TRAVEL

Best places for you to kick-back, relax, and enjoy summertime in Chicago

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Last week, I had the opportunity to visit friends in Chicago. Having lived in Texas for a couple years now, one forgets how nice summer can actually be in other parts of the country. 

Best places for you to kick-back, relax, and enjoy summertime in Chicago

Since I attended school in Chi-town (2009-2012), quite a bit has changed. Whereas, the concrete paths along the river, which often reeked of urine (much like several city blocks of San Francisco), were once an afterthought, now the newly renovated Riverwalk is a premier destination.

Best places for you to kick-back, relax, and enjoy summertime in Chicago
  • On the Water

City Winery

Last October, I completed my engagement trip at the City Winery on the Riverwalk. It was pretty cold and we were the last patrons to visit, before they shut down for the season. 

Even though there wasn’t any other clientele enjoying the vino, I could tell City Winery’s newest location was going to be a big hit. We ended up having so much fun with the Riverwalk to ourselves on that autumn Sunday, we missed our flight back home to Texas!

Best places for you to kick-back, relax, and enjoy summertime in Chicago

On our most recent trip to the Winery, we could barely grab a seat. And now they’ve introduced “River Domes” to protect its patrons from inclement weather. The patio is definitely dog friendly, but I’m not sure about the River Domes. 

Needless to say, my, how time have changed. The Second City is a town of constant evolution. After all, it is literally built on the ashes of its former self.

Best places for you to kick-back, relax, and enjoy summertime in Chicago

After revisiting the prime real estate and reminiscing over rozays on the Riverwalk, I was inspired to write about some more of my favorite patio spots in Summertime Chi.

Best places for you to kick-back, relax, and enjoy summertime in Chicago
  • For Views

J. Parker

The view from J. Parker’s rooftop patio is second to none – overlooking Lincoln Park and North Avenue Beach. The rooftop bar is located on top of the boutique Hotel Lincoln.

Best places for you to kick-back, relax, and enjoy summertime in Chicago
Best places for you to kick-back, relax, and enjoy summertime in Chicago

Cindy's Rooftop

Cindy’s Rooftop sits atop The Chicago Athletic Association Hotel. I had the opportunity to visit during Sunday brunch where a DJ spun for the day crowd. 

The place is definitely hip. I recommend going early as there will likely be a line in the hotel lobby.

Best places for you to kick-back, relax, and enjoy summertime in Chicago
Best places for you to kick-back, relax, and enjoy summertime in Chicago
  • For Chilling

Nomi Garden

“Bark Hyatt” aka the Nomi Garden on the seventh floor of Park Hyatt is one of my favorite dog-friendly patios. 

The only other luxury hotel I know of that is so accommodating to our four-legged friends is Hotel Van Zandt back home in Austin, Texas.

Best places for you to kick-back, relax, and enjoy summertime in Chicago
  • For Food

Carmine's & Tavern on Rush

Carmine’s and Tavern on Rush are located right next to each other in Viagra Triangle. Both spots harbor wonderful patio cafes to enjoy some good food and drink. And both locations are a short walk to Oak Street Beach. 

For my money, I believe Carmine’s provides some of the best bang-for-your-buck dishes in the Gold Coast.

Best places for you to kick-back, relax, and enjoy summertime in Chicago
Best places for you to kick-back, relax, and enjoy summertime in Chicago
Best places for you to kick-back, relax, and enjoy summertime in Chicago

Big Star

Big Star is one of my all-time favorite patios in the city. Great people watching. And of course, I love the fact that you can have your dog by your side while wolfing down tacos and margaritas

As a Texan resident, I can certify Big Star’s tacos are some of the best in the country.

Best places for you to kick-back, relax, and enjoy summertime in Chicago
  • For Happy Hour

Benchmark

When I lived here, I spent many happy hours at Benchmark in Old Town enjoying the open air through its retractable roof. It's always fantastic to catch a sunset here. If you can, try to visit before 11 P.M., as they close the roof at this time due to the local noise ordinance.

Best places for you to kick-back, relax, and enjoy summertime in Chicago

Best places for you to kick-back, relax, and enjoy summertime in Chicago

Steakbar

Nowadays, Steakbar (same owners as Benchmark), which is located right next door to Benchmark, may be the more popular destination for the avocado-toast-loving generation. Steakbar may not have a retractable roof, but it has a sidewalk patio and floor-to-ceiling windows on the second floor. 

Best places for you to kick-back, relax, and enjoy summertime in Chicago
  • For a Nightcap

Fountainhead

Many visitors to Chicago may never make it as far north as Ravenswood/Lincoln Square, but if you do, make sure to stop into the low-key beer and whiskey purveyor Fountainhead. I lived out this way during my school days so this bar was home base. 

But even if I hadn’t lived in this area, I would’ve made the trip just for their food

When I was a broke graduate student, I tended to order Anchor Steam, as it was randomly the cheapest beer on their menu. But now that I’m an alumni, saddled with student loans, nevermind, I’d still probably order Anchor Steam from this wonderful whiskey bar.

Best places for you to kick-back, relax, and enjoy summertime in Chicago
Best places for you to kick-back, relax, and enjoy summertime in Chicago

There's no place I'd rather visit in the summer than Chicago. Between the lake shore, the parks, the patios, and the people, Chicago transforms into a summer paradise from June to August. If it's your first time visiting, you have to try a deep dish pizza . Heck, even if you're a grizzled veteran, you can't leave the city without having a good slice of pie.

Best places for you to kick-back, relax, and enjoy summertime in Chicago

"Baby do you remember when / Fireworks at Lake Michigan / Oh, now I'm coming home again." - Kanye West

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Photo Credits:

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