Best of Chicago Roof Top Bars: Part 1

The summer in Chicago comes and goes way too fast. By the time the weather is consistently warm, fall is just a month a way. When it is a nice hot day in Chicago, you can rest assure every roof top bar in Chicago will be at capacity with locals enjoying their drinking time outside with a view. No matter which rooftop you might choose to climb, it’s a wise idea to get their early and expect a wait. Luckily a number of hotels and restaurants have expanded their business to the sky in the past decade and Chicago has some scenic rooftop bars with summer cocktails and great food. We’re going to focus on all the best rooftop bars Chicago has to offer. So grab your summer drink of choice and map out your Chicago roof top bar crawl.

Vertigo Sky Lounge

Vertigo Sky Lounge is geared more for the night club type of crowd. It is definitely in the “swanky” category, basically a club on a rooftop. This might not be for everyone, but luckily there are plenty other rooftops to choose from however, this roof top bar is the only year round indoor/outdoor lounge in Chicago.  In the summer time the fire pit is blazing. During the winter it’s the only outdoor rooftop in the city. We’re not exactly sure why people would put themselves through that, but we’re not here to judge only to blog. Each night features a different DJ. Since it does have the word “lounge” in it’s name, it offers it’s guests a lot of comfy chairs and couches to… you guessed it.. lounge around in. Like with most of the rooftop bars in Chicago, it can be tough to find a spot, so we recommend making a reservation and getting there early. Many of the negative reviews we’ve heard are in regards to the loud music. On the other hand some people really like the music. Again it depends on the type of vibe you’re interested in. The drink menu is pretty standard, and there is  a focus on bottle service if you’re that kind of baller.

View Pictures of Vertigo Sky Lounge
[Best_Wordpress_Gallery id=”22″ gal_title=”Chicago Roof Top Bars | Vertigo Lounge”]


This Peruvian restaurant is all about awesome food with a view. For the foodie who enjoys eating outside this is the place to be. All the items on the menu are focused on capturing the true Peruvian experience. Even the drinks are inspired by Peru. The Mixologist at Tanta create a menu of delicious cocktails inspired from Peruvian ingredients. Some of the signature cocktails include: Picso Sour, el piscolero, La Rusa, and Inca-nela. Be warned these cocktails are absolutely delicious, but are very strong. If we we’re to write about the food it would take us an entire post to do it justice. let’s just say the food holds up to the complex and delicious flavors the country of Peru has to offer.  Even if the wait for eating outside is ridiclous, eat inside because the food is worth it. The actual roof top offers a respectable view of River North, but isn’t very spacious, but the view is fantastic. The bar itself stays true to the overall South American theme.

View Pictures of Tanta
[Best_Wordpress_Gallery id=”23″ gal_title=”Chicago Roof Top Bar | Tanta”]

Fountain Head

Located where the Ravenswood, Lincoln Square and North Center neighborhoods meet, Fountainhead focuses on everything local. From the farms that produce the food to the distillers that make the liquor, Fountain Head strives to focus on where their products came from. In the about us section of the Fountain head’s website, their mission is to understand all the have to offer from the source. They have relationships with all their producers that provide them their product. The result is a menu based on serving meals at their peak time. Everything from food to drink is seasonal. Speaking of seasonal, let’s get back tot he point of this post. The rooftop bar is gorgeous. Further away from downtown, Fountain Head rooftop is more low key than the other bars mentioned in this post. Keeping up with the locally sourced vibe, the rooftop is called “Rooftop Garden”. Yes, thre is actually a garden up on the roof. Really ties the whole being outside and enjoying a nice day theme all together with that fresh flowers and plant smell.

View Pictures of Fountain Head
[Best_Wordpress_Gallery id=”24″ gal_title=”Chicago Rooftop Bar | Fountain Head”]


Located in the Near North Side neighborhood, Drumbar is all about the fancy cocktail. It has the look and feel of an old school speak easy bar. Leather couches and chairs, even the menus are made out of leather. The bar reminds you of Ron Burgundy saying “Rich Mahogany”.  The title of their website is ” A Legal Drinking Establishment” keeping up with the speak easy atmosphere. Sip on some fancy hand crafted cocktails made by professional mixologists and feel like your in an episode of Madmen. The cocktail menu can be a bit overwhelming, but we’ve heard the following are the drinks to try: Another Man’s Rhubarb, Chico Guapo and  ooo! What’s That? (the name alone would make us order it). Since this bar is located right off Michigan Avenue, it can be a little difficult to land a table or place to sit. So once again we really recommend getting their early and expecting to wait a little while. Also, for the price conscious traveller (this is a hostel website after all) this might not be the most ideal spot as the drinks are on the pricey side. Delicious specialty drinks come with a price unfortunately.

View Pictures of Drumbar
[Best_Wordpress_Gallery id=”25″ gal_title=”Chicago Roof Top Bar | Drumbar”]

Roof on the Wit

Located in Downtown Chicago, Roof on the Wit is the winner of best view in our opinion. To be fair it does have the advantage of being located  right off the Chicago river. Much like Vertigo Lounge, the Roof on the Wit is all about the social scene.  It got #1 in the 2015 Nightclub & Bar top 100 for Chicago and #26 in all the USA as rated by That should really let you know this isn’t the spot for a nice quiet casual drink, but more for those who like a lively energetic crowd.  Like Vertigo Lounge they have live DJ performances each night. During the day it’s more laid back and quiet, so if you want to get a great view of the Chicago River and sip your poison of choice in a more low key style, head over in the early after noon. They open at 2 p.m. every day of the week. Just in case you want some food with your bottle service, they offer bite sized dishes of all kinds including oysters, dips, and sliders.

View Pictures of Roof on the Wit
[Best_Wordpress_Gallery id=”26″ gal_title=”Chicago Roof Top Bar | Roof on the Wit”]
Gene’s Sausage Shop & Delicatessen

Alcohol isn’t the only thing that goes well with rooftops, specialty meats and rooftops are an awesome summer match. Gene’s Sausage Shop has a fantasic roof top where patrons can enjoy cold adult beverages and preservative free dried meats and Bratwursts. Similar to Drumbar, Gene’s rooftop is surrounded by gardens that grow herbs and tomatoes that are actually used in the menu. You can’t have grilled meats and warm weather without beer. Gene’s has a wide variety of beers on tap and are constanlty changing out the rotation. They have 7 different kinds of Bratwurst, this place is essentially summer on a roof. It’s pretty far from downtown in the Lincoln Square neighborhood, so your chances of getting a table in a timely manner are a little higher. For like the 50th time in this post we emphasize that on a a nice day any roof top will be very full, so be prepared for a wait. Patience is a virtue especially in Chicago during the summer.

View More Pictures of Gene’s Sausage Shop