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Family-Friendly Chicago Itinerary Including Grant Park Dessert, Navy Pier, Lincoln Park & Starbucks Roastery: May 9-12, 2025

Viewed by 104 travelers

Day 1: Hotel, Grant Park & Dessert

Chicago, USA on May 9, 2025

1:00pm

Check-in & Settle at Hyatt Regency O'Hare

Arrive at the hotel and get settled with your family, preparing for an active afternoon.
Included, 30m

2:00pm

Explore Grant Park

Visit Chicago’s iconic Grant Park to enjoy outdoor sculptures, gardens, and lakeside views with the family from 2pm to 3:30pm.
Free, 1h30m

3:30pm

Dessert at Jeni's Splendid Ice Creams in Grant Park area

Treat your family to delicious artisan ice cream at nearby Jeni's Splendid Ice Creams, perfect for a sweet pause before departing.
USD8 per person, 30m

4:00pm

Early Dinner at Gibsons Bar & Steakhouse O'Hare

Enjoy a hearty American meal with kid-friendly options at this nearby renowned steakhouse open until 9pm.
USD30 per person, 1h

5:00pm

Return to Hotel to Relax

Head back to Hyatt Regency O'Hare and unwind for the evening after a beautiful afternoon outdoors and dessert treat.
Free, 1h
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Day 2: Navy Pier & Night Visit

Chicago, USA on May 10, 2025

8:00am

Breakfast at Yolk - O'Hare Area

Start your day with a delicious breakfast at a nearby family-friendly cafe.
USD15 per person, 1h

9:00am

Morning Leisure & Hotel Amenities

Relax and enjoy hotel amenities or take a short outing before your scheduled evening plans.
Free, 7h30m

5:30pm

Travel to Navy Pier

Take the Blue Line and then walk or taxi to Navy Pier for your evening activities.
USD5 per person, 30m

6:00pm

Dinner at Riva Crabhouse

Enjoy lakeside seafood dining with kid-friendly options at Navy Pier.
USD25 per person, 1h30m

7:30pm

Ride the Centennial Wheel

Experience stunning views aboard the iconic Ferris wheel during twilight or nighttime, adding magic to the experience.
USD16 per adult, USD10 per child, 1h

8:30pm

Visit Buckingham Fountain at Night

Take a short taxi or transit ride to Buckingham Fountain to see its colorful nighttime water and light show, open until 10pm some evenings.
Free, 45m

9:15pm

Return to Hyatt Regency O’Hare

Travel back to your hotel for rest after a delightful day.
USD5 per person, 1h
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Day 3: Lincoln Park Outdoor Fun

Chicago, USA on May 11, 2025

12:00pm

Relaxed Morning & Early Afternoon

Enjoy hotel amenities or nearby cafes to recharge for your evening plans.
Free, 5h

5:00pm

Travel to Lincoln Park

Use CTA or taxi to reach Lincoln Park for an evening of biking and zoo visits.
USD5 per person or taxi USD25, 1h

6:00pm

Bike Ride Around Lincoln Park

Rent bikes and explore park trails in a fun family outing.
USD12 per bike per hour, 1h

7:00pm

Visit Lincoln Park Zoo

Explore the free zoo open until 8pm and engage kids with animal encounters.
Free, 1h

8:00pm

Dinner at Café Ba-Ba-Reeba!

Enjoy Spanish tapas with family-friendly options at this nearby popular spot, open until 9:30pm.
USD25 per person, 1h

9:00pm

Return to Hyatt Regency O’Hare

Take a taxi or CTA back to your hotel to rest after a lively evening.
Taxi USD25 or included pass, 1h
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Day 4: Coffee & Architecture Exploration

Chicago, USA on May 12, 2025

9:00am

Prepare for Downtown Visit

Get ready and pack before heading out to explore downtown Chicago.
Free, 1h

10:00am

Starbucks Reserve Roastery Visit

Experience unique coffee tastings and kid-friendly treats at the flagship store open until 10pm.
Free; purchases optional, 1h30m

11:30am

Walk to Chicago Riverwalk

A pleasant 10-minute walk along the river to start your architecture river cruise.
Free, 30m

12:00pm

Chicago Architecture River Cruise

Discover Chicago’s iconic buildings on a guided 90-minute river cruise, fun and educational for the family.
USD53 per adult, USD41 per child, 1h30m

1:30pm

Lunch at Beatrix

Enjoy fresh, healthy fare with family-friendly options near the riverwalk, perfect to recharge after the cruise.
USD20 per person, 1h30m

3:00pm

Willis Tower Skydeck

Visit the observation deck for panoramic city views and the glass ledge experience; last entry at 3:30pm.
USD35 per adult, USD28 per child, 1h

4:30pm

Return to Hyatt Regency O’Hare

Take the Blue Line back to your hotel, concluding your memorable family trip to Chicago.
Included in day pass, 45m
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