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

Viewed by 81 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: Lincoln Park & Outdoor Fun

Chicago, USA on May 11, 2025

9:00am

Breakfast at Yolk - O'Hare Area

Grab a filling breakfast locally to fuel up for a day of outdoor exploration in Lincoln Park.
USD15 per person, 1h

10:30am

Visit Lincoln Park Zoo

Explore the free Lincoln Park Zoo where kids can see animals from around the world and enjoy family-friendly outdoor exhibits and playgrounds.
Free, 2h

12:30pm

Picnic Lunch at Lincoln Park

Pick up picnic fare from a local deli or café to enjoy a relaxing outdoor meal in the park's scenic area.
USD15 per person, 1h

1:30pm

Afternoon at North Avenue Beach or Outdoor Parks

Head to North Avenue Beach for some lakefront fun, playgrounds, and open spaces suitable for kids or enjoy nearby outdoor parks for family activities.
Free, 2h

3:30pm

Return to Hyatt Regency O'Hare

Travel back to the hotel after a day full of fresh air and family-friendly outdoor fun.
Included, Evening
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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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