Family-Friendly Chicago Itinerary with Navy Pier and Iconic Sites, May 9-12, 2025

Day 1: Navy Pier & Pizza

Chicago, USA on May 9, 2025

1:00pm

Check-in & Settle at Hyatt Regency O'Hare

Settle into your hotel before heading out to explore Chicago’s waterfront.
Included, 30m

1:30pm

Transit to Navy Pier

Travel via taxi/Uber (approx. 30 mins) or CTA bus and train to Navy Pier, an iconic family-friendly lakeside destination with attractions and scenic views.
Taxi approx. USD30; CTA USD3.50 per person, 30m

2:00pm

Explore Navy Pier

Enjoy walking along the pier, visiting shops, and stopping by family attractions including the Centennial Wheel.
Free entry, 1h

3:00pm

Giordano’s for Late Lunch

Walk or take a short taxi (5 mins) to Giordano’s at Navy Pier for famous Chicago deep-dish pizza in a welcoming setting for families.
USD25 per person, 1h

4:00pm

Return to Hotel

Take a taxi or CTA back to Hyatt Regency O'Hare to relax after the afternoon adventure.
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
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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 catch bus #22 or short taxi to Lincoln Park Zoo, a free, engaging spot 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, perfect for family learning and fun.
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

Take a leisurely walk around Lincoln Park or head to nearby lakefront paths to unwind before returning.
Free, 45m

7:30pm

Return to Hotel

Use taxi or CTA to travel back via Clark/Lake Blue Line to airport area and hotel.
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 space, a treat for adults and kids alike.
Free, 1h15m

12:15pm

Lunch at Beatrix on the Riverwalk

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

1:45pm

Chicago Architecture River Cruise

Embark on a 90-minute boat tour showcasing the city’s architectural highlights, a fascinating and educational family activity.
USD53 adult, USD41 child, 1h30m

3:15pm

Willis Tower Skydeck or Millennium Park

Choose to visit the Skydeck for panoramic city views or Millennium Park for a relaxing walk before heading to the airport.
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 the hotel to collect luggage.
USD7 + taxi approx. USD15, 50m
View Hotel Availability