MyWeekendlyAI concierge
theme.summer-weekend.label · Chicago

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Loved by 4.5k locals271 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.

  • Wrigley Field

    Family

    Wrigleyville

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

  • 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.

Live & on stage

  • Lollapalooza

    Grant Park · Jul 30 – Aug 2 · Festival

  • Pitchfork Music Festival

    Union Park · Jul 18–20 · Indie

  • Chicago Blues Festival

    Millennium Park · Jun 5–7 · Blues / Free

  • Christkindlmarket

    Daley Plaza · Nov 21 – Dec 24 · Holiday

Frequently asked

  • Standouts right now: Millennium Park, Chicago Riverwalk, Wrigley Field. 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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