Activities To Enjoy Alone In Chicago

Everyone needs alone time now and again, and some things are just better enjoyed on your own. So why not indulge yourself with these pretty great solo activities? Whether you check out a movie or a museum, treat yourself to a fancy treatment or meal, combining several of these will make for a pretty great day out in Chicago.

Take the architectural boat tour

Never found time for one of the most popular tourist activities in the city? The Chicago Architecture Foundation River Cruise is as good as the reviews say it is, so don’t worry about anyone else’s schedule and just do it. Learning more about the many famous buildings along the Chicago River is a fun and rewarding experience, and you can impress your friends with your knowledge afterwards.

Pamper yourself in a River North hotel

Chow down at the French Market

With so many great food vendors under one roof, you can put together your own customised tasting menu at the Chicago French Market. How about an aromatic salad from Saigon Sisters, a Mac & Cheese side from Wood Fire Counter, a Strawberry Dream crêpe from FliP Crepes or an artisan truffle from Lolli & Pops? That’s barely scratching the surface. You also won’t have to share a single bite.

Go to the movies

Going to the movies on your own is massively underrated. You don’t have to be self-conscious about how many snacks you want, you can watch whatever you choose and you don’t have to answer any questions during the movie. Chicago has some great movie theaters, such as the Music Box Theatre in Wrigleyville, which has midnight movies and weekend matinees featuring rare and classic films, alongside the best of modern cinema.

Take a wellness class at the Chicago Botanic Garden

What better way to relax and find your own thoughts than by taking a wellness class in the beautiful surroundings of the Chicago Botanic Garden? Outdoor yoga (remember to bring a mat), tai chi and even walking classes are open to all ages and fitness levels. Held in different parts of the gardens each time, the focus is on feeding your mind, body, and soul.

Retail therapy on the Magnificent Mile

Shopping can be a wonderful, fun activity or a joyless and tiresome chore. That’s often down to who you’re shopping with, so remove any outside influence by going it alone. Head to the Magnificent Mile and take your sweet time browsing literally dozens of stores, trying on whatever you want and buying it too.

Get lost in a museum

We all browse museums at different speeds, enjoying certain pieces and exhibitions more than others, so why not go without being hurried or slowed down by anyone else? World famous Chicago museums such as the Art Institute of Chicago, the Field Museum or the Museum of Science and Industry are all best enjoyed at your own pace, taking time to appreciate the wonders within or just to enjoy the peace.

Take on all three floors of Myopic Books

Another activity best enjoyed solo is looking for that classic book you’ve always wanted, especially in a used book store with over 70,000 titles littered across three floors. In Wicker Park’s Myopic Books, it’s easy to spend hours browsing shelves, flipping through old books and just soaking up the atmosphere. Stick around for a reading or even live music.

Did you know – Culture Trip now does bookable, small-group trips? Pick from authentic, immersive Epic Trips, compact and action-packed Mini Trips and sparkling, expansive Sailing Trips.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.