Epic Two-Week US Adventure: From Chicago to New York City

Day 1: Arrival in Chicago

Chicago, Illinois on June 16, 2025

9:00AM

Breakfast at Lou Mitchell's

Start your adventure with a classic Chicago breakfast at Lou Mitchell's, famous for its homemade pastries and hearty pancakes.
USD20, 1.5 hours

11:00AM

Visit Millennium Park

Explore Millennium Park, home to the iconic Cloud Gate sculpture, a must-see photo spot.
USD0, 2 hours

1:00PM

Lunch at Portillo's

Indulge in Chicago-style hot dogs and Italian beef sandwiches at Portillo's, a local favorite.
USD15, 1 hour

2:30PM

Art Institute of Chicago

Visit the Art Institute, one of the oldest and largest art museums in the U.S., featuring masterpieces by van Gogh and Grant Wood.
USD25, 2.5 hours

5:00PM

Skydeck Chicago

Experience breathtaking views of the city from the Willis Tower's Skydeck, where you can also step out onto 'The Ledge'.
USD30, 1.5 hours

7:00PM

Dinner at Giordano's

Savor Chicago's famous deep-dish pizza at Giordano's, renowned for its stuffed crust.
USD30, 1.5 hours
View Hotel Availability

Day 2: Explore Chicago

Chicago, Illinois on June 17, 2025

8:30AM

Breakfast at Wildberry Pancakes and Cafe

Enjoy delicious pancakes and fresh fruit at Wildberry, well-loved by locals.
USD15, 1 hour

10:00AM

Navy Pier

Stroll through Navy Pier and enjoy the shops, restaurants, and a beautiful view of Lake Michigan.
USD0, 2 hours

12:30PM

Lunch at The Purple Pig

Feast on Mediterranean fare and charcuterie boards at The Purple Pig, known for its friendly ambiance.
USD25, 1.5 hours

2:00PM

Shedd Aquarium

Explore aquatic life at Shedd Aquarium, one of the largest indoor aquariums in the world.
USD40, 2.5 hours

5:00PM

Walk the Magnificent Mile

Shop or window shop along Michigan Avenue, also known as the Magnificent Mile, filled with iconic stores.
USD0, 1.5 hours

7:00PM

Dinner at RPM Italian

Pamper yourself with delicious Italian cuisine at RPM Italian, featuring fresh, seasonal ingredients.
USD50, 2 hours
View Hotel Availability

Day 3: Culture & History

Chicago, Illinois on June 18, 2025

9:00AM

Breakfast at the Bongo Room

Try the famous caramel pecan roll and other breakfast specialties at the Bongo Room.
USD15, 1.5 hours

11:00AM

Visit the Field Museum

Explore the Field Museum to see Sue the T-Rex and other fascinating exhibits.
USD25, 2.5 hours

2:00PM

Lunch at The Art of Pizza

Enjoy a slice of Chicago's best pizza at The Art of Pizza, a favorite amongst locals.
USD15, 1 hour

3:30PM

Museum of Science and Industry

Discover interactive, science-based exhibits at the Museum of Science and Industry, one of the largest of its kind.
USD25, 3 hours

6:30PM

Dinner at The Capital Grille

Savor a delicious steak dinner at The Capital Grille, known for its dry-aged steaks.
USD60, 2 hours
View Hotel Availability

Day 4: Day Trip from Chicago

Chicago, Illinois on June 19, 2025

8:00AM

Breakfast at Jewel-Osco's Lattes & More

Grab a quick breakfast at Jewel-Osco, focusing on fresh and fulfilling options.
USD5, 1 hour

9:00AM

Day Trip to Oak Park

Visit Oak Park to see Frank Lloyd Wright's home and studio and other unique architecture.
USD0, 4 hours

1:00PM

Lunch at Winberie's Restaurant

Enjoy lively dishes at Winberie's, a perfect lunch stop after a day of sightseeing.
USD20, 1 hour

3:00PM

Return to Chicago and relax

Rest and freshen up before dinner.
USD0, 1.5 hours

5:00PM

Dinner at The Haka

Experience a unique dining experience with a mix of global flavors at The Haka.
USD35, 1.5 hours
View Hotel Availability

Day 5: Final Day in Chicago

Chicago, Illinois on June 20, 2025

8:30AM

Breakfast at Toast

Enjoy a cozy breakfast featuring egg dishes and fresh pastries at Toast.
USD15, 1 hour

10:00AM

Visit Lincoln Park Zoo

Explore Lincoln Park Zoo, a free zoo in Chicago with beautiful gardens and diverse animals.
USD0, 2 hours

1:00PM

Lunch at The Grill on the Alley

Delight in upscale American cuisine with a classic touch at The Grill on the Alley.
USD35, 1.5 hours

3:00PM

Final Shopping

Spend some time shopping or picking up souvenirs in the local boutiques before leaving for New York City.
USD0, 2 hours

5:00PM

Dinner at Joe's Seafood, Prime Steak & Stone Crab

Indulge in a luxurious dinner with fresh seafood and prime steaks.
USD70, 2 hours

7:30PM

Travel to New York City

Fly to New York City, enjoying the evening flight to your exciting destination.
USD150, 3 hours
View Hotel Availability

Day 6: New York City Excursion

New York City on June 21, 2025

9:00AM

Breakfast at Ess-a-Bagel

Start your NYC adventure with a delicious New York bagel experience at Ess-a-Bagel.
USD10, 1 hour

10:30AM

Visit Central Park

Walk through the scenic paths of Central Park, ideal for relaxation and people-watching.
USD0, 2 hours

1:00PM

Lunch at The Loeb Boathouse

Dine at The Loeb Boathouse, situated within Central Park, allowing beautiful views of the lake.
USD30, 1.5 hours

2:30PM

Visit the Metropolitan Museum of Art

Spend hours exploring incredible art collections that span thousands of years at the Met.
USD25, 3 hours

6:00PM

Dinner at Carmine's

Enjoy family-style Italian dining at Carmine's, perfect for sharing with friends and family.
USD40, 1.5 hours
View Hotel Availability

Day 7: Iconic NYC Highlights

New York City on June 22, 2025

8:30AM

Breakfast at The Brooklyn Diner

Savor classic diner staples at The Brooklyn Diner, perfect to fuel your day.
USD15, 1 hour

10:00AM

Visit the Statue of Liberty

Take a ferry to visit the Statue of Liberty and enjoy panoramic views of the Manhattan skyline.
USD25, 3 hours

2:00PM

Lunch at Fraunce's Tavern

Dine in a historic tavern frequented by George Washington, now serving classic American fare.
USD20, 1.5 hours

3:30PM

Walk Brooklyn Bridge

After lunch, enjoy a walk across the Brooklyn Bridge, experiencing iconic views and great photo ops.
USD0, 1.5 hours

6:00PM

Dinner at The River Café

Dine at The River Café with stunning views of the Manhattan skyline, perfect for a romantic evening.
USD90, 2 hours
View Hotel Availability

Day 8: Times Square & More

New York City on June 23, 2025

9:00AM

Breakfast at Café Grumpy

Experience artisan coffee and freshly baked pastries at Café Grumpy, a local favorite.
USD10, 1 hour

10:30AM

Visit Empire State Building

Head to the Empire State Building to enjoy incredible views from the observation deck.
USD40, 2 hours

1:00PM

Lunch at Shake Shack

Grab a quick and delicious burger and milkshake at Shake Shack, a tasty NYC classic.
USD15, 1 hour

2:30PM

Explore Times Square

Immerse yourself in the bustling atmosphere of Times Square, famous for its bright lights and entertainment.
USD0, 2 hours

5:00PM

Dinner at Ruby Foo's

End your day with a relaxing dinner at Ruby Foo's while experiencing modern Asian cuisine.
USD35, 2 hours
View Hotel Availability

Day 9: Cultural Immersion

New York City on June 24, 2025

8:30AM

Breakfast at Jack's Wife Freda

Start your day with Mediterranean-inspired breakfast dishes at Jack's Wife Freda, known for its cozy vibe.
USD15, 1 hour

10:00AM

Visit the Museum of Modern Art (MoMA)

Explore the vast collection of modern and contemporary art at MoMA, a must for art lovers.
USD25, 3 hours

1:00PM

Lunch at The Oyster Bar

Enjoy the freshest seafood at The Oyster Bar in Grand Central Terminal.
USD30, 1.5 hours

3:00PM

Walk through Chelsea Market

Explore the gourmet food market at Chelsea Market, where you can sample a variety of local foods.
USD0, 2 hours

6:00PM

Dinner at Blue Note Jazz Club

Catch a live jazz performance while enjoying dinner at the famous Blue Note Jazz Club.
USD70, 2.5 hours
View Hotel Availability

Day 10: Leisure Day in NYC

New York City on June 25, 2025

9:00AM

Brunch at Sarabeth's

Enjoy a leisurely brunch at Sarabeth's, known for its scrumptious brunch options and pastries.
USD40, 1.5 hours

11:00AM

Visit the High Line

Walk along the High Line, a revitalized elevated park, offering unique views of the city.
USD0, 2 hours

1:30PM

Lunch at Eataly

Dine at Eataly, an Italian marketplace offering diverse dining options and delicious artisanal goods.
USD30, 1.5 hours

3:00PM

Explore Lower East Side Tenement Museum

Learn about the city's rich immigrant history at the Tenement Museum.
USD25, 2 hours

6:00PM

Dinner at Katz's Delicatessen

Experience the iconic pastrami sandwich at Katz's, famous for its deli experience.
USD20, 1.5 hours
View Hotel Availability

Day 11: Shopping & Relaxation

New York City on June 26, 2025

9:00AM

Breakfast at The Breakfast Club

Start your day with comforting breakfast choices at The Breakfast Club.
USD15, 1 hour

10:30AM

Visit SoHo for Shopping

Explore the trendy boutiques and shops in SoHo, perfect for unique shopping experiences.
USD0, 3 hours

1:30PM

Lunch at Buddakan

Savor modern Asian dishes in a stunning atmosphere at Buddakan.
USD45, 1.5 hours

3:00PM

Visit the 9/11 Memorial

Pay respects at the 9/11 Memorial and Museum, a poignant tribute to the past.
USD20, 2 hours

6:00PM

Dinner at Nobu

Experience a renowned culinary adventure at Nobu, celebrated for its innovative Japanese-Peruvian fusion dishes.
USD100, 2 hours
View Hotel Availability

Day 12: Final Day in NYC

New York City on June 27, 2025

9:00AM

Breakfast at The Pancake House

Enjoy wood-fired pancakes and a cozy atmosphere at The Pancake House.
USD15, 1 hour

10:30AM

Walk through the West Village

Experience the charm of NYC's West Village with its picturesque streets and quirky shops.
USD0, 2 hours

1:00PM

Lunch at Momofuku Noodle Bar

Taste delicious ramen and other fine noodle dishes at Momofuku, a trending eatery.
USD20, 1.5 hours

3:00PM

Final Shopping at Hudson Yards

Spend your last afternoon shopping at Hudson Yards, experiencing high-end retail.
USD0, 2 hours

6:00PM

Dinner at The Spotted Pig

Close your NYC adventure with a relaxing dinner at The Spotted Pig, known for its Michelin-starred menu.
USD45, 2 hours
View Hotel Availability

Day 13: Departure Day

New York City on June 28, 2025

9:00AM

Breakfast at The Smith

Enjoy a final breakfast with a classic American menu at The Smith.
USD20, 1 hour

10:30AM

Leisure Time

Take the last stroll around your favorite spots or do any last-minute shopping.
USD0, 2 hours

1:00PM

Check-out and Farewell

Prepare for your departure to the airport to catch your flight home.
USD0, 1 hour
View Hotel Availability