Chicago

Savor Summer at Chicago’s Essential Waterfront Restaurants

Pretend like you're vacationing on the coast.

Photo courtesy of Pizzeria Portofino
Photo courtesy of Pizzeria Portofino
Photo courtesy of Pizzeria Portofino

Nothing beats summer in Chicago. The al fresco dining is arguably what leads to the locals’ winter amnesia. But thanks to the Chicago River and Lake Michigan, the city gives guests the opportunity to transport themselves to another world. Along the shimmering water, under a shaded corner, winter (and the last two years spent inside) feel like a distant memory. Take advantage of the city’s unique topography at one of the 15 best places to enjoy the water. Make a reservation whenever possible and plan around the fireworks.

Photo courtesy of Robert's Pizza & Dough Co.
Photo courtesy of Robert’s Pizza & Dough Co.
Photo courtesy of Robert’s Pizza & Dough Co.

Robert’s Pizza & Dough Co.

Streeterville
$$
Somehow the chaos of a noisy downtown evaporates when you make your way to the dining area for Robert’s Pizza & Dough Co. Besides having one of the best pizzas in the city (a brick oven-baked, thin-crust evolved from its owner’s 20 year-old obsession to fine tune his dough recipe for the ultimate crust) its subtle ambiance will leave you wanting more. The restaurant is located on a beautiful, tree-lined terrace and bordered by the Chicago River where boaters can pull up to to pick-up their food. The restaurant boosts plenty of indoor and outdoor seating. Its patio is dog-friendly and if you dine in on Wednesday or Saturday evening in the summer, you’ll catch the dazzling display of fireworks from Navy Pier.

Bar Mar by José Andrés

Loop
$$$
Located in the heart of Chicago’s downtown business district, Bar Mar is the upscale dining the area needs. Come with work colleagues, girlfriends or make it a trip to see and be seen. Its high, airy ceilings bring complimentary light and energy to a modern menu focused on surf and turf. Expect classics like fried calamari, lobster rolls and ceviche at Chef Jos√© Andr√©s’ newest restaurant in Chicago.

Pizzeria Portofino
Pizzeria Portofino
Pizzeria Portofino

Pizzeria Portofino

River North
$$
Don’t let the name deceive you. Pizzeria Portofino is more than just a pizza place. It offers a number of seafood and pasta dishes, inspired by its Italian namesake. The restaurant is located on a busy stretch of real estate that’s perfect for people watching (on land and water). Guests arriving via water can park their boat at the restaurant or pull up and carry out directly onto their boats from the Marina Menu.

Photo courtesy of Cielo Rooftop at Azul
Photo courtesy of Cielo Rooftop at Azul
Photo courtesy of Cielo Rooftop at Azul

Cielo Rooftop at Azul

Near North Side
$$
Cielo Rooftop at Azul is one of the city’s largest open-air rooftops and perfect for big groups. The Latin American inspired bar and restaurant features views of the Chicago skyline on one side and views of the Chicago River on the other. The waterfront bar offers a seafood focused menu by Chef Michael Hernandez that includes lobster empanadas, street tacos and ceviche.

Photo by Troy Walsh
Photo by Troy Walsh
Photo by Troy Walsh

The Kitchen

River North
$$
The Kitchen’s expansive indoor and outdoor dining space offers killer views of the Chicago River alongside an international-inspired menu by Chef Michael Bertozzi. Its farm-to-table options include a foie gras burger, a mortadella melt with pistachio gremolata and swiss fondue; and tuna tiradito with yuzu kosho, avocado and cilantro. Their drink menu is designed for slow slips on a hot summer day and includes non-alcoholic options.

Theater on the Lake - Restaurant/Events/Theater
Theater on the Lake – Restaurant/Events/Theater
Theater on the Lake – Restaurant/Events/Theater

Theater on the Lake

Lincoln Park
$$
Enjoy a breezy and breathtaking view of the City at Theater on the Lake. The upscale bar has a number of indoor and outdoor options where you can watch runners, bikers and walkers enjoy the lakefront path-while also keeping an eye on how well your favorite Chicago sports team is doing. Gaze directly east and you’ll be hypnotized by the lake’s rolling waves. Turn south and watch the sky change behind a skyline that includes the iconic Hancock building. The menu includes burgers, brisket and chicken tacos. Expect local craft beers, spirits and wine on the drink menu.

Reggie’s on the Beach

Jackson Park
$$
Most of the city’s waterfront dining is concentrated on the Northside. However, Reggie’s on the Beach is doing something about that. The Southside bar brings its seasonal offerings to the 63rd Street beach. The music venue and eatery serves up wings, burgers, and blackened catfish salad alongside a number of free shows. Every Thursday and Sunday night, guests are treated to the sounds of reggae, blues, jazz, funk and jam. Guests can even rent a jet ski, kayak or paddleboard from the beachfront locale. Seating is first come, first serve.

Small Cheval
Small Cheval
Small Cheval

Small Cheval Riverside

Loop
$$
Au Cheval in the West Loop gave the city one of its best burgers. Its sister restaurant, Small Chevall, allows more people to experience the juicy and decadent burger via its riverfront location. The no frills counter gives guests the opportunity to dine indoors, complete with views of the river, or grab and go where they can find their own cozy spot on the riverwalk to enjoy their meal. The tiny outpost is quintessential Chicago-everything you need without the hassle.
Reservations not accepted.

River Roast
River Roast
River Roast

River Roast

River North
Whether you’re out for a midweek patio power lunch or an alfresco date night, executive chef Cedric Harden’s expansive riverside tavern is a must-try outdoor dining experience during the summer months. Small bites like buttery shrimp and crab brioche toast piled with ripe avocado and shrimp mousse and pork meatballs swimming in tomato sauce, spicy giardiniera, pillowy ricotta gnocchi set the stage for the main event: one of the restaurant’s substantial roasts, carved table-side and dressed to impress.

Chicago Cut Steakhouse
Chicago Cut Steakhouse
Chicago Cut Steakhouse

Chicago Cut

River North
$$$$
Stop by this stylish chophouse for breathtaking riverfront views and perfectly seared USDA Prime steaks (or the vegan vegetable risotto) to match. The timeless hideaway and adjoining open-air patio is a favorite among local celebrities and other big shots-if you’re lucky, that juicy, dry-aged Delmonico might even come with a star sighting or two.

City Winery Chicago Riverwalk
City Winery Chicago Riverwalk
City Winery Chicago Riverwalk

City Winery Chicago Riverwalk

Loop
This festive downtown outpost is positioned directly along Chicago’s riverwalk and comes outfitted with plentiful umbrella-shaded seating for comfortable outdoor dining and imbibing. Score wine through the concept’s unique tap system, and dine on a curated lineup of gourmet sandwiches and salads and a rotating selection of sorbets and gelatos to help you stay cool.

Riva
Riva
Riva

Gibsons Italia

West Loop
Sleek contemporary stylings, cheffy housemade pastas, high-end chops flown in farm-fresh from Australia and Japan, and a postcard-perfect waterside setting combine to make this one of the Windy City’s top upscale dining destinations. Consider this date night gold.

RPM Seafood
RPM Seafood
RPM Seafood

RPM Seafood

River North
Lettuce Entertain You Enterprises’ sprawling, multi-level seafood emporium debuted to much fanfare just before the pandemic and has flung open their gleaming riverside doors yet again, welcoming Chicagoans back with safely spaced open-air seating and a plethora of culinary delights. Look for a finely stocked raw bar, sushi grade tartare, and a surf and turf combo for the ages: hand-cut Creekstone filet paired with plump Alaskan King Crab.

Beatnik West Town
Beatnik West Town
Beatnik West Town

Beatnik on the River

Loop
The downtown offshoot of the popular West Town hangout mirrors its sister location’s bohemian-chic vibe with a bounty of lush greenery, Mediterranean-accented cosmopolitan fare, and vibrant, loungey decor. Add a sundrenched patio with plenty of room, a shimmering riverside backdrop, and a cooling breeze and you’ve got your new brunchtime no-brainer.

Metropolitan Brewing
Metropolitan Brewing
Metropolitan Brewing

Metropolitan Brewing

Avondale
Head up north and grab a seat on this friendly neighborhood taproom’s inviting patio to experience house-brewed beer done right: crisp German-style lagers served along a quiet stretch of the Chicago river with a side of good, old-fashioned fresh air. Food is BYOB — takeout and delivery options abound — and adventurous drinkers are more than welcome to ditch the wheels and paddle on over instead, hitching up their kayak to the adjoining pier before grabbing a well-deserved cold one.Want more Thrillist? Follow us on Instagram, Twitter, Pinterest, YouTube, TikTok, and Snapchat.

Ximena N. Beltran Quan Kiu is a Thrillist contributor and communications specialist based in Chicago.

Chicago

Robyn DaCultyre Is Doing It for the Culture

"The cool thing about Ohio is that there is literally a place for everyone."

Photo by Kayode Omoyosi
Photo by Kayode Omoyosi
Photo by Kayode Omoyosi

I was introduced to Robyn DaCultyre at an Untitled Queen show at C’mon Everybody in late January, and it was one of the most unique drag shows I’d seen in a while. Afterwards, I tracked down this self-described “drag creature” and video chatted about her drag origin story, the state of drag in her native Ohio, and the dual identities that make up her persona. Thrillist: I want to ask you about how Robyn DaCultyre came about and your point of view behind your performance.

Robyn DaCultyre: I’ve been travelling around the country from a young age in ministry and Christian studies. I moved to Chicago right after high school. Four years later, moved back to Columbus and decided I didn’t really want to do church anymore; that wasn’t where my heart was.

I had a really low point in my life and had a suicide attempt and then really found drag and started doing drag as a coping mechanism and way to let off steam. I started in July of 2019, and it was really a lot of punk and metal music. I created this drag creature of sorts and they were really out of this world and celestial and all of those fun alien type terms.

And then we went into a global pandemic and I had a lot of time to figure out who I wanted to be. Digitally I was still doing a lot of drag creature-esque numbers and all of that, but I had this moment where we’re on the front lines getting hit with pepper spray and rubber bullets and pepper spray-all of those lovely things. And I said, I have this platform and I need to start showcasing what’s happening.

Untitled [Queen] stepped in at the right time and messaged me and said, “I’m doing this show for Independence Day called Untitled in America with 52 different performers and I want you to be a part of it.” It was at that moment I was able to take the footage I had been recording on the front lines and incorporate it into digital content. I did a song called Black Like Me by Mickey Guyton that talks about white picket fences, but if you want to see how America is, then you should try being Black like me. The imagery of what’s literally happening in Columbus in that digital performance really spearheaded me into focusing on people who look like me.

Nina Simone is one of my biggest inspirations, and one of her quotes that resonates with me is that it’s the duty of the artist to resonate with the times. My art is politically charged. I like to entertain, but there will definitely be a time when you come to a show expecting to have your drink and be chill and that might not be the case.

How did the name Robyn DaCultyre come about?

I was smoking with Ursula Major, who was on season one of Dragula, and the first time I introduced myself to her I was Robyn Banks, which is my drag name originally. She said, “Well, do you just not want to be original at all?” [Laughs] And I sat with that for a couple of months, and I got really stoned one day and was listening to Janelle Monae, and she talks about doing it for the culture, and I said “I do it for the culture, too!” And the rest is history.

And you started a series called Melanated.

We started Melanated last February. I told the idea to my show director that there were no shows specifically run by Black people that only featured Black entertainers. I wanted to do this show for a night and she said, Why don’t we do it once a week for the whole month? The first show happens, and it’s a sold out crowd, and [my director] comes back and says we should do this every month. So I sucked it up and here we are a year later.

Melanated is the only fully Black show in all of the state. It’s a horrible marketing tool and not something I want to promote, but it is just a fact. It amazes me that we are the 13th largest city in America and there’s nothing here that’s fully focused on Black entertainers. The name also comes from Janelle Monae; she says she’s highly melanated and I said, that works.

Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)

You refer to yourself as a drag creature, as opposed to drag queen or king…

This is actually the first time I’m making this public. I am in this place where I want to separate the alternative creature from who this melanated goddess or whatever is. DaCultyre is definitely the person who runs Melanated and then Robyn is this drag creature that is out of this world and really loves punk and alternative music. And both intertwine to make Robyn DaCultyre.

You also do pageants. Tell me about that.

In 2020 I was appointed by Nina West, who is from Columbus, as the representative from Ohio for National Entertainer of the Year in Louisville, Kentucky. I placed ninth out of 13 contestants and I really fell in love with the system and fell in love with the pageantry and loved the idea of reigning and being different. I want to show that we as alternative performers, as bearded performers, you can come into these systems and shake things up.

Is there a uniquely “Ohio” style of drag?

No, and I think that’s one of the things that makes it so amazing is that everyone has their own unique style, and it’s all pretty much accepted. I started as a performer and a drag creature and there was space that was afforded to me and I transitioned to more glamor and pageantry and that’s afforded to me as well. I’ve been a bearded entertainer for a year now. The cool thing about Ohio is that there is literally a place for everyone.

I think I have everything I need. Is there anything else I didn’t ask you about that you want to bring up, or‚Ķ

I don’t think so. Are there any generic questions you haven’t asked?

Generic questions‚ĶI think I asked all of them already [laughs]. I like to ask what you’d be doing if you weren’t doing drag?

It’s a great question. I have a day job that is very demanding so I need drag to get away. I’m also very creative and artistic. I used to do web design and all these other things to pull into my creativity. Drag is the longest thing I’ve stuck with in all parts of my life, so I don’t think it’s going anywhere anytime soon.

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John deBary¬†is a drinks expert and writer. His first cocktail book,¬†Drink What You Want, is available now, and his next book,¬†Saved by the Bellini, is expected in early 2023. He is also the co-founder and president of the¬†Restaurant Workers’ Community Foundation, which is dedicated to improving the lives of hospitality industry professionals through advocacy, grant making, and impact investing.

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