Sitting on Lake Michigan, Chicago is a city that not only boasts of its position to this stunning lake but it also prides itself on being one of the largest cities in the US boasting many hotels with lake views. Experience luxury and convenience at hotels in downtown Chicago with stunning skyline views, and easy access to top solo activities in Chicago. Known locally as the Windy City, Chicago is an eclectic destination that is punctuated by a love for music and the arts. This city has managed to shake off a dark past of crime, transforming this history into a thrilling tale. Stories of gangsters like Al Capone have reverberated across the world and Chicago started it all. This fascinating city has a lot to offer. If you’re travelling alone, check out the top things to do alone in Chicago and make the most of your solo adventure.
1. Sail through architectural wonders on Chicago's River (from USD 44.0)
If you love architecture and history, you will enjoy this cruise along the Chicago River and Lake Michigan. You will see some of the most iconic buildings and landmarks of Chicago, such as the Wrigley Building, the Tribune Tower, the Willis Tower, the Marina City Towers, and the new Vista Tower.
You will learn about the 130-year-long history of Chicago’s skyline and how it has evolved. You will also have a chance to admire the views of the lake and the city from a comfortable boat with an open-air deck or a climate-controlled interior.
Chicago River: 1.5-Hour Guided Architecture Cruise
Duration: 1.5 hour
2. Explore the Museum of Contemporary Art (from USD 22.0)
Don’t pass up the opportunity to explore the Museum of Contemporary Art in downtown Chicago if you have an appreciation for contemporary art. This museum presents the creations of prominent artists spanning different mediums and styles, ranging from painting and sculpture to photography and video.
By visiting, you’ll be exposed to the newest developments and imaginative concepts in contemporary art, alongside iconic pieces by influential figures like Jasper Johns, Andy Warhol, Cindy Sherman, and others. Additionally, you can immerse yourself in special exhibitions, performances, and dynamic events that evolve throughout the year.
Chicago Museum of Contemporary Art Tickets
Duration: 1 to 3 hours
3. Chicago crime and mob tour (from USD 46.0)
This city, known for its tainted gangster past, offers an array of places to go alone in Chicago. However, the locals have chosen to take this history and turn it into an unforgettable tour. You’ll have the chance to visit the actual scenes where mobsters like Al Capone and Hymie Weiss implemented their criminal plans. A knowledgeable guide will narrate the tales of these dastardly criminals as you’re taken around the locations of their crimes. As part of the tour, you’ll get to see the courthouses that witnessed the trying of these cases. The tour culminates in a visit to the infamous 1929 Valentine’s Day Massacre.
Chicago Criminals, Mobsters and Gangsters Bus History Tour
Duration: 90 to 120 minutes
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4. Skydeck Chicago (from USD 44.0)
If you’re thinking about what to do alone in Chicago, this is one visit that ought to be on your bucket list. The Skydeck is a viewpoint on the 103rd floor of Chicago’s Willis Tower. This is famous for being the city’s highest point and is a place you go to get a panoramic view of Chicago. The highlight of this tour is the glass balcony that stretches outwards from the building. This all-glass section allows you to see the whole city from a height of over 1,000 feet (304 metres). If heights aren’t your thing, you can simply take a look at the exhibits that showcase Chicago’s history and culture.
Tip from Trip101 local expert
If you want to stand above the Chicago skyline you can't go wrong with visiting the Skydeck Chicago. Whether you go alone or with someone, you will get beautiful views of the city and also some great photos or selfies. Make sure to watch the weather and cloud cover so that you can get the best possible views when you walk out onto glass over 100 stories above ground!
Chicago: Skydeck Chicago Admission Ticket
Duration: 90 to 120 minutes
5. Chicago helicopter tour (from USD 179.0)
You really haven’t seen Chicago until you get a bird’s eye-view of the city at night. This tour would make for an unforgettable climax to your trip to the Windy City. Hop onto a helicopter at Vertiport Chicago. You can opt to start your tour at dusk and get a photo-worthy view of the sunset. This tour will give you a different view of the landmarks in the city, making you fully appreciate the beauty that is Chicago. As your expert pilot manoeuvres the aircraft, you’ll get to see sites like the majestic Willis Tower from above. However, the highlight is when you get to see Lake Michigan from the air. This 15-minute ride is truly unforgettable.
Chicago by Night Helicopter Tour
Duration: 30 minutes
6. Chicago film tour (from USD 30.0)
Are you a movie lover? Then this tour is especially for you. The film tour is a two-hour coach ride that offers a glimpse of the locations where popular films were shot. For instance, you’ll get to see where movies like The Dark Knight and Transformers were filmed. Get information on Chicago’s 100-year long cinema history that is glittering with a whopping 75 productions that have been filmed here. A guide will skilfully narrate this history to you, pointing out the specific locations.
Chicago Film Tour
Duration: 2 hours
7. Chicago grand tour (from USD 73.0)
Immerse yourself in the life of Chicago by signing up for this exciting tour. It is four hours of fascinating views around the city while riding a coach. The thrill starts on Lake Shore Drive, a scenic route in which you’ll get a view of stunning sites like Adler Planetarium’s sky dome, Field Museum of Natural History and former US president, Barack Obama’s childhood home. This entourage snakes its way to the city’s North Side when you pass by Richard J Daley Center and catch a glimpse of the Picasso sculpture. At the climax of this tour, you’ll have a chance to ascend one of Chicago’s tallest buildings and head to the John Hancock Observatory where you’ll get a panoramic view of the city.
Chicago Tour, 360 Chicago Observation Deck Admission Ticket
Duration: 4 hours
8. Chicago city tour and river cruise (from USD 76.0)
Combine the allure of touring the city on a coach with the thrill of seeing Chicago on a yacht. This tour includes both of these on a four-hour trip. You start on a bus which takes you around Chicago’s most famous sites. As you marvel at the city, an animated guide will bring everything you see to life, giving you an inkling of the history of each attraction. Among the sites you’ll pass is President Obama’s former home. After two-hours of site seeing, you’ll be taken to the Chicago River where a sleek yacht will be waiting to offer a different vantage point of Chicago.
Chicago City Tour and Chicago River Cruise
Duration: 4 hours
9. Tommy's Gun Garage (from USD 68.0)
Tommy Gun’s Garage is a 20s-themed restaurant that offers not just dinner, but an interactive show as well. This is a place where you get to experience a taste of the gangster-ridden 1920s life in Chicago. It’s a wonderful place to enjoy a night filled with fun and dancing. The whole venue takes you back to the past with everything is designed to make you feel like you’ve walked into the 20s. This includes a memorabilia of events like the St. Valentine’s Day Massacre. Their menu doesn’t let you down either. You can choose from a sumptuous steak, chicken or fish dish and end the night with a comedy show that includes audience participation.
Skip the Line: Tommy Gun's Garage Dinner and Show Ticket
Duration: 3 hours
10. Chicago walking tour (from USD 28.0)
There’s no better way to experience Chicago than on foot. This walking tour will allow you to dive right into the culture and history of this great city. The walking tour involves two hours of strolling through the historic sites, admiring the architectural masterpieces from over a century ago. On this tour, you’ll get to visit the Chase Tower Plaza, Chicago Temple, and Chicago Cultural Center. Also on this trip, your guide will take you to the fascinating underground passages known as the Chicago Pedway System. This is a network of tunnels that connect buildings in the downtown area.
Chicago Loop and Pedway Architecture Tour
Duration: 1 hour 30 minutes
11. Chicago Segway tour (from USD 71.0)
There are many ways to see Chicago but few are as fun-filled and unique as touring on a Segway. Ride these two-wheeled vehicles through the streets of Chicago, accompanied by a guide and a few other eager tourists. Beforehand, you’ll get a half-hour training on how to use the Segway. Once you’ve gotten a hang of it, you’ll start your tour, taking you past sites like the Buckingham Fountain, Lincoln Park, and Museum Campus. You’ll also glide past Lake Michigan on Lakeshore Drive and catch a glimpse of Navy Pier.
Chicago Segway Tour
Duration: 3 hours
12. Famous tastes of Chicago (from USD 70.0)
You won’t have properly toured Chicago until you try out the popular cuisines in the city. And there’s no better way to indulge in these mouth-watering treats than on a food tour. The Famous Tastes of Chicago tour will not only fill your belly but will also fill your mind with fun facts about the history and culture of Chicago and how it influenced the dishes loved by the locals. The tour has six stops in some of the oldest restaurants in the city. You’ll get to try out the famous deep dish pizza at Pizano’s Pizza and stuff your face with chocolate at The Goddess and the Baker café among other iconic eateries.
Famous Tastes of Chicago Food Tour
Duration: 3 hours
The best of Chicago
Embarking on these solo adventures in Chicago is not only an excellent way to explore the best of the Windy City but also an opportunity to make new friends. Whether you choose to partake in one or all of these exciting activities, you’ll find a range of fun things to do alone in Chicago. Experience Chicago at its best and enjoy a memorable visit.
Frequently asked question about things to do alone in Chicago
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