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6 Days Exploring Chicago's Landmarks and Cuisine Itinerary
Last updated: 2024 Jun 14Welcome to the Windy City
Morning
Start your day with a visit to Millennium Park. This iconic park is home to the famous Cloud Gate sculpture, also known as 'The Bean'. It's a great spot for photos and offers a beautiful view of the city skyline. Enjoy a leisurely stroll through the park's gardens and take in the public art installations.
Afternoon
Head over to Art Institute of Chicago, one of the oldest and largest art museums in the United States. Spend a few hours exploring its vast collection, which includes works by famous artists such as Monet, Van Gogh, and Picasso. For lunch, walk to The Purple Pig, known for its Mediterranean-inspired small plates and extensive wine list.
Evening
In the evening, catch a show at Chicago Theatre. This historic theater hosts a variety of performances, from Broadway shows to concerts. Afterward, dine at Girl & the Goat, one of Chicago's most popular restaurants offering innovative dishes in a lively atmosphere.
Bedtime
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Millennium Park
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Art Institute of Chicago
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Chicago Theatre
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Architectural Marvels and Riverwalk
Morning
Begin your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Experience breathtaking views from one of the tallest buildings in the Western Hemisphere. Don't miss The Ledge, where you can step out onto glass boxes extending 4.3 feet outside the building.
Afternoon
Next, explore Chicago Riverwalk, a scenic promenade along the Chicago River. Enjoy lunch at Portillo's Hot Dogs, famous for its Chicago-style hot dogs and Italian beef sandwiches. Afterward, take an architectural boat tour to learn about the city's iconic buildings from a unique perspective on the water.
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Skydeck Chicago at Willis Tower (Sears Tower)
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Chicago Riverwalk
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Museums and Lakefront Leisure
Morning
Visit Field Museum in the morning. This natural history museum is home to Sue, the largest and most complete T-Rex skeleton ever discovered. Explore exhibits on ancient cultures, gems, minerals, and more.
Afternoon
Spend your afternoon at Shedd Aquarium, located on Lake Michigan's shore. Discover thousands of aquatic animals from around the world in this renowned aquarium. For lunch nearby, try Lou Malnati's Pizzeria for some classic deep-dish pizza.
Evening
In the evening, take a stroll along Navy Pier (not on wishlist but highly recommended), which offers stunning views of Lake Michigan and features attractions like rides and shops. End your day with dinner at Joe's Seafood, Prime Steak & Stone Crab, known for its exceptional seafood dishes.
Bedtime
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Field Museum
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Shedd Aquarium
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Cultural Gems and Nightlife
Morning
Start your day with a visit to Adler Planetarium. Explore exhibits about space exploration and enjoy spectacular views of Chicago’s skyline from this lakeside location.
Afternoon
Next up is Museum of Science and Industry, where you can easily spend several hours exploring interactive exhibits on everything from space travel to genetics. For lunch nearby, head over to The Publican, which offers hearty American fare with an emphasis on pork dishes.
Evening
In the evening, enjoy live music at House of Blues. This iconic venue hosts performances by top artists across various genres in an intimate setting. Before or after catching some tunes here have dinner at nearby restaurant: RPM Italian
Bedtime
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Adler Planetarium
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Museum of Science and Industry
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House of Blues
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Exploring the Loop and Historic Architecture
Morning
Begin your day with a visit to Chicago Cultural Center. This stunning building is known for its beautiful architecture and free art exhibits. Don't miss the world's largest Tiffany stained-glass dome.
Afternoon
Afterward, head to Chicago Loop, the city's bustling downtown area. Explore its historic buildings, including Rookery Building, an architectural masterpiece designed by Frank Lloyd Wright. For lunch, enjoy a meal at Avec, a cozy spot offering Mediterranean-inspired dishes.
Evening
In the evening, visit Chicago Theatre for another show or performance if you missed it earlier in your trip. Alternatively, explore more of the Loop's nightlife. Dine at Gene & Georgetti, one of Chicago's oldest steakhouses known for its classic American fare.
Bedtime
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Chicago Cultural Center
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Chicago Loop
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Rookery Building
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Chicago Theatre
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Lakefront Adventures and Farewell
Morning
Start your final day with a visit to Lincoln Park & Zoo. This free zoo is home to a wide variety of animals and is located within Lincoln Park, which offers beautiful gardens and walking paths.
Afternoon
Next, head to 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city from 1,000 feet above. For lunch nearby, try Frontera Grill, known for its delicious Mexican cuisine created by celebrity chef Rick Bayless.
Evening
Spend your last evening in Chicago at Navy Pier, enjoying the attractions and stunning views of Lake Michigan. End your trip with dinner at Smoque BBQ, where you can savor some of the best barbecue in the city.
Bedtime
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Lincoln Park & Zoo
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360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Navy Pier
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