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Family-Friendly Chicago Outdoor and Iconic Attractions Itinerary: May 9-12, 2025

Viewed by 57 travelers

Day 1: Arrival & Grant Park

Chicago, USA on May 9, 2025

1:00pm

Check-in & Refresh at Hyatt Regency O'Hare

Settle into your hotel and prepare for an afternoon outdoor visit to one of Chicago’s favorite parks.
Included, 1h

2:00pm

Explore Grant Park

Enjoy the expansive green spaces, playgrounds, and fountains at Grant Park while taking in views of the city skyline and Lake Michigan, perfect for family relaxation.
Free, 2h

4:00pm

Early Dinner at Giordano's O'Hare

Feast on the iconic Chicago-style deep-dish pizza located conveniently near your hotel, great for satisfying family appetites.
USD20 per person, 1h
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Day 2: Navy Pier & Lakefront

Chicago, USA on May 10, 2025

9:00am

Breakfast at Yolk - O'Hare Area

Enjoy a delicious, hearty breakfast just minutes from your hotel to prepare for a day along the lakefront.
USD15 per person, 1h

10:30am

Morning Free Time

Spend the morning relaxing or exploring local neighborhoods and parks at your own pace.
Varies, 7h

5:30pm

Dinner at Riva Crabhouse on Navy Pier

Savor fresh seafood and kid-friendly dishes in a lively waterfront venue with panoramic views of Lake Michigan.
USD25 per person, 1h30m

7:00pm

Ride the Centennial Wheel and Walk Navy Pier

Experience spectacular sunset views from the Centennial Wheel and enjoy the vibrant atmosphere of Navy Pier’s waterfront promenade.
USD16 per adult, USD10 per child, 1h30m

8:30pm

Return to Hyatt Regency O'Hare

Return to your hotel after a memorable evening by the lake.
Included, Evening
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Day 3: Evening Lincoln Park Fun

Chicago, USA on May 11, 2025

9:00am

Morning Leisure at Hotel or Local Area

Enjoy a relaxing morning at the hotel or explore nearby parks and amenities at your leisure before evening fun.
Free, 8h

6:00pm

Visit Lincoln Park Zoo

Explore the Lincoln Park Zoo in the light evening hours where the zoo is open until 6pm on Sundays and later on selected days; check schedule for extended hours if available for May 11th, enjoy animal exhibits and playgrounds ideal for families.
Free, 1h

7:30pm

Dinner at Café Ba-Ba-Reeba!

Dine on Spanish tapas with family-friendly options nearby Lincoln Park, a cozy spot to enjoy flavorful meals after zoo time.
USD25 per person, 1h30m

9:00pm

Evening Stroll in Lincoln Park

Enjoy a relaxed walk around the park or nearby Conservatory grounds to wind down your evening in nature.
Free, 1h

10:00pm

Return to Hyatt Regency O'Hare

Head back to your hotel to rest after a pleasant evening of sightseeing.
Included, Night
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Day 4: Coffee, Architecture & Willis Tower

Chicago, USA on May 12, 2025

8:00am

Breakfast at Hyatt Regency O'Hare

Enjoy a relaxed breakfast at the hotel to start your last day in Chicago comfortably.
USD15 per person, 1h

9:30am

Visit Starbucks Reserve Roastery Chicago

Explore the world-class coffee experience with unique drinks and treats in a spacious and exciting environment that can entertain all family members.
Varies by order, 1h

10:30am

Chicago Riverwalk Architecture Walking Tour

Take a 1.5-hour guided walking tour to see Chicago’s stunning architectural highlights along the river, perfect for adults while kids enjoy the sights and riverfront views.
USD40 per adult, USD25 per child, 1h30m

12:00pm

Lunch at Beatrix in River North

Dine on fresh, wholesome meals with a number of kid-friendly choices conveniently located near the Chicago Riverwalk.
USD20 per person, 1h

1:00pm

Willis Tower Skydeck

Ascend to the iconic Willis Tower Skydeck for panoramic city views and exciting glass ledge experience; last entry by 3:30pm, with hours till 4pm.
USD35 per adult, USD28 per child, 1h

2:00pm

Stroll Along Lakefront Shorewalk

Spend your remaining afternoon enjoying a peaceful walk along Lake Michigan’s scenic shorewalk or browsing local shops.
Free, 2h

4:00pm

Return to Hyatt Regency O'Hare

Conclude your Chicago adventure by heading back to your hotel to prepare for departure or relax.
Included, Evening
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