Family-Friendly Chicago Itinerary: May 9-12, 2025 with Added Lunch on Day 2

Day 1: Grant Park & Iconic Fountains

Chicago, USA on May 9, 2025

1:00pm

Check-in & Settle at Hyatt Regency O'Hare

Arrive at your hotel and prepare to start your Chicago adventure comfortably.
Included, 1h

2:00pm

Travel to Grant Park via Blue Line

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

3:00pm

Explore Grant Park & Buckingham Fountain

Enjoy the grandeur of Buckingham Fountain, one of the world's largest, with operating water shows during afternoon hours.
Free, 45m

3:45pm

Visit Centennial Fountain

Short stroll to the peaceful Centennial Fountain and its lovely surrounding gardens; perfect for family photos and relaxation.
Free, 30m

4:15pm

Return to Hyatt Regency

Take Blue Line from Jackson Station back to O'Hare and walk to your hotel to rest or freshen up.
Included in day pass, 45m

5:00pm

Dinner at Giordano's near O'Hare

Enjoy Chicago’s famous deep-dish pizza in a family-friendly atmosphere just minutes from your hotel.
USD20 per person, 1h
View Hotel Availability

Day 2: Lunch & Evening Navy Pier

Chicago, USA on May 10, 2025

8:00am

Breakfast at Yolk - O'Hare Area

Start your day with a tasty and hearty breakfast close to your hotel for family energy.
USD15 per person, 1h

9:00am

Free Morning and Early Afternoon

Relax, explore nearby or rest at the hotel until lunchtime.
Free, 3h30m

12:30pm

Lunch at Wildberry Pancakes and Cafe

Savor delicious American breakfast and lunch options with kid-friendly menu choices, located near Millennium Park; open from 7am to 3pm.
USD20 per person, 1h30m

2:00pm

Return to Hotel or Leisure Time

Head back to the hotel by Blue Line or enjoy light activities nearby to rest before the evening.
Included in day pass, 1h30m

5:30pm

Depart for Navy Pier & Millennium Park

Walk 7 minutes to O'Hare Station, board Blue Line to Washington Station, then transfer or walk to Navy Pier.
Included in day pass, 30m

6:00pm

Dinner at Riva Crabhouse on Navy Pier

Enjoy lakeside dining with seafood and kid-friendly options suitable for the family while soaking up the lively evening atmosphere.
USD25 per person, 1h30m

7:30pm

Centennial Wheel Ride at Navy Pier

Experience stunning evening views of Lake Michigan and the city skyline from the iconic Ferris wheel.
USD16 per adult, USD10 per child, 1h

8:30pm

Visit Crown Fountain at Millennium Park

Witness the interactive video art fountain illuminated at night, engaging for kids and adults alike; open until 10pm in warmer months.
Free, 30m

9:00pm

Return to Hyatt Regency

Take CTA lines back to O'Hare to end the day comfortably.
Included in day pass, 45m
View Hotel Availability

Day 3: Lincoln Park Zoo & Water Fountain

Chicago, USA on May 11, 2025

9:00am

Morning Leisure

Enjoy a slow start at the hotel or nearby cafes.
Free, 5h

2:45pm

Travel to Lincoln Park Zoo via CTA

Take Blue Line from O'Hare to Washington, transfer to Brown Line to Armitage, then walk 12 minutes to the zoo.
Included in day pass, 1h15m

4:00pm

Explore Lincoln Park Zoo

Visit one of Chicago’s charming, free-entry zoos with exhibits the kids will love, open until 6pm.
Free, 1h

5:00pm

Lincoln Park Water Fountain Fun

Let the children play at the nearby interactive water fountain area, perfect for an afternoon cool-down.
Free, 30m

5:30pm

Dinner at Café Ba-Ba-Reeba!

Experience delicious Spanish tapas with kid-friendly options close to Lincoln Park Zoo in a lively setting.
USD25 per person, 1h30m

7:00pm

Evening Lincoln Park Walk

Take a calming family stroll around nearby park areas or conservatory before heading back.
Free, 1h

8:00pm

Return to Hyatt Regency

Take Brown and Red Lines back to O'Hare station and walk to the hotel.
Included in day pass, 1h
View Hotel Availability

Day 4: Architecture, Lunch & Skydeck Views

Chicago, USA on May 12, 2025

8:00am

Breakfast at Hyatt Regency

Enjoy a nourishing breakfast at your hotel before heading out for the day’s adventures.
USD15 per person, 1h

9:30am

Starbucks Reserve Roastery

Visit this flagship location downtown for a unique coffee tasting experience and treats the whole family can enjoy.
Varies, 1h

10:30am

Chicago Riverwalk Architecture Tour

Take an engaging 1.5-hour guided walking tour exploring Chicago’s renowned architecture along the scenic riverwalk, suitable for families.
USD40 per adult, USD25 per child, 1h30m

12:30pm

Lunch at Beatrix

Relax and enjoy healthy, fresh meals at this family-friendly restaurant near the riverwalk with a great kids menu from 12:30pm to 2:00pm.
USD20 per person, 1h30m

2:00pm

Willis Tower Skydeck

Head to the iconic Willis Tower to experience breathtaking city views and the famous glass ledge experience before last entry at 3:30pm.
USD35 per adult, USD28 per child, 1h

3:00pm

Lakefront Shorewalk

Enjoy a family-friendly walk along Lake Michigan’s shoreline allowing the kids to stretch their legs and admire the lakeside views.
Free, 1h

4:00pm

Return to Hyatt Regency O'Hare

Take the Blue Line back to the airport hotel to rest or prepare for your onward journey.
Included in day pass, 45m
View Hotel Availability