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Winter weekend · Chicago

Winter weekend in Chicago

Wintering in Chicago — cosy dinners, skating, holiday lights and the small rooms that feel right when it's freezing out.

Frequently added to plansEditor's pick

Top spots in Chicago

  • Wrigley Field

    Family

    Wrigleyville

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

  • Millennium Park

    Outdoors

    Loop

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

  • Art Institute of Chicago

    Culture

    Grant Park

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

  • Pilsen Mural Walk

    Culture

    Pilsen

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

Where to eat

  • Au Cheval

    $$

    Diner / Burgers · West Loop

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

  • Lou Mitchell's

    $

    Diner · West Loop

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

  • Alinea

    $$$$

    Modernist tasting · Lincoln Park

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

  • Girl & The Goat

    $$$

    Modern American · West Loop

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

  • Pequod's Pizza

    $$

    Deep-dish · Lincoln Park

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

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

Winter weekend in other cities