New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
10 Days Exploring Iconic Landmarks and Cuisine Itinerary
Last updated: 2024 Jun 30Welcome to Chicago's Iconic Sights
Morning
Start your day with a visit to Millennium Park, one of Chicago's most iconic landmarks. Here, you can marvel at the famous Cloud Gate sculpture, also known as 'The Bean,' and enjoy the serene Lurie Garden. Afterward, head over to The Magnificent Mile for some upscale shopping and sightseeing along this bustling street.
Afternoon
In the afternoon, take a guided tour of the Art Institute of Chicago. This world-renowned museum houses an extensive collection of art from various periods and cultures. To enhance your experience, join the Chicago: Art Institute of Chicago Guided Tour which provides insightful commentary on key artworks.
Evening
Conclude your day with a visit to Navy Pier. This lively entertainment hub offers stunning views of Lake Michigan, various dining options, and exciting attractions. For dinner, enjoy a meal at Giordano's, famous for its deep-dish pizza.
Bedtime
Find amazing hotels in Chicago.
Popular
Millennium Park
click to access prices
Popular
The Magnificent Mile
click to access prices
Popular
Art Institute of Chicago
click to access prices
Popular
Chicago Art Institute of Chicago Guided Tour
click to access prices
Popular
Navy Pier
click to access prices
Architectural Marvels and Cultural Gems
Morning
Begin your second day with a trip to the Skydeck Chicago at Willis Tower (Sears Tower). From here, you can enjoy breathtaking views of the city from one of the tallest buildings in the Western Hemisphere. Don't miss stepping out onto The Ledge for an exhilarating experience.
Afternoon
After lunch at Portillo's, explore more architectural wonders with a visit to the historic Rookery Building. Then embark on the popular Chicago River: 1.5-Hour Guided Architecture Riverboat Tour, which offers fascinating insights into Chicago's architectural history while cruising along the river.
Evening
In the evening, immerse yourself in local culture at Second City, where you can catch a comedy show featuring some of Chicago's best talent. For dinner, head over to Lou Malnati's Pizzeria for another taste of authentic deep-dish pizza.
Bedtime
Find amazing hotels in Chicago.
Popular
Skydeck Chicago at Willis Tower (Sears Tower)
click to access prices
Popular
Rookery Building
click to access prices
Popular
Chicago River 1.5-Hour Guided Architecture Riverboat Tour
click to access prices
Popular
Second City
click to access prices
Exploring Museums and Local Flavors
Morning
Kick off your third day with a visit to the impressive Field Museum. This natural history museum boasts extensive exhibits on everything from ancient civilizations to dinosaur fossils. Consider joining the guided tour for an in-depth exploration.
Afternoon
After grabbing lunch at The Purple Pig, continue your cultural journey with a stop at the renowned Shedd Aquarium. Home to thousands of aquatic animals, this aquarium offers engaging exhibits and shows that are perfect for all ages.
Evening
Wrap up your day by exploring the vibrant nightlife at House of Blues. Enjoy live music performances while savoring Southern-inspired cuisine for dinner at their restaurant. End your night with drinks at their lively bar.
Bedtime
Find amazing hotels in Chicago.
Popular
Field Museum
click to access prices
Popular
Shedd Aquarium
click to access prices
Popular
House of Blues
click to access prices
Historic Landmarks and Scenic Views
Morning
Start your day with a visit to Grant Park, often referred to as 'Chicago's front yard.' This expansive park is home to Buckingham Fountain, one of the largest fountains in the world. Take a leisurely stroll through the park and enjoy its beautiful gardens and public art installations.
Afternoon
In the afternoon, head over to Chicago Cultural Center. This stunning building offers free art exhibits, concerts, and cultural events. Don't miss the chance to see the world's largest Tiffany stained-glass dome. Afterward, join the Chicago: Underground Pedway & Downtown Secrets Walking Tour for an intriguing exploration of Chicago's hidden underground pathways.
Evening
Conclude your day with a visit to Marina City, an iconic architectural complex known for its unique design. Enjoy dinner at Smith & Wollensky, located along the Chicago River, offering prime steaks and seafood with a view.
Bedtime
Find amazing hotels in Chicago.
Popular
Grant Park
click to access prices
Popular
Chicago Cultural Center
click to access prices
Popular
Chicago Underground Pedway & Downtown Secrets Walking Tour
click to access prices
Popular
Marina City
click to access prices
Artistic Inspirations and Urban Adventures
Morning
Begin your day with a trip to Adler Planetarium, where you can explore fascinating exhibits about space and astronomy. The planetarium also offers stunning views of the Chicago skyline from its lakeside location.
Afternoon
After lunch at The Gage, continue your artistic journey with a visit to Museum of Science and Industry. This massive museum features interactive exhibits on everything from space exploration to historical artifacts. Enhance your experience by joining the guided tour available at the museum.
Evening
In the evening, head over to Chicago Theatre for a tour of this historic venue or catch a live performance if available. For dinner, dine at The Dearborn, known for its modern American cuisine in a stylish setting.
Bedtime
Find amazing hotels in Chicago.
Popular
Adler Planetarium
click to access prices
Popular
Museum of Science and Industry
click to access prices
Popular
Chicago Theatre
click to access prices
Sporting Venues and Skyline Views
Morning
Kick off your day with a visit to Wrigley Field, one of baseball's most iconic stadiums. Take a guided tour of this historic ballpark to learn about its rich history and see behind-the-scenes areas.
Afternoon
After lunch at Wildberry Pancakes and Cafe, head over to 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy panoramic views of Chicago from this observation deck located on the 94th floor of the John Hancock Center. For an added thrill, try TILT - an enclosed moving platform that tilts you out over Michigan Avenue.
Evening
Wrap up your day with some relaxation at Chicago Riverwalk. This scenic promenade along the Chicago River offers beautiful views, public art displays, and various dining options. Enjoy dinner at City Winery, where you can savor delicious food paired with their house-made wines while enjoying live music.
Bedtime
Find amazing hotels in Chicago.
Popular
Wrigley Field
click to access prices
Popular
360 Chicago Observation Deck (Formerly John Hancock Observatory)
click to access prices
Popular
Chicago Riverwalk
click to access prices
Exploring Brooklyn's Hidden Gems
Morning
Start your day in Brooklyn with a visit to Brooklyn Bridge Park. This waterfront park offers stunning views of the Manhattan skyline and the iconic Brooklyn Bridge. Take a leisurely walk along the park's pathways and enjoy the scenic beauty.
Afternoon
After lunch at Juliana's Pizza, head over to Brooklyn Museum. This renowned museum features an extensive collection of art, including works from ancient civilizations to contemporary pieces. Enhance your visit by joining a guided tour that provides deeper insights into the exhibits.
Evening
Conclude your day with a stroll through Dumbo, a trendy neighborhood known for its cobblestone streets, art galleries, and vibrant nightlife. Enjoy dinner at The River Café, offering exquisite cuisine with breathtaking views of the Manhattan skyline.
Bedtime
Find amazing hotels in New York.
Popular
Brooklyn Bridge Park
click to access prices
Popular
Brooklyn Museum
click to access prices
Popular
Dumbo
click to access prices
Manhattan's Iconic Landmarks
Morning
Begin your day with a visit to Central Park, one of New York City's most famous landmarks. Explore its vast green spaces, picturesque bridges, and serene lakes. Consider taking the New York City: Private Central Park Pedicab Tour for a unique and informative experience.
Afternoon
After lunch at Tavern on the Green, head over to Metropolitan Museum of Art (The Met). This world-class museum houses an extensive collection of art from various cultures and time periods. Enhance your visit by joining a guided tour that highlights key artworks and exhibits.
Evening
In the evening, make your way to Times Square, the bustling heart of Manhattan known for its bright lights and vibrant atmosphere. Enjoy dinner at Carmine's, famous for its family-style Italian dishes, before exploring the area's numerous entertainment options.
Bedtime
Find amazing hotels in New York.
Popular
Central Park
click to access prices
Popular
New York City Private Central Park Pedicab Tour
click to access prices
Popular
Metropolitan Museum of Art (The Met)
click to access prices
Popular
Times Square
click to access prices
Historical Sites and Cultural Experiences
Morning
Kick off your day with a visit to Statue of Liberty & Ellis Island Guided Tour. This iconic landmark is a symbol of freedom and democracy. The guided tour provides historical insights into both Liberty Island and Ellis Island, where millions of immigrants first arrived in America.
Afternoon
After lunch at Eataly Downtown, continue your exploration with a trip to the somber yet powerful National September 11 Memorial & Museum. This museum offers an in-depth look at the events of 9/11 through artifacts, testimonies, and multimedia displays. Consider joining a guided tour for additional context.
Evening
Wrap up your day by visiting Rockefeller Center. Take in panoramic views from the Top of the Rock Observation Deck or explore nearby attractions such as Radio City Music Hall. For dinner, dine at Del Frisco's Double Eagle Steakhouse, known for its prime steaks and elegant ambiance.
Bedtime
Find amazing hotels in New York.
Popular
NYC Statue of Liberty and Ellis Island Guided Tour
click to access prices
Popular
National September 11 Memorial & Museum
click to access prices
Popular
Rockefeller Center
click to access prices
Farewell to New York's Highlights
Morning
Start your final day in New York with a visit to One World Trade Center. Take the elevator up to the One World Observatory for breathtaking views of the city and beyond. The interactive exhibits and presentations provide a deeper understanding of this iconic building and its significance.
Afternoon
After lunch at Le District, head over to Museum of Modern Art (MoMA) Entry Ticket. This world-renowned museum features an impressive collection of modern and contemporary art, including works by Picasso, Van Gogh, and Warhol. Enhance your visit by joining a guided tour that offers insights into the key pieces on display.
Evening
Conclude your trip with a visit to Broadway. Catch a show at one of the many theaters in this famous district. For dinner, enjoy a meal at Sardi's, known for its pre-theater dining experience and celebrity caricatures adorning the walls. End your night with drinks at The Rum House, a classic cocktail bar located nearby.
Bedtime
Find amazing hotels in New York.
Popular
One World Trade Center
click to access prices
Popular
NYC Museum of Modern Art (MoMA) Entry Ticket
click to access prices
Popular
Broadway
click to access prices
Top Chicago Travel Videos
Adjacent Cities
Find the right stay during your trip.