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Chicago, IllinoisDate ideas56° Overcast

Date ideas in Chicago

Romantic dinners, drinks, shows and views.

18 places

The top 18

Romantic and intimate places, plus shows, live music and galleries, ranked by our own engine.

  1. Medieval Torture Museum4.9· 6.7kMuseum · Theatre District

    1. Medieval Torture Museum

    Atmospheric museum of authentic medieval instruments and reconstructions; educational and photo-friendly.
  2. Chicago Symphony Orchestra4.9· 3.8kLive music · Jewelers Row

    2. Chicago Symphony Orchestra

    World-class symphony performances in an elegant, historic concert hall.
  3. Alla Vita4.8· 4.6kRestaurant · Fulton River District

    3. Alla Vita

    Modern Italian fare, house-made pastas and an elevated wine-focused dining experience.
  4. Lyric Opera of Chicago4.8· 2.7kTheatre · West Loop Gate

    4. Lyric Opera of Chicago

    Historic, upscale opera house offering world-class productions and elegant theatrical experiences.
  5. Civic Opera House4.8· 2.1kLive music · West Loop Gate

    5. Civic Opera House

    Historic Art Deco opera house with world-class performances and striking architecture.
  6. Jazz Showcase4.8· 1.1kLive music · Printer's Row

    6. Jazz Showcase

    Historic, intimate jazz club with live performances and craft cocktails.
  7. United Center4.7· 23kLive music · West Haven

    7. United Center

    High-energy arena for major sports, concerts, and iconic Chicago events.
  8. The Chicago Theatre4.7· 10kTheatre · Theatre District

    8. The Chicago Theatre

    Ornate historic theater with iconic marquee, guided tours, and lively ticketed performances.
  9. RPM Italian4.7· 7.0kItalian · River North

    9. RPM Italian

    Polished modern Italian with house-made pastas, steaks, extensive wine list
  10. Chicago Cultural Center4.7· 5.7kGallery · Jewelers Row

    10. Chicago Cultural Center

    Historic landmark with free galleries, ornate architecture, rotating exhibits and performances.
  11. Stan Mansion4.8· 935Theatre · Palmer Square

    11. Stan Mansion

    Historic, versatile event space for weddings, concerts, and conventions with modern AV.
  12. Gibsons Italia4.7· 4.0kItalian · Fulton River District

    12. Gibsons Italia

    Upscale Italian steakhouse with seafood specialties, extensive wine list, lively atmosphere.
  13. Kingston Mines4.7· 3.7kLive music · Park West

    13. Kingston Mines

    Historic, high-energy blues club with nonstop live music and strong cocktails.
  14. Thalia Hall4.7· 3.6kLive music · Pilsen

    14. Thalia Hall

    Historic music hall with eclectic live shows, craft cocktails, and lively crowds.
  15. The Salt Shed4.7· 3.2kLive music · Pulaski Park

    15. The Salt Shed

    Lively live-music venue with craft beer and energetic crowd, local acts
  16. Rosa's Lounge4.8· 800Live music · Pacific Junction

    16. Rosa's Lounge

    Intimate historic blues club with live Chicago acts, strong drinks, energetic vibe.
  17. Francesca's On Chestnut4.7· 2.9kItalian · Streeterville

    17. Francesca's On Chestnut

    Upscale cozy Italian spot with handmade pastas and a curated wine list.
  18. Auditorium Theatre4.7· 2.9kTheatre · Printer's Row

    18. Auditorium Theatre

    Historic performance venue showcasing diverse live music, theater and dance productions.

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