10 Things To Do Alone In Chicago - Updated 2021

things to do alone in Chicago

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. 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 these suggestions of tours you can sign up in Chicago.

1. Chicago crime and mob tour (from USD 46.0)

This city is known for its tainted gangster past. 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: 1 hour 30 minutes

1134 reviews

2. 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

153 reviews

3. Skydeck Chicago (from USD 30.0)

If you’re eager to get a bit of a thrill, 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.

Travel tip by Chicago Local Expert - John
Posted on: Feb 10, 2021

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!

Skydeck Chicago Admission Ticket

Duration: 3 hours

974 reviews

4. 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

10 reviews

5. 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

10 reviews

6. 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

10 reviews

7. 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

8. 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 reviews

9. 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

10 reviews

10. 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

218 reviews

The best of Chicago

Get the best of the Windy City by taking part in one or all of the tours above. If you’re travelling alone, this is the best way to make new friends. Experience Chicago at its best and enjoy a memorable visit.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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