New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
15-Day Chicago Adventure Itinerary
Last updated: 2024 Jun 14Welcome to the Windy City
Morning
Start your day with a visit to Millennium Park, one of Chicago's most iconic attractions. Stroll through the park and take in the famous Cloud Gate sculpture (also known as 'The Bean'), Lurie Garden, and Crown Fountain. The park is a great introduction to the city's vibrant culture and architecture.
Afternoon
Head over to Art Institute of Chicago, which is just a short walk from Millennium Park. This world-renowned museum houses an extensive collection of art from around the globe. Spend a few hours exploring its impressive exhibits and don't miss the famous 'American Gothic' painting by Grant Wood.
Evening
Dine at Alinea, one of Chicago's most celebrated restaurants. Known for its innovative and artistic approach to cuisine, Alinea offers a unique dining experience that will be a highlight of your trip.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Exploring Chicago's Architecture
Morning
Begin your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Enjoy breathtaking views of the city from one of the tallest buildings in the Western Hemisphere. The glass-floored ledge offers an exhilarating experience as you look down on the city below.
Afternoon
Take an architectural boat tour along Chicago River. This tour provides an excellent overview of Chicago's architectural history and its stunning skyline. You'll learn about the city's famous buildings and their architects while cruising along the river.
Evening
Enjoy dinner at Girl & the Goat, a popular restaurant known for its inventive dishes and vibrant atmosphere. Make sure to try some of their signature small plates.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Cultural Gems and Local Flavors
Morning
Visit Field Museum, one of the largest natural history museums in the world. Explore fascinating exhibits like Sue the T-Rex and learn about different cultures and natural wonders.
Afternoon
Head over to Shedd Aquarium located nearby on Museum Campus. Discover marine life from around the world in this impressive aquarium that features everything from beluga whales to colorful coral reefs.
Evening
Have dinner at Joe's Seafood, Prime Steak & Stone Crab, where you can indulge in delicious seafood dishes and prime steaks in an elegant setting.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Parks and Entertainment
Morning
Spend your morning exploring Lincoln Park & Zoo. This beautiful park offers scenic walking paths along with a free zoo that houses animals from all over the world.
Afternoon
Take some time to relax at Chicago Riverwalk. Enjoy a leisurely stroll along this picturesque waterfront area filled with cafes, public art installations, and beautiful views of downtown Chicago.
Evening
End your day with dinner at Lou Malnati's Pizzeria, where you can savor authentic deep-dish pizza – a must-try when visiting Chicago.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Historic Chicago
Morning
Start your day with a visit to Chicago Cultural Center. This stunning building is known for its beautiful architecture and hosts free art exhibits and cultural events. Don't miss the world's largest Tiffany stained-glass dome.
Afternoon
Head over to Chicago Board of Trade Building, an iconic skyscraper that represents the city's financial history. You can take a guided tour to learn about its architectural significance and historical importance.
Evening
Dine at Portillo's Hot Dogs, a Chicago institution known for its classic Chicago-style hot dogs, Italian beef sandwiches, and chocolate cake shakes.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Sports and Skyline Views
Morning
Visit Wrigley Field, one of the oldest baseball stadiums in the United States. Take a guided tour to learn about the history of the Chicago Cubs and explore this historic ballpark.
Afternoon
Spend your afternoon at 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy panoramic views of the city from this observation deck located on the 94th floor of the John Hancock Center.
Evening
Have dinner at Gibsons Bar & Steakhouse, a classic Chicago steakhouse known for its prime steaks, seafood, and lively atmosphere.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Museums and Music
Morning
Explore Museum of Science and Industry, one of the largest science museums in the world. Discover interactive exhibits on topics ranging from space exploration to genetics.
Afternoon
Visit Adler Planetarium, located on Museum Campus. Learn about astronomy and space science through engaging exhibits and shows in their state-of-the-art theaters.
Evening
Enjoy live music at House of Blues. This iconic venue offers great food along with performances by talented musicians across various genres.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Shopping and Comedy
Morning
Start your day with some shopping along The Magnificent Mile. This famous shopping district is home to numerous high-end stores, boutiques, and department stores.
Afternoon
Take a break at The Purple Pig, known for its Mediterranean-inspired small plates. Enjoy a leisurely lunch before continuing your exploration.
Evening
End your day with laughter at Second City, one of the most famous comedy clubs in the world. Catch a show featuring talented comedians who often go on to become household names.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Architectural Marvels and Local Eats
Morning
Start your day with a visit to Rookery Building. This historic building is a masterpiece of architecture designed by Daniel Burnham and John Root, with later renovations by Frank Lloyd Wright. Take a guided tour to appreciate its intricate design and historical significance.
Afternoon
Head over to Marina City, an iconic residential complex known for its unique corncob-shaped towers. Explore the area and enjoy the views of the Chicago River.
Evening
Dine at The Publican, a highly-rated restaurant known for its farm-to-table approach and communal dining experience. Enjoy dishes that highlight local ingredients and flavors.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Historic Landmarks and Scenic Views
Morning
Wrigley Building is your first stop today. This historic skyscraper is one of Chicago's most recognizable landmarks. Take some time to admire its beautiful architecture and explore the surrounding area.
Afternoon
Tribune Tower is just a short walk away. This neo-Gothic skyscraper houses fragments from famous buildings around the world embedded in its walls. Learn about its history and significance in Chicago's architectural landscape.
Evening
Avec Restaurant awaits you for dinner. Known for its Mediterranean-inspired small plates, this cozy spot offers a delightful dining experience with flavors that will tantalize your taste buds.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Science, Industry, and Deep-Dish Pizza
Morning
Museum of Science and Industry is on today's agenda. Spend your morning exploring this vast museum with interactive exhibits on various scientific topics.
Afternoon
Frederick C. Robie House, designed by Frank Lloyd Wright, is your next stop. Take a guided tour to learn about this architectural gem located in Hyde Park.
Evening
Lou Malnati's Pizzeria will be your dinner destination tonight. Enjoy some of Chicago's best deep-dish pizza at this beloved local institution.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Aquatic Wonders and Classic Cuisine
Morning
Begin your day at Adler Planetarium. Located on Museum Campus along Lake Michigan, it offers fascinating exhibits about space exploration as well as stunning views of both the lakefront skyline from outside or inside through their telescopes during special events!
Afternoon
Afterward head over towards Navy Pier where you can visit Navy Pier. This iconic attraction features rides like Ferris wheel providing panoramic vistas across cityscape while also hosting numerous shops restaurants entertainment options making perfect place spend leisurely afternoon soaking up atmosphere!
Evening
For dinner make way towards Portillo's Hot Dogs another staple within culinary scene offering variety delicious comfort foods including famous hot dogs Italian beef sandwiches more ensuring satisfying end wonderful day exploring all things aquatic classic cuisine related!
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Art and Entertainment
Morning
Start your day with a visit to Chicago Theatre. This iconic venue is known for its stunning architecture and rich history. Take a guided tour to learn about its significance in Chicago's entertainment scene.
Afternoon
Head over to Grant Park, often referred to as 'Chicago's front yard.' This large urban park offers beautiful gardens, walking paths, and public art installations. It's a great place to relax and enjoy the outdoors.
Evening
Dine at Au Cheval, a highly-rated restaurant known for its gourmet burgers. Enjoy a delicious meal in a cozy setting.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
History and Scenic Views
Morning
Biograph Theater is your first stop today. This historic theater is famous for being the site where notorious gangster John Dillinger was shot by the FBI. Learn about its intriguing history through guided tours.
Afternoon
Water Tower Place is next on your list. This shopping center offers a variety of stores and dining options. Spend some time exploring the shops or simply enjoy the vibrant atmosphere.
Evening
Frontera Grill awaits you for dinner. Known for its authentic Mexican cuisine crafted by celebrity chef Rick Bayless, this restaurant offers a delightful dining experience with bold flavors.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Final Day in Chicago
Morning
Chicago Riverwalk is the perfect place to start your final day in Chicago. Enjoy a leisurely stroll along this picturesque waterfront area filled with cafes, public art installations, and beautiful views of downtown Chicago.
Afternoon
Palmer House Hilton is next on your itinerary. This historic hotel has hosted numerous celebrities and dignitaries over the years. Take some time to explore its elegant interiors and learn about its storied past.
Evening
End your trip with dinner at Smoque BBQ, where you can indulge in mouthwatering barbecue dishes that are sure to leave you satisfied.
Bedtime
Find amazing hotels in Chicago, Illinois, USA.
Adjacent Cities
Find the right stay during your trip.