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Family-Friendly Chicago Itinerary with L Train Travel: May 9-12, 2025

Viewed by 95 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

L Train from O'Hare to Jackson Station

Take the Chicago L Blue Line from O'Hare Airport to Jackson Station, about 45-50 minutes, enjoying a smooth and scenic ride into the city.
USD5 per person, 50m

2:20pm

Walk to Grant Park

Walk 10 minutes from Jackson Station south to Grant Park, enjoying city sights along the way.
Free, 15m

2:35pm

Explore Grant Park

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

3:35pm

Deep Dish Pizza at Giordano's

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

4:40pm

L Train Blue Line back to O’Hare

Return by Blue Line train to the Hyatt Regency O'Hare for some rest after an exciting afternoon out.
USD5 per person, 50m
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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

L Train Blue Line to Washington Station then Uber to Navy Pier

Take the Blue Line from O'Hare to Washington Station (approx 50 minutes), then a short 10-minute Uber ride to Navy Pier for a convenient arrival.
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

L Train Blue Line back to O'Hare

Take the Blue Line train back to Hyatt Regency O'Hare, wrapping up the night comfortably by train.
USD5 per person, 50m
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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

L Train Blue Line to Fullerton Station

Take the Blue Line from O'Hare to Fullerton Station (approx 55 minutes) for access to Lincoln Park neighborhood.
USD5 per person, 55m

6:00pm

Walk to Lincoln Park Zoo and Bike Rental

Walk 15 minutes to Lincoln Park Zoo, free and great for kids, then rent bikes nearby to explore the scenic trails and lakefront paths.
Zoo is free, bike rental USD12 per hour, 1h45m

7:45pm

Dinner at Café Ba-Ba-Reeba!

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

9:00pm

L Train Blue Line back to O'Hare

Return to the hotel on the Blue Line, comfortably ending the day’s outing.
USD5 per person, 55m
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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

L Train Blue Line to Washington Station

Take the Blue Line into downtown Chicago, arriving at Washington Station for a convenient starting point.
USD5 per person, 50m

10:50am

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

12:20pm

Walk to Chicago Riverwalk

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

12:50pm

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

2:20pm

Lunch at Beatrix Restaurant

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

3:50pm

Willis Tower Skydeck Visit

Visit the iconic Skydeck for amazing panoramic views; last entry at 3:30pm is past so adjust visit to 2:30pm if preferred, otherwise enjoy nearby Millennium Park.
USD35 adult, USD28 child, 1h

4:50pm

L Train Blue Line back to Hyatt Regency O’Hare

Take the Blue Line subway from downtown back to the hotel comfortably and efficiently.
USD5 per person, 50m
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