Chicago is a city that loves to show off. Its stunning skyline, iconic landmarks, and fascinating neighborhoods make it a perfect spot for engaging tours and experiences. Whether you’re interested in architecture, theater, literature, sports, or ghost stories, Chicago has something to offer. We particularly enjoy the Chicago: 45-Minute Family-Friendly Architecture River Cruise, which offers a relaxing way for families to learn about Chicago’s famous buildings with live commentary. It’s a great blend of education and fun—plus, you can enjoy locally sourced food on board.
For a touch of Chicago’s arts and culture, the Chicago Theatre Tour Experience provides an inside look at one of the city’s most photogenic venues. For history and literary lovers, the American Writers Museum offers a deep dive into over 400 years of American writing, with interactive exhibits that appeal to all ages. And if you’re after something a little spooky, the Ghosts & Hauntings of the Windy City Walking Tour takes you through Chicago’s darker tales of gangsters and Victorian-era spirits.
Below is a quick overview. We’ve selected a mix of outdoor adventures, insider tours, cultural visits, and even active options, all designed to give you a well-rounded experience of Chicago.
1. Chicago: 45-Minute Family-Friendly Architecture River Cruise
This 45-minute cruise down the Chicago River is an ideal way to see the city’s skyscrapers and historic buildings with your family. The boat features live, family-friendly commentary that explains what makes Chicago’s architecture so impressive—think of the Wrigley Building, Tribune Tower, and the Marina City towers. The best part? You can relax and enjoy a locally sourced food and drinks menu from the onboard full-service bar, making it a hassle-free outing for all ages.
What makes this tour stand out is its balance of education and entertainment. The guides are knowledgeable but keep it lively enough for kids. Pre-purchasing your tickets helps you skip the long lines, especially during peak times. The reviews show a high approval rating of 4.7/5 from over 2,100 reviews, with many families appreciating its easy pace and engaging commentary.
Ideal for families, first-time visitors, or anyone wanting a quick, scenic overview of downtown Chicago. The 45-minute duration means it’s easy to fit into a busy day without feeling overwhelmed.
Bottom Line: A family-friendly, informative cruise that combines architecture, relaxation, and local food. Perfect for a quick, enjoyable glimpse of Chicago’s iconic skyline.
2. The Chicago Theatre Tour Experience
This 1-hour tour unlocks the secrets of Chicago’s most-photographed venue, the historic Chicago Theatre. The tour , as described here, takes you behind the scenes to marvel at the six-story “C-H-I-C-A-G-O” sign and the beautiful murals and architecture that have made it a Chicago icon.
During the tour, you’ll walk in the footsteps of legendary performers and see the grand auditorium, which still retains its vintage charm. One of the highlights is meeting a famous Rockettes’ dancer, which adds a unique personal touch. The guide’s stories reveal the theatre’s history, from its golden age to modern-day performances, making it a rich experience for theater fans and history buffs alike. Guests often comment that the decor is “beautifully preserved” and that the guide is both friendly and knowledgeable.
At $26 per person, this tour offers excellent value for anyone interested in Chicago’s arts scene or iconic landmarks. Many reviews praise it for being informative and fun, with the guide adding a lively touch to the experience.
Bottom Line: An engaging, insider look at Chicago’s premier theatre, ideal for theater lovers or those wanting to learn more about Chicago’s entertainment history.
3. Chicago: American Writers Museum Flexible Date Entry Ticket
This flexible-entry ticket provides access to the American Writers Museum, where you can spend as little or as much time exploring over 400 years of American writing. The museum’s interactive exhibits include timelines, videos, and a “word waterfall,” plus opportunities to write your own stories on vintage typewriters. It’s a fantastic visit for book lovers, students, or anyone curious about American authors such as Dickinson, Poe, Dr. Seuss, and Prince.
What makes this experience worth considering is its flexible access—you can visit over a span of 1 to 14 days, fitting it into your schedule. Kids under 13 enter free, making it family-friendly. The museum also offers creative activities like short story or poem writing, which makes for a lively, hands-on experience. Guests appreciate the educational value and interactive approach, making it suitable even if you’re not a dedicated reader.
For $0, this is an excellent free activity if you’re looking to deepen your understanding of American literature and enjoy a quiet, inspiring space. It’s especially good for rainy days or low-key afternoons.
Bottom Line: An interactive cultural experience for all ages that celebrates American writers and offers plenty of opportunities to get creative.
4. Chicago: Ghosts & Hauntings of the Windy City Walking Tour
This 1-hour walk through Northside Chicago is packed with stories of mobsters, serial killers, and Victorian spirits. Led by US Ghost Adventures, this tour explores Lincoln Park’s haunted sites, including the forgotten burial ground beneath the neighborhood and the Victorian woman in white seen at Lincoln Park Zoo. It’s a spooky, fun way to see a different side of Chicago, perfect for those who enjoy history with a dash of supernatural.
The guide is praised for storytelling skills that keep the group engaged. The tour covers Chicago’s darker history, with stories of gangsters like Al Capone and ghostly sightings. Many reviews mention it’s “very informative” and “fun,” with some visitors ending the tour in a local pub to keep the spooky vibe going. The tour costs $27 and is ideal for fans of ghost stories, history, or those looking for a slightly eerie adventure.
Keep in mind, this tour is best suited for those comfortable with walking and spooky tales. It’s a lively, spooky experience that blends history with ghostly legends.
Bottom Line: Perfect for fans of ghost stories or Chicago’s darker past, offering a spirited way to explore the city’s history with a supernatural twist.
5. Chicago: Full-Day or Half-Day Bike Rental
For a flexible way to see Chicago at your own pace, renting a bike is hard to beat. With options for full-day or half-day rentals, you can explore the lakefront, Lincoln Park, or downtown streets on your schedule. The rental includes a helmet, bike lock, and detailed map, ensuring you’re well-equipped to navigate the city.
You can choose from a hybrid bike, a Fujifilm Sportif 2.1 road bike, or an electric bike if you want assistance with hills. The route options are endless—biking along Lake Michigan’s shoreline offers stunning views, while the city streets reveal eclectic neighborhoods. For families, child trailers and junior bikes make it accessible for all ages.
Guests appreciate the ease of use and the freedom it provides to customize their sightseeing. The cost, at $24 per person, offers good value, especially if you’re planning to spend multiple hours exploring. The only downside is that you’ll need to plan your route, but that’s part of the fun.
Bottom Line: An excellent way to see Chicago on your terms, ideal for active travelers who want to combine sightseeing with some exercise.
6. Chicago: Chicago White Sox Baseball Game Ticket
Nothing beats experiencing America’s favorite pastime live in Chicago. With tickets to a Chicago White Sox game at Guaranteed Rate Field, you’ll witness the excitement of Major League Baseball firsthand. The ticket price starts around $21, making it accessible for many fans.
The game typically lasts about three hours, with plenty of chances to cheer for home runs and enjoy concessions. The lively crowd, colorful atmosphere, and the chance to see top teams make this a memorable outing. Mobile tickets simplify entry, and you can often pick from different game dates depending on your schedule.
This experience is perfect for sports enthusiasts or families looking for a fun, relaxed day. While tickets are affordable, the real value is in the atmosphere—there’s nothing like experiencing a game in person.
Bottom Line: A fun, affordable way to enjoy Chicago’s baseball culture—ideal for sports fans or families seeking a lively, casual outing.
7. Michigan Avenue Rendezvous Walking Tour with Smartphone App
This two-hour walking tour uses a smartphone app to explore Michigan Avenue’s secrets and highlights. The self-guided format lets you discover hidden gems and iconic landmarks at your own pace, guided by engaging location-based prompts and a fun scavenger hunt style.
While it’s lower-rated at 3/5 from 3 reviews, the flexible format appeals to independent travelers who enjoy exploring on their own terms. It’s a budget-friendly option at $18 per person, perfect for those who want a guided experience without a fixed schedule. The app provides historic facts, trivia, and challenges that make it interactive and engaging.
Ideal for tech-savvy travelers or those short on time, this tour offers a different way to see Chicago’s most famous shopping street and surrounding areas.
Bottom Line: A flexible, budget-friendly self-guided tour for explorers comfortable with using smartphone apps and seeking a personalized experience.
8. Midwest Multi-city Gym Pass
If your trip involves staying active, this Midwest Gym Pass offers access to many top gyms across the region for just $21 per person. The pass is valid for 30 days and includes 1, 2, or 5 visits, making it perfect for fit travelers wanting to maintain their routine. It’s a great way to explore Chicago’s fitness scene, from boutique studios to larger gyms.
The pass doesn’t restrict your workout times, giving you the flexibility to exercise when it suits you. Plus, you can cancel up to 2 hours before class if your plans change. It’s especially useful for travelers who want to combine sightseeing with some wellness or for those eager to try different gyms in the city.
The reviews are excellent, with a 4.8/5 rating, and users appreciate the convenience and variety. This pass suits active travelers, fitness enthusiasts, or anyone looking to stay healthy during a trip.
Bottom Line: A practical option for active travelers who want to combine their Chicago visit with fitness, ensuring they stay energized throughout their stay.
How to Choose Your Perfect Chicago Tour
When deciding which experience suits you best, consider your interests, budget, and available time. For families or those wanting a quick overview, the Chicago: 45-Minute Family-Friendly Architecture River Cruise offers a relaxing, educational outing. If you love theater or architecture, the Chicago Theatre Tour provides an insider’s look. Literature fans should not miss the American Writers Museum, while history buffs who enjoy a scare might prefer the Ghosts & Hauntings Tour.
Active travelers and sports fans can rent bikes or catch a White Sox game, combining sightseeing with physical activity or entertainment. For a self-guided option, the Michigan Avenue tour offers a flexible way to explore at your own pace.
Finally, if staying fit during your trip matters, the Midwest Gym Pass is a smart way to keep your workout routine on track. Always book early if you’re visiting during peak seasons to secure the best times and seats.
Final Thoughts
Chicago offers a wide range of tours and experiences that cater to diverse interests. From family-friendly cruises and cultural museums to ghost walks and active bike rentals, there’s something for all. For first-timers, a river cruise combined with a theater tour offers a great introduction, while history lovers might enjoy the ghost tour or the American Writers Museum.
For travelers wanting to explore independently, self-guided tours and bike rentals provide flexibility and value. And sports fans should not miss the chance to see a White Sox game for a lively local experience. Whichever you choose, booking early and tailoring your activities to your interests will ensure a memorable time in the Windy City. Enjoy your trip—and don’t forget your camera!