Chicago, affectionately known as the “Windy City,” is a vibrant metropolis that offers an unparalleled array of fun and exciting activities. From the majestic shores of Lake Michigan to the bustling Chicago River, the city’s unique blend of natural beauty and urban sophistication makes it a must-visit destination for anyone seeking adventure and culture.

You’ve seen the movies, you’ve heard the name, but whether it’s your first time or your tenth time, if you’re visiting Chicago, you’re going to want to have a game plan. The Windy City is great for its incredible architecture — they invented skyscrapers, you know — but Chicago is so much more – from its storied past to the friendly people, buzzing atmosphere, to its culinary delights, and diverse neighborhoods. There are almost too many fun things to do in Chicago, which makes it no surprise that it was voted The Best Big City in the U.S. for an astounding seventh year in a row! “Over 520,000 travelers from around the world cast their votes and once again crowned Chicago as the nation’s “Best Big City”, according to the annual Readers’ Choice Awards.

The heart of Chicago’s appeal lies in its stunning architecture. A cruise along the Chicago River offers awe-inspiring views of towering skyscrapers and historic buildings, each with its own story. The city’s architectural tours are not just educational; they’re a captivating experience, showcasing the innovation and design prowess that have shaped Chicago’s skyline. Whether you’re marveling at the Willis Tower or the neo-Gothic Tribune Tower, the city’s architectural grandeur is a feast for the eyes.

But Chicago’s allure extends far beyond its buildings. Lake Michigan, with its expansive, crystal-clear waters, invites residents and visitors alike to its shores for a plethora of activities. Whether it’s sunbathing at one of the city’s many beaches, taking a leisurely bike ride along the Lakefront Trail, or embarking on a thrilling sailing adventure, the lake is Chicago’s natural playground.

Chicago also features good public transport, making it a breeze to get around. However, while most people don’t think of Chicago as a city on the water, it most certainly is: Just take one look out on Lake Michigan and you’ll believe us! Or the historic Chicago River that runs right through it. So, if you’re hoping to experience this majestic city and have some fun from the water whether on Lake Michigan or the Chicago River (and have some fun while you’re on land, too) you’ve come to the right place. As Thrillist recommends, “Come nightfall, hit the Chicago River or Lake Michigan for some memorable jaunts with Chicago City Cruises.” Here’s a short list we’ve put together of some of the best sights to see and the most fun things to do in Chicago, Illinois.

Fun Things to Do in Chicago on Lake Michigan

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Chicago Seadog Lakefront Speedboat Tour – If you’re in the mood for some action and adventure, you can’t go wrong with an exciting and fun speedboat tour on Lake Michigan. On the Chicago Seadog Lakefront Speedboat Tour, you’ll enjoy Chicago’s iconic skyline from Lake Michigan as you depart from Navy Pier at a fast clip, since the Lakefront Speedboat Tour is the best way to view Chicago from the water. The Seadog offers fun for the whole family (and the dog, too!) combining an exciting speedboat ride along the shoreline with informative and amusing descriptions of the world-famous Chicago skyline. Oh, and did we mention that the Seadog is BYOB? Yep, feel free to bring your own drinks to enjoy on the water — just no glass containers, please!

Fun Things to Do in Chicago on The Chicago River

Chicago Seadog River & Lake Architectural Tour – Looking to enjoy Chicago’s world-famous skyline at a more mellow pace? We’ve got you covered: The Chicago Seadog River & Lake Architectural Tour is an exciting architecture cruise along the Chicago River. Taking off from Navy Pier, this 75-minute narrated cruise is the premier way to get up-close and personal views of Chicago’s unique architecture and famous landmarks. There’s also live narration along the city’s shore, and (of course) you’ll still get to experience the speed of the Seadog afterward during a short speedboat ride on Lake Michigan. Maybe “mellow” was the wrong word to describe the pace, let’s go with FUN!

Fun Chicago Sites

The Bean (Cloud Gate) – Okay, you probably saw this one coming, and while we know it’s a bit touristy if you haven’t had your picture taken next to this incredible sculpture, it’s definitely worth a trip! Located in the heart of downtown Chicago, it’s one of Chicago’s most popular sights and reflects the city’s famous skyline and the surrounding green space. Plus, it’s in Millennium Park, which features fountains, peaceful gardens, free events, street art, skating rinks, rock climbing, park space, and much more.

Millennium Park with Cloud Gate (The Bean) sculpture in background.jpg

Wrigley FieldSports are another integral part of Chicago’s identity. The city’s passionate fans rally behind their teams, from the historic Wrigley Field, home of the Chicago Cubs, to the roaring crowds at Soldier Field, cheering for the Bears. The spirit of competition and camaraderie at these games encapsulates the city’s love for sports and its unwavering support for its athletes. Wrigley Field is the oldest park in the National League and the second-oldest in Major League Baseball and was designated a National Historic Landmark in 2020. Plus, even if you don’t catch a game while you’re in town, you can hang out in the surrounding Wrigleyville neighborhood, which is full of sports bars, restaurants, and other fun things to do. (You might even catch a little Cubs fever while you’re there!)

MuseumsChicago’s cultural vibrancy is palpable in its museums, theaters, and music venues. The Art Institute of Chicago, with its renowned collections, houses nearly 300,000 works of art in fields ranging from Chinese bronzes and contemporary design to textiles, installation art, and more. It stands as a testament to the city’s artistic spirit. There’s also the Field Museum, located on Chicago’s iconic Lake Michigan shore, which boasts a whopping collection of nearly 40 million artifacts and specimens.

Meanwhile, the lively sounds of blues and jazz fill the air in historic venues, offering a glimpse into the genres’ deep roots in Chicago’s cultural landscape. The city’s theaters, from the grand Chicago Theatre to the innovative stages of the Second City, showcase a wide range of performances, reflecting the city’s rich theatrical tradition.

Fun Chicago Restaurants, Bars, and Breweries

From Michelin-starred restaurants to iconic deep-dish pizza joints, Chicago is home to a ton of incredible restaurants, and the city is famous for several great dishes, including Chicago Italian Beef, deep-dish pizza, and its world-renowned hot dogs. There’s also a slew of hip cocktail bars, old-school watering holes, and distilleries. Love a good pint? You’re in business: Chicago has no shortage of world-renowned craft breweries, which are usually more pet- and kid-friendly than bars and restaurants (just make sure to check ahead of your visit), including Revolution Brewing, Maplewood Brewery & Distillery, Dovetail Brewery, and many more.


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Chicago’s blend of natural beauty, architectural marvels, culinary delights, cultural richness, and sports fervor creates a dynamic environment where fun and adventure are always around the corner. Whether you’re seeking inspiration, relaxation, or exhilaration, Chicago promises an unforgettable experience, making it truly the best city to explore and enjoy.

FAQs – Fun Things to Do in Chicago (2024 & 2025)

What are other fun outdoor activities in Chicago?

Fun things to do in Chicago depend on the time of year. During the warm months, there are lots of things to do on the water. Since it’s on Lake Michigan, Chicago offers many different cruises, charters, and other fun activities on the water. In the cold months, you may be limited to more “indoor” activities or fun things such as ice skating.

What are other fun indoor activities in Chicago?

Fun indoor activities in Chicago may include exploring the plethora of museums in the city, or even the world-famous buildings such as The Willis Tower or The Chicago Theater.

What else is Chicago famous for?

Chicago is famous for many things, but one thing is that it is a cultural hotspot for the arts, including architecture, music, and food. Its cultural impact reaches way further than the Midwest, with a global impact on many different industries. Hence, enjoy the museums, concerts, food, sites, and other fun things to do while in town!

What are family-friendly activities in Chicago?

Fun family-friendly activities in Chicago include visiting the sites such as the Bean or Willis Tower, visiting museums, or perhaps riding the famous Centennial Wheel at Navy Pier to get some amazing views of the city and Lake Michigan.

What types of “things to do” does City Cruises offer in Chicago?

City Cruises has several fun things to do in Chicago, in addition to our Seadog cruises, we also offer Dining Cruises on Lake Michigan or the Chicago River, as well as architectural tours from the water.

What Are Some Unique Culinary Experiences in Chicago?
Chicago is not just famous for its deep-dish pizza and hot dogs. The city offers a diverse culinary scene, including food tours, tasting experiences at local breweries and distilleries, and fine dining at Michelin-starred restaurants.

Where Can I Experience Chicago’s Music and Nightlife?
Chicago’s vibrant music scene includes everything from jazz and blues to indie and electronic music. Explore famous venues like the House of Blues, The Green Mill, or catch a live performance at one of the city’s many nightclubs.

Are There Any Historic Landmarks to Visit in Chicago?
Chicago is rich in history. Visitors can explore landmarks such as the Chicago Water Tower, the Pullman National Monument, or take a historic neighborhood tour to delve into the city’s past.

What Are the Best Shopping Destinations in Chicago?
The Magnificent Mile is just the beginning. Chicago offers diverse shopping experiences, from luxury boutiques to vintage shops and local markets like the Randolph Street Market.

Can I Explore Chicago’s Art Scene?
Yes, Chicago’s art scene is thriving. Visit renowned institutions like the Art Institute of Chicago, explore contemporary galleries in the West Loop, or discover street art in neighborhoods like Pilsen.

What Outdoor Recreational Activities Are Available in Chicago?
Beyond water activities, Chicago offers biking along the Lakefront Trail, hiking in nearby forest preserves, and enjoying the city’s many parks, like Millennium Park and Lincoln Park.

Where Can I Find Unique Theater or Comedy Experiences in Chicago?
Chicago is known for its improv comedy scene and theaters. Catch a show at The Second City, or enjoy a play at the Chicago Theatre or Steppenwolf Theatre.

Are There Educational Activities for Kids in Chicago?
Chicago has many educational attractions for children, including the Chicago Children’s Museum, the Museum of Science and Industry, and the Field Museum, which are both fun and educational.

What Are Some Seasonal Events in Chicago?
Chicago hosts various events throughout the year, like the Chicago Air and Water Show, Lollapalooza music festival, and seasonal celebrations like the Christkindlmarket during winter.

How Can I Experience Chicago’s Architectural Beauty?
Apart from architectural tours, visitors can admire Chicago’s skyline from observation decks like the Skydeck Chicago in Willis Tower or take a self-guided walking tour of the city’s architectural landmarks.

What Unique Experiences Does the Chicago River Offer?

  • Discover architectural boat tours showcasing the city’s iconic skyline and historical buildings.
  • Enjoy kayaking adventures on the river for a unique perspective of the city.
  • Explore riverfront dining and entertainment options along the Riverwalk.

Are There Recreational Activities Available on Lake Michigan?

  • Engage in water sports like jet skiing, paddle boarding, and sailing.
  • Relax on beaches like North Avenue Beach and Oak Street Beach.
  • Experience fishing charters for a day of angling on the lake.

What Types of Cruises Can I Experience on Lake Michigan?

  • Join themed cruises for special occasions like fireworks displays, dinner cruises, or jazz nights.
  • Opt for luxury yacht experiences for a more upscale adventure.
  • Participate in educational cruises focusing on the ecology and history of Lake Michigan.

How Can I Explore Chicago’s Waterways with City Cruises?

  • Discover various sightseeing tours that offer a narrated journey through Chicago’s history and architecture.
  • Enjoy brunch, lunch, or dinner cruises with stunning views of the city.
  • Book private events or special occasion cruises for celebrations.

What Are Some Romantic Activities to Do on the Water in Chicago?

  • Plan a sunset cruise on Lake Michigan for a memorable evening.
  • Experience a dinner cruise with fine dining and dancing under the stars.
  • Rent a private boat for a more intimate exploration of Chicago’s waterways.

Are There Family-Friendly Water Activities in Chicago?

  • Join interactive pirate-themed cruises for a fun adventure with children.
  • Explore the Shedd Aquarium for educational marine experiences.
  • Visit Navy Pier for family-oriented water rides and attractions.

Can I Learn to Sail or Boat on Lake Michigan?

  • Enroll in sailing or boating classes offered by various clubs and organizations along the lakefront.
  • Join group sailing excursions to learn the basics in a fun environment.

What Are the Best Ways to View the Chicago Skyline from the Water?

  • Opt for evening cruises to see the skyline illuminated at night.
  • Take a photography tour on the water to capture stunning views of the city.
  • Enjoy a kayak trip at dusk for a serene and picturesque experience.

How Accessible Are Water Activities for Visitors?

  • Many water-based activities offer rentals and lessons for beginners.
  • Accessible boat tours are available for individuals with mobility challenges.
  • Beaches and waterfront areas are generally well-connected by public transportation.

Original post date: July 20, 2023