While Chicago is an incredible city for dating, romantic escapades, and family fun, there’s something special about enjoying some much needed ‘me’ time. So, why not ditch the plus one for the day and explore these fantastic ideas for solo dates around the city? After all, what can be better than treating yourself to some independent adventures? Keep scrolling for our top picks of the best things to do alone in Chicago!
1. Book a massage that feels like you’re in a tropical paradise like Tulum
Our favorite spot for self-care solo dates? The NOW Massage. They offer an affordable yet uniquely designed spa experience that rivals high-end and exclusive day spas. Originating in Los Angeles, and hailed by Forbes as “L.A.’s most stunning self-care oasis,” The NOW has expanded to several locations around Chicago, including Lincoln Park, Lincoln Square, West Loop, South Loop, Wicker Park, Lakeview, and Naperville.
Gara Post, Co-Founder & Chief Creative Officer of The NOW Massage, identified a void in the marketplace, sharing, “The NOW’s unique design aesthetic is inspired by exotic destinations from around the world and my travels to places like Tulum and Greece back in 2015. With my background in design, we are constantly looking at ways to elevate and maintain our unique design aesthetic as we grow The NOW from coast to coast.”
The massage boutiques evoke a vacation-like atmosphere with breezy beachside decor, featuring natural wood surfaces, exposed beams, sheepskins, and rawhides, along with an eye-catching crystal grid found in every spa. Guests can indulge in signature massages like The NOW for relaxation, The HEALER for stress reduction, and The STRETCH for sports-injury recovery. Additional add-ons include Herbal Heat Therapy, Deep Tissue, Fresh Eyes, Hemp Calm Balm, Gliding Cupping, and Gua Sha. Simplifying booking, The Ritual Membership offers monthly or bi-monthly massages and exclusive perks.
2. Take a stroll to clear your mind
Chicago is filled with incredible architecture and beautiful places to take a solo stroll. There are so many options for a walk, including the gorgeous lakefront trail, the longest street in Chicago, our plentiful parks, and, of course, all 77 neighborhoods across the city. Whether spending the day in the West Loop’s Fulton Market or strolling along Devon Avenue in West Rogers Park and stopping for some delicious Indian food along the way, a solo walk is the best way to find something you would have missed while driving. Not to mention, it’s one of our favorite ways to clear our mind!
3. Find something free to do
The best things in life are free, right? Thankfully, Chicago offers a plethora of opportunities to spend the day doing things that won’t cost you a dime, from world-class museums to a massive indoor garden, spectacular public art, special annual events, and more! Even our fabulous zoo is free! Check out everything there is to do in Chicago for free here.
4. Step into another world at one of Chicago’s best immersive experiences
If you’re ready to step into a whole other world at one of Chicago’s top immersive experiences, look no further. Explore imaginative worlds and escape Chicago without crossing city limits, courtesy of these captivating and immersive experiences. From solving a mysterious murder at the Clue Walking experience, getting served gastronomic delights by a miniature chef during your five-course 3D animated dinner at Le Petit Chef, or enter the metaverse at Verse: The Art of the Future which fuses art and technology.
Check them all out here!5. Take a solo adventure to one of our ‘Bucket List’ adventures in Chicago!
At Secret Chicago, we’ve curated a list of must-try bucket list experiences that you absolutely should check out, whether you’re a lifelong Chicagoan, a recent transplant, or just visiting our beautiful city. From exploring our marvelous street art murals to ice skating at Maggie Daley Park, these are a few of our top things to do in Chicago that just so happen to be perfect outings if you’re hitting the city solo!
Discover our full bucket list here!
6. Go on a coffee date at one of the best independent coffee shops in the country
There’s little we love more than finding a new coffee shop around town, and what can be better than indulging in a fabulous cup of coffee by yourself?! Chicago has some of the best independent coffee shops, and one just happens to be rated the best in Chicago according to USA Today’s Best Independent Coffee Shop (2023) list. These artisanal shops were narrowed down by an expert panel who looked at cozy atmospheres, friendly baristas, and unique menus. Topping the list was Chicago’s Big Shoulders Coffee owned by husband-and-wife duo who oversee five popular locations around the city!
Click to find Chicago’s Big Shoulders Coffee near you!
7. Plan a luxurious solo staycation at one of the world’s top hotels
Chicagoans get to enjoy plenty of luxe hotels, but one has recently been named one of the ’10 Best New Hotels in the United States’ by USA Today! Why not savor it solo for a little peace and quiet? Chicago’s extravagant St. Regis opened in 2023, offering lavish amenities and unique restaurants. Among them is a Tuscan-inspired restaurant already generating buzz and securing a spot on the coveted Michelin Guide’s ‘Most Anticipated Restaurants for 2024’ list.
USA Today shared, ‘The St. Regis never spares any detail, as illustrated by its new location in Chicago. There’s an expansive riverfront terrace, dog-friendly accommodations next to beautiful Lakeshore East Park, an entire wellness floor, and two unique restaurants featuring Japanese fusion and Tuscan steakhouse cuisines.’
Learn more about the St. Regis Chicago here. Looking for a weekend getaway or to take a day trip to Michigan or Wisconsin, check out this list!
8. Take yourself out to dinner
It’s no secret that Chicago has some of the best dining options in the country, so why not take yourself out on a date to indulge in a fantastic meal? If you don’t feel comfortable sitting out front and center, cozy up to the bar at a new restaurant for a delicious drink and dinner. Whether you’re in the mood for trying out our newest restaurants to hit the scene, Michelin-starred spots or a Chicago diner that serves up one of the world’s best burgers, you’ll find some of the best options in our city!
Read up on all of our top spots for food and drink in the city here!
9. Check out one of these wonderful book shops
During the winter months, there’s nothing better than getting cozy with a new book, and we absolutely love the mission of finding the perfect one! In Andersonville, explore Women & Children First, boasting a grand collection of new, indie, and books featuring up-and-coming writers. You can also visit The Understudy, a unique theater-based bookstore and coffee shop where scripts, biographies, theatrical-themed novels, and art books await. Don’t miss other must-visit book shops like Sandmeyer’s Bookstore, a former old printing press, Volumes Bookcafe in Wicker Park, 57th Street Books on the South Side, and more!
10. Go to a fabulous Broadway show!
Have you ever wanted to catch a Broadway show but hesitate because your friends or significant other might not share the same interest?! Discover the magic of solo Broadway dates! We’ve curated a list of the best Broadway shows in Chicago this winter, featuring the return of Hamilton and the delightful Mrs. Doubtfire, played by Rob McClure, reprising his Tony-nominated role alongside his real-life co-star and wife, Maggie Lakis.
See the full list of Broadway shows happening right now in Chicago
11. Romanticize your life at an enchanting Candlelight Concert
I’ll take a Candlelight Concert date for one please! Candlelight concerts bring the most beautiful setting to venues all over the Windy City to hear mesmerizing musical performances celebrating pop, jazz, classical and more genres. Find one that speaks to you this winter!
View every upcoming concert in Chicago here!
12. Venture to one of these historic theaters for a solo movie date!
Take yourself to the movies and enjoy whatever the hell you want! Whether it’s the latest blockbuster, indie flick, a romantic comedy, or an action-packed adventure, Chicago is brimming with historic theaters for you to get comfortable while indulging in a 2+ hour solo movie experience!