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Thinking outside of the box to plan a date night will provide endless spots for Chicago couples. With constant sporting events, rooftop bars and coffee shops there are plenty of spots around the city of 2 million people to have a date night that will fit each couple.Game Night: Rather than going to a sporting event, spend the night at Headquarters Bearcade in River North or Lakeview location for a date night filled with competition. With TV’s playing games and full audio for Bulls and Blackhawk’s games this spot will pull out the competitive spirit for any couple. With more than 65 vintage arcade and pinball tiles along with 16 beers on tap Headquarts is a playful spot.Rooftop Bar: With a full drink menu and appetizers available at Packing House in the trendy meatpacking district of West Loop, there are plenty of views to swoon over. It is a mile away from downtown and the skyline view wont disappoint.Tacos: With 7 different types of taco’s available, Antique Taco in Wicker Park is a great spot of couples to share a few different tacos together. The husband and wife team running the restaurant bring their inspiration to give normal tacos a run for their money.Movie Night: Catching a movie might be the most traditional date night idea, but going to the Regal Webster Place 11 Movie Theater works out perfect because it is right across the street from Webster’s Wine Bar. Plan on going to the early movie to provide time to walk across the street to Webster’s Wine Bar and get a glass of wine from one of their 500 labels in the wine cellar after the movie.Dinner: Nestled in Streeterville right before walking to Navy Pier, Quay is a romantic spot to start any date night. The main dining room at Quay is notably one of the best in Chicago. Make dinner reservations before 7:00pm so you can finish your meal in time to walk to Navy Pier and catch the fireworks on Wednesday and Saturday nights.Tour: Take a 2-hour bus tour around a few different Chicago neighborhoods to experience Chicago as it was in the 1920’s and 19030’s. With the newly renovated bus you will tour Chinatown, Greek Town, Pilsen, Little Italy and Lincoln Park. The tour guides tell stories about Capone, and get to know Chicago’s jazz-age during the Prohibition Era.Read More