Romantic Weekend Getaway in Chicago for Couples

Day 1: City Landmarks

Chicago, USA on May 24, 2025

8:30am

Breakfast at Wildberry Pancakes and Cafe

Start your day with a delicious breakfast featuring pancakes, omelets, and fresh coffee in a cozy downtown setting. Opens at 7:00am, perfect for early risers.
USD25, 1h

9:30am

Explore Millennium Park

Enjoy iconic sights like Cloud Gate (The Bean), Crown Fountain, and Jay Pritzker Pavilion, a lovely outdoor space to take romantic photos. The park is open daily from 6:00am to 11:00pm.
Free, 1h30m

11:00am

Visit the Art Institute of Chicago

Explore one of the oldest and largest art museums in the US, featuring Impressionist paintings and modern art, perfect for art-loving couples. Open 10:30am to 5:00pm, closed Wednesday.
USD30, 2h

1:30pm

Lunch at The Gage

Enjoy upscale American cuisine with a lively atmosphere across from Millennium Park. Open daily from 11:30am to 10:00pm.
USD50, 1h

3:00pm

Relax at Maggie Daley Park

Take a walk or rent a tandem bike in this beautiful park adjacent to Millennium Park, featuring gardens, playgrounds, and mini golf.
Free, 1h

5:00pm

Navy Pier Stroll and Rides

Visit Chicago’s iconic Navy Pier, enjoy waterfront views, the Centennial Wheel, and lively atmosphere as the sun sets. Open from 10:00am to 10:00pm.
USD15 for rides, 2h

7:30pm

Dinner at Riva Crabhouse on Navy Pier

Delight in fresh seafood with stunning lake views, perfect for a romantic dinner. Open daily from 11:30am to 10:00pm.
USD70, 1h30m
View Hotel Availability

Day 2: Nature and Shopping

Chicago, USA on May 25, 2025

8:00am

Breakfast at Batter & Berries

Enjoy gourmet breakfast and brunch favorites including stuffed French toast and fresh juices. Open from 8:00am.
USD25, 1h

9:30am

Lincoln Park Zoo Visit

Explore one of the nation’s oldest free zoos with a charming variety of animals and beautiful gardens. Zoo is open from 10:00am to 5:00pm.
Free, 1h30m

11:30am

Walk Along the Chicago Lakefront Trail

Take a leisurely scenic walk along Lake Michigan’s shores heading towards the Magnificent Mile.
Free, 1h

12:30pm

Lunch at Eataly Chicago

Savor a variety of Italian dishes and fresh pasta in a lively market setting in the Magnificent Mile. Open 11:00am to 9:00pm.
USD45, 1h

1:45pm

Shopping and Exploring Magnificent Mile

Browse luxury shops, unique boutiques and enjoy the vibrant urban atmosphere along Michigan Avenue.
Varies, 2h

4:00pm

Chicago Architecture Foundation River Cruise

Embark on a 90-minute guided boat tour showcasing Chicago’s architectural landmarks along the Chicago River. Cruises run through mid-October, typically departing every 30 minutes until 6:00pm.
USD50, 1h30m

6:00pm

Dinner at The Purple Pig

Enjoy Mediterranean-inspired dishes with a focus on sharing plates, a cozy spot ideal for couples. Dinner service from 5:00pm to 10:00pm.
USD60, 1h30m
View Hotel Availability