Whether you’re an urbanite or a tourist, Chicago has a lot of unique and interesting date ideas. So, even if you’re stuck with the weather, you’ll never be stuck for something to do!

Top 5 Date Ideas in Chicago
Top 5 Date Ideas in Chicago

The city’s rich history makes it a great place to take your date. Check out the Shedd Aquarium or go on a gangster and ghost tour to learn more about the city’s dark past.

1. Dinner and a Movie

If you’re looking for a fun, unique date idea in Chicago, dinner and a movie can be the perfect option. It’s a great way to bond over a delicious meal and get to know your date.

One of the best things about this date idea is that it doesn’t require much time or money. It can take up two or four hours of your evening, so you have plenty of time to chat and spend quality time together.

If you don’t want to head to the movie theater, check your local parks and universities for showings on the lawn. You can usually find a few classic flicks here and it’s a great way to relax outside and enjoy the weather.

2. Art Institute of Chicago

Chicago’s Art Institute, a world-class museum that’s consistently ranked among the top museums in the country by TripAdvisor travelers, is located in a historic Beaux Arts building that was erected for the 1893 World’s Columbian Exposition. Its massive Renzo Piano-designed Modern Wing was opened in this century and significantly expanded its galleries.

The Museum is home to a collection of art that spans centuries and cultures. Its mission is to collect and preserve works of art representing the world’s diverse artistic traditions, for the inspiration and education of the public, and in accordance with the highest ethical standards and practices.

The museum is home to a world-class art collection that consists of European painting and sculpture as well as Asian art and other genres. It also boasts one of the largest collections of impressionist and post-impressionist paintings outside France.

3. Headquarters Beercade

Head back in time and play classic sized arcade games at Headquarters Beercade, a retro wonderland that offers craft beers, cocktails and thoughtful bar food. The 80s-inspired venue features whimsical artwork, a wall display of thousands of cassette tapes and a menu that reflects its Chicago roots.

With a name coined from the frothy head of draft beer, plus the quarters that are usually pumped into them to play, HQ lines the space with 70+ vintage arcade games and pinball machines. Open 365 nights a year, it appeals to those looking for an alternative to the monotonous.

Melding together a love of over 45 vintage video games, a cicerone curated craft beer list and a classically inspired signature cocktail list, Headquarters raises the bar on the arcade bar concept. With a BYOF (bring your own food) policy, HQ is a great spot to take a break from the hustle and bustle of River North.

4. Rooftop Bars

Chicago has an impressive list of swanky, trendy rooftop bars that boast incredible views over the city skyline and Lake Michigan. They’re buzzing with vibrant lounges and are open year-round, so you can enjoy a swanky sunset drink anytime you want.

A roof top bar is a romantic setting and a great place to go for a date. They have a great menu of small plates and crafted cocktails that will impress your date.

Cindy’s is one of the best roof top bars in Chicago with a beautiful view over Millennium Park, “The Bean,” and Lake Michigan. This upscale bar is part of the historic Chicago Athletic Association Hotel and offers an impressive menu and hand-crafted cocktails.

5. Sports

Whether you’re a die-hard fan or just want to watch the game, sports is a big part of Chicago culture. We have several major professional teams, including baseball’s Cubs, White Sox, Bears and Blackhawks; American football’s Chicago Bears; and basketball’s Bulls, Sky, and Fire.

A few of these are based in the city, but many are outside the borders. We also have a wide network of sports clubs, from volleyball on North Ave Beach to roller skating near Lake Michigan.

During the nineteenth century, the YMCA and other reformers used sports to teach lessons in discipline, teamwork, self-sacrifice, and leadership. New athletic games, reformers argued, offered a cleaner alternative to saloon-centered activities like dogfighting and bear baiting.