10 Days of Food and Museums in Chicago & New York Itinerary

Begin your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Experience breathtaking views of the city from one of the tallest buildings in the world. Afterward, grab breakfast at Au Cheval, known for its delicious brunch options.

Head over to Chicago Riverwalk for a scenic stroll along the river. You can also take an architectural boat tour to learn more about Chicago's famous buildings. For lunch, stop by Portillo's Hot Dogs for a taste of classic Chicago-style hot dogs.

Spend your evening at House of Blues, enjoying live music in this iconic venue. Before the show, have dinner at The Purple Pig, which offers Mediterranean-inspired small plates.

Visit Field Museum in the morning. This natural history museum is home to Sue, the largest and most complete T-Rex skeleton ever discovered. Afterward, enjoy breakfast at Frontera Grill, known for its delicious Mexican cuisine.

In the afternoon, explore Navy Pier, one of Chicago's top attractions. Take a ride on the Ferris wheel or simply enjoy the views of Lake Michigan. For lunch, try some BBQ at Smoque BBQ.

End your day with dinner at Joe's Seafood, Prime Steak & Stone Crab, where you can indulge in some of the best seafood and steaks in town.

Start your day with a visit to Museum of Science and Industry. This museum offers interactive exhibits that are fun for all ages. Afterward, have breakfast at a local favorite spot near Hyde Park.

Head over to explore more historic sites like Chicago Cultural Center and take a walk through Grant Park afterward. For lunch, dine at another iconic spot:  Gibsons Bar & Steakhouse.

Conclude your evening with an unforgettable dining experience at  Alinea, one of only 14 Michelin three-star restaurants in America.

Begin your last day in Chicago with a visit to Adler Planetarium. This planetarium offers stunning views of the stars and the Chicago skyline. Afterward, enjoy breakfast at Palmer House Hilton, known for its historic charm and delicious morning offerings.

Spend your afternoon exploring Lincoln Park & Zoo. This free zoo is home to a variety of animals and is located within the beautiful Lincoln Park. For lunch, head over to The Purple Pig for some Mediterranean-inspired dishes.

End your day with a visit to Second City, one of the most famous comedy clubs in the world. Enjoy a night of laughter and entertainment. Before the show, have dinner at Gibsons Bar & Steakhouse, known for its prime steaks and elegant atmosphere.

Central Park is a perfect place to start your first day in New York. Take a leisurely stroll or rent a bike to explore this iconic park. For breakfast, stop by Russ & Daughters Cafe for some classic New York bagels and lox.

Metropolitan Museum of Art (The Met) awaits you in the afternoon. Spend several hours exploring its vast collection of art from around the world. For lunch, dine at The Modern, which offers contemporary American cuisine right inside The Met.

Broadway is synonymous with New York's vibrant theater scene. Catch an evening show on Broadway for an unforgettable experience. Before heading to the theater, enjoy dinner at Jean-Georges, known for its exquisite French cuisine.

Statue of Liberty & Ellis Island are must-see landmarks that offer insight into America's history. Take a ferry ride to these iconic sites and spend your morning exploring them. Afterward, have breakfast at Balthazar, which offers delicious French pastries and breakfast dishes.

One World Trade Center provides breathtaking views of New York City from its observation deck. Spend some time here reflecting on history and enjoying the panoramic views. For lunch, head over to Katz's Delicatessen for an authentic New York deli experience.

Times Square comes alive in the evening with its bright lights and bustling atmosphere. Explore this iconic area before having dinner at Carbone, known for its Italian-American cuisine.

Start your day with a visit to Museum of Modern Art (MoMA) which houses an impressive collection of modern art from around the world. Enjoy breakfast at their on-site cafe before diving into their exhibits.

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Start your day with a visit to Brooklyn Museum. This museum is one of the oldest and largest in the country, featuring an extensive collection of art from various cultures. After exploring the museum, enjoy breakfast at Momofuku Noodle Bar, known for its innovative Asian-inspired dishes.

In the afternoon, head over to Prospect Park. Designed by the same architects who created Central Park, this beautiful park offers plenty of green space for a relaxing stroll. For lunch, stop by Peter Luger Steak House, a legendary spot known for its mouth-watering steaks.

End your day with a visit to Brooklyn Bridge Park, where you can enjoy stunning views of the Manhattan skyline. Before heading back, have dinner at Gramercy Tavern, which offers contemporary American cuisine in a cozy setting.

Chelsea Piers Sports & Entertainment Complex is a great place to start your last day in New York. Enjoy some recreational activities or simply take in the views along the Hudson River. For breakfast, stop by Shake Shack for some classic American fare.

High Line is an elevated park built on a historic freight rail line. Spend your afternoon walking along this unique green space and enjoying its gardens and public art installations. For lunch, dine at Blue Hill at Stone Barns, which offers farm-to-table dining just outside the city.

Empire State Building is an iconic landmark that provides breathtaking views of New York City from its observation deck. End your trip with dinner at Le Bernardin, known for its exquisite seafood dishes.