Chicago Family Itinerary with Train and Subway Transit, May 9-12, 2025

Day 1: Pizza & Navy Pier

Chicago, USA on May 9, 2025

1:00pm

Check-in & Settle at Hyatt Regency O'Hare

Arrive at hotel and get settled before exploring the city.
Included, 30m

1:30pm

Late Lunch at Giordano's Deep-Dish Pizza

Take a taxi/Uber (25 mins) or Metra train from O'Hare to Union Station, then a short taxi (10 mins) to Giordano’s for Chicago’s famous deep-dish pizza, family-friendly and filling.
USD25 per person, 1h

2:45pm

Transit to Navy Pier

From Giordano’s, take a short taxi/Uber (10 mins) or use CTA buses for a comfortable trip to Navy Pier, ideal for the family.
Taxi approx. USD15-$20; CTA USD3.50 per person, 15m

3:00pm

Explore Navy Pier

Enjoy lakeside walking, shopping, and family-friendly recreation at this iconic Chicago destination.
Free entry, 45m

3:45pm

Centennial Wheel Ride

Take a fun Ferris wheel ride offering stunning city and lake views, great for kids and adults alike.
USD16 adult, USD10 child, 30m

4:15pm

Return to Hotel

Use taxi/Uber or CTA bus back to O'Hare area, about 25 mins by taxi or 45-50 mins via bus and train options.
Taxi approx. USD25-$30, 25m
View Hotel Availability

Day 2: Grant Park & Dinner

Chicago, USA on May 10, 2025

8:00am

Breakfast at Yolk near Hyatt Regency O’Hare

Start your day with a hearty breakfast near the hotel featuring breakfast favorites suitable for kids and adults.
USD15 per person, 1h

9:00am

Morning Relaxation at Hotel

Enjoy hotel amenities and relax prior to evening exploration.
Free, 7h30m

4:00pm

Travel to Downtown via Metra Union Pacific North Line

Take a short taxi/Uber to Rosemont Metra station, then board the Union Pacific North Line train to Ogilvie Transportation Center (approx. 30 mins), then a short taxi or walk to Grant Park.
USD7 per person, 1h

5:30pm

Stroll Grant Park

Enjoy a peaceful family walk in the lush surroundings of Grant Park, featuring gardens and sculptures.
Free, 1h15m

6:45pm

Buckingham Fountain Light and Water Show

Experience the beautiful illuminated water display at a landmark fountain, a memorable evening event.
Free, 30m

7:15pm

Dinner at The Gage

Dine at The Gage offering upscale American fare with kid-friendly options in a cozy setting.
USD30 per person, 1h15m

8:30pm

Return via Metra and Taxi

Return to Ogilvie Station by taxi or walking, then take the Metra train back to Rosemont station and taxi to hotel.
USD7 per person + taxi approx. USD15, 1h
View Hotel Availability

Day 3: Lincoln Park Zoo

Chicago, USA on May 11, 2025

3:00pm

Travel to Lincoln Park Zoo

From Hyatt Regency O’Hare, take the Blue Line subway downtown to Clark/Lake (approx. 45 min). Then transfer to bus #22 or take a short taxi (approx. 15 min) to Lincoln Park Zoo.
USD5-$7 per person, 1h

4:00pm

Visit Lincoln Park Zoo and Conservatory

Discover the free zoo with animals and stroll through the enchanting conservatory gardens, exciting for children.
Free, 1h30m

5:30pm

Dinner at Café Ba-Ba-Reeba!

Enjoy Spanish tapas style dining with kid-friendly plates in Lincoln Park’s vibrant food scene.
USD25 per person, 1h15m

6:45pm

Evening Walk in Lincoln Park

Relax with a casual walk around Lincoln Park or along nearby lakefront trails to unwind.
Free, 45m

7:30pm

Return to Hotel

Take a taxi or bus back to Clark/Lake to board Blue Line subway to O’Hare, then walk to hotel, approx. 1 hour total.
USD10-$20 per person, 1h
View Hotel Availability

Day 4: River Cruise & Skydeck

Chicago, USA on May 12, 2025

9:00am

Pack and Check-out

Prepare for check-out and store luggage if needed for day activities.
Free, 1h

10:00am

Travel Downtown via Metra

Take a taxi/Uber to Rosemont Metra station, board the Union Pacific North Line to Ogilvie Transportation Center downtown (approx. 30 mins), then walk 10 minutes to Starbucks Reserve Roastery.
USD7 per person, 50m

10:50am

Starbucks Reserve Roastery Visit

Experience an immersive coffee experience with treats, perfect for coffee lovers and casual browsing.
Free, 1h15m

12:15pm

Lunch at Beatrix on the Riverwalk

Enjoy a lovely family-friendly lunch with fresh, varied options along Chicago’s scenic Riverwalk.
USD20 per person, 1h30m

1:45pm

Chicago Architecture River Cruise

Take a 90-minute boat tour highlighting Chicago’s architectural marvels on the scenic river cruise.
USD53 adult, USD41 child, 1h30m

3:15pm

Willis Tower Skydeck or Millennium Park

Choose between visiting the famous Skydeck or relaxing in Millennium Park, both a short walk or taxi ride away.
Skydeck USD35/28 child; Millennium Park free, 1h

4:15pm

Return to Hyatt Regency O'Hare

Travel back by short taxi or walk to Ogilvie, then take Metra to Rosemont station and taxi/Uber to hotel for luggage pickup.
USD7 per person + taxi approx. USD15, 50m
View Hotel Availability