Mom deserves a Mother’s Day that is as unique as she is. We’re all guilty of buying last-minute flowers and scented candles, but planning a special Mother’s Day in Chicago doesn’t have to be stressful. Based on my experience living in Chicago for about 15 years, I’ve put together a list of fun and unexpected ways to celebrate Mother’s Day around the city that all appear in my book Secret Chicago. Whether she’s a music lover, art fan, or just needs a day to recharge, surprise her with one of these unique Mother’s Day ideas.
Join the Circus Together
Has mom ever told you to run away and join the circus? You can do that in Logan Square! Aloft Circus Arts is a circus training school hidden in an unassuming Evangelical church built in 1908.
While Aloft trains circus professionals and offers classes in skills like trapeze and aerial silks, you don’t need a pro to attend. Sign up for a stretching and flexibility class with mom, or buy her tickets to Aloft’s monthly student showcase called Sanctuary and let their talented performers dazzle you.
Treat Her to a Chicago Staycation
From grand historic hotels to trendy boutique properties, there is no shortage of incredible hotel options for a Chicago staycation. But how many hotels can boast an exclusive speakeasy inside? The Old Chicago Inn, is a bed and breakfast located in the Lakeview neighborhood. The greystone building built in 1906 offers nine guest rooms and a lobby decorated with vintage charm.
The real secret to the Old Chicago Inn is in the basement—it houses a private speakeasy called Room 13! From the 1920s décor to classic cocktails made only using alcohol brands that were available during Prohibition, Room 13 is the closest you can get to the Jazz Age. Entrance to Room 13 is reserved for members and for hotel guests, so you’ll have to book a room to treat mom to this blast from the past!
Brunch with a View—and a Side of History
It’s no secret that Cindy’s, the rooftop restaurant at the Chicago Athletic Association in the Loop, offers one of the best views in town. Who wouldn’t want to enjoy Mother’s Day brunch with a view of Lake Michigan and Millennium Park?
Before you head straight to the elevator, take a moment to soak in the once-exclusive space. The Chicago Athletic Association (CAA) was a private men’s club for the city’s wealthiest residents. Names like Wrigley and Marshall Field once graced these halls. You’ll notice the club’s “C” logo around the building from stained glass to antique door handles. Does it look familiar? CAA member and Chicago Cubs owner William Wrigley borrowed the team’s “C” logo from the club logo in 1937. That’s one way to impress your sports fan mom.
Bliss Out with a Spa Day
Despite being a busy city, Chicago has plenty of places to relax. Yet some are more unique than others. The InterContinental Chicago in Streeterville is worth a stay for access to the spa and historic pool alone. The original 1920s pool on the 14th floor features stunning Spanish tiles, stained-glass windows, and a fountain. You can mom can take a lap where Esther Williams and Johnny Weissmuller once swam! Learn more about InterContinental Chicago’s history and design.
Don’t want to get wet? You can enjoy the benefits of three days at the sea in under an hour in a salt cave. Chicago’s salt caves are man-made, but halotherapy (salt therapy) dates back to the Middle Ages. Salt caves expose you to the minerals in salt which supposedly treat various issues and is a relaxing way to spend 45 minutes. In addition to offering beer soaks, Piva Beer Spa in West Town offers halotherapy sessions. In the Chicago suburbs, you can find salt therapy in Glenview, Arlington Heights, La Grange, and more.
Admire an Art Gallery
Maybe she’s been to the Art Institute of Chicago, but has mom stepped inside a restored piece of architectural history? With 1.5 million annual visitors, the Art Institute can be a bustling place. Yet the Chicago Stock Exchange Trading Room is a quiet, elegant secret hidden on the museum’s east side.
Go down a few steps and enter the wood doors to step back into 1894. Louis Sullivan and Dankmar Adler built the Trading Room as part of the Chicago Stock Exchange. Looking at the chalkboard, you can imagine traders shouting deals across the room. When the building was demolished in 1972, the Art Institute reconstructed this room with the help of preservationists like Richard Nickel, and John Vinci. Thanks to them, we can admire the sumptuous restored details like intricate stenciling and stained-glass skylights.
Stroll a Park Together
Maybe mom would love nothing more than to get outside in Chicago with you on Mother’s Day. There are plenty of free options from Jackson Park in Hyde Park to Garfield Park Conservatory. Washington Square Park in the tony Gold Coast neighborhood is home to the distinguished Newberry Library. Yet the park has a radical past! Once known as Bughouse Square, Chicago’s oldest park allows anyone to make a speech at any time. Back before TV, socialists, atheists, and eccentrics jumped on soap boxes here to speak their truth. If mom has a rebellious streak, this is the park for her!
Or admire the monuments and works of art in Grant Park in the Loop. Agora, an artwork by Polish sculptor Magdalena Abakanowicz, is a group of 106 sculptures at the park’s south end. The nine-foot-tall pieces are all unique and poised in motion. Walk through the sculptures together and ponder the artist’s meaning.
Raise a Glass
If your mom is anything like mine, she loves wine. You can taste honey wine, or mead, at Wild Blossom Meadery in Beverly. Celebrate Mother’s Day in Chicago at Wild Blossom, the first meadery in Illinois. Their honey comes from bee colonies all over the area, and they offer mead flavors from hibiscus nectar to chocolate honey buzz. Treat mom to a mead tasting on Wild Blossom’s lovely patio adjacent to the Dan Ryan Woods. Take a tour of Wild Blossom with me and WGN!
For a zero-proof beverage, treat mom to afternoon tea at any number of elegant spots like Russian Tea Time or the Langham. My vote is for tea at the Drake Hotel in the Gold Coast, a Chicago classic since 1920. You’ll sit next to a fountain decked with flowers in the hotel’s Palm Court while a harpist plays and nibble on delicious bites. If it’s your first time, check out my 10 tips for afternoon tea etiquette.
Groove to the Music
On my mom’s last visit to Chicago, we headed straight to the Blues Heaven Foundation in the South Loop for a tour. In the 1950s and ’60s, the building was once home to the iconic rhythm and blues label Chess Records sound in the 1950s and ’60s. “At Last” by Etta James and “One Bourbon, One Scotch, One Beer” by John Lee Hooker are just some of the iconic songs recorded here. The Rolling Stones even named a song for the address! Tour the building where music magic happened and see artifacts from musicians like Buddy Guy and Chuck Berry. Hearing the Chess songs play in the room they were recorded in gave me chills.
If mom is more of a jazz lover, head Uptown to the Green Mill. The bar has served jazz legends, gangsters, and film stars since 1907. In the early days of film, Charlie Chaplin and Gloria Swanson stopped by after filming at Essanay Studios. Al Capone had a favorite booth at the Green Mill during Prohibition, and his crew’s unfortunate encounter with Green Mill singer Joe E. Lewis was portrayed in the film The Joker is Wild. Today, the Green Mill is alive with the sound of music every night of the week.
Shop Sustainably
Chicago has more breweries than any other city in the U.S., but only one runs on food waste. Whiner Beer Co. is located inside the Plant, a former meatpacking facility in the Back of the Yards that’s been converted to a small business incubator focused on sustainability and waste reduction. The facility is working on getting off the grid and will be powered by biogas from an anaerobic digester. Support the 15 businesses at the Plant at the Turtle Stop, which also sells sustainable grocery and cleaning items and gifts.
On Mother’s Day, Whiner Beer Co. is hosting a Mother’s Day brunch. The taproom is inside the Plant facility. Stop by from noon to 3 p.m. for a rotating menu of Mexican-inspired Texas barbecue as well as Whiner’s delicious brews.
Want to discover other hidden places in Chicago? Check out my books Secret Chicago: A Guide to the Weird, Wonderful, and Obscure and Chicago Scavenger!
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Jessica Mlinaric founded Urban Explorer in 2010 to inspire curious travelers by highlighting arts and culture, history, and hidden gems in Chicago and beyond. She is the author of ‘Secret Chicago’ and ‘Chicago Scavenger.’ Jessica has visited 20+ countries and 30+ U.S. states. She has more than 16 years of experience as a marketing strategist and works as a freelance writer and photographer.
