Whether you are looking for food, drinks, dancing or just lounging, you can bet there is a rooftop in Chicago that has exactly what you want. In a city that savors our warm months (there aren’t many), we have to have plenty of rooftop options to make sure everyone who wants to be on one can be. And even though there have always been a lot of rooftop choices in Chicago, it seems like there are more and more each week. It makes sense! If you live in the city, it’s the perfect escape from the craziness at street level, and if you are visiting, it’s the best way to take in the amazing views that Chicago has to offer. With so many options, it can be daunting to find the right one for you, but this list will help you pick the perfect spot.

1. Cindy’s Rooftop: If you are going for the “see & be seen” type of rooftop, Cindy’s is it. It’s been a hot spot in Chicago for the past few years, for a number of reasons. It sits on Michigan Avenue, across from Millenium Park in Chicago’s Loop, and has impeccable views of Lake Michigan and the Chicago skyline. It sits atop the newly renovated Chicago Athletic Hotel, which is a pretty cool place in and of itself. Be forewarned, this place is crowded at most times of the day (reservations are a good idea) and drinks and food are a little pricey. It’s worth it though, I promise. 
2. Devereaux Chicago: This rooftop has it all. A hip party scene during the day (pool included) and a sleek trendy scene at night. Devereaux is located in Chicago’s Gold Coast neighborhood and sits atop the Viceroy hotel. It’s a space used by hotel guests, other tourists and locals, which makes for a fun crowd. While they do have a pool, which is great for those hot summer days, I don’t suggest bringing the kiddies. It’s definitely an adult crowd ready to drink and relax. The cocktails and food are both good, even though (again) a little on the pricey side. (It’s Chicago – you just have to get used to spending $16 for a nice drink.) 
3. the J. Parker: This rooftop is definitely more of a chill locals scene. It’s located in Chicago’s Lincoln Park neighborhood, so it’s a little off the beaten tourist path. It sits atop yet another hotel, the Hotel Lincoln – which is adorable and very kitschy. It may not be in the heart of the city, but that is probably why it has the best views. You get to see the entire skyline (Lake Michigan and the Lincoln Park zoo included) completely uninterrupted. If you are avoiding crowds, I recommend going in the early afternoon during the week. If you are seeking a crowd, Saturdays and Sundays, during the day, are where it’s at. 
4. Wrigleyville Rooftops: If family fun is what you seek, don’t be discouraged, there are lots of rooftop options for you. Head north of the city to Wrigley Field to take in a ball game. But, you don’t have to settle for the stadium experience. You can get above the cheering fans and watch from a birds eye view. Wrigleyville Rooftops actually consists of multiple properties lining two sides of Wrigley Field. Most are all inclusive, meaning you get your “ticket” to watch the game, plus unlimited food and drink. It’s a fun way to watch a classic baseball team, while enjoying a great view of the city and an unforgettable rooftop experience. 
5. Terrace 16: You are probably sensing a theme, as I tell you that Terrace 16 also sits atop a hotel. (Apparently that’s hot real estate in Chicago!) This time it’s the Trump Hotel, literally in the center of the city. Despite whether you have a positive or negative view about the man whose name is on the building, Terrace 16 is an incredible spot. The views are unparalleled – looking north (toward’s Michigan Avenue), south (towards the Loop) and east (towards the river and lake). It’s a great spot to take out of town visitors to really wow them with the city. The drinks are great, the food is yummy and the prices, well you guessed it, high. But it’s worth it for the incredible views. My recommendation: come early on a Wednesday or Saturday evening, and stay for the fireworks show. Best view of the twice weekly fireworks show in the entire city.

   

Well, what are you waiting for? Go up on the roof and enjoy summertime in Chicago!

Signed with Style,