With the weekends affording many of us time to take a break from our work lives, we must fill them with memories. Whether exploring the parks, spending valuable time with friends and family, or enjoying an event somewhere in Chicago, weekends are designed to be enjoyed! Luckily, in such a sensational city like Chicago, options are abundant. To ensure you can make your weekend fun, we’ve rounded up some of the best things to do in Chicago this weekend, January 17th through the 19th.
“Shucked”
Don’t miss the final weekend of the Tony Award-winning musical Shucked at CIBC Theatre in Chicago! This captivating show follows a woman who leaves her hometown to discover why the corn is dying in her small town. Featuring a score by Grammy Award-winning songwriters Brandy Clark and Shane McAnally, Shucked is directed by Tony Award winner Jack O’Brien.
📍 Location: 1207 Clarence Ave, Berwyn, IL 60402
🗓️ Dates: January 17-19th
SIDEBAR Happy Hour w/ MICHELE MCGUIRE
Fitzgerald’s is hosting a Happy Hour Concert featuring Michele McGuire! Join us at Fitzgerald’s Sidebar for a free show, where you can enjoy menu items from Babygold Barbecue, including $1 shrimp and oysters. Reservations are available, but walk-ins are also welcome.
📍 Location: 1207 Clarence Ave, Berwyn, IL 60402
🗓️ Dates: January 17th
Friday Nights at Casa Chi
Casa Chi, located within the InterContinental Chicago Magnificent Mile, is the perfect place to kick off your weekend in Chicago. Every Friday, from 7 to 9 PM, the lounge features live music, providing an immersive experience with a rotating lineup of talented guitarists playing samba, bossa nova, and Latin-inspired tunes. Casa Chi has quickly become a favorite among live music enthusiasts, thanks to its intimate setting, world-class cocktails, and vibrant atmosphere.
Guests can choose from over 142 unique selections of mezcal and tequila, along with creative cocktails, tasting flights, and sake. The menu offers vibrant dishes such as ceviche and sizzling Ishiyaki hot stones with Wagyu Beef Ribeye and Scallops Anticucho, all designed to complement the music and drinks perfectly.
📍 Location: Casa Chi
🗓️ Dates: January 17th
Live music Saturday with Myles Hayes at Bar Pendry
Listen to the sounds of Chicago live at Bar Pendry with Myles Hayes, complete with seasonal cocktails and small bites by the cozy fireplace! A perfect Saturday weekend in Chicago.
📍 Location: Bar Pendry
🗓️ Dates: January 18th, from 4-6 p.m.
Maggie Daley Park Ice Ribbon Celebrates 10th Anniversary
The Maggie Daley Park Ice Ribbon is set to open for its 10th winter season on November 15. This quarter-mile winding track, twice the length of an average ice rink, offers breathtaking views of Chicago’s lakefront and skyline. Skaters can bring their own skates or rent them on-site. To avoid long lines and secure your spot on this iconic Chicago winter destination, it’s recommended to make reservations in advance.
📍 Location: Maggie Daley Park, Downtown Chicago
🗓️ Date: November 15, 2024—until 2025
Sip cocktails at a speakeasy in a secluded lounge
We love the allure of a cool, hidden gem. While there are many spots in Chicago, you should check out upstairs at Nisos this weekend in Chicago/ The Lounge is an alluring, hidden cocktail lounge (hint: look for the bookshelf) tucked away on the second floor of Nisos Prime. The 2,000-square-foot room offers a wondrous, carefree late-night speakeasy full of animation and melody Wednesdays—Saturdays while transporting guests to the nightlife of the Mediterranean.
Check out the Hamptons of the Midwest
Chicago actually has its own romantic and bucolic destination: Harbor Country, haphazardly labeled “The Hamptons of the Midwest.” Harbor Country is a region in Southwestern Michigan. It’s a favored weekend getaway destination for those looking to relish in a tranquil retreat with beaches, bed and breakfasts, and wineries.
Grab Bottomless Brunch
Chicago food is seriously on another level, and nothing makes that more apparent than the city’s endlessly delicious list of bottomless brunch options. This popular weekend activity typically involves breakfast delicacies, bottomless mimosas, and perhaps endless Bloody Marys if you feel extra spicy.
It’s one of the best things to do in Chicago this weekend, centered around festivity and fun. With this in mind, we’ve rounded up a few of the best spots to enjoy an exciting bottomless brunch in Chicago!
See ‘Harry Potter And The Cursed Child’
Potterheads rejoice! The world’s most famous wizard will be heading to a Chicago Broadway theater today!
The Tony Award-winning play Harry Potter and the Cursed Child will embark on its first-ever North American tour, debuting in Chicago from September to February 2025. The play debuted at London’s Palace Theatre in 2016 and on Broadway in April 2018.
Escape the city to a charming town for a weekend getaway
The small town is a storybook setting with historic 1800s architecture that is dazzling as you stroll Main Street, coined “Helluva Half Mile,” which sprawls with more than 125 independently owned business shops. It will make you feel as if you have fallen straight into the scene of an Emily Henry novel.
Dine at one of the best new restaurants
Deciding where to dine on a Friday or Saturday night can be daunting. Whether you’re with a group of friends or having a date night, everyone is opinionated when selecting a restaurant. From arbitrary TikTok recommendations to Instagram reels, narrowing down the Chicago dining scene is easier said than done. That’s why we’ve done it for you with this unequivocal list of the best new restaurants in Chicago you need to try this weekend! Now, let’s hope there is a reservation open.