Chicago isn’t just all skyscrapers and sports it’s also full of charm, creativity, and aesthetic corners that are perfect for a girls’ getaway or solo self-care trip. Whether you’re brunching in a flower-covered café, snapping photos in a pink museum, or indulging in a luxe spa session, the city has so many ways to lean into your feminine side.
In this guide, I’ve rounded up my favorite girly things to do in Chicago from sweet treats to style havens and glittering views. If you’re planning a bachelorette weekend, girls’ trip, or just craving a bit of sparkle in the Windy City, this list is for you.
Here’s an expanded and more detailed version of the café and brunch section to better guide your readers and make their trip planning easier:
Pretty Cafes & Insta-Worthy Brunch Spots
1. The Pink Squirrel (Logan Square)
The moment I stepped into The Pink Squirrel, I felt like I was inside a retro Barbie dream. This charming bowling bar is decked out in blush tones, neon lights, and cozy pink booths, with vintage flair from the ‘50s and ‘60s. The main draw? Their boozy milkshakes. I ordered the Strawberry Shortcake with vodka and whipped cream served in a sundae glass topped with sprinkles and a cherry.
What I loved most was how it doubles as a vibe and a venue you can rent out mini duckpin bowling lanes for a fun girls’ night. It’s not just cute, it’s interactive. Pro tip: go on a weekday evening to avoid the crowds and get better photo ops under the neon glow.
Address: 2414 N Milwaukee Ave
Photo Tip: Snap your milkshake in front of the pink mural near the entrance.
Price: $12–$16 per milkshake
2. Maison Parisienne (Gold Coast)
Looking for a little slice of Paris in Chicago? Maison Parisienne is a French café tucked into a quiet street near the Gold Coast mansions. It’s effortlessly elegant with floral arrangements, pastel walls, and delicate tableware that feels straight out of a French lifestyle magazine.
The highlight here is their fresh, flaky pastries and buttery quiches. I went for a Lavender Latte and their Tarte aux Pommes (apple tart), and the flavors were as lovely as the ambiance. It’s an ideal spot for a slow morning, journaling, or catching up with a friend over croissants.
Address: 2224 N Clark St
Try This: Lavender latte + almond croissant combo
Vibe: Feminine, calm, and totally Parisian
3. Beatnik on the River (Downtown)
Beatnik on the River isn’t just brunch it’s an experience. Set along the Chicago Riverwalk, this bohemian haven is packed with velvet daybeds, hanging plants, hand-carved wood, and global-inspired décor that feels like Marrakech met Bali in the middle of downtown Chicago.
The menu blends Mediterranean, Middle Eastern, and Latin flavors. I recommend the shakshuka with a side of house-made pita it was so flavorful and warming. Don’t skip their craft cocktails either (even the mocktails are photogenic!). Perfect for a mid-morning date, birthday brunch, or solo journal session in style.
Address: 180 N Upper Wacker Dr
Pro Tip: Request outdoor seating in warm months it overlooks the river with serious picnic-in-the-city energy.
Photo Tip: The vintage mirrors and mosaic floor inside are Insta favorites.
Spa Days, Blowouts & Self-Care Time
4. AIRE Ancient Baths (River West)
Tucked inside a restored industrial building, AIRE Ancient Baths is hands down the most luxurious spa experience I’ve had in Chicago. Picture candlelit stone walls, flickering lanterns, and serene music echoing as you dip between warm, cold, and saltwater baths. It feels like you’ve stepped into another century in the best way possible.
What makes AIRE so special is how immersive it is. You can book a thermal bath session alone or pair it with deep tissue or hot stone massages. My favorite? The wine bath ritual, where you literally soak in antioxidant-rich red wine extract (yes, really).
Address: 800 W Superior St
Tip: Arrive early and don’t rush each session is timed but you’ll want every minute.
Price: $$–$$$ (Thermal bath starts around $90, treatments go up from there)
5. Drybar (Lincoln Park)
A girls’ weekend in Chicago needs a glam-up stop and Drybar never misses. Whether you’ve got a fancy dinner, rooftop plans, or just want that “main character” feeling, a professional blowout is a game-changer. Their stylists are super friendly and efficient, and they use Drybar products that smell so good.
I usually go for the Cosmo-Tai, which gives you beachy curls with volume, but they also offer sleek straight styles and soft waves. Book in advance, especially on weekends!
Address: 1611 N Sheffield Ave
Must-Know: They don’t do cuts or color just styling!
Bonus: The yellow hairdryer chandelier is adorable for a quick snap post-glow-up.
6. Scratch Goods (West Loop)
Looking for something a little quirky and wellness-inspired? Scratch Goods is a skincare studio and shop where you can literally put on a face mask with your besties. They host rotating mask bar sessions where you choose your clay, blend your own, and apply it together while sipping tea and learning about ingredients.
It’s fun, informative, and leaves your skin baby-soft. I went with a group of friends and we were giggling in clay masks one minute and buying serums the next.
Address: 847 W Randolph St
Best For: Girlfriend dates, bachelorette wellness mornings
Price: $$ (Mask bar starts around $35)
Cute Things to Do With Your Besties
7. WNDR Museum (West Loop)
WNDR Museum is where art meets interactive fun. Think neon light rooms, mirror installations, kinetic floors, and even a “Confetti Dome” that made me feel like a kid again. Every corner is a photo opportunity, but it’s also thoughtfully designed to make you reflect and play.
Go in with a phone battery fully charged, because you’ll want to document everything. They change up the installations seasonally, so it’s never the same twice!
Address: 1130 W Monroe St
Can’t-Miss: The Infinity Mirror Room by Yayoi Kusama
Tip: Get tickets in advance; weekends sell out fast.
8. Afternoon Tea at The Drake Hotel (Magnificent Mile)
Channel your inner Bridgerton with afternoon tea at The Drake. It’s served in their elegant Palm Court with a harpist playing in the background, floral centerpieces on every table, and waitstaff in tuxedos. You’ll be served delicate finger sandwiches, buttery scones, and mini desserts on silver-tiered trays.
I brought my mom here on a girls’ day, and we both loved the experience it’s posh without being pretentious. Dress up a little, and soak it in.
Address: 140 E Walton Pl
Best For: Mother-daughter days, birthdays, bridal showers
Bonus: Snap a pic near the grand staircase before or after
9. Candle-Making at Paddywax Candle Bar (Wicker Park)
Nothing says cozy + crafty like pouring your own candle at Paddywax Candle Bar. You walk in, choose a vessel and fragrance (I went with amber & smoke), and get guided through the process by a cheerful instructor. You can bring wine if you want to turn it into a true girls’ night!
Best part? You take your candle home the same day, and every time you burn it, it’ll remind you of the memories.
Address: 1639 N Damen Ave
Good To Know: Candles take 2 hours to cool plan to explore the neighborhood or grab dinner nearby
Price: $$ ($45–$55 depending on vessel size)
Shop ‘Til You Drop (Stylishly)
10. Southport Corridor (Lakeview)
If Michigan Avenue is Chicago’s Rodeo Drive, then Southport Corridor is its stylish little sister charming, walkable, and full of personality. It’s where I go when I want to stroll and shop without feeling rushed or overwhelmed. You’ll find a mix of trendy national brands like Madewell and Lululemon alongside local gems like Krista K Boutique (great for fashion-forward finds) and Art Effect (quirky gifts and accessories).
It’s also sprinkled with cafes, bakeries, and even a cute old-school theater if you want to catch a rom-com post-shopping. Basically, it’s my favorite place to spend a Saturday with a friend and a latte in hand.
Location: Southport Ave between Belmont & Irving Park
Tip: Look out for neighborhood sidewalk sales in spring/summer for boutique bargains
Snack Stop: Stop by Do-Rite Donuts for a pistachio old-fashioned
11. Alice & Wonder (Lincoln Park)
Alice & Wonder is my definition of a girly shopping haven: it’s pink, playful, and full of heart. Founded by a Chicago local, the boutique offers curated pieces that are both trendy and wearable think floral skirts, graphic tees, and pastel-colored accessories.
They also carry adorable Chicago-themed merchandise, perfect if you’re visiting and want a stylish souvenir that’s not a touristy T-shirt. I picked up a “Chi Babe” sweatshirt on my last visit and wear it every time I travel it’s cozy and a convo starter.
Address: 956 W Webster Ave
Gift Idea: Their greeting cards and candles make cute birthday or bridesmaid gifts
Vibe: Feminine, modern, and 100% Instagrammable
12. Nordstrom on Michigan Avenue
For a one-stop shopping experience that still feels glam, Nordstrom on the Mag Mile delivers. You’ll find designer bags, luxury beauty counters (Chanel, Dior, YSL you name it), a massive shoe floor, and a killer selection of occasion dresses.
But what makes it stand out is the little extras: a personal stylist service, an in-house café (get the tomato soup + grilled cheese), and even a mini champagne bar upstairs if you need to “celebrate your finds.” I’ve spent full afternoons here without even realizing the time.
Address: 55 E Grand Ave
Perfect For: Last-minute outfits, makeup splurges, bridal accessories
Bonus: Toast to your haul with a glass of bubbly before you leave!
Sunset Views & Girly Nights Out
13. Cindy’s Rooftop (Loop / Millennium Park)
I always recommend Cindy’s Rooftop for golden hour it’s a dreamy spot that overlooks Millennium Park, Lake Michigan, and the Art Institute’s green roof. The entire space feels like a glass greenhouse, filled with hanging plants, warm wood, and cushy lounge seating.
The drinks are a little pricey, but the views more than make up for it. I usually go for the Frosé or their rotating seasonal cocktails. If you’re lucky, you’ll catch one of those cotton-candy sunsets that reflects off The Bean.
Address: 12 S Michigan Ave (Inside Chicago Athletic Association Hotel)
Best Photo Spot: Head to the far end of the balcony, facing east at sunset
Tip: Make a reservation or arrive right at opening it fills up fast, especially in summer
14. LondonHouse Cupola (Downtown/Riverwalk)
If you’re dressing up for one ultra-glam evening in Chicago, this is the place. The LondonHouse Cupola is one of the most beautiful skyline viewpoints I’ve ever experienced and it feels like a secret. You’ll climb a spiral staircase from the rooftop bar to reach a domed glass cupola where you can sip champagne under the stars with 360° views of the city.
It’s romantic, upscale, and feels like a scene from a movie. I wore a flowy dress and heels and didn’t want to leave. They usually reserve this spot for hotel guests or private events, but it’s worth asking when you book!
Address: 85 E Wacker Dr
Vibe: Glam, romantic, a little exclusive
Note: Lighting is low bring a phone light or plan for moody evening pics
15. Chicago Magic Lounge (Andersonville)
For something unique (and a little mysterious), spend an evening at the Chicago Magic Lounge. It’s hidden behind a fake laundromat front and opens into a vintage-style cabaret space where illusionists perform right at your table. There’s live jazz, velvet seating, and delicious cocktails think speakeasy meets magic show.
I came here not knowing what to expect and was blown away by the talent and vibe. It’s interactive, flirty, and so much more memorable than a standard night at a bar.
Address: 5050 N Clark St
What to Expect: Table-side tricks, stage performances, and a stunning lounge bar
Girls Night Tip: Book a dinner + show package in advance and dress up it’s a fun excuse to be a little extra
Seasonal Girly Things To Do in Chicago
- Spring: Tulip season at Maggie Daley Park or a flower class at Flowers for Dreams
- Summer: Rosé picnics on North Avenue Beach or mural hopping in Wicker Park
- Fall: Apple cider donuts at Lincoln Park Farmer’s Market
- Winter: Ice skating at the Ribbon + hot cocoa at Cocoa + Co.
FAQs
What are the best neighborhoods in Chicago for cute, girly experiences?
Lincoln Park, Wicker Park, and Gold Coast are packed with pretty cafes, unique boutiques, and picture-worthy places.
Is Chicago good for a girls’ trip?
Absolutely! With its mix of food, shopping, spas, and nightlife, it’s perfect for bachelorettes or weekend getaways.
Where can I take Instagram photos in Chicago?
Try the WNDR Museum, LondonHouse rooftop, Garfield Park Conservatory, or murals in West Loop.
Any girly things to do in Chicago that are free?
Yes! Walk the Lakefront Trail at sunset, browse Lincoln Park Zoo, or snap pics at Cloud Gate (The Bean).
Final Thoughts + Plan Your Perfect Day
I’ve visited Chicago many times, and this list is what I’d plan for a perfect girly day: café hopping, a boutique browse, candle-making or a massage, and rooftop views at golden hour. Whether you’re visiting with friends, sisters, or just treating yourself, I hope this gives you a fun, feminine way to explore one of my favorite cities.
