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3-Day Chicago Adventure Itinerary
Last updated: 2024 Jun 14Exploring Iconic Chicago
Morning
Start your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). This iconic landmark offers breathtaking views of the city from its observation deck. Spend some time taking in the panoramic views and snapping photos. Afterward, head to Lou Malnati's Pizzeria for a classic Chicago deep-dish pizza experience.
Afternoon
In the afternoon, take a stroll along Chicago Riverwalk. This scenic walkway along the Chicago River is perfect for a leisurely walk and offers stunning views of the city's architecture. Stop by The Purple Pig for a delightful lunch featuring Mediterranean-inspired small plates.
Evening
End your day with some live jazz at House of Blues. This legendary venue hosts incredible performances that will immerse you in Chicago's vibrant music scene. For dinner, enjoy a meal at Gibsons Bar & Steakhouse, known for its prime steaks and classic American fare.
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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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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Cultural Gems and Jazz Beats
Morning
Begin your day with a visit to Art Institute of Chicago, one of the oldest and largest art museums in the United States. Explore its vast collection of artworks from around the world. For breakfast, stop by Au Cheval, famous for its delicious breakfast options and renowned burgers.
Afternoon
After exploring the museum, head to Millennium Park to see the iconic Cloud Gate sculpture (The Bean) and enjoy the beautiful park surroundings. Grab lunch at The Publican, known for its farm-to-table dishes and communal dining experience.
Evening
In the evening, catch a show at Chicago Theatre, an architectural gem that hosts various performances throughout the year. For dinner, dine at Girl & The Goat, offering innovative dishes crafted by celebrity chef Stephanie Izard.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.69Millennium Park
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4.69Millennium Park
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Landmarks and Local Flavors
Morning
Kick off your day with a visit to 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy stunning views of Lake Michigan and the city skyline from this observation deck. Afterward, have breakfast at Eataly Chicago, where you can savor Italian pastries and coffee.
Afternoon
Spend your afternoon exploring Navy Pier, one of Chicago's most popular attractions featuring shops, restaurants, and entertainment options. For lunch, head to Portillo's Hot Dogs to try their famous Chicago-style hot dogs.
Evening
Conclude your trip with an evening visit to Second City, renowned for its comedy shows that have launched many famous comedians' careers. Enjoy dinner at Bavette's Bar & Boeuf, known for its elegant ambiance and delectable steakhouse fare.
Bedtime
Find amazing hotels in Chicago.
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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4.48Navy Pier
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4.48Navy Pier
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