Ashley HomeStore - Chicago

Embark on a journey back in time to the days of infamous mobsters like Al Capone, Bugs Moran, and John Dillinger with Untouchable Tours. This unique experience takes patrons to various famous areas in Chicago where notorious gangsters would hang out during the days of Prohibition. During the tour, you'll return to Prohibition-era Chicago and visit the hotspots where Al Capone and his allies and enemies became famous. The guides are actors who adopt the persona of a 1920s gangster and accurately recount the crimes and activities in Chicago during the 1920s and '30s. You'll hear about the exploits of Capone, Moran, Dillinger, and other notorious gangsters. Some sites included are the St. Valentine's Day Massacre, the Biograph Theatre, and Holy Name Cathedral. The tour is educational and highly entertaining, and you even have the chance to win prizes at the end.

The Empty Bottle sounds like an excellent spot to catch some live music. They offer affordable drinks, reasonable cover, and a fun crowd. It's interesting to note that the bar started as a cat-filled hole-in-the-wall in 1992 but later moved two blocks up the street to a slightly larger and better-equipped venue. They've been putting on great shows for the past 20 years and have managed to maintain their success thanks to their low prices, lack of attitude, and loyal customer base.

If you're looking for a romantic date spot in Chicago, consider ROOF on theWit. This lounge within the Wit Hotel offers a breathtaking city view from its outdoor patio and hangover space. Whether you're in the mood for steak or pizza, their dinner menu offers a wide range of delicious entrees. ROOF is a luxurious retreat that can be found on the 27th floor, offering unique hand-crafted cocktails, delectable cuisine, stunning views of the skyline, and vibrant design and entertainment. It has been crowned Hotel Bar of the Year by the Nightclub & Bar Awards and recognized by Travel+Leisure as one of the top 3 rooftop bars in the world. Guests can indulge in the finest acoustic music series, world-class DJs, and live runway shows.