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"After a delicious sit-down dinner, join Vito, Gloves, da gangsters and da flappers for non-stop comedy and dangerous fun! You will be transported back to the 1920s, by da boss's 1928 Model A Ford, Roaring Twenties music, memorabilia and pictures of da gangsters and coppers of da time. The mugs and molls dance and sing the Charleston and other musical selections from 1920’s composers like Cole Porter, George Gershwin, Fats Waller and Duke Ellington."
• 1.5 miles from hotel.
"Located at Fullerton Avenue and Lake Shore Drive, Theater on the Lake is a historic building that offers breathtaking views of Lake Michigan and Chicago's skyline. Designed in 1913 and constructed in 1920, Theater on the Lake, is a Prairie style structure constructed in brick with sweeping steel arched pavilions throughout. Theater on the Lake offers 4 venue options as well as the opportunity of full use of the building. Polishing this existing jewel on Lake Michigan shore elevates it to the level of the other major iconic architectural gems. Theater on the Lake is a partnership between Lakefront Hospitality Group and the Chicago Park District. Located in the historic Theater on the Lake building at Fullerton, The Lakefront Restaurant is an upscale tavern with intimate tables, communal seating and a lounge area. Chef Cleetus Friedman presents seasonal Midwestern fare made with the freshest choice ingredients. While the beverage program highlights the craft beer and spirit scene with a diverse wine list of like-minded producers, Chef Cleetus will also utilize the venue to showcase his portfolio of beer and wine collaborations."
• Prime time performances Tues-Friday at 7:00 pm.
• 2019 season tickets are free, but attendees must reserve online ahead of time.
• 6.7 miles from hotel
"The Second City is an improvisational comedy enterprise and historically first on-going improvisational theater troupe, continually based in Chicago. It also has training programs and live theatres in Toronto and Los Angeles. The Second City Theatre opened on December 16, 1959, and has since become one of the most influential and prolific comedy theatres in the world. The Second City has produced television programs in both Canada and the United States, including SCTV, (SNL), Second City Presents, and Next Comedy Legend. Since its debut, The Second City has consistently been a notable starting point for comedians, award-winning actors, directors, and others in show business, including Bill Murray, Gilda Radner, John Candy, John Belushi, Dan Aykroyd, Del Close, Eugene Levy, Catherine O'Hara, Nia Vardalos, Ryan Stiles, Mike Myers, Steve Carell, Tina Fey, Amy Poehler, Stephen Colbert, and many others."
• Ticket prices range depending on show – General admission $25-$50
• About 4 miles from the hotel
"Meet at a downtown pizzeria & tavern to start your tour. Hear the history of tavern style pizza while devouring slices and a drink at the first stop. Our bus then picks you up and takes you through several neighborhoods where you’ll get the chance to literally eat your way through Chicago. You’ll sit down at pizzerias to sample a wide range of styles and toppings from some of the most accomplished pizzerias in the world."
• $80 per person
• 3.5 hours / Sat. nights @ 7 pm
• Start downtown and explore neighborhoods like Lakeview, Logan Square, and the Gold Coast
• Transportation is included for tour; Tour starts 0.5 miles away from Hilton Chicago Hotel
"See the city as you’ve never seen it before on our classic Lake Michigan boat tour. Enjoy stunning views of Chicago’s downtown as you cruise the coastline of one of the Great Lakes. Our Classic Lake Tours depart daily from Navy Pier, spring through autumn. Whether you’re local or visiting for the first time, taking in the striking views of Chicago’s skyline from Lake Michigan makes for a perfect day."
• 40-minute boat ride
• Departs at Navy Pier – 2 miles from the hotel
• Adults $23-$25, children $8-$10, infants free
• Spring through Autumn – April is weather dependent and typically only operates on Saturdays and Sundays
• Discount codes are available on website for $2 off adult and $1 off children
"Escape into Chicago's underworld on a crime and mob tour with stops off-and-on the luxury, climate-controlled bus. Some of the world’s most famous criminals, mobsters and gangsters bamboozled their way through Chicago. Explore several historic crime scenes by foot, including where Chicago gangsters John Dillinger and Hymie Weiss stood just before their deaths."
• Off and on bus tour
• 2 hours - Night tour starting at 8:00 pm
• $45.00 per person
• Starting location is 2 miles from the hotel
"Enjoy the best rooftop dining Chicago has to offer. The jewel in the crown of The Chicago Athletic Association Hotel, Cindy's is our rooftop restaurant and open-air terrace with panoramic views of Millennium Park,the Art Institute, Lake Michigan, and beyond. Created out of thin air, the aery atmosphere gives contrast to the Association’s history as a men’s club, yet carries an unmistakable look of having always been here. With seasonal freshness reflected in both food and drink, this Chicago restaurant truly offers some of the best cuisine while donning the relaxed ambience of a Great Lakes beach house with a view. Executive Chef Christian Ragano brings family style classic comfort food, bio-dynamic wines and award-winning cocktails with large format apothecaries."
• 0.6 miles from the hotel