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16 Mar 2025Updated last time
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3 Days in Chicago Itinerary

3 Days in Chicago: A Perfect Itinerary

Welcome to the thrilling city of Chicago, a metropolis teeming with culture, cuisine, and captivating landmarks. This 3-day itinerary is designed to help you make the most of your time in the Windy City, ensuring you experience some of its most iconic attractions and hidden gems. Your journey begins at Millennium Park, home to the spectacular 'Cloud Gate' sculpture. Stroll through the park, appreciating its blend of art, architecture, and landscape design. Next, visit the Art Institute of Chicago, one of the oldest and largest art museums in the United States, boasting an impressive collection ranging from ancient artifacts to modern masterpieces. Continue your adventure at Navy Pier, a vibrant hotspot offering stunning views of Lake Michigan, a plethora of dining options, and a variety of attractions including the Centennial Wheel. On the second day, ascend to the Skydeck at Willis Tower for unparalleled panoramic views of Chicago from the 103rd floor. Experience the heart-pounding 'Ledge', a glass balcony extending outside the building. Then, dive into a world of discovery at the Museum of Science and Industry, one of the largest science museums globally. Here, highlights like the U-505 submarine and coal mine replica await. Finally, immerse yourself in nature at Lincoln Park Zoo, one of the nation’s oldest zoos and a free attraction perfect for families. Wander through lush grounds and marvel at a variety of animal exhibits. In these three days, you'll find Chicago's charm is in its diversity, offering a spectrum of activities for every traveler. Enjoy the adventure!


Recommended Activities

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    Millennium Park

    Home to the iconic 'Cloud Gate' sculpture, also known as 'The Bean', Millennium Park is a vibrant space where art, architecture, and landscape design come together. It's perfect for a leisurely stroll, outdoor concerts, and enjoying public art installations.
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    Art Institute of Chicago

    Renowned for its impressive collection of artworks, including pieces by Grant Wood, Edward Hopper, and Georges Seurat, this museum offers an extensive range of exhibits from ancient artifacts to modern masterpieces.
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  • This popular landmark offers stunning views of Lake Michigan, a variety of dining options, shops, and attractions like the Centennial Wheel. It's a fun destination for all ages, making it perfect for a day of entertainment and relaxation.
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    Willis Tower Skydeck

    The Skydeck at Willis Tower offers breathtaking 360-degree views of Chicago from the 103rd floor. The 'Ledge', a glass balcony extending outside the building, provides a thrilling experience for visitors.
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    Museum of Science and Industry

    This museum is one of the largest science museums in the world, featuring fascinating exhibits on everything from space exploration to genetics. Highlights include the U-505 submarine and a replica coal mine.
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    Lincoln Park Zoo

    One of the oldest zoos in the U.S., Lincoln Park Zoo is free to the public and features a wide variety of animals and exhibits in a picturesque setting. It's a great place for families and animal lovers alike.
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Restaurants

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    Alinea (Chicago, IL)

    Alinea (Chicago, IL)

    Known for its innovative and avant-garde approach to dining, Alinea offers a multi-sensory experience with dishes that are as visually stunning as they are delicious.
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    The Aviary

    4.3
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    The Aviary

    Specializing in creative cocktails and small bites, The Aviary is part of the Alinea Group and offers a unique, high-end bar experience with a focus on molecular gastronomy.
    4.3
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  • SafeHouse

    A spy-themed restaurant that requires a password for entry, SafeHouse offers a fun and interactive dining experience with clever spy gadgets and secret passageways.
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    Three Dots and a Dash

    4.1
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    Three Dots and a Dash

    This tiki bar offers a tropical escape with its exotic cocktails and Polynesian-inspired decor, making it a fun and unusual spot to unwind.
    4.1
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    Geja’s Cafe

    4.2
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    Geja’s Cafe

    Famous for its romantic atmosphere, this fondue restaurant offers a unique dining experience where you can cook your own food at the table.
    4.2
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Hotels

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    The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

    The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

    This hotel offers a blend of modern luxury with art deco elegance, featuring a rooftop terrace and direct access to The Shops at North Bridge.
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    The Publishing House Bed and Breakfast, IL

    4.9

    The Publishing House Bed and Breakfast, IL

    Housed in a historic building that was once a publishing house, this bed and breakfast features stylish, literary-themed rooms and a cozy atmosphere.
    4.9
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    The Godfrey Hotel Chicago

    4.3

    The Godfrey Hotel Chicago

    Known for its unique architecture and stunning rooftop bar, The Godfrey offers a chic and contemporary stay in the heart of the city.
    4.3
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    Virgin Hotels Chicago

    4.5

    Virgin Hotels Chicago

    This innovative hotel offers a modern, tech-savvy experience with features like app-based room controls, making it a great choice for the modern traveler.
    4.5
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    Longman & Eagle

    4.6

    Longman & Eagle

    Combining rustic charm with modern amenities, this boutique hotel above a Michelin-starred restaurant offers a unique, indie vibe and personalized experience.
    4.6
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Local Events & Happenings

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    Lollapalooza

    Lollapalooza

    The event will take place at Grant Park in Chicago.
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    Whiplash In Concert with Chicago Philharmonic

    Whiplash In Concert with Chicago Philharmonic

    The event will take place at The Auditorium in Chicago.
    Map IconThe Auditorium in Chicago (0.4 mi)
    Calendar Icon14 Sep 2025
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    Steven Wilson: The Overview Tour

    Steven Wilson: The Overview Tour

    We continue to closely monitor official public health guidance and adjust our policies accordingly. A risk of COVID-19 transmission exists in any public space where people are present. Event participants assume all potential risk related to exposure....
    Map IconThe Auditorium in Chicago (0.4 mi)
    Calendar Icon18 Sep 2025
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    Wardruna: World Tour 2025 - Part ll

    Wardruna: World Tour 2025 - Part ll

    We continue to closely monitor official public health guidance and adjust our policies accordingly. A risk of COVID-19 transmission exists in any public space where people are present. Event participants assume all potential risk related to exposure....
    Map IconThe Auditorium in Chicago (0.4 mi)
    Calendar Icon21 Sep 2025
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    The Princess Bride: An Inconceivable Evening with Cary Elwes

    The Princess Bride: An Inconceivable Evening with Cary Elwes

    The event will take place at The Auditorium in Chicago.
    Map IconThe Auditorium in Chicago (0.4 mi)
    Calendar Icon28 Sep 2025
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    Colter Wall and Friends

    Colter Wall and Friends

    We continue to closely monitor official public health guidance and adjust our policies accordingly. A risk of COVID-19 transmission exists in any public space where people are present. Event participants assume all potential risk related to exposure....
    Map IconThe Auditorium in Chicago (0.4 mi)
    Calendar Icon2 Oct 2025
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    Air Play Moon Safari

    Air Play Moon Safari

    The event will take place at The Auditorium in Chicago.
    Map IconThe Auditorium in Chicago (0.4 mi)
    Calendar Icon6 Oct 2025
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