Family-Friendly Chicago Itinerary with Architecture Tour and Evening Activities: May 9-12, 2025

Day 1: Grant Park & Iconic Fountains

Chicago, USA on May 9, 2025

1:00pm

Check-in & Settle at Hyatt Regency O'Hare

Arrive and get comfortable at your hotel before heading out for a mid-afternoon adventure.
Included, 1h

2:00pm

Travel to Grant Park via Blue Line

Walk 7 mins to O'Hare CTA Station, take Blue Line to Jackson Station, then walk about 10 minutes east to Grant Park.
USD5 per person, 1h

3:00pm

Visit Buckingham Fountain

Enjoy the grandiosity and water displays at one of the world's largest fountains, perfect for photos and family fun.
Free, 45m

3:45pm

Explore Centennial Fountain

Take a short stroll to this beautiful fountain and surrounding gardens, a calm spot for family relaxation and pictures.
Free, 30m

4:15pm

Return to Hyatt Regency

Return by Blue Line to your hotel to rest or prepare for dinner.
Included with day pass, 45m

5:00pm

Dinner at Giordano's near O'Hare

Savor Chicago’s famous deep-dish pizza just a few minutes from your hotel in a family-friendly setting.
USD20 per person, 1h
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Day 2: Lunch & Evening Navy Pier

Chicago, USA on May 10, 2025

8:00am

Breakfast at Yolk - O'Hare Area

Get a hearty start at a local breakfast spot close to your hotel, perfect for families.
USD15 per person, 1h

9:00am

Morning Leisure

Relax or enjoy hotel amenities before lunch, perfect time for resting or light exploring nearby.
Free, 3h30m

12:30pm

Lunch at Weber Grill Restaurant near Hyatt Regency O'Hare

Enjoy delicious grilled fare in a family-friendly atmosphere just steps from your hotel, open 11am–9pm.
USD20 per person, 1h30m

2:00pm

Leisure, Hotel Rest or Nearby Activities

Rest or explore nearby shops and amenities near the hotel until it’s time to leave for the evening.
Free, 3h30m

5:30pm

Depart for Navy Pier & Millennium Park

Take the Blue Line from O’Hare Station to Washington Station, then transfer or walk to Navy Pier for evening activities.
Included in day pass, 30m

6:00pm

Dinner at Riva Crabhouse on Navy Pier

Dine lakeside with the family enjoying seafood and kid-friendly options amid lively evening views.
USD25 per person, 1h30m

7:30pm

Ride the Centennial Wheel

View Chicago's spectacular skyline and Lake Michigan from the iconic Ferris wheel at Navy Pier.
USD16 per adult, USD10 per child, 1h

8:30pm

Visit Crown Fountain

Explore this interactive video fountain at Millennium Park illuminated at night, fun for all ages.
Free, 30m

9:00pm

Return to Hyatt Regency

Take the CTA back to O’Hare, ending your family fun day with a restful return to the hotel.
Included in day pass, 45m
View Hotel Availability

Day 3: Evening Zoo & Bike Stroll

Chicago, USA on May 11, 2025

12:00pm

Morning & Early Afternoon Leisure

Enjoy a relaxing morning and early afternoon at the hotel or nearby cafes, allowing your family to recharge.
Free, 6h

5:30pm

Travel to Lincoln Park

Take the Blue Line from O'Hare to Washington, transfer to Brown Line to Armitage, or take taxi for convenience to Lincoln Park area.
USD5 per person or taxi approx. USD25, 1h

6:30pm

Bike Stroll around Lincoln Park

Rent bikes from a nearby Divvy station and enjoy a leisurely family bike ride through Lincoln Park paths, taking in scenic views and fresh air; opens until dusk.
USD12 per bike per hour, 1h15m

7:45pm

Visit Lincoln Park Zoo (Evening Visit)

Explore the free zoo during extended hours for a memorable family experience with animals in a cooler evening setting; zoo closes at 8pm.
Free, 30m

8:15pm

Dinner at Café Ba-Ba-Reeba!

Enjoy family-friendly Spanish tapas with kid options nearby, a perfect way to end the evening; kitchen open until 9:30pm.
USD25 per person, 1h

9:15pm

Return to Hyatt Regency

Travel back to your hotel for a well-earned rest after an active and fun evening.
Included in day pass or taxi approx. USD25, 1h
View Hotel Availability

Day 4: Architecture and Skyline Views

Chicago, USA on May 12, 2025

8:00am

Breakfast at Hyatt Regency

Have a nourishing breakfast at your hotel to start your exciting last day in Chicago.
USD15 per person, 1h

9:30am

Travel Downtown to Chicago Riverwalk

Take Blue Line from O’Hare to Washington, then walk to the riverwalk area to start the architecture tour.
USD5 per person, 1h

10:30am

Chicago Architecture River Cruise

Embark on the famous Chicago Architecture Foundation Center River Cruise with your family to explore iconic buildings and learn about Chicago’s architectural legacy; tours last about 90 minutes.
USD53 per adult, USD41 per child, 1h30m

12:00pm

Lunch at Beatrix

Dine on fresh and healthy dishes with a kid-friendly menu located near the riverwalk, open for lunch until 2pm.
USD20 per person, 1h30m

1:30pm

Family Bike Stroll on Chicago Riverwalk

Rent bikes from a Divvy station and enjoy a scenic, family-friendly ride along the Chicago Riverwalk, viewing notable skyline views and waterfront landmarks.
USD12 per bike per hour, 1h30m

3:00pm

Willis Tower Skydeck

Experience breathtaking panoramic views and the thrilling glass ledge at Willis Tower before the last entry at 3:30pm. A highlight for the whole family.
USD35 per adult, USD28 per child, 1h

4:00pm

Return to Hyatt Regency O'Hare

Take the Blue Line back to your hotel to conclude your memorable Chicago trip.
Included in day pass, 45m
View Hotel Availability