Chicago Rooftop Cubs Game: Skybox on Sheffield

Buy me some peanuts and Cracker Jacks. I don’t care if I ever get back ’cause it’s Root Root Root for the Cubbies…

What’s a Rooftop, you ask? Why would you not just go to the famous, historic Wrigley Field? Well, here’s my take, and recommendation, on doing something different for game day: a Rooftop Cubs Game.

When I was 20, I distinctly remember coming to a Cubs game, enjoying a few at the establishments around Wrigley Field and saying, “I could totally live here when I move to Chicago”. Five years later, I could never live there. I love to visit Wrigleyville, but I would go crazy having to deal with Wrigleyville mayhem daily. It might be my age, my lack of tolerance for drunken 20-year-olds or the fact that I savor peace and quiet (damn you, upstairs neighbors), but my desire to live in the Cubs-obsessed, alcohol-induced, but ever-so-charming neighborhood of Wrigleyville are over. However, this past weekend, I enjoyed one of my best days in the neighborhood at a Rooftop Cubs Game through Skybox on Sheffield. Root root root for the Cubbies.


Outside view of Skybox on Sheffield (taken from my tour of Wrigley!)


Wrigley Field is centered in the middle of what on non-game days is a quiet, residential, neighborhood with a deeply loyal community. To this day, the Cubs play the fewest night home games than any other team out of respect for the Wrigleyville residents. The field is surrounded by apartment buildings crammed with young twenty-somethings and Cubs-lovers in each apartment, who eagerly await Opening Day (usually by drinking too much at the neighborhood bars or partaking in the weekly bar crawls that last a full 16 hours). Up until the 1980’s, those local residents would congregate on their roofops to get whatever glimpse or sound byte they could of those Cubbies during game days.

In the early 1990s, building owners got smart. They began building up their rooftops with stadium seating and started to charge attendees. The building owners were making full profit from their admissions, angering Cubs management who weren’t seeing any of it. So the dispute began. Like any typical Chicago debate, the buildings owners were petty and argued that they were just “having parties” on the rooftops and charging for the food and drink as part of the party package – that just so happened to occur every times there was a home game. The Cubs management passively responded by putting up wind tarps, blocking the rooftop-goers views of the game, claiming that it was “windy” for their customers. Passive turned to aggressive. Negotiations began and ultimately resulted in an agreement that the Cubs would receive 17% of the profit. Which, rumor has it, was about $5 million last year. Smart move, Cubbies.



The Wrigley Rooftops are a thriving business and a great way to experience a Cubs game, especially if you’re with a big group. Depending on what you would typically spend at a game, you can score an incredible deal on daily coupon sites such as Groupon ($60 for ticket and unlimited food/drink). Just make sure you buy the right one! I purchased to go with a group, but actually bought it for the wrong Rooftop. Each has a different name and many are run by different companies, so be sure to get the name right :). You don’t want to pull a Moyer. But huge shout out to Skybox on Sheffield for not making it a big deal and letting me right in anyways. I couldn’t have been more appreciative! You can also purchase directly on any of their sites – for this one.


Goose Island, one of the most well-established and loved Chicago-based breweries, specially brews three different beers just for the Skybox on Sheffield customers. These craft beers come with Cubs-themed names and definitely added to the experience. And, they were delicious! I’d go back just for the Skybox White, Cubby Blueberry and 424 Golden Ale, though there were other options as well. Beer and full bar included in the price of the ticket!

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The Four Goose Island Beers: Cubby Blueberry, 424 Golden Ale, India Pale Ale and Skybox White.


One of three, easily accessible bars. No lines, no hassle! And it’s already paid for – it literally feels free!


We started with tacos and mini soft pretzels, both scrumptious appetizers that definitely got us looking forward to the grill bar. While there were definitely lines for the grill station, the food was freaking fantastic.They had burgers, chicken burgers, pulled pork sandwiches, brats, hot dogs, and veggie burgers including “gluten free” options (no bun), multiple sides and were very generous with portions. I stuck with a bun-free burger that came with grilled onions, spicy aioli and side of corn black bean relish. Healthy but delicious options at a baseball game? Yes, please.


The grill bar. You had to wait in line, but the food was DELICIOUS.

You could even get a real, Chicago-style hotdog!


The boys chowing down.


From others’ experiences, Skybox on Sheffield is one of the fancier Rooftop options. It’s incredibly well done, and has a great mix of people. We loved our bartenders (thanks, Jaime!), and felt like there was a sophisticated, but fun feel to the box. The Rooftop had three different levels of seating – two outdoor and one indoor, which would have been incredibly convenient had it started raining.

Customer Service

As I mentioned earlier, I bought a ticket to the wrong Skybox. They let me in without a problem since someone in our group wasn’t attending and didn’t make it a hassle for me at all. For this, I am very grateful and believe that this is a true mark of great customer service. My stupid mistake aside, the bartenders and cooks were so outgoing, knowledgeable and seemed to really enjoy being there!

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Can you guess why the entrance stamp is 424? (Answer: the distance away from home plate!)

Bang For Your Buck

I thought it was absolutely worth the money we paid. You can find rooftop deals for anywhere between $60-$150, which you end up paying close to that between time spent at bars, the ticket price itself, the $8 beers and and $8 hotdogs. I rate this a GREAT bang for your buck, especially for travelers seeking fun city adventures in the United States.

Overall, I absolutely loved my Wrigley Rooftop experience and can’t wait to do it again. I would definitely go through Skybox on Sheffield, though I do want to try out some of the others! One looked like it had a dance party going on…maybe for a Saturday game :). If you’re in Chicago this summer, getting to Wrigley or a Rooftop for a Cubs game is a MUST!


Rooftop or Wrigley – what do you prefer?


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I'm Emily - a twenty-something female travel-enthusiast - here to serve and inspire you. Need help planning your next trip? Email me at emily [at] letsroamwild [dot] com and tag your own travel pics to share with the world @letsroamwild.

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