The 7 Best Romantic Restaurants in Chicago

The month of love is here! Whether you are looking for a special place to celebrate Valentine’s Day or simply a memorable place for a date night in the Windy City any time of the year, here are six of my favorite romantic restaurants in downtown Chicago and one close-by, which all deliver extraordinary dining experiences. Each has a different vibe, but what they all have in common are outstanding cuisine, stunning views and remarkable service.

Excellent Choices for Valentine’s Day Restaurants in Chicago

Signature Room on 95th
Located on the 95th floor of the John Hancock Center, the Signature Room is pretty much on everyone’s list of the most romantic restaurants in Chicago. Over the years, it has been the setting for thousands of special date nights, anniversary celebrations or proposals, and it’s easy to see why. Its two-story windows with seriously stunning views of Chicago, in my opinion, the city’s best, offer a magical back drop.

Tip: Signature Lounge on the 96th floor, connected to the restaurant via a central staircase or accessible directly from the bottom of the building via elevator, offers a lower key experience, but equally fantastic views. Time your visit for late afternoon to catch the sun setting over the city while you enjoy a cocktail or a glass of champagne. On the weekends, there is live jazz, which adds to the experience.

Best romantic restaurants in Chicago - Signature Room at the 95th
The Signature Room is known as one of the best romantic restaurants in Chicago and offers some of the best views of the skyline anywhere in the city. Photo courtesy of Signature Room on the 95th.

You won’t be quite as high if you visit Everest, located on the 40th floor of the historic Chicago Stock Exchange building. However, the views are still amazing and the dining experience is exceptional. This one Michelin star restaurant, part of the Lettuce Entertain You Enterprises restaurant group, serves contemporary French food and is famous for its attentive service and impressive world-class wine collection. Everest is celebrating its 30th anniversary this year, which says a lot in a city with an incredible culinary scene and new comers popping up all the time.

Best romantic restaurants in Chicago - Everest
Everest serves outstanding contemporary French cuisine in a classic setting. Photo courtesy of Lettuce Entertain You Restaurants.

If you are in the mood for Italian, head to Spiaggia, considered by many to be the city’s finest Italian restaurant. Spiaggia, known for amazing contemporary Italian food and spectacular views of Lake Michigan and the Magnificent Mile, is a Chicago dining institution when it comes to special occasions.

Best romantic restaurants in Chicago - Spiaggia
The main dining room at Spiaggia. Photo courtesy of Spiaggia.

The two-star Michelin restaurant Sixteen most certainly qualifies as an over-the-top experience. The food and service are remarkable and so are the views of downtown Chicago including the Chicago River, the Wrigley Clock Tower and Lake Michigan.

Tip: Weather permitting, start or end your evening with cocktails on the terrace located just outside the restaurant. It’s a great spot to view Navy Pier fireworks too!

Best romantic restaurants in Chicago - Sixteen
Sixteen is one of the most romantic restaurants in Chicago and a great choice for a memorable dining experience. Photo courtesy of Sixteen.

NoMi is a contemporary and chic, yet approachable establishment. Aside from delightful fare focused on local suppliers and delicious sushi, this restaurant offers great views of Michigan Avenue, the Water Tower Square and even Lake Michigan. I find it especially romantic during Christmas time when it’s snowing and Chicago’s Magnificent Mile is lit up even more than usual.

Tip: In summer months, try the NoMi Garden located just outside the double doors at the entrance, a memorable rooftop setting to enjoy cocktails or a romantic outdoor dinner.

Best romantic restaurants in Chicago - NoMi
NoMi dining room offers great views of the Chicago’s Magnificent Mile and the Water Tower Square. Photo courtesy of NoMi.

Let me explain right away: this bar/eatery might not be what some would consider a “classic romantic” atmosphere. Cindy’s is not quiet, subdued, dimly lit, but rather hip, energetic and noisy. Why am I recommending this place? Because it can definitely qualify for a sexy date night. The bar area is an exciting place to hang out before your dinner; the food, offered in larger portions, is meant to be shared; and, the best part, views from its roof-top terrace overlooking Chicago’s Millennium Park including the famous Bean sculpture and Lake Michigan are to die for.

Tip: In the summer, make sure to coordinate your visit with the Navy Pier fireworks schedule, usually on Wednesday and Saturday nights. In the winter, snuggle up next to the large fire pits located at each end of the terrace. Either way, a memorable experience is guaranteed.

Best romantic restaurants in Chicago - Cindy's Rooftop Restaurant
Looking for a unique view of Chicago’s famous Bean? Head to the terrace at Cindy’s. Photo courtesy of Cindy’s.

North Pond Restaurant
You will need to grab an Uber if you are staying downtown, but the ride is short and definitely worth it. The North Pond Restaurant is located in Lincoln Park, just north of the city’s beloved zoo, overlooking the North Pond. Housed in a Frank Lloyd Wright-style building, which used to be a warming center for the pond ice skaters, the restaurant claims they have one of the loveliest settings in the city and I have to agree. North Pond offers gorgeous views of the Chicago skyline which change with the seasons, as does the restaurant menu which relies heavily on local ingredients.

Tip: Try to score a table by the big glass windows. Keep in mind they have an amazing brunch, too, in case you want to return the following morning.

Best romantic restaurants in Chicago - North Pond
North Pond Restaurant will not only delight you with its menu, but also with beautiful views of the Chicago’s skyline from Lincoln Park. Photo courtesy of North Pond Restaurant.

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Main photo courtesy of Signature Room.

Know Before You Go

  • Chicago’s nickname is “The Windy City.”
  • Make sure to visit Millennium Park so that you can see the world-famous Bean!
  • Avoid visiting in the winter if you aren’t a fan of cold weather! The weather warms up around May.

This post was written by Hilton Suggests Team Member, Vera H. Are you interested in traveling to Chicago? Let us know if we can help you with any other recommendations. Tweet us for more great local travel tips!

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