Family-Friendly Chicago Itinerary with Lakefront Shore and Evening Activities: May 9-12, 2025

Day 1: Arrival & Local Parks

Chicago, USA on May 9, 2025

1:00pm

Check-in & Rest at Hyatt Regency O'Hare

Settle in at your hotel and refresh before heading out for family-friendly outdoor time.
Included, 1h

2:00pm

Visit Rosemont Community Park

Play, relax, and enjoy green space suitable for children just a short drive from your hotel.
Free, 1h30m

3:30pm

Early Dinner at Giordano's O'Hare

Try Chicago's legendary deep-dish pizza in a family-friendly environment near the hotel.
USD20 per person, 1h
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Day 2: Lakefront & Evening Tour

Chicago, USA on May 10, 2025

3:30pm

Walk Along Chicago Lakefront Shore

Explore the beautiful Lakefront Shorewalk from the Museum Campus north toward Navy Pier, enjoying scenic views and playgrounds accessible for families.
Free, 1h30m

5:30pm

Dinner at The Gage

Dine in a lively downtown spot offering diverse cuisine that appeals to both kids and adults.
USD25 per person, 1h

6:30pm

Chicago Riverwalk Evening Architecture Tour

Take a guided walk or boat tour along the river to view iconic city architecture illuminated after dusk.
USD40 per adult, USD25 per child, 1h15m

8:00pm

Willis Tower Skydeck at Night

Experience breathtaking nighttime cityscape from the Skydeck, open till 10pm.
USD35 per adult, USD28 per child, 1h

9:00pm

Return to Hyatt Regency O'Hare

Relax back at the hotel after a packed scenic evening.
Included, Evening
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Day 3: Navy Pier & Lakeside Fun

Chicago, USA on May 11, 2025

10:00am

Breakfast at Hyatt Regency O'Hare or nearby cafe

Enjoy a relaxing breakfast near your hotel to prepare for the day ahead.
USD15 per person, 1h

11:00am

Rest and pool time at hotel

Unwind and recharge with some leisure time before your evening out.
Included, 6h

6:00pm

Dinner at Riva Crabhouse on Navy Pier

Savor fresh seafood and family-friendly dishes with stunning views of Lake Michigan.
USD25 per person, 1h30m

7:30pm

Evening Stroll and Centennial Wheel Ride at Navy Pier

Enjoy a lakeside walk along Navy Pier and ride the Centennial Wheel to capture spectacular city and lake views at sunset.
USD16 per adult, USD10 per child, 1h

8:30pm

Walk along Lakefront Shore near Navy Pier

Take a peaceful walk along the nearby Lakefront path, ideal for family enjoying the gentle lake breeze and city lights.
Free, 30m

9:00pm

Return to Hyatt Regency O'Hare

Head back to your hotel after a relaxing lakeside evening.
Included, Evening
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Day 4: Lincoln Park & Science

Chicago, USA on May 12, 2025

8:00am

Breakfast at Yolk - O'Hare Area

Start the day with hearty breakfast favorites near your hotel.
USD15 per person, 1h

9:00am

Lincoln Park Zoo

Explore an engaging, free zoo with diverse animal exhibits perfect for children; opens at 10am, so enjoy nearby walk or playground before entry.
Free, 2h

11:00am

Lincoln Park Conservatory

Discover tropical and exotic plants in this beautiful garden setting adjacent to the zoo.
Free, 1h

12:00pm

Lunch at Café Ba-Ba-Reeba!

Enjoy flavorful Spanish tapas with kid-friendly options for a delightful meal in Lincoln Park.
USD20 per person, 1h

1:00pm

Museum of Science and Industry

A fun, interactive science museum with exhibits to entertain all ages, open until 4pm.
USD23 per adult, USD14 per child, 3h

4:00pm

Relaxing Walk Along Lakefront Shore near Museum Campus

Enjoy scenic views and fresh air with a family-friendly stroll along Lake Michigan’s beautiful shores to wind down your trip.
Free, 1h

5:00pm

Return to Hyatt Regency O'Hare

Head back to your hotel to rest and pack for departure.
Included, Evening
View Hotel Availability