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Family Adventure From Chicago: New York, Niagara Falls, and Orlando Itinerary

Viewed by 108 travelers

Day 1: Departure from Chicago

Chicago, USA on May 5, 2025

2:00PM

Begin Journey

Catch your flight from Chicago to New York. Ensure you arrive at the airport at least 2 hours before departure.
USD200, Duration depends on flights
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Day 2: Explore New York

New York, USA on May 6, 2025

8:00AM

Breakfast at Ellen's Stardust Diner

Enjoy breakfast with singing waitstaff at this iconic diner; their famous French toast is a must-try!
USD50, 1 hour

9:30AM

Visit Central Park

Explore this massive urban park where your kids can play, go paddle boating, or visit the Central Park Zoo.
USD20 (Zoo entry), 2.5 hours

12:00PM

Lunch at Shake Shack

Grab a classic burger and shake combo at this beloved fast-casual chain, perfect for families.
USD40, 1 hour

1:30PM

Explore the American Museum of Natural History

Kids will love the dinosaurs and space exhibits at this fascinating museum.
USD80 (family ticket), 3 hours

5:00PM

Dinner at Carmine's Italian Restaurant

Savor family-style Italian dishes at this popular spot that’s perfect for larger groups.
USD100, 1.5 hours

7:00PM

Times Square

Experience the dazzling lights and energy of Times Square in the evening.
Free, 1 hour
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Day 3: More NYC Adventures

New York, USA on May 7, 2025

8:00AM

Breakfast at Junior's Restaurant

Famous for their cheesecake, this diner will kickstart your day with delicious breakfast options.
USD60, 1 hour

9:30AM

Visit the Statue of Liberty

Catch the ferry from Battery Park to experience this iconic symbol of freedom.
USD70 (family ticket), 3.5 hours

1:00PM

Lunch at Hudson Eats

A variety of eateries offering everything from sushi to tacos with a river view!
USD50, 1 hour

2:30PM

Explore the Intrepid Sea, Air & Space Museum

Your kids will be amazed by aircraft carriers and the space shuttle in this hands-on maritime museum.
USD80 (family ticket), 3 hours

6:00PM

Dinner at The Hard Rock Cafe

Dine in a rock-and-roll atmosphere featuring American classics that everyone can enjoy.
USD80, 1.5 hours
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Day 4: Travel to Niagara Falls

Niagara Falls, USA on May 8, 2025

8:00AM

Take Amtrak Train to Niagara Falls

Enjoy a scenic train ride that will take about 9 hours, passing beautiful landscapes.
USD100 per person, 9 hours

5:00PM

Check-in at a Local Hotel - The Giacomo Hotel

Stay at a trendy 4-star hotel conveniently located near Niagara Falls state park.
USD200 per night, 1 hour

7:00PM

Dinner at The Top of the Falls Restaurant

Dine with a view of the falls, enjoying American cuisine, especially known for its signature salmon dish.
USD120, 1.5 hours
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Day 5: Explore Niagara Falls

Niagara Falls, USA on May 9, 2025

8:00AM

Breakfast at the Hotel

Enjoy a hearty breakfast at the hotel before heading out to explore.
Included in hotel cost, 1 hour

9:00AM

Maid of the Mist Boat Tour

Experience the falls up close on this boat tour; rain ponchos are provided!
USD100 (family ticket), 2 hours

12:00PM

Lunch at Niagara Falls State Park

Pack a picnic & enjoy lunch in nature surrounded by stunning views.
USD40, 1 hour

1:00PM

Cave of the Winds

Walk along wooden platforms to get even closer to the Bridal Veil Falls; prepare to get wet!
USD80 (family ticket), 2 hours

4:00PM

Visit the Butterfly Conservatory

Stroll through a lush garden filled with thousands of butterflies; great for photos!
USD40 (family ticket), 1.5 hours

6:30PM

Dinner at Rainforest Cafe

An exciting dining experience for kids with animatronic animals and jungle decor.
USD80, 1.5 hours
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Day 6: Travel to Orlando

Orlando, USA on May 10, 2025

6:00AM

Breakfast at the Hotel

Finish off with one last breakfast at The Giacomo before checking out.
Included in hotel cost, 1 hour

9:00AM

Flight to Orlando

Catch a direct flight to Orlando, approximately 2 hours.
USD200, 2 hours

12:00PM

Check-in at Hyatt Regency Grand Cypress

Enjoy the luxury of this 4-star resort as your base for exploring Orlando.
USD250 per night, 1 hour

1:00PM

Lunch at Disney Springs

Enjoy a variety of food choices at this outdoor shopping and dining area.
USD60, 1.5 hours

3:00PM

Explore Disney Springs

Visit shops, entertainment, and play areas for the kids before heading back to the hotel.
Free, 2 hours

6:00PM

Dinner at T-Rex Cafe

A dinosaur-themed restaurant sure to excite the kids with its atmosphere and kids' menu.
USD80, 1.5 hours
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Day 7: Theme Park Fun

Orlando, USA on May 11, 2025

8:00AM

Breakfast at Crossroads at House of Blues

Begin your day with a southern-style breakfast at this music-centered restaurant.
USD60, 1 hour

10:00AM

Visit Walt Disney World (Magic Kingdom)

Experience iconic rides and attractions suitable for both kids, like Pirates of the Caribbean.
USD500 (family ticket for two days), 1 day

12:30PM

Lunch in the Park

Grab quick service meals inside the park; avoid long lines for maximum fun!
USD100, 1 hour

6:00PM

Dinner at Be Our Guest

Enjoy French-inspired cuisine in the Beast's castle; reservations are necessary!
USD120, 1.5 hours
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Day 8: More Theme Park Fun

Orlando, USA on May 12, 2025

8:00AM

Breakfast at the Hotel

Relax and enjoy breakfast at Hyatt Regency's buffet before heading out.
Included in hotel cost, 1 hour

10:00AM

Visit Walt Disney World (Epcot)

Experience the World Showcase and enjoy attractions like Soarin’ and Test Track.
Included in previous park ticket, 1 day

1:00PM

Lunch in the Park

Try diverse cuisine around the world at various stands featured in Epcot.
USD80, 1.5 hours

6:00PM

Dinner at The Coral Reef Restaurant

Dine with views of an aquarium filled with colorful fish — a hit for kids!
USD120, 1.5 hours
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Day 9: Leisure Day

Orlando, USA on May 13, 2025

8:30AM

Breakfast at the Hotel

Another tasty buffet breakfast to fuel up for the day.
Included in hotel cost, 1 hour

10:30AM

Visit Universal Studios Florida (Optional Day Pass)

Explore rides and shows based on Universal movies, particularly fun for the teenager.
USD350 (family ticket), 1 day

12:30PM

Lunch at The Leaky Cauldron (Universal)

Try some British fare inside the Wizarding World of Harry Potter, a special experience!
USD80, 1 hour

6:00PM

Dinner at The Cheesecake Factory

Enjoy a family-friendly extensive menu with something for everyone — don’t forget the cheesecake!
USD100, 1.5 hours
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Day 10: Final Day in Orlando

Orlando, USA on May 14, 2025

8:00AM

Breakfast at the Hotel

Indulge in breakfast at your leisure at the hotel before checking out.
Included in hotel cost, 1 hour

10:00AM

Relax by the Pool

Spend a final relaxing morning at the hotel pool — kids will love it!
Free, 2 hours

12:30PM

Lunch at The Boathouse (Disney Springs)

Enjoy waterfront dining and try their famous lobster roll for a memorable farewell meal.
USD120, 1.5 hours

3:00PM

Flight Home to Chicago

End your wonderful trip with a flight back to Chicago, cherishing amazing memories.
USD200, Duration depends on flights
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