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Weekend plan

Date Night in Chicago — Curated for Two

Rooftop cocktails, low-lit dinners, jazz at 10 — paced like a real night out.

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Friday

  1. 6:30 PM
    London House Rooftop
    Nightlife · Loop

    Rooftop — Riverwalk rooftop with Wrigley views.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Loop — short walk from your other stops
    • ·A fall-perfect atmosphere
  2. 8:00 PM

    Geja's Cafe

    Date night · $$$ · Lincoln Park

    Low-lit dinner — Candlelit basement fondue — Chicago date-night classic.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Lincoln Park — short walk from your other stops
    • ·A fall-perfect atmosphere
  3. 10:30 PM
    Live Jazz Bar
    Nightlife · Old town

    Cocktails and a trio — solo at the bar or a date-night standby.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Old town — short walk from your other stops
    • ·A fall-perfect atmosphere

Saturday

  1. 11:00 AM

    Hutch

    Brunch · $$ · Wicker Park

    Slow brunch — Country fried steak benedict — Southern brunch with strong cocktails.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Wicker Park — short walk from your other stops
    • ·A fall-perfect atmosphere
  2. 4:00 PM
    360 Chicago
    Outdoors · Streeterville

    View — 94th-floor TILT over Magnificent Mile.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Streeterville — short walk from your other stops
    • ·A fall-perfect atmosphere
  3. 8:00 PM

    Pequod's Pizza

    Deep-dish · $$ · Lincoln Park

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

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Lincoln Park — short walk from your other stops
    • ·A fall-perfect atmosphere
  4. 11:00 PM
    The Aviary
    Nightlife · West Loop

    Cocktail bar — Grant Achatz's haute-cocktail theatre.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in West Loop — short walk from your other stops
    • ·A fall-perfect atmosphere

Remix

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Every plan below is freshly built from Chicago's top curated picks.