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5 Unique Date Ideas in the Chicago Loop

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Posted  10 months ago  in  Eat & Drink  by  Brittany Tepper

While we can’t guarantee you’ll meet your soul mate, these five unique date ideas are sure to blow your date away in the heart of the Windy City.


May Your Love Last at Long as The Palmer House Hilton, America's Longest Continually Operating Hotel

The Palmer House is a result of the love between Chicago’s first power couple, Potter and Bertha Palmer. Introduced by Chicago icon Marshall Field, the couple married on July 28, 1870. Potter’s wedding gift to Bertha – The Palmer House Hotel – is to this day the most extravagant wedding gift in Chicago history. While you may not be able to match Potter Palmer’s lavish romantic gestures, a drink or meal under the hotel’s breathtaking ceiling in Lockwood Restaurant and Bar is sure to impress any date. If you are looking to add some extra magic to your night, reserve tickets to the Magic Parlour, an intimate magic show with award-winning, third-generation magician Dennis Watkins in one of the hotel’s historic parlour rooms.

Spark Some Friendly Competition at Flight Club

Nothing sparks romance like some friendly competition. Flight Club, located on the corner of Wacker and Clark, is the perfect spot for couples looking for a playful night out. The new two-story restaurant is the Loop’s first “social darts” experience, taking the somewhat dated game of darts to a whole new sleek and trendy level. Once you arrive, the host will guide you to your oche area where you will be assigned a leaderboard that will not only snap your photo and record your score but guide you through a variety of fast-paced games. Competition getting too fierce? With multiple throw lines, you can make the game as easy or hard as you choose. The bar offers an impressive menu of drinks including a variety of beautiful signature cocktails. The Taurus looks more like a piece of art than a cocktail with an edible illustration on top of a pomegranate, brandy, and gin mixture. The food menu ranges from shareable flat breads to dry aged steak, making it as versatile as you need it to be.

Take Your Date to New Heights at Skydeck Chicago

We can’t think of a date that is more “Chicago” than Pie in the Sky at Skydeck Chicago. Share a famous Giordano’s Chicago style deep-dish pizza 103 floors above the Loop at the iconic Willis Tower. You and your date will have exclusive after-hours access to The Ledge, Skydeck Chicago’s glass box that extends 4.3 feet from the Skydeck at 1,353 feet in the air. The unforgettable meal includes a deep-dish pizza, salad, dessert, and, of course, a breathtaking view of the city at night. We recommend checking that your date isn’t afraid of heights before investing $100 per person for this exclusive experience, but if you both are Chicago-loving thrill seekers, this date will take your relationship to whole new heights.

Dinner and a Show Never Gets Old in the Loop's Theatre District

Nothing is quite like dinner and a show in the Loop’s Theatre District. Whether you’re looking for a suspenseful drama or a star-studded musical, the Loop offers a variety of productions that are sure to spark conversation. Stop by HotTix in Block Thirty Seven for half-price theatre tickets to productions in the Loop and beyond.

This February, we recommend seeing Christina Anderson’s play How to Catch Creation at the Goodman Theatre This “sterling world-premiere production” is “an entertaining and emotional escape” - Daily Herald. Change can happen in a heartbeat. A young writer’s life turns upside down when her girlfriend drops some unexpected news. Fifty years later, four artists feel the reverberations of that moment—and its unexpected consequences—as their lives intersect in pursuit of creative passion and legacy. In this bold, imaginative work, Christina Anderson, “a gifted playwright you want to pay attention to” (Variety), dissects the universal act of creation to inspire the dreamers and idealists in us all.

Before the show, treat your date to a meal at one of the many Loop restaurants offering prix fixe menus for theatre-goers. Italian Village, just a few blocks from the Goodman Theatre, offers a three course Prix Fixe Theatre Menu. Enjoy a romantic meal as you dine under the twilight skies of a recreated Tuscan village.

Share your love of literature at the American Writers Musesum

Roses are red, violets are blue. The American Writers Museum is the perfect date spot for you! Words can express love better than roses and chocolates ever will, and the American Writers Museum is full of words - and love. Share your love of literature with the one you love and let the wise words of your favorites writers stoke your romantic fire. Feeling inspired? Write a love letter to yours truly on one of our many vintage typewriters and watch the sparks fly as the keys clack!