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Date Night Done Right

Make The Magnificent Mile the venue for your next date! Whether it’s your first date or your 50th anniversary, no one can resist a night on the along one of the Great Avenues of the World. Check out our guide to the best places for a date on The Mag Mile.

  • Lou Malnati's

    Show your love in the most delicious way possible with a heart-shaped pizza from Lou Malnati’s! Chicago’s classic deep dish pizza spot offers a special heart-shaped pizza year round. All you have to do is ask!

  • Cindy's

    Looking for a romantic spot to watch the fireworks from Navy Pier? Head to Cindy’s, the new rooftop restaurant and bar atop the Chicago Athletic Association Hotel. The great food, cocktails, and unbelievable view make it a popular hotspot.

  • Chocolate at The Peninsula Chicago

    Few things pair perfectly with a date quite like chocolate does. Luckily, the Peninsula Hotel offers a Chocolate Bar experience Friday and Saturday evenings, complete with an array of chocolate bites and a Chocolate Martini.

  • Lookingglass Theatre

    For a night out at the theater, venture out to the Lookingglass Theatre, housed in Chicago’s historic Water Tower Water Works building. Located right on The Magnificent Mile, the theater features a variety of shows, including one based off of Moby Dick and another inspired by classic vaudeville. The flexible main stage allows for a complete transformation unique to each play, transporting the audience into the realm of the story.

  • LondonHouse Rooftop Lounge

    For a night you’ll both remember the rest of your lives, book a Proposal Experience on the LondonHouse Rooftop Lounge. The experience features a private Cupola, complete with rose petals, a bottle of Dom Perignon, and a breathtaking backdrop of the city skyline for the big moment.



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