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Whether you’re a local or planning a visit for your first date, Chicago has plenty of romantic options. From bars to beaches, the Windy City has something for every kind of couple.
One of the best ways to get acquainted is by taking a stroll around one of the city’s parks. You can also check out the Lincoln Park Zoo, where you’ll be able to play with cute animals and enjoy a relaxing evening outdoors.
Soaring high above the city, Chicago's rooftop bars are a must-see for anyone looking to get a taste of the dazzling views. They offer an unforgettable view of the city's famous landmarks and a refreshing cocktail to boot.
One of the city's most Instagram-worthy rooftop bars is Cindy’s, a bar and restaurant that’s part of the Chicago Athletic Association hotel. It has sweeping views of Millennium Park, "The Bean," and Lake Michigan.
In addition to a rooftop patio, Cindy's also features a soaring, glass-enclosed dining area where you can dine and drink on elevated comfort foods and cocktails. It’s no wonder Travel + Leisure ranked this bar among the top 50 in the world!
At this new AMC theater, which is set to open Thursday evening, you can combine your meal and movie in one. A full menu is available to order from a console at your seat, and your food is delivered directly to your plush leather recliner.
It also boasts a full bar that you can purchase drinks at without buying a movie ticket. This is something that's only found at a few other AMC multiplexes in the city, and it's an excellent choice for your first date.
The AMC Dine-In Block 37 is the best place to go if you're looking for a new date night destination in Chicago. This 11-screen cinema, located in the Loop, has everything you'd expect from a modern cinema, including premium formats like Dolby Cinema and RealD 3D. It's also got remote ticketing, large, reserved seats and a full service Dine-In.
Navy Pier is a quintessential Chicago landmark that draws in millions of visitors every year. It was originally designed to be both a commercial shipping pier and a recreational space.
A great date destination, the pier is home to some of the city's best entertainment and dining options. It also has a wide variety of activities that are perfect for kids and families.
Whether you're going to the Children's Museum, taking in a show at Cirque Shanghai, or enjoying the views from the Miller Lite Beer Garden, there are plenty of ways to entertain your partner.
Art is always a great date night activity, and Navy Pier offers a rotating schedule of contemporary art to excite your imagination and inspire your date. Plus, the pier's Skydeck offers a bird's-eye view of the city that will set your date's jaw on end.
The Waterfall Glen Forest Preserve is one of the most ecologically-diverse parcels of open space in DuPage County. It contains prairies, savannas and oak-maple woodlands that contain more than 700 native plants.
The preserve also contains wetlands and riverbeds where many animals live year-round or during their migrations. The 2,500-acre site is home to more than 300 species of mammals, birds, fish, amphibians, reptiles and invertebrates.
While hiking is the best way to experience Waterfall Glen, you can also enjoy the bluff overlooks at Rocky Glen waterfall and Sawmill Creek. It’s a little more difficult to access these sites, but the views are well worth it.
If you're looking for something different than the classic dinner and a movie, a visit to a bookstore is always a good choice. In fact, some bookstores even double as cafes where you can enjoy a coffee or pastry alongside your book.
The best bookstores are those that make a point to keep their spaces interesting by having regular events, hosting writers and other literary personalities, or donating a portion of their profits to a worthy cause. Housing Works Bookstore in NYC, for instance, donates 100% of its profits to fight HIV/AIDS and homelessness.
Barcelona-based critic Jorge Carrion offers a similar view in Bookshops, his collage-like memoir of his pilgrimages to bookstores around the world. He combs his archive of business cards, receipts, and travel journals for vignettes, combining commercial markers with literary history to illustrate why a bookstore must remain a place for reading and reflection rather than simply selling books.
If you're looking for a fun date idea in Chicago, a happy hour bar crawl is the way to go. You can find a variety of options, from a classy speakeasy-style watering hole to a sports bar that serves 90 draft beers.
A gin-focused cocktail bar that bases its style and drinks on the time when Prohibition took effect, Scofflaw is a good choice for a classy date night in Chicago's Logan Square neighborhood. The Victorian-style salon, barstool seating and cozy patio make for an elegant atmosphere.
The restaurant serves a range of dishes that are sure to woo your date, from oysters by the bivalve to an upscale French fry tower. And don't forget to stop by their beer and wine selections -- they also have a solid cocktail menu.
Known as the Windy City, Chicago draws tens of millions of visitors each year. From world-class museums to stunning public parks, there’s no shortage of things to do and see in the Windy City.
A recent trend among kitty-loving patrons has been the opening of cat cafes in some of the country’s most populous cities. While the concept is nothing new, gaining regulatory approval for such an establishment can be a challenge.
Currently, there are two cat cafes in the Chicago area: one at the Tree House Humane Society’s state-of-the-art facility in Rogers Park and another tucked away in the more modestly named Windy Kitty Cat Cafe on Lincoln Avenue in the heart of Lincoln Park. Both offer a variety of beverages and a few quirky features, but the real reason to check them out isn’t just for the drinks. The most important thing to remember when it comes to visiting a cat cafe is to have realistic expectations.
If you want to impress your date with a high-end outdoor movie experience, Rooftop Movies in Millennium Park is the place to go. This terrace features tropical decor, lawn games, a state-of-the-art LED screen and a range of seating options, including loveseats.
If your partner loves wildlife, the Lincoln Park Zoo is the perfect first date idea. With more than 200 unique animal species from around the world, this is a chance to have fun while enjoying nature together.
Another great date idea is to take a pottery class and spend time with your loved one. It’s a hands-on activity that will make you feel closer to your date and also bring out your creative side.
If you're looking for a little romance, the Museum of Contemporary Art is a great place to go on a date. Located on the Magnificent Mile, this institution features thought-provoking exhibits that challenge you and your date to think about art in a different way.
The museum is also home to a unique sculpture garden, a thriving theater, and an award-winning gift store that sells art-related items. Its permanent collection consists of works by some of the world's most influential artists, including Lee Bontecou, Mark Rothko, Agnes Martin, and Andy Warhol.
The museum is committed to offering educational programs that encourage children, teens, and adults to engage in contemporary art. For example, Teens of Contemporary Art (TOCA) is an open gathering of high school students interested in contemporary art, where they explore exhibitions, participate in workshops and discussions about modern art, and plan events.
If you're looking for a unique and exciting way to spend your date night, take a helicopter tour of Chicago. You'll get to see the city from a new perspective and will have some amazing photos to show off!
Helicopter tours are a great way to experience the city's architecture from a different perspective. They offer a breathtaking view of the city's skyline and landmarks like Wrigley Field, Navy Pier, and the Lincoln Park Zoo.
This 45-minute helicopter flight for up to three people will give you and your date dramatic panoramic views of the city's most iconic landmarks. You'll also learn about the history and architecture of the city from a professional pilot.
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