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Family-Friendly Chicago Itinerary with Navy Pier Exploration and Deep-Dish Pizza: May 9-12, 2025

Viewed by 94 travelers

Day 1: Lunch & Navy Pier

Chicago, USA on May 9, 2025

1:00pm

Check-in & Settle at Hyatt Regency O'Hare

Unpack and get ready to explore Chicago in the afternoon.
Included, 30m

1:30pm

Transit from Hyatt Regency O’Hare to Navy Pier via Blue and Red Lines

Walk to O'Hare Blue Line station, take Blue Line train toward downtown to Clark/Lake station (~45 mins), then transfer to Red Line southbound to Grand station (~5 mins), then walk about 12 minutes east to Navy Pier area.
USD5 per person for unlimited day pass, 1h

2:30pm

Lunch at Riva Crabhouse on Navy Pier

A family-friendly restaurant right on Navy Pier offering seafood as well as kid-friendly options with great lake views, perfect for a leisurely lunch close to the pier attractions.
USD25 per person, 1h

3:30pm

Explore Navy Pier

Enjoy attractions like the Centennial Wheel, the Chicago Shakespeare Theater, and waterfront walks along Navy Pier.
Centennial Wheel USD18 per person, 1h

4:30pm

Return to Hyatt Regency O’Hare

Walk back to Grand station, take Red Line northbound to Clark/Lake, transfer to Blue Line toward O’Hare (~1h total).
Included in day pass, 1h
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Day 2: Grant Park & Dinner

Chicago, USA on May 10, 2025

8:00am

Breakfast at Yolk near Hyatt Regency O’Hare

Family-friendly breakfast spot with hearty and diverse options to energize for the day.
USD15 per person, 1h

9:00am

Relax at the Hotel

Enjoy the hotel’s amenities to rest and prepare for the evening's city exploration.
Free, 7h30m

4:30pm

Blue Line L Train from O’Hare to Jackson station

Travel about 45 minutes to downtown Chicago for your evening outing.
USD3 per person, 45m

5:15pm

Walk 10 minutes to Grant Park

Explore Chicago’s iconic park and beautiful Buckingham Fountain at dusk.
Free, 15m

5:30pm

Stroll Grant Park & See Buckingham Fountain

Enjoy gardens, walking paths, and the famous fountain’s early evening light show.
Free, 1h

6:30pm

Dinner at The Gage

Delicious American cuisine with a family-friendly menu, conveniently near Grant Park.
USD30 per person, 1h15m

7:45pm

Return Blue Line from Jackson to O’Hare

After dinner, catch the train back to your hotel for a restful night.
USD3 per person, 45m
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Day 3: Lincoln Park Zoo

Chicago, USA on May 11, 2025

2:00pm

Transit from Hyatt Regency O’Hare to Lincoln Park Zoo

Take Blue Line to Clark/Lake, transfer to Red Line northbound to Fullerton station (~1h total), then walk 10 minutes to the zoo.
USD3 per person, 1h

3:10pm

Visit Lincoln Park Zoo & Conservatory

Explore the free zoo and gardens, great for children and adults alike, featuring diverse animals and plants.
Free, 1h30m

4:40pm

Dinner at Café Ba-Ba-Reeba!

Family-friendly Spanish tapas restaurant near Lincoln Park, offering a lively atmosphere and varied dishes.
USD25 per person, 1h

6:00pm

Return to Hyatt Regency O’Hare

Take Red Line back to Clark/Lake, then Blue Line to O’Hare, approximately 1 hour total transit time.
USD3 per person, 1h
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Day 4: Riverwalk & Skydeck

Chicago, USA on May 12, 2025

9:00am

Pack and Check-out

Get ready for your last day; leave luggage at the hotel for collection after sightseeing.
Free, 1h

10:00am

Blue Line L Train to Washington station

Take approximately 45 minutes downtown to access the Riverwalk area.
USD3 per person, 45m

10:45am

Walk to Starbucks Reserve Roastery

Enjoy a 15-minute walk to this unique coffee experience with delicious treats for the family.
Free, 15m

11:00am

Visit Starbucks Reserve Roastery

See coffee roasting in action and try specialty drinks while kids enjoy snacks.
Free, 1h

12:00pm

Lunch at Beatrix on Chicago Riverwalk

Family-friendly restaurant with fresh ingredients and kid options, set along the scenic riverwalk.
USD20 per person, 1h

1:00pm

Chicago Architecture River Cruise

90-minute tour departing from Michigan Ave and Wacker Drive dock, exploring Chicago’s famed architecture from the river.
USD53 adult, USD41 child, 1h30m

2:30pm

Walk to Willis Tower Skydeck

A 15-minute walk to Willis Tower for breathtaking panoramic views and the famous glass Skydeck ledge.
USD35 adult, USD28 child, 1h

3:45pm

Return to Hyatt Regency O’Hare

Return by walking to Washington station then Blue Line train to O’Hare (approx. 45 minutes).
USD3 per person, 45m
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