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Chicago Adventure 5 Days Itinerary
Last updated: 2024 Jun 14Welcome to the Windy City
Morning
Start your Chicago adventure 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 a leisurely stroll. For breakfast, head over to Lou Malnati's Pizzeria for some of the best deep-dish pizza in town.
Afternoon
After exploring Millennium Park, make your way to Art Institute of Chicago. This world-renowned museum houses an impressive collection of art from around the globe. Plan to spend a few hours here. For lunch, enjoy a meal at The Purple Pig, known for its delicious Mediterranean-inspired dishes.
Evening
In the evening, take a walk along Chicago Riverwalk. The Riverwalk offers stunning views of the city skyline and is lined with bars and restaurants. For dinner, dine at Girl & the Goat, one of Chicago's most popular restaurants offering innovative small plates.
Bedtime
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4.69Millennium Park
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4.69Millennium Park
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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History and 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 world. Afterward, grab breakfast at Au Cheval, famous for its mouth-watering burgers.
Afternoon
Next, explore Chicago's architectural marvels with a visit to Chicago Board of Trade Building and then take an architectural boat tour along the Chicago River. For lunch, stop by Portillo's Hot Dogs for a taste of classic Chicago-style hot dogs.
Evening
In the evening, catch a show at Chicago Theatre, an iconic venue that hosts a variety of performances. Before the show, enjoy dinner at Bavette's Bar & Boeuf, known for its steakhouse fare and speakeasy vibe.
Bedtime
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.87Chicago Board of Trade Building
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4.87Chicago Board of Trade Building
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Museums and More
Morning
Start your day with a visit to Field Museum, one of the largest natural history museums in the world. Don't miss Sue, the largest T-Rex skeleton ever discovered! For breakfast or brunch, head over to The Publican, which offers hearty farm-to-table dishes.
Afternoon
Afterward, explore more scientific wonders at Adler Planetarium. The planetarium offers fascinating exhibits about space and astronomy. For lunch, try some delicious Mexican cuisine at Frontera Grill, created by celebrity chef Rick Bayless.
Evening
Spend your evening enjoying live music at House of Blues, where you can listen to some great blues bands while dining on Southern-inspired dishes from their menu.
Bedtime
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4.56Field Museum
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4.56Field Museum
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4.61Adler Planetarium
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4.61Adler Planetarium
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Parks and Zoos
Morning
Begin your day with a relaxing stroll through Grant Park, often referred to as 'Chicago's front yard'. It's an excellent place for morning walks or jogs. Afterward, have breakfast at Giordano's where you can try another style of deep-dish pizza.
Afternoon
Head over to explore nature and wildlife at Lincoln Park & Zoo. This free zoo is home to various animals and beautiful gardens. For lunch nearby, stop by Smoque BBQ for some mouth-watering barbecue dishes.
Evening
In the evening, visit Navy Pier where you can enjoy rides like Centennial Wheel or simply walk around enjoying various attractions there including shops & eateries before having dinner at seafood haven -Joe's Seafood Prime Steak & Stone Crab
Bedtime
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4.70Grant Park
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4.70Grant Park
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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Final Day in Chicago
Morning
Start your final day in Chicago with a visit to Museum of Science and Industry. This museum is one of the largest science museums in the world and offers interactive exhibits that are both educational and fun. For breakfast, stop by Avec Restaurant for a delightful meal to kickstart your day.
Afternoon
After exploring the museum, head over to 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy panoramic views of the city from this observation deck located on the 94th floor. For lunch, indulge in some classic Italian cuisine at RPM Italian, known for its modern take on traditional dishes.
Evening
In the evening, take a leisurely walk along The Magnificent Mile, Chicago's premier commercial district. It's a great place for shopping, dining, and people-watching. For your final dinner in Chicago, dine at Gibsons Bar & Steakhouse, renowned for its prime steaks and lively atmosphere.
Bedtime
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4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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