Things to do in Chicago

    Discover amazing Chicago activities and premium in-home experiences.

    Cradled by the breezes of Lake Michigan, Chicago rises in an energetic sweep of gleaming towers and historic neighborhoods, where every block thrums with a rhythm all its own. Here, bold city spirit meets Midwest warmth—inviting you to savor skyline sunsets, soulful jazz drifting from open doors, and the irresistible pull of deep-dish comfort beneath wide Midwestern skies.

    Popular Activities in Chicago

    Chicago Underground Pedway and Loop Secrets Tour

    Explore the hidden Pedway and stunning interiors while uncovering quirky stories beneath downtown Chicago

    5.0 2.8K reviews
    $32/ person

    Dazzling Interiors of Chicago's Loop Walking Tour

    Explore hidden architectural gems and ornate lobbies with a guided 2-hour stroll through the Loop

    5.0 2.8K reviews
    $32/ person

    Chicago Ghosts, Gangsters, and True Crime Walking Tour

    Explore Chicago’s darker past with ghost stories, gangster lore, and true crime on a relaxed 2-hour city walk

    5.0 2.8K reviews
    $32/ person

    All That Glam: Chicago’s Art Deco Masterpieces

    Explore Chicago’s glamorous Art Deco interiors with stories of the Roaring ’20s

    5.0 2.8K reviews
    $32/ person

    New Orleans Historic Donut & Beignet Tour

    Taste top donuts and beignets as you explore Magazine Street history in a 2-hour walking tour

    5.0 1.3K reviews
    $58/ person

    West LA Donut Walking Tour

    Taste baked and artisan donuts across West Hollywood on a relaxed 2-hour stroll

    5.0 1.3K reviews
    $58/ person

    Washington DC Historic Donut Tour

    Sample delicious donuts as you explore historic DC landmarks

    5.0 1.3K reviews
    $58/ person

    Miami: Wynwood Art, Culture, & Donut Tour

    Sample donuts and churros as you explore Wynwood's art scene on a 2-hour walk

    5.0 1.3K reviews
    $58/ person

    Miami South Beach Donuts, Pastelitos & Patisserie Tour

    Sample artisanal donuts, Latin-inspired treats, and Cuban coffee across South Beach

    5.0 1.3K reviews
    $58/ person

    Savannah Historic Downtown Donuts and Sweet Treats Tour

    Taste Savannah’s best donuts and pastries while exploring historic downtown

    5.0 1.3K reviews
    $58/ person

    Chicago Downtown Donut Tour

    Taste top donuts and uncover sweet history on a 2-hour downtown walking tour

    5.0 1.3K reviews
    $58/ person

    Chicago West Loop Donuts & Pastry Tour

    Sample creative donuts and hear West Loop stories on a 2-hour guided stroll

    5.0 1.3K reviews
    $58/ person

    Harvard Square Historic Donut Tour in Boston

    Taste signature donuts while exploring Harvard Square's history

    5.0 1.3K reviews
    $58/ person

    Downtown Detroit Donut & Pastry Tour

    Taste Detroit’s best donuts and pastries on a 2-hour stroll

    5.0 1.3K reviews
    $58/ person

    Brooklyn Donut Tour: Williamsburg & Greenpoint

    Sample iconic Brooklyn donuts on a 2-hour walk through Williamsburg and Greenpoint

    5.0 1.3K reviews
    $58/ person

    East Village Historic Donut & Pastry Tour in New York City

    Taste classic and artisan donuts while exploring East Village landmarks and music history

    5.0 1.3K reviews
    $58/ person

    Times Square Donut Tour in New York City

    Taste standout donuts while exploring Times Square and Rockefeller Center with a local guide

    5.0 1.3K reviews
    $58/ person

    Union Square and Greenwich Village Donut Tour

    Taste top donuts while exploring Union Square and Greenwich Village

    5.0 1.3K reviews
    $58/ person

    Portland Downtown Donut Tour

    Sample four donut shops and uncover Portland's sweet history

    5.0 1.3K reviews
    $58/ person

    Downtown Philadelphia Donut Tour

    Taste top donuts and explore Philly's sweet spots on a guided downtown stroll

    5.0 1.3K reviews
    $58/ person

    Nashville Downtown Donut Walking Tour

    Taste signature donuts as you explore Nashville’s downtown on a relaxed stroll

    5.0 1.3K reviews
    $58/ person

    Seattle Downtown Donut Tour

    Taste top donuts and uncover sweet local history on a 2-hour walking tour

    5.0 1.3K reviews
    $53/ person

    Art Institute of Chicago Skip-the-Line Private Tour

    Explore masterpieces with a private guide and skip the ticket lines.

    Art Institute of Chicago Semi-Private Skip-the-Line Tour

    Skip lines and explore masterpieces with an expert guide in a small group for a more personal, flexible visit

    $62/ person

    Chicago's Original Gangster Tour

    Experience Chicago as it was during the 1920s and 1930s!

    4.6 348 reviews

    Chicago Winery Tour and Tasting

    Learn About Winemaking in the Heart of Chicago

    4.6 279 reviews
    $29/ person

    Miami Wynwood Walls Food & Graffiti Art Walking Tour

    Sample Miami favorites and explore Wynwood Walls on a guided 3-hour food and art walk

    4.9 5.4K reviews
    $11/ person

    Chicago Highlights and Attractions Walking Tour

    Cover Chicago's icons in 2 hours with a guide, from the Magnificent Mile to Millennium Park.

    4.9 5.4K reviews
    $12/ person

    Chicago Food and Walking Tour

    Taste Chicago classics and explore top landmarks on a guided 5-hour tour

    4.9 5.4K reviews
    $12/ person

    Chicago West Loop Food Tour with 5 Tastings

    Taste Chicago's West Loop with guided stops at acclaimed eateries and artisan spots

    4.9 4.3K reviews
    $84/ person

    Chicago Willis Tower Skydeck Tour With Donut Tasting

    Savor a donut and enjoy 103rd-floor views as you learn how Chicago rose from the Great Fire

    Luxury Chicago Helicopter Tour in Twin Engine Aircraft

    See Chicago's top landmarks by air on a private, air-conditioned helicopter flight

    4.9 58 reviews
    $1,903

    Key West Southernmost Sweet Treats Tour

    Savor donuts, Key lime pie, and local favorites on a guided 2-hour tasting tour of Key West

    5.0 1.3K reviews
    $58/ person

    See Chicago's Skyline & Stories by Boat

    Discover Chicago's iconic skyline and rich history on a narrated lake and river cruise

    4.9 560 reviews
    $40/ person

    Historical and Architectural River Tour

    Discover Chicago architecture and fireboat history on a guided river cruise.

    4.9 560 reviews
    $37/ person

    Chicago Happy Hour Cruise On Lake And River

    Sail past the Chicago skyline on a 2-hour 21+ cruise with drinks for purchase and Thursday brewery or Friday live music

    4.9 560 reviews
    $67/ person

    Chicago Bike Tour with West Side Food Tastings

    Sample Chicago favorites while cycling through vibrant Near West Side neighborhoods on a fun 4-hour guided ride

    4.9 5.4K reviews
    $110/ person

    Chicago Private Luxury Yacht Rental for Up to 12

    Charter a 47 ft yacht to cruise the Chicago River or Lake Michigan with BYOB and skyline views

    4.6 114 reviews
    $1,936

    18-Foot Private Pontoon Cruise on the Chicago River

    Captain your own pontoon on the Chicago River for two hours with training and life vests provided

    4.6 114 reviews
    $271/ boat

    2-Hour Private 22 Ft Pontoon Cruise on the Chicago River

    Drive your own pontoon on the Chicago River with BYOB and a quick lesson

    4.6 114 reviews

    Explore the Vibrant Heart of Chicago

    Chicago is a city where architectural marvels meet vibrant neighborhoods, offering an urban tapestry rich with history and culture. As you stroll along the shores of Lake Michigan, you'll feel the gentle breeze that brings life to this bustling metropolis. The skyline is a masterpiece in itself, showcasing iconic structures like Willis Tower and John Hancock Center against a backdrop of endless blue waters.

    In summer, Millennium Park becomes your playground—home to outdoor concerts at Jay Pritzker Pavilion and reflective moments by Cloud Gate (affectionately known as "The Bean"). Autumn paints Lincoln Park's trees in fiery hues, perfect for leisurely walks or picnics near its tranquil lagoon. Winter transforms Navy Pier into a wonderland adorned with twinkling lights while spring invites you to explore the lush Garfield Park Conservatory.

    Dive into Chicago’s culinary scene by sampling deep-dish pizza or savoring flavors from around the world in neighborhoods like Pilsen and Chinatown. Catch live jazz echoing through historic clubs or discover art at renowned institutions such as The Art Institute of Chicago. Whether you're cruising down the river on an architecture tour or cheering at Wrigley Field under sunny skies, every moment here feels uniquely alive—a testament to why this city captures hearts time after time.

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