Redhead Piano Bar is a fun time with stiff drinks. There is no cover, so get to the party early. There is one piano player (no duelers here) singing fantastic covers and entertaining a crowd. The martinis are delicious and the vibe, while energetic, is still one where you can hear your friends talk.
The Second City is a must when visiting Chicago. They have various stages and shows but Depraved New World currently playing is hilarious and gives a bonus improv boost at the end. It’s a well-coordinated comedic sketch show that flows together well with lots of laughs. Although you can order food at the comedy club, Corcoran’s across the street is a good option as well.
Eno is a warm and welcoming wine bar right next to Michael Jordan’s Steakhouse which offers several tasty wine flights with decadent cheese and chocolate pairings. It’s the perfect spot to try for an afternoon treat or an early evening snack before an evening out. It is across from the highly suggested, but also hard to get into The Purple Pig, so a good suggestion if you don’t wish to wait.
Barrelhouse Flat is a perfect place for a delicious craft cocktail and a variety of tasty plates served late. Following the popularity of speakeasies popping up across the U.S., this place is not hidden but has the same Jazz Age flair. Plus, the service is spot on.
Other notable mentions are Wells on Wells, Suite Lounge, and Plum Market (for wine tastings) all located in Old Town in North Chicago. Also, The Gage is a lovely lunch place after a trip to the Art Institute.
Travel tip: Sign up for the hop-on/hop-off tour so that you can get to the good stops and plans your walks from the neighborhood you’re in. The buses pick up in several locations including right by ‘The Bean’ in Millennium Park and will take you around to Navy Pier (get your free bag of popcorn), Shedd Aquarium, Water Tower, Magnificent Mile, and Willis Tower just to name a few.
Have you been to Chicago? Share your favorite with me on Twitter: @mscourtneybeth using the hashtag #chicagotipsforCourtney!