Last Updated on October 3, 2026 by Themigonikitchen

A Chicago Girls’ Trip Guide: Where to Eat, Drink & Explore

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There’s something so special about a getaway with your favorite girlfriends—and Chicago is easily one of the best cities in North America for a girls’ trip. Between world-class shopping, incredible dining, scenic lake views, and aesthetic coffee shops on every corner, the Windy City has everything you need for an unforgettable weekend away.

Whether you’re planning a birthday weekend, a long-overdue catch-up, or a quick 48-hour escape, here is a curated guide to the best spots for a Chicago girls’ trip!

Aesthetic Coffee & Morning Fuel

Chicago’s coffee scene is top-tier, featuring inventive flavors and beautiful spaces perfect for catching up.

• Sawada Coffee (West Loop): Famous for its moody, rustic aesthetic and Military Latte (a combination of matcha, espresso, cocoa powder, and vanilla syrup). It’s set in a cool shared space with Green Street Smoked Meats.
• Drip Collective: Perfect for adventurous coffee lovers. Don’t miss their Banana Miso Latte or beautiful Ube Latte.
• Oud Cafe & Tabeeb Coffee: Two incredible Palestinian-owned coffee shops serving unique Middle Eastern lattes (think cardamom, pistachio, and fresh mint) along with sweet treats like the Za’atar Nutella Donut.

Trendy Brunch & Bottomless Drinks

No girls’ trip is complete without a leisurely brunch in a gorgeous setting.

• Beatnik on the River: A total must for a stylish brunch. Situated right along the Chicago River, its bohemian, lushly decorated patio feels like stepping into a Mediterranean oasis. Pair incredible cocktails with river views.
• The Publican (Fulton Market): Ideal for foodies who love a lively, European hall vibe. Their pastry basket is phenomenal, and the bottomless drip coffee will keep you energized for a day of exploring.

Fun Cocktails, Speakeasies & Evening Views

When the sun goes down, Chicago’s cocktail scene shines.

• Three Dots and a Dash: Tucked away down an alleyway in River North, this hidden tropical tiki bar serves up elaborate, fun, shareable tiki cocktails in a wildly atmospheric subterranean space.
• Raised, An Urban Rooftop Bar: Grab a drink at this popular rooftop bar with beautiful views of the city. Rooftop bars are plentiful in Chicago and for good reason, who wouldn’t want a view of the picture perfect skyline with a drink in hand?
• Lake Michigan Sunset Cruise: Trade crowded bars for a scenic boat ride. Seeing the Chicago skyline lit up at golden hour from the water is hands-down one of the best experiences to share with friends. Bonus – most of these cruises feature a bar with drinks for purchase, if you still want that cocktail!
• Creepies (West Loop): A chic, French-inspired bistro with amazing energy, brie-filled gougères, and Parisian gnocchi.

Boutique Shopping & Hidden Treasures

Skip the generic high-street chains and explore these unique neighborhood gems:

• Alice and Wonder: The ultimate destination for trendy, Chicago-inspired apparel, cute accessories, and gifts.
• P.O.S.H.: A charming European-inspired boutique filled with hotel silver, vintage flea market finds, and imported homewares.
• L.A. Burdick Chocolates: Grab their famous handmade chocolate mice as sweet souvenirs to take back home.

Iconic Food Stops You Can’t Miss

• Tavern-Style Pizza at Zarella’s: Skip the heavy deep-dish and opt for Chicago’s true local favorite—crispy, thin, cracker-crust tavern pizza cut into squares. The Vodka Sauce pizza is an absolute winner.
• Mr. Beef on Orleans (or Portillo’s): Grab a legendary Italian Beef sandwich at the spot made famous by The Bear. If you want a quick option with less of a wait, head to Portillo’s for a classic Chicago-style hot dog and beef sandwich!

Relaxation & Cultural Highlights

• Garfield Park Conservatory: A stunning, plant-filled indoor glasshouse that offers a tranquil escape from the bustling city streets. Easily accessible by CTA with a direct stop, so no worries about pricey rideshares.
  • Pro Tip: Check if your local botanical garden membership (like the Dallas Arboretum) grants you free reciprocal entry!
• Millennium Park Walk: Go early in the morning to grab photo-op shots at Cloud Gate (“The Bean”) without the crowds.
• Architecture River Cruise: Chicago is hailed as an architecture lover’s dream. There are so many stunning types of architecture within the city and the best way to see them is by cruise of course! The architecture cruises are a fun, informative and scenic way to see the city’s historical buildings.
• The Chicago Art Institute: Listed as one of Trip Advisors “Best of the Best US Attractions” in 2025 for good reason, this art museum is one of the most outstanding in the country. Explore the artwork as a group and pick out your favorites.