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Chicago Family Trip Itinerary with Detailed Transport Options, May 9-12, 2025

Viewed by 93 travelers

Day 1: Pizza & Navy Pier

Chicago, USA on May 9, 2025

1:00pm

Check-in & Settle at Hyatt Regency O'Hare

Arrive and get settled into your room at Hyatt Regency O’Hare before heading out for afternoon activities.
Included, 30m

1:30pm

Late Lunch at Giordano's Deep-Dish Pizza

Travel by taxi or Uber from Hyatt Regency O’Hare directly to Giordano's (approx. 25-minute drive) for classic Chicago deep-dish pizza enjoyed by all ages.
USD25 per person, 1h

2:45pm

Taxi/Uber to Navy Pier

Take a taxi or Uber for a quick 10-minute ride to Navy Pier, ensuring comfortable travel with kids and plenty of luggage space.
USD15-$20 approx., 15m

3:00pm

Explore Navy Pier

Enjoy the lakefront views, open-air shops, and family-friendly atmosphere of Navy Pier’s famous attractions.
Free entry, 45m

3:45pm

Centennial Wheel Ride

Ride the Ferris wheel for panoramic views of Chicago skyline and Lake Michigan, a highlight for the kids.
USD16 adult, USD10 child, 30m

4:15pm

Return by Taxi or Uber to Hyatt Regency O'Hare

For convenience with family, take a direct taxi/Uber back to the hotel, about 25-minute drive.
USD25-$30 approx., 25m
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Day 2: Buckingham Fountain Evening & Dinner

Chicago, USA on May 10, 2025

8:00am

Breakfast at Yolk near Hyatt Regency O’Hare

Enjoy a family-friendly breakfast close to your hotel with hearty options to start the day.
USD15 per person, 1h

9:00am

Relax at Hotel

Spend the daytime relaxing at Hyatt Regency O’Hare or enjoying hotel amenities.
Free, 7h30m

4:30pm

Travel Downtown via Blue Line Subway

Walk 10 minutes to the O'Hare Blue Line station and take the subway toward downtown Chicago (approx. 45 minutes) exiting near Grant Park.
USD5 per person, 1h

5:30pm

Stroll Grant Park

Explore Grant Park’s gardens and sculptures, enjoying fresh air and open spaces perfect for families.
Free, 1h15m

6:45pm

Buckingham Fountain Light and Water Show

Witness the iconic fountain’s illuminated evening show, making for spectacular family memories.
Free, 30m

7:15pm

Dinner at The Gage

Walk a short 5-minute distance to The Gage for American-style dinner with kid-pleasing menu options.
USD30 per person, 1h15m

8:30pm

Return to Hyatt Regency O'Hare via Blue Line Subway

Make an easy 45-minute subway ride back to O'Hare station and then walk to your hotel.
USD5 per person, 1h
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Day 3: Lincoln Park Zoo Visit

Chicago, USA on May 11, 2025

3:00pm

Travel to Lincoln Park Zoo by Blue Line & Bus

Take the Blue Line subway from O’Hare to the Washington station downtown (approx. 45 minutes), transfer to bus #22 toward Lincoln Park Zoo for a 15-minute ride. The trip offers cost-effective public transit suitable for families.
USD5-$7 per person, 1h

4:00pm

Explore Lincoln Park Zoo & Conservatory

Visit the free-admission zoo, engaging kids with animals and beautiful conservatory gardens nearby.
Free, 1h30m

5:30pm

Dinner at Café Ba-Ba-Reeba!

Walk about 10 minutes to this lively tapas restaurant serving kid-friendly small plates with delicious Spanish flavors.
USD25 per person, 1h15m

6:45pm

Evening Walk in Lincoln Park

Enjoy a relaxing post-dinner stroll within Lincoln Park or along the nearby lakefront trail.
Free, 45m

7:30pm

Return to Hyatt Regency O'Hare by Taxi or Bus + Blue Line

Take a taxi or bus back to the Blue Line station, then the subway to O’Hare, approximately 1-hour total trip with minimal walking.
USD10-$20 per person, 1h
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Day 4: River Cruise & Skydeck

Chicago, USA on May 12, 2025

9:00am

Pack and Check-out

Prepare for checkout and last day excursions; store bags at the hotel if needed.
Free, 1h

10:00am

Travel Downtown by Blue Line Subway

Walk to O'Hare station and take the Blue Line subway downtown (about 45 minutes).
USD5 per person, 50m

10:50am

Visit Starbucks Reserve Roastery

Enjoy a unique coffee experience and tasty treats at this flagship location within walking distance in River North.
Free, 1h15m

12:15pm

Lunch at Beatrix on the Riverwalk

Walk about 10 minutes to this bright and fresh spot with diverse menu options ideal for a family lunch.
USD20 per person, 1h30m

1:45pm

Chicago Architecture River Cruise

Walk 5 minutes to embark on a 90-minute guided boat tour showcasing Chicago’s legendary architecture along the river.
USD53 adult, USD41 child, 1h30m

3:15pm

Willis Tower Skydeck or Millennium Park Exploration

Walk or take a short taxi ride (5-10 minutes) to Willis Tower for skydeck views or Millennium Park for outdoor art and space. Choose based on family energy and interests.
Skydeck USD35/28 child; Millennium Park free, 1h

4:15pm

Return to Hyatt Regency O'Hare

Use the Blue Line subway from downtown to O’Hare station and walk to the hotel (approx. 1hr total), convenient for luggage pickup and departure.
USD5 per person, 50m
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