3-Day Weekend Girls Trip in Chicago: Food, Culture & Fun

Day 1: Explore Downtown

Chicago, USA on May 3, 2025

9:00am

Breakfast at Wildberry Pancakes and Cafe

Start your trip with delicious, hearty breakfast classics and unique pancakes located near Millennium Park, perfect to fuel your day.
USD15-25, 1h15m

10:30am

Millennium Park Visit

Explore the iconic Cloud Gate sculpture (The Bean) and enjoy the beautiful outdoor art and gardens in this famous urban park. Open daily from 6:00am to 11:00pm.
Free, 1h30m

12:15pm

Art Institute of Chicago

Visit one of the oldest and largest art museums in the US, housing classic and contemporary artwork including Grant Wood’s American Gothic. Open 10:30am-5:00pm.
USD25, 2h

2:30pm

Lunch at Giordano's

Enjoy famous deep-dish Chicago-style pizza in a cozy downtown setting.
USD20-30, 1h

4:00pm

Riverwalk Stroll

Take a scenic walk along the Chicago Riverwalk, watching the city views and bridges, perfect for photo ops and light shopping.
Free, 1h

6:00pm

Dinner and Drinks at Cindy’s Rooftop

Savor seasonal cocktails and American cuisine with amazing views of Millennium Park from this rooftop restaurant. Usually open until 11:00pm.
USD40-60, 2h

8:30pm

Evening Entertainment at a Jazz Club

End your night with live jazz music at Andy’s Jazz Club, open until 1:00am, to experience Chicago’s vibrant music scene.
USD20-40 cover plus drinks, 2h
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Day 2: Shopping & Waterfront Fun

Chicago, USA on May 4, 2025

8:30am

Breakfast at Little Goat Diner

Enjoy creative and hearty breakfast dishes with a modern twist in this trendy diner owned by Stephanie Izard.
USD15-25, 1h

10:00am

Shopping on Michigan Avenue (Magnificent Mile)

Explore extensive shopping options from luxury boutiques to flagship stores along the Magnificent Mile, open typically from 10:00am to 9:00pm.
Varies, 3h

1:00pm

Lunch at The Purple Pig

Relish Mediterranean-inspired small plates and an extensive wine list in a vibrant, casual atmosphere on the Magnificent Mile.
USD25-40, 1h30m

3:00pm

Navy Pier visit

Enjoy the iconic Navy Pier attractions including the Centennial Wheel, boat tours, and shops. Open from 10:00am to 10:00pm on weekends.
Wheel ticket USD18, others vary, 2h

6:00pm

Dinner at Riva Crabhouse on Navy Pier

Savor fresh seafood and stunning lake views in a relaxed setting perfect after a day of sightseeing.
USD40-60, 2h

8:30pm

Sunset Lake Michigan Cruise

Cap your day with a sunset cruise around Lake Michigan providing beautiful city skyline views. Cruises typically depart around 8:30pm, lasting 1.5 hours.
USD35-50, 1h30m
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Day 3: Neighborhood Charm

Chicago, USA on May 5, 2025

9:00am

Breakfast at Ann Sather

Famous for fluffy cinnamon rolls and classic breakfast fare, this cozy spot is a Wicker Park favorite. Opens at 8:00am daily.
USD15-20, 1h

10:30am

Wicker Park Boutique & Street Art Walk

Discover unique shops, local boutiques, and colorful street art murals while strolling the edgy and artsy neighborhood streets.
Free to explore, 2h

12:30pm

Lunch at Big Star

Enjoy mouthwatering tacos and craft cocktails in an upbeat setting with a lively patio, open daily from 11:30am.
USD20-30, 1h

2:00pm

Lincoln Park Zoo and Conservatory

Visit the free Lincoln Park Zoo and nearby Conservatory to unwind surrounded by nature before heading home. Zoo open 10:00am–5:00pm, Conservatory until 5:00pm.
Free, 2h

5:00pm

Early Dinner at Alinea (Reservation Required)

Wrap up your trip with an unforgettable fine dining experience at Alinea, renowned for its innovative molecular gastronomy. Reservations required well in advance.
USD250+, 2h
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