians and genres.
“You’ll never feel out of place in events like this since there’s a band or singer out there that will play the kind of music you like,” Eskew stated.
Additionally, he recommends visiting local markets to learn more about Chicago’s businesses.
“In these local markets, you’ll get to see Chicago’s vendors and the many products or services they offer.”
For Eskew, engaging with locals at these events is the best way to truly experience the city.
“I think being a part of such events where you connect with a lot of the locals is the best and only way to really see more of Chicago,” he said.
Must-Do Activities on a Business Trip
Amanda Benson, owner of Dusty Trail RVH, shared her top recommendations for those visiting Chicago on a business trip. She began with a must-see attraction:
“You can’t leave Chicago without experiencing the iconic Willis Tower Skydeck,” she said. “Step out onto ‘The Ledge’ — a glass box extending 4.3 feet from the building’s 103rd floor for mind-blowing views of the city skyline.”
Next, Benson suggested taking a break from meetings to explore the Riverwalk.
“This pedestrian waterfront path offers stunning city views, restaurants, bars and even a kayak rental spot,” she said. “It’s the perfect way to unwind after a long workday.”
Of course, no business trip to Chicago would be complete without indulging in the city’s famous deep-dish pizza. In particular, Benson recommends heading to classics like Lou Malnati’s, Pequod’s or Giordano’s for a deliciously indulgent slice (or two!) of this Chicago staple.
Finally, Benson suggests visiting Millennium Park.
“Explore Millennium Park, home to the famous Cloud Gate sculpture, also known as ‘The Bean,” she said. “Snap photos, enjoy the gardens, and catch a free concert or event if one is happening during your visit.”
Discover Iconic Architecture & Cultural Spots
When visiting Chicago, Farhan Zafar from bookonboard.com highlighted several must-do experiences to make your trip memorable.
“First and foremost, explore the iconic architecture that defines the city’s skyline,” he recommended. “Take an architecture river cruise to see renowned buildings, like the Willis Tower, the John Hancock Center and the historic Wrigley Building up close.”
Farhan also encourages visitors to immerse themselves in the city’s cultural scene by visiting world-class museums.
“The Art Institute of Chicago houses an impressive collection spanning centuries and continents,” he said. “Don’t miss the Museum of Science and Industry, known for its interactive exhibits and historic artifacts.”
And, food lovers should not miss Chicago’s diverse culinary scene, which is famous for its deep-dish pizza, Chicago-style hot dogs and inventive fine dining options. Specifically, Farhan recommends strolling through neighborhoods like Pilsen or Wicker Park to sample ethnic cuisines and trendy eateries.
Or, for outdoor enthusiasts, Chicago offers beautiful parks and lakefront trails that are perfect for walking, biking or simply enjoying the scenery.
“Millennium Park is a must-visit, home to the iconic Cloud Gate sculpture, also known as ‘The Bean,’” he said.
Visitors can also catch a live performance at one of Chicago’s many theaters or comedy clubs, which showcase everything from Broadway hits to improv comedy.
“With its blend of culture, cuisine and entertainment, Chicago offers something for every visitor to enjoy,” he shared.
Whether you’re exploring the diverse neighborhoods, indulging in the local culinary scene or enjoying the vibrant music festivals, Chicago promises a memorable experience.
