An Anniversary Dinner in Chicago: Best Dining Spots at the Top


Skyscrapers make for more than just impressive skylines. They’re home to impressive rooftop restaurants and bars too. There’s nothing more romantic than sitting under the night sky as the bright lights of the city illuminate the face of your loved one smiling back at you. Consider having your anniversary dinner in Chicago, home to many rooftop oases where you can celebrate with a drink, a dessert, or an indulgent meal.


On the 70th floor of a residential building is an unsuspecting restaurant with absolutely unmatched views of the city just waiting for you to take them in. Cite is located atop Lake Pointe Tower, the only residential building located east of Lakeshore Drive. Thanks to its location, you’ll revel in sweeping panoramic views of every Chicago icon, including the Willis Tower, Navy Pier, the John Hancock building, and North Avenue Beach. The endless views of Lake Michigan and the gentle swaying of the skyscraper will make you feel as though you’ve boarded a cruise ship that’s been sailing across the sea for days. The circular restaurant is surrounded by floor to ceiling windows. It’s no doubt that the views are the star of this show, which is why it’s a go-to for couples celebrating an anniversary dinner in Chicago. There are a few bar seats for those who arrive early, but if you’d like to revel in the views a bit longer, grab a dining room seat for a long meal. Shift your glance from the city lights to the menu where you can indulge in caviar and bone marrow for starters, or wagyu New York strip and king crab legs for entrées.


If you’re looking for something a bit more secluded for a pre- or post-dinner drink or bite, head over to Drumbar atop the Raffaello Hotel. Located just off the Magnificent Mile, you’ll find fantastic views of Lake Michigan and the iconic John Hancock building. You’ll be happy to find a cozy seat outdoors or inside this posh place. The classic greenery and white picket fences on the intimate terrace contrast with the moody interior, complete with leather seats and a checkered floor. The drinks taste fantastic. Sip on a classic concoction such as an old fashioned or a unique house cocktail such as a Generally Mackin,’ a mix of brandy, bell pepper, cayenne, lime, and fajita seasoning. Beverages are out of the ordinary, but who wants ordinary on a special occasion like this?

The Terrace at the Trump

For an anniversary dinner in Chicago, where the views and the food go head-to-head, make your way over to The Terrace at the Trump. “Dress to impress” was coined here. The sophisticated patio on the 16th floor of the glistening Trump International Hotel and Tower has now become a staple in the Chicago dining scene, and for good reason. While the views aren’t of the bird’s-eye variety, you’ll be pleasantly surprised by the beauty of your surroundings. Nestled on the Chicago river, you’ll find gorgeous glimpses of the boats, bridges, and, of course, architecture. You’ll get up close and personal with the iconic clock tower of the Wrigley Building as well as the soaring historic Tribune Tower. Cheers to great company with a glass of boutique wine while you ponder over the small menu, which is filled with favorites including soft shell crab, grouper ceviche, and pork belly pastor.

The Terrace at the Trump

401 North Wabash Avenue Chicago IL 60611

(312) 588-8600

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