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Family-Friendly Chicago Itinerary with Train and Uber Travel Options: May 9-12, 2025

Viewed by 156 travelers

Day 1: Hotel Arrival & Grant Park Walk

Chicago, USA on May 9, 2025

1:00pm

Check-in & Settle at Hyatt Regency O'Hare

Arrive at the hotel and get settled with your family, preparing for an afternoon outing.
Included, 30m

1:30pm

Travel to Grant Park via Uber

Take a family-friendly Uber ride from Hyatt Regency O'Hare to Grant Park for convenience and ease, about 40 minutes with moderate traffic.
USD40 approx, 40m

2:15pm

Explore Grant Park

Enjoy a scenic walk through Grant Park’s gardens and fountains with art installations that kids and adults will enjoy.
Free, 1h15m

3:30pm

Deep Dish Pizza at Giordano's

Dine on authentic Chicago deep dish pizza nearby, perfect for the whole family.
USD25 per person, 1h

4:30pm

Uber back to Hyatt Regency O’Hare

Take an Uber back to the hotel to rest after an exciting afternoon out.
USD40 approx, 40m
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Day 2: Navy Pier & Night Out

Chicago, USA on May 10, 2025

8:00am

Breakfast at Yolk near Hyatt

Start the day with a hearty breakfast at a local spot offering kid-friendly meals.
USD15 per person, 1h

9:00am

Relax at Hotel

Spend the morning enjoying hotel amenities or nearby indoor activities.
Free, 8h30m

5:30pm

Travel to Navy Pier via Train and Short Uber

Take the Blue Line train from O'Hare station to Clark/Lake (approx 45-50 minutes), then switch lines or take a short Uber 10 minutes to Navy Pier for a smooth, family-friendly journey.
USD5 per person for train + USD15 Uber, 1h15m

6:45pm

Dinner at Riva Crabhouse, Navy Pier

Savor seafood with kid-friendly options, enjoying lake views at Navy Pier.
USD25 per person, 1h30m

8:15pm

Centennial Wheel Ride

Take in breathtaking views on the Ferris wheel during dusk or night, a highlight for children.
USD16 adult, USD10 child, 45m

9:00pm

Uber to Buckingham Fountain

A quick 10-minute Uber ride to Buckingham Fountain to witness its illuminated evening water show.
USD15, 30m

9:30pm

Return to Hyatt Regency O'Hare by Uber

Finish the night with a comfortable Uber ride back to the hotel.
USD45 approx, 40m
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Day 3: Lincoln Park Adventures

Chicago, USA on May 11, 2025

12:00pm

Morning Leisure at Hotel

Unwind in the morning enjoying hotel amenities or nearby indoor play areas for kids.
Free, 5h

5:00pm

Uber to Lincoln Park

Take an Uber directly to Lincoln Park for a convenient family evening outing.
USD30 approx, 30m

5:30pm

Bike Rental and Ride

Rent bikes to explore Lincoln Park's scenic trails and lakefront paths, fun for all ages.
USD12 per bike per hour, 1h30m

7:00pm

Walk Around Lincoln Park Zoo

Visit the free zoo area open until 8pm to enjoy animal exhibits with the kids.
Free, 1h

8:00pm

Dinner at Café Ba-Ba-Reeba!

Enjoy family-friendly Spanish tapas in a lively atmosphere, serving until 9:30pm.
USD25 per person, 1h

9:15pm

Uber return to Hyatt Regency O'Hare

Comfortably return to the hotel by Uber after a fun-filled day.
USD30 approx, 30m
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Day 4: Coffee, River Cruise & Skyline Views

Chicago, USA on May 12, 2025

9:00am

Prepare and Pack

Get ready and pack your belongings before heading out downtown.
Free, 1h

10:00am

Starbucks Reserve Roastery Visit

Enjoy unique coffee flavors and family treats at the famous Reserve store open till late.
Free to enter; purchases optional, 1h30m

11:30am

Walk to Chicago Riverwalk

Walk 10 minutes along the river towards your cruise departure point, enjoying city views.
Free, 30m

12:00pm

Chicago Architecture River Cruise

Board a fun, educational 90-minute boat tour to discover Chicago’s famous architecture with the family.
USD53 adult, USD41 child, 1h30m

1:30pm

Lunch at Beatrix Restaurant

Eat fresh, wholesome food with kid-friendly options steps from the Riverwalk.
USD20 per person, 1h30m

3:00pm

Willis Tower Skydeck Visit

Visit the iconic Skydeck for amazing panoramic views; last entry at 3:30pm daily.
USD35 adult, USD28 child, 1h

4:15pm

Blue Line Train to Hyatt Regency O’Hare

Take the Blue Line subway from downtown back to the hotel comfortably and efficiently.
USD5 per person, 45m
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