Chicago offers tons of unique experiences, but nothing beats enjoying them with a friend. Here are some of our favorite happenings perfect for a BFF day—whether you’re booking a spa day, dining at one of the city’s most fabulous restaurants, heading to a Candlelight concert, or checking out a one-of-a-kind experience for a fun evening!
Keep scrolling for our list of the top things to do with your best friend in Chicago! Who’s ready for a night out with your nearest and dearest?
1. Share frozen cocktails, lake views, and lobster pasta at Shore Club Chicago
Whether you’re planning a brunch date with friends or a full day by the lake, Shore Club Chicago has plenty of reasons to put it on your summer bucket list. Groups can share dishes like the overflowing Mezze Platter, Spicy Tuna Crispy Rice, and Coconut Crusted Shrimp, or order heartier entrées. We especially loved the Lobster & Shrimp Fettuccine and Seared Atlantic Salmon while overlooking Lake Michigan.
Pair it all with a customizable spritz from the tableside Spritz Bar Cart, sample six signature frozen cocktails with the Frozen Flight featuring Mango Margarita, Piña Colada, Strawberry Daiquiri, Peachy Lychee, Spritzicle, and Freaky Tiki, or split a bottle of rosé with friends—we recommend The Beach by Whispering Angel. Then grab a spot in the Patio Lounge or Oasis, where you can relax or play games. Get ready to soak up the summer vibes from day to night!
📍 Shore Club Chicago – 1603 N Jean Baptiste Pointe du Sable Lake Shore Dr.
2. Sip wine and laugh the night away at this unique Chicago comedy experience
Comedy comes before snobbery at this innovative standup and wine tasting event in Chicago. Six different wines are brought to the table as the comedian onstage guides you through the notes, even offering up suggestions for food pairings. It’s not about becoming an expert, it’s just about laughing and having fun with your friends
📅 25 July, 5 September & 9 October
📍 Chop Shop, Chicago
🎟️ Tickets: From $68 per person
3. Have a pool day with friends that feels like you’re at a private beach club
Head to Wicker Park’s only public rooftop pool that has skyline views, street-style tacos, and frozen cocktails, so if you’re looking for a fantastic way to end summertime Chi, this is the place. Solana on the 6th floor of the Robey Hotel is one of our favorite places to enjoy all-day lounging, and you don’t need to be a hotel guest to do it. Plus, there’s a daytime special you don’t want to miss. From 11:00 a.m. to 3 p.m., enjoy those delicious street-style tacos, including Carne Asada, Al Pastor, Pollo, Pescado, or Roasted Mushrooms for only $3.
4. Bask in the light of a Candlelight concert
Candlelight Concerts are great for friends looking to disconnect from their screens and share a truly special moment together in some of Chicago’s most stunning architectural gems. Whether your group is into the classical brilliance of Vivaldi or wants to hear tributes to modern artists, the vibe is effortlessly cool and inclusive. Thousands of flickering candles create a relaxed, Instagram-worthy atmosphere where you can just sit back, vibe to the music, and enjoy a high-end cultural experience without any of the usual stuffiness.
📅 Throughout the year
📍 Various locations
🎟️ Tickets: From $40 per person
5. Bandit in the West Loop is the ultimate happy hour spot for drinks, bites & bathroom selfies
Looking for a fun happy hour spot in Chicago? Bandit in the West Loop is perfect for after-work drinks, group hangs, and epic bathroom selfies. The vibe is playful and unapologetically over-the-top, especially in the bathrooms, where the guys’ room is covered floor-to-ceiling in Britney Spears posters, while the girls’ bathroom features Justin Timberlake photos with “Cry Me a River” written across the walls. It’s safe to say we spent some time there admiring Justin’s best fan photos over the years.
As for food, don’t skip the Diplomat sliders, gooey cheese sticks, poke bowl, steak tacos, loaded nachos, and crispy wings — especially on Wing Wednesday when they’re just $1 each. Pair it with $10 well drinks, a Thirsty Thursday pitcher special, or the $15 Burger & High Life combo on Miller Monday for the ultimate happy hour lineup.
Some standout cocktails included the Bandit Smash (tin cup bourbon, sage, lemon, pineapple, mint), The Samantha (Grey Goose, cranberry, lemon, cucumber, sage, and basil), and the Spicy Fella (Patrón, cardamom, pineapple, serrano, and lime).
6. Unleash your inner child at this new Minecraft experience
Looking for a fun group outing near Chicago? The immersive Minecraft experience is the perfect spot to explore with friends, whether you grew up playing the game or just want something different to do together. Step inside a life-sized blocky world filled with interactive challenges, iconic biomes, and photo-worthy moments as you work together to complete missions and explore the experience. From battling mobs to collecting resources and uncovering hidden surprises, it’s a nostalgic adventure that’s even better with a group.
7. Grab your friends and get ready to get covered in color
The Color Vibe 5K is less about racing and more about having fun together, with a colorful 3.1-mile course, music, photo ops, and a new burst of color around every mile. Come dressed in your brightest outfits, dance your way through the course, and leave with some seriously colorful memories.
📅 Saturday, September 5
🎟️ Learn more here!
8. Treat yourself to a calming girls night out with a soothing sound bath
Treat yourself to the ultimate girls night with a serene floating meditation and sound bath at The St. Regis Chicago. Set under a soft glow at the indoor pool, you’ll unwind on floating beds as calming sound bowls and guided meditation help you reset and recharge. End the evening with a champagne toast and a take-home gift.
Learn more about future sessions here!
📅 Throughout the year
📍 St. Regis Chicago
🎟️ Secure your spot here.
9. Give your verdict at The Jury Experience
The Jury Experience is the ultimate high-stakes challenge for a group of friends who love a good true crime deep dive or a heated group chat debate. You and your crew become the actual jury, working together to dissect forensic evidence and witness testimony. Whether you’re trying to crack a complex murder mystery or arguing the ethics of an AI car crash, this 60-minute immersive show turns your night out into a collaborative brain-teaser.
📅 Various dates
📍 Edlis Neeson Theater – MCA
🎟️ From $46 per person
10. See a play at the legendary Steppenwolf Theatre in Lincoln Park
Plan a night out with friends at Chicago’s iconic Steppenwolf Theatre, one of the city’s most celebrated destinations for live performances. Known for its bold productions and award-winning talent, the theater offers everything from thought-provoking dramas to contemporary plays in an intimate setting that makes every show feel immersive.
Located in Lincoln Park, it’s the perfect excuse to grab drinks at the on-site Front Bar before settling in for an unforgettable evening of theater. Catch upcoming productions like Catch as Catch Can, comedian Alex Edelman’s new show What Are You Going to Do, and more.
11. Play high-tech mini golf just outside Chicago
Looking for a fun night out with friends? Puttshack is a great pick if you’re looking for a night out with some healthy competition! With glowing mini golf courses, music and automatic scoring, you can just focus on having a blast. Order a few shareable bites like the Puttshack Poutine and Mediterranean Lamb Skewers, and don’t skip out on the creative cocktails.
📍 Find it in Oak Brook and Skokie
12. Chill at The Jazz Room
The Jazz Room at The Den Theatre is the perfect spot for a night out with friends, transporting you back to the golden age of jazz. With its 1920s speakeasy vibe, atmospheric lighting, and intimate seating, you can sip cocktails while professional musicians perform soul-stirring tributes to legends like Frank Sinatra and Louis Armstrong.
📅 Various dates
📍 The Den Theatre
🎟️ From $47 per person
13. Have a luxurious spa day
Booking a spa day with friends is hands-down one of our favorite ways to unwind and relax! It makes us feel like we’re on vacation, even if it’s only for the day since many of the city’s top spas can be found in some of our favorite hotels with incredible views. You and your friends can enjoy the most relaxing treatments from facials and massages to manis, and pedis. One of our favorite parts is visiting the steam rooms or saunas before or after our treatments.
If you want to splurge, check out AIRE Ancient Baths for an incredible treatment. Plan to soak in their several thermal baths inspired by ancient civilizations in various temperatures in a historic candlelit former factory.
If we don’t want to break the bank, we head to The NOW Massage for an affordable yet uniquely designed spa experience that rivals high-end, exclusive day spas. The soothing decor and relaxing sound of waves crashing always transports us straight to Tulum, making it the perfect escape without leaving the city.
Check out our favorite spas all over the city here!
14. Let loose at WhirlyBall Chicago
WhirlyBall Chicago is an excellent spot for a high-energy outing with friends, offering a hilarious mix of bumper cars, lacrosse, and basketball. It’s impossible not to have a blast as you zip around the court competing for bragging rights, and the fun continues off-court with bowling, multi-level laser tag, and a great selection of craft beers.
📅 Open every day
📍1825 W. Webster Ave., Chicago, IL 60614
15. Have a giggle at a comedy club
Chicago’s comedy scene is legendary, and catching a show with friends is the ultimate way to experience the city’s sharp wit. From the iconic improv stages of The Second City and iO Theater to the intimate stand-up vibes at Zanies and the Laugh Factory, there’s a venue for every sense of humor. Take a look at our list of the best comedy clubs in Chicago for inspiration.
16. Visit Little India
You can spend hours hopping between tasty restaurants for authentic butter chicken and dosas in Little India, browsing shops filled with colorful saris and intricate jewelry, and grabbing some world-class street snacks. It’s an absolute must-visit neighborhood that’s perfect for a group that loves to eat well and explore somewhere unique together.
