Family-Friendly Chicago Itinerary: Navy Pier, Parks & Architecture May 9-12, 2025

Day 1: Lunch & Navy Pier

Chicago, USA on May 9, 2025

1:00pm

Check-in & Settle at Hyatt Regency O'Hare

Settle into your hotel before heading out for lunch and sightseeing.
Included, 30m

1:30pm

Lunch at Giordano’s near Navy Pier

Enjoy iconic Chicago deep-dish pizza prior to sightseeing at Navy Pier, a perfect introduction to the city’s culinary highlights.
USD25 per person, 1h

2:30pm

Walk or taxi to Navy Pier

Travel a short distance to Navy Pier to enjoy family-friendly attractions and scenic lakeside views.
Free entry; Taxi approx. USD10, 15m

2:45pm

Explore Navy Pier

Stroll along the pier, visit shops, and ride the Centennial Wheel for stunning city and lake views.
Centennial Wheel USD18 per person, 1h15m

4:00pm

Return to Hotel

Take a taxi or public transit back to Hyatt Regency O'Hare to rest after an afternoon of fun.
Taxi approx. USD30; CTA USD3.50 per person, 30m
View Hotel Availability

Day 2: Grant Park & Dinner

Chicago, USA on May 10, 2025

8:00am

Breakfast at Yolk near Hyatt Regency O’Hare

Enjoy classic breakfast favorites in a family-friendly atmosphere close to your hotel.
USD15 per person, 1h

9:00am

Relax at Hotel

Rest and enjoy hotel amenities before the evening outing.
Free, 7h30m

4:00pm

Travel Downtown via Metra

Take a taxi to Rosemont Metra station, then ride the Union Pacific North Line train to Ogilvie Transportation Center downtown, then short taxi or walk to Grant Park.
USD7 per person, 1h

5:30pm

Stroll Grant Park

Enjoy the beautiful gardens and sculptures amid this green oasis in Chicago.
Free, 1h15m

6:45pm

Buckingham Fountain Light and Water Show

Experience an enchanting light and water show at the famous fountain, a perfect family moment.
Free, 30m

7:15pm

Dinner at The Gage

Savor upscale American fare with kid-friendly options in a warm and inviting downtown venue.
USD30 per person, 1h15m

8:30pm

Return to Hotel

Take Metra back to Rosemont and taxi to hotel; rest for next day.
USD7 + 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

Take Blue Line subway downtown to Clark/Lake station, then bus #22 or taxi to Lincoln Park Zoo, an engaging free zoo perfect for kids.
USD5-$7 per person, 1h

4:00pm

Visit Lincoln Park Zoo and Conservatory

Explore animals at this no-cost zoo and enjoy beautiful botanical gardens, great for family fun and education.
Free, 1h30m

5:30pm

Dinner at Café Ba-Ba-Reeba!

Taste delicious, kid-friendly Spanish tapas in a lively yet relaxed Lincoln Park setting.
USD25 per person, 1h15m

6:45pm

Evening Stroll

Leisurely walk around Lincoln Park or nearby lakefront paths before returning to hotel.
Free, 45m

7:30pm

Return to Hotel

Use taxi or CTA to return to airport area and hotel via Clark/Lake Blue Line.
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

Get ready for the day and check out of your hotel, storing luggage if needed.
Free, 1h

10:00am

Travel Downtown via Metra

Take taxi to Rosemont station, then Metra train to Ogilvie Transportation Center, then a short walk to the Starbucks Reserve Roastery.
USD7 per person, 50m

10:50am

Starbucks Reserve Roastery Visit

Enjoy a unique coffee and snack experience in this immersive roastery, enjoyable for the entire family.
Free, 1h15m

12:15pm

Lunch at Beatrix on the Riverwalk

Taste fresh and varied dishes in a family-friendly restaurant on the scenic Chicago Riverwalk.
USD20 per person, 1h30m

1:45pm

Chicago Architecture River Cruise

Enjoy a 90-minute boat tour highlighting Chicago’s famed architecture in an engaging, educational family-friendly format.
USD53 adult, USD41 child, 1h30m

3:15pm

Willis Tower Skydeck or Millennium Park

Visit Skydeck for stunning city views or explore Millennium Park for a gentle stroll before heading back.
Skydeck USD35/28 child; Millennium Park free, 1h

4:15pm

Return to Hyatt Regency O'Hare

Take taxi or walk to Ogilvie, then Metra to Rosemont and taxi/Uber to hotel to collect luggage.
USD7 + taxi approx. USD15, 50m
View Hotel Availability