Best Chicago Happy Hour Specials

The nice and hot summer weather is back in Chicago and you’re looking for a place to cool down or maybe grab a few drinks at. Summer time is no stranger to a good Chicago happy hour special. With so many different places to pick from, where should you start your happy hour adventure? Well, grab a few friends and get ready to enjoy some of the best Chicago happy hour specials that you could find this summer!

Monday Night Sunset Cocktail Cruise

Have you ever sailed around the city for your Chicago happy hour celebration? If not, then you need to try out this Monday night happy hour cruise on board the Anita Dee II! This cruise will sail you around Chicago giving you the best views of the city that you won’t get anywhere else. Order up all the drinks that you want at one of the full-service cash bars on board. Enjoy drinks, great company, and a view while you sail throughout Chicago with one of the best happy hour plans you could find. No other happy hour event is going to treat you to an experience while giving you views of the amazing windy city. Don’t miss out on this great cruise and give your Monday nights an upgrade!

Tuesday Night Chicago Happy Hour Cruise

If Monday night doesn’t look too good for you, then check out this Tuesday night happy hour cruise also on aboard the Anita Dee II! Don’t settle for the typical Tuesday night plans and enjoy your night aboard this happy hour cruise. This cruise is going to sail you around Chicago aboard a multileveled yacht and give you amazing views of the city. View the Chicago skyline as the sun sets and see the city’s biggest landmarks as you sail. While you sail, you will be able to order as many drinks as you like from one of the full-service cash bars on board. Complete this happy hour cruise by heading to the outside deck and snapping pictures of the city as you sail along creating unforgettable memories with your friends. Make this summer one to remember by hopping aboard this Tuesday night cruise!

Brando’s Speakeasy

Come out to one of Chicago’s best karaoke bars and enjoy their happy hour specials and a large selection of songs to perform. At Brando’s Speakeasy, you will be able to select from over 300,000 songs to perform. Sing out loud and grab some drinks as you relax in this comfy bar. Brando’s happy hour goes on every Monday through Thursday from 5 pm until 7 pm and gives you a huge variety of items to pick from.

From $5 to $3 drink specials and half price brewery beer, Brando’s Speakeasy is going to quench your thirst no matter what you’re craving. Not only will you able to purchase cheap drinks, but you can also enjoy Brando’s $3 flatbreads and pizzas as well as $5 cheese and meat trays! This Chicago happy hour is going to take care of your after work drinking needs.


If you want to enjoy a Chicago happy hour that’s a bit later, then check out the happy hour going on at drumBAR. This rooftop bar is located on the 18th floor of the Raffaello Hotel in Chicago’s Gold Coast neighborhood. This moody yet energetic bar has an intimate indoor lounge area and a beautiful outdoor terrace with views of Lake Michigan and the Hancock building. At the drumBAR, you can enjoy their daily happy hour special from 8 pm until 10 pm that offers $8 select cocktails and $8 champagne! You can enjoy drumBAR’s happy hour special on any day you want so make sure to grab some friends and head out to this rooftop bar to start your night. The drumBAR was also voted the best rooftop bar in Chicago in 2012, so you know you’re in for a great time!

Lowcountry & Clark Street Karaoke Bar

Located beneath the Southern seafood restaurant Lowcountry, Clark Street’s Karaoke Bar offers up a great happy hour special. As long as you’re at the bar, everyday is happy hour before 7 pm with a food purchase! While you enjoy some of the great dishes offered, you can also enjoy half priced drafts and cocktails as well.

Sample some of the best Southern seafood that you could find in Chicago and enjoy a couple of drinks with your friends to start your day. Once you’re full of food and drinks, check out one of the karaoke rooms. Sing your heart out to one of the many songs available in one of the five different private karaoke rooms available. This karaoke bar is one of the best karaoke bars that you could find in Chicago with an amazing happy hour special!

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