10-Day Adventure in America: Chicago, Cleveland, and Niagara Falls

Day 1: Explore Chicago

Chicago, IL on April 1, 2025

9:00 AM

Breakfast at Lou Malnati's

Start your day with a famous Chicago deep-dish pizza at Lou Malnati's.
Located in Lincoln Park, a short rideshare from downtown.
USD 20, 1.5 hours

11:00 AM

Visit Millennium Park

Stroll through Millennium Park to see the iconic Cloud Gate sculpture and enjoy the vibrant atmosphere.
Walk or take a quick 'L' ride from Lou Malnati's.
Free, 2 hours

1:00 PM

Lunch at The Olive Garden

Enjoy a hearty Italian lunch at The Olive Garden near the park.
Located a short walk away.
USD 25, 1 hour

3:00 PM

Art Institute of Chicago

Explore incredible art pieces ranging from ancient to modern at the Art Institute.
5-minute walk from restaurant.
USD 25, 2 hours

5:30 PM

Skydeck Chicago

Take in unparalleled views of the city from the Skydeck on Willis Tower.
Short 'L' ride to the nearby tower.
USD 30, 1.5 hours

7:30 PM

Dinner at Portillo's

Indulge in a classic Chicago-style hot dog at Portillo's.
A short ride from the Skydeck.
USD 15, 1 hour
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Day 2: More of Chicago

Chicago, IL on April 2, 2025

8:30 AM

Breakfast at Wildberry Pancakes

Fuel up with pancakes and delicious brunch options at Wildberry.
Located in the Loop, a quick ride from your hotel.
USD 15, 1.5 hours

10:00 AM

Navy Pier

Visit Navy Pier for shops, rides, and scenic views of Lake Michigan.
Take a short bus ride to Navy Pier.
Free (additional costs for rides), 3 hours

1:00 PM

Lunch at Harry Caray's Tavern

Enjoy a classic American lunch at Harry Caray's with views of the lake.
Located at Navy Pier itself.
USD 25, 1 hour

3:00 PM

Chicago Architecture Boat Tour

Experience the city's stunning skyline from a unique perspective on a boat tour.
Embark from near Navy Pier.
USD 40, 2 hours

5:30 PM

Shopping on Magnificent Mile

Explore high-end stores and boutiques along this famous shopping street.
A short walk from the boat tour drop-off.
Free (shopping costs vary), 2 hours

7:30 PM

Dinner at Alinea

Savor an exquisite fine dining experience at Alinea, one of Chicago's best.
Book a table well in advance (reservations required).
USD 290 (tasting menu), 3 hours
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Day 3: Travel to Cleveland

Cleveland, OH on April 3, 2025

9:00 AM

Breakfast at Cloud Gate Cafe

A quick breakfast with coffee and pastries at Cloud Gate Cafe before departure.
Five-minute walk from the hotel.
USD 10, 1 hour

10:30 AM

Drive to Cleveland

Depart for Cleveland, enjoying scenic views along the way.
Rental car is recommended for this journey.
USD 50 (gas cost approx.), 5 hours

3:30 PM

Check-In at Hotel

Settle into your accommodation and freshen up.
Choose a centrally located hotel in Downtown Cleveland.
Varies by booking, 1 hour

5:00 PM

Dinner at The Greenhouse Tavern

Enjoy a delicious farm-to-table dinner at The Greenhouse Tavern.
Located in downtown Cleveland.
USD 30, 1.5 hours

7:00 PM

Evening Walk at the Waterfront

Take a leisurely evening walk along the Cleveland Waterfront.
A short distance from your hotel.
Free, 1 hour
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Day 4: Discover Cleveland

Cleveland, OH on April 4, 2025

8:30 AM

Breakfast at The Breakfast Club

Indulge in a hearty breakfast at this local favorite.
Located a short walk from downtown.
USD 15, 1.5 hours

10:00 AM

Rock and Roll Hall of Fame

Explore the history of rock music at this iconic museum.
Located by the waterfront; easy to reach.
USD 28, 2 hours

12:30 PM

Lunch at Slyman's Restaurant

Savor a famous corned beef sandwich at Slyman's.
A short drive from the museum.
USD 20, 1 hour

2:00 PM

Visit Cleveland Museum of Art

Admire the world-renowned collection at the Cleveland Museum of Art.
Located in University Circle, a short drive away.
Free, 2 hours

4:30 PM

Explore Tremont Neighborhood

Wander through the charming streets of this unique neighborhood.
Short drive from the museum.
Free, 1.5 hours

6:30 PM

Dinner at Mabel's BBQ

Treat yourself to some amazing barbecue at Mabel's.
Located within the Tremont neighborhood.
USD 25, 1.5 hours
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Day 5: Niagara Falls Journey

Niagara Falls, NY on April 5, 2025

8:00 AM

Breakfast at the Hotel

Enjoy a quick breakfast at your hotel before heading to Niagara Falls.
On-site at your downtown Cleveland hotel.
Included, 1 hour

9:30 AM

Drive to Niagara Falls

Set off on your drive to the magnificent Niagara Falls.
Continue on I-90E for scenic views.
USD 40 (gas cost approx.), 2.5 hours

12:30 PM

Lunch at Top of the Falls Restaurant

Have lunch overlooking the falls at Top of the Falls Restaurant.
Located within Niagara State Park.
USD 30, 1.5 hours

2:00 PM

Maid of the Mist Boat Tour

Get up close to the roaring falls on the Maid of the Mist boat tour.
Board from the Niagara Falls base.
USD 25, 2 hours

4:30 PM

Explore Niagara Falls State Park

Wander the beautiful walking paths and viewpoints of the park.
Easily accessible from the boat tour.
Free, 2 hours

6:30 PM

Dinner at The Hard Rock Cafe

Enjoy a casual meal with a rock and roll vibe at The Hard Rock Cafe.
Short drive from the State Park.
USD 35, 1.5 hours
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Day 6: Niagara Falls Exploration

Niagara Falls, NY on April 6, 2025

9:00 AM

Breakfast at the Hotel

Enjoy breakfast at your hotel overlooking the falls.
On-site dining at your hotel.
Included, 1 hour

10:30 AM

Cave of the Winds Tour

Experience the thrill of standing right next to the Bridal Veil Falls.
Accessed through Niagara Falls State Park.
USD 18, 2 hours

1:00 PM

Lunch at The Rainbow Room

Dine with stunning views of the falls at The Rainbow Room.
Located in the park area.
USD 30, 1.5 hours

3:00 PM

Jet Boat Ride

Feel the rush on a thrilling jet boat ride through the Niagara River.
Located at Niagara River's launch point.
USD 60, 2.5 hours

6:00 PM

Dinner at Wine on Third

Savor local wine and a seasonal dinner at Wine on Third.
Located in downtown Niagara Falls.
USD 40, 2 hours

8:30 PM

Evening Illumination of the Falls

End your day with the beautiful illumination of the falls at night.
Easily accessed from dinner location.
Free, 1 hour
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Day 7: Return to Chicago

Chicago, IL on April 7, 2025

8:00 AM

Breakfast at the Hotel

Enjoy a final breakfast at your hotel in Niagara Falls.
On-site dining.
Included, 1 hour

9:30 AM

Drive Back to Chicago

Travel back to Chicago, reminiscing about the journey.
Take the same route back.
USD 40 (gas cost approx.), 5 hours

2:00 PM

Lunch at Portillo's in Chicago

Enjoy Chicago's famous hot dogs one last time.
Located near the hotel.
USD 15, 1 hour

3:30 PM

Visit Shedd Aquarium

Explore the wonders of marine life at this incredible aquarium.
A short 'L' ride from the restaurant.
USD 40, 2 hours

6:00 PM

Dinner at Giordano's

Relish a delicious stuffed deep-dish pizza at Giordano's.
Short travel from the aquarium.
USD 25, 1.5 hours
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Day 8: Chicago's Culture

Chicago, IL on April 8, 2025

9:00 AM

Breakfast at The Bongo Room

Start your day at The Bongo Room with delicious pancakes and coffee.
Located in Wicker Park.
USD 20, 1.5 hours

11:00 AM

Chicago History Museum

Delve into Chicago's rich history at the fascinating museum.
A short ride from the breakfast spot.
USD 15, 1.5 hours

1:00 PM

Lunch at The Chicago Diner

Experience famous vegan comfort food and classic diner fare.
Nearby the history museum.
USD 25, 1 hour

3:00 PM

Visit Lincoln Park Zoo

Enjoy the free admission to Lincoln Park Zoo and meet amazing animals.
Short drive or ride from the diner.
Free, 2 hours

6:00 PM

Dinner at House of Blues

Dig into Southern-inspired dishes while taking in live music.
Located in downtown Chicago.
USD 35, 2 hours
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Day 9: Final Day in Cleveland

Cleveland, OH on April 9, 2025

8:00 AM

Breakfast at The Breakfast Club

Return to The Breakfast Club for a delicious breakfast to kickstart your day.
Located downtown.
USD 15, 1.5 hours

10:00 AM

Visit the Cleveland Botanical Garden

Relax in scenic gardens and learn about plant species.
Short drive to University Circle.
USD 15, 2 hours

12:30 PM

Lunch at Blue Point Grille

Enjoy oysters and fresh seafood with a riverside view.
Located in downtown Cleveland.
USD 35, 1.5 hours

2:30 PM

Explore Playhouse Square

Walk around the largest performing arts center outside of New York City.
Take a short walk or drive.
Free, 1.5 hours

5:00 PM

Dinner at The Capital Grille

Indulge in a refined dining experience at this classy steakhouse.
A short ride from Playhouse Square.
USD 60, 2 hours
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Day 10: Departure

Cleveland, OH on April 10, 2025

8:00 AM

Breakfast at The Capital Grill

Enjoy a refined breakfast before your departure.
On-site dining at hotel.
USD 20, 1 hour

9:30 AM

Check-Out and Departure

Complete your check-out and prepare to head back home.
Arrange transport to the airport.
Varies by travel, 2 hours
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