MyWeekendlyAI concierge
theme.winter-weekend.label · Chicago

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Loved by 1.9k locals183 plans built this week

Top spots in Chicago

  • Millennium Park

    Outdoors

    Loop

    Anish Kapoor's Bean (Cloud Gate), free concerts at Pritzker Pavilion.

  • Chicago Riverwalk

    Outdoors

    Loop

    Walk or kayak past the city's famous architecture on river level.

  • Art Institute of Chicago

    Culture

    Grant Park

    American Gothic, Nighthawks and one of the world's great impressionist collections.

  • Wrigley Field

    Family

    Wrigleyville

    Ivy-covered walls and Old Style beer — catch a Cubs day game.

  • Pilsen Mural Walk

    Culture

    Pilsen

    Mexican-American street art along 16th and 18th Streets.

  • North Avenue Beach

    Family

    Lincoln Park

    Boathouse-shaped beach pavilion and skyline-backed swims.

Where to eat

  • Alinea

    $$$$

    Modernist tasting · Lincoln Park

    Grant Achatz's three-star theater on a plate.

  • Pequod's Pizza

    $$

    Deep-dish · Lincoln Park

    Caramelized cheese crust — the locals' deep-dish pick.

  • Au Cheval

    $$

    Diner / Burgers · West Loop

    Two-hour wait for the country's most-talked-about cheeseburger.

  • Girl & The Goat

    $$$

    Modern American · West Loop

    Stephanie Izard's wood-fired plates, share everything.

  • Lou Mitchell's

    $

    Diner · West Loop

    Route 66 diner since 1923 — fluffy omelets and free Milk Duds.

Frequently asked

  • Standouts right now: Millennium Park, Chicago Riverwalk, Art Institute of Chicago. The shortlist is curated by people who live in Chicago and refreshed regularly so it reflects what's actually open and worth your time.

More Chicago weekend ideas

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