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Chicago’s Top Spots for Dinner and a Show

No need to overthink plans — find food and entertainment under one roof

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For many, the idea of heading out to a sprawling venue with hundreds or thousands of people in attendance for a concert or theater performance is still a little overwhelming. A more intimate setting, with comfortable seats and some good food and adult beverages, is a better option.

Some of the best meals in Chicago may be enjoyed at establishments specializing in dinner and a show. From contemporary burlesque performances to live blues, country, Latin, or soul, the entertainment matches the eats for a well-rounded night out at the following destinations.

As of June 11, Chicago restaurants have fully reopened and the city has lifted restrictions on capacity, masking, and social distancing. For updated information on coronavirus cases, please visit the city of Chicago’s COVID-19 dashboard. Studies indicate that there is a lower exposure risk when outdoors, but the level of risk involved with patio dining is contingent on restaurants following safety guidelines. The latest CDC guidance for vaccinated diners during the COVID-19 outbreak is available here; dining out still carries risks for unvaccinated diners and workers. Find a local vaccination site here.

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Artango Bar & Steakhouse

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Situated in a busy little corridor of Lincoln Square, this Argentine-focused steakhouse is for certain aiming to be on your hot list for date night. Artango is decadent with its romantic aura; the lights are low, the tables are candlelit, and the soundtrack is always South American. On weekends, that soundtrack comes alive as Argentine musical duos or trios take up space at the entrance, welcoming in guests. On the menu: ceviche, slow-grilled steaks, seafood paella.

Dorian’s

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Note: Dorian’s has remained closed during the pandemic. Ownership hopes to reopen in mid-July.

Part live music venue, part restaurant, part...record store? Dorian’s is a unique find in Bucktown. While you’re waiting to be admitted into the lounge, peruse the well-curated vintage vinyl selection ranging from Elvis to Ella Fitzgerald. Inside, the intimate space is lively with blues, jazz, or R&B shows Thursday through Saturday. The food is meant to share: Choose from chicken bao, mushroom won tons, chicken liver mousse, and cheese and charcuterie. Expect a new menu when the venue reopens.

Dorian’s could reopen in July.
Barry Brecheisen/Eater Chicago

Bordel | Cabaret & Cocktail Bar

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Pre-pandemic, this sexy Wicker Park hang had gotten so hot that Hamilton performers dropped by on the regular for impromptu performances. The cabaret-style Bordel, with its secret entrance, lush red booths, and enticing dance music, is still quite tempting with a variety of acts that are mostly Spanish influenced. Flamenco dancers, burlesque performers, and bands are the main attraction. Just be prepared for showtime to happen at any time. The food menu is provided by the downstairs Mama Delia marketplace and café. There are a variety of conservas and imported hams from Spain for noshing.

Bub City

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Every Wednesday is live-band karaoke at Bub City, the country-western barbecue restaurant resuscitated from Lincoln Park to River North by Lettuce Entertain You Enterprises. The original location opened near Halsted and North more than 25 years ago, and when LEYE decided to reopen it, they added the live music component courtesy of Joe’s on Weed Street owner Ed Warm. The menu has been updated as well with offerings such as baby-back ribs, pulled-pork shoulder, and a house-made pastrami sandwich. There’s also a suburban Rosemont location.

Andy's Jazz Club & Restaurant

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This River North venue dates back to the 1950s and had earned a reputation as one of the best places to listen to jazz in the city. At one point, Andy’s was an after-work haven for Sun-Times and Tribune staffers, but golden age of newspapers has past. The food does not take center stage here; the music is the undisputed queen. Dining is reservation only, and while the chops and salads aren’t memorable, the overall entertainment package makes Andy’s notable. 

Untitled Supper Club

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This upscale dining destination certainly feels like it belongs in another era. Specifically, it aims for a Prohibition-era vibe with its attention to detail in each of its featured rooms, from the cabaret lounge to whiskey bar featuring one of the largest selections in the Midwest. As far as entertainment, catch a weekly peek at “Unbridled,” the risqué burlesque show, or sit back and be entertained by local bands performing blues, jazz or soul. The cuisine is globally influenced with offerings such as house-made pastas, grilled branzino, steaks, and chicken Milanese. 

City Winery

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Prince’s last Chicago show was at City Winery and that alone serves as this West Loop venue’s claim to fame. Yes, it’s hosted many other famous artists, but no one on that level. This place showcases every genre under the sun, and the most popular shows are by neo-soul, jazz, blues, and folk artists. The food menu in the music hall is just as varied albeit an abbreviated version from the restaurant. There’s burrata & prosciutto flatbread, plus steak frites, duck tostadas, and mushroom and goat cheese risotto balls. They’ve made the task of choosing simpler for finicky diners by adding a prix-fixe food and wine pairing option. 

The Darling

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We don’t want to spoil all the cool little surprises the Darling has in store for you once you’ve entered the hidden library for drinks and dinner. It’s on the first floor of this two-level West Loop building, and it’s quite the tempting gem. Burlesque performers appear spontaneously, and their costumes are so elaborate that you’ll feel underdressed no matter what you’re wearing. That’s only half the fun. The other half is experiencing the elaborately dressed cocktails as well as indulgent, shareable platters of seafood, flatbreads, or miniature desserts.

Babygold BBQ

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El Che Steakhouse owner/chef John Manion teams up with the famed FitzGerald’s venue to open his first barbecue joint. Adjacent to FitzGerald’s, BabyGold BBQ is family friendly with grilled meats and vegetables (brisket, baby-back ribs, barbecue-spiced cauliflower), a smoked shrimp salad po’boy, char-grilled oysters, and cornbread topped with cajun honey butter. There’s live music daily — sometimes free and for all ages — ranging from blues to alt rock.

Babygold BBQ is part of FitzGerald’s.
Barry Brecheisen/Eater Chicago

Pier 31 Restaurant

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Summertime is when this South Side venue reigns for its lineup of jammin’ bands and deejays on its festive back deck facing Margaret Taylor Burroughs Beach. There’s reggae every Saturday afternoon, and guests are also treated to salsa, old school R&B, jazz, and more. There is excessive dancing, too, so it can get a little intimidating, but it’s also fun to watch the action from your table. Sustenance includes grilled burgers, a Chicago-style hot dog, salmon burger, and chipotle black bean burger.

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Artango Bar & Steakhouse

Situated in a busy little corridor of Lincoln Square, this Argentine-focused steakhouse is for certain aiming to be on your hot list for date night. Artango is decadent with its romantic aura; the lights are low, the tables are candlelit, and the soundtrack is always South American. On weekends, that soundtrack comes alive as Argentine musical duos or trios take up space at the entrance, welcoming in guests. On the menu: ceviche, slow-grilled steaks, seafood paella.

Dorian’s

Note: Dorian’s has remained closed during the pandemic. Ownership hopes to reopen in mid-July.

Part live music venue, part restaurant, part...record store? Dorian’s is a unique find in Bucktown. While you’re waiting to be admitted into the lounge, peruse the well-curated vintage vinyl selection ranging from Elvis to Ella Fitzgerald. Inside, the intimate space is lively with blues, jazz, or R&B shows Thursday through Saturday. The food is meant to share: Choose from chicken bao, mushroom won tons, chicken liver mousse, and cheese and charcuterie. Expect a new menu when the venue reopens.

Dorian’s could reopen in July.
Barry Brecheisen/Eater Chicago

Bordel | Cabaret & Cocktail Bar

Pre-pandemic, this sexy Wicker Park hang had gotten so hot that Hamilton performers dropped by on the regular for impromptu performances. The cabaret-style Bordel, with its secret entrance, lush red booths, and enticing dance music, is still quite tempting with a variety of acts that are mostly Spanish influenced. Flamenco dancers, burlesque performers, and bands are the main attraction. Just be prepared for showtime to happen at any time. The food menu is provided by the downstairs Mama Delia marketplace and café. There are a variety of conservas and imported hams from Spain for noshing.

Bub City

Every Wednesday is live-band karaoke at Bub City, the country-western barbecue restaurant resuscitated from Lincoln Park to River North by Lettuce Entertain You Enterprises. The original location opened near Halsted and North more than 25 years ago, and when LEYE decided to reopen it, they added the live music component courtesy of Joe’s on Weed Street owner Ed Warm. The menu has been updated as well with offerings such as baby-back ribs, pulled-pork shoulder, and a house-made pastrami sandwich. There’s also a suburban Rosemont location.

Andy's Jazz Club & Restaurant

This River North venue dates back to the 1950s and had earned a reputation as one of the best places to listen to jazz in the city. At one point, Andy’s was an after-work haven for Sun-Times and Tribune staffers, but golden age of newspapers has past. The food does not take center stage here; the music is the undisputed queen. Dining is reservation only, and while the chops and salads aren’t memorable, the overall entertainment package makes Andy’s notable. 

Untitled Supper Club

This upscale dining destination certainly feels like it belongs in another era. Specifically, it aims for a Prohibition-era vibe with its attention to detail in each of its featured rooms, from the cabaret lounge to whiskey bar featuring one of the largest selections in the Midwest. As far as entertainment, catch a weekly peek at “Unbridled,” the risqué burlesque show, or sit back and be entertained by local bands performing blues, jazz or soul. The cuisine is globally influenced with offerings such as house-made pastas, grilled branzino, steaks, and chicken Milanese. 

City Winery

Prince’s last Chicago show was at City Winery and that alone serves as this West Loop venue’s claim to fame. Yes, it’s hosted many other famous artists, but no one on that level. This place showcases every genre under the sun, and the most popular shows are by neo-soul, jazz, blues, and folk artists. The food menu in the music hall is just as varied albeit an abbreviated version from the restaurant. There’s burrata & prosciutto flatbread, plus steak frites, duck tostadas, and mushroom and goat cheese risotto balls. They’ve made the task of choosing simpler for finicky diners by adding a prix-fixe food and wine pairing option. 

The Darling

We don’t want to spoil all the cool little surprises the Darling has in store for you once you’ve entered the hidden library for drinks and dinner. It’s on the first floor of this two-level West Loop building, and it’s quite the tempting gem. Burlesque performers appear spontaneously, and their costumes are so elaborate that you’ll feel underdressed no matter what you’re wearing. That’s only half the fun. The other half is experiencing the elaborately dressed cocktails as well as indulgent, shareable platters of seafood, flatbreads, or miniature desserts.

Babygold BBQ

El Che Steakhouse owner/chef John Manion teams up with the famed FitzGerald’s venue to open his first barbecue joint. Adjacent to FitzGerald’s, BabyGold BBQ is family friendly with grilled meats and vegetables (brisket, baby-back ribs, barbecue-spiced cauliflower), a smoked shrimp salad po’boy, char-grilled oysters, and cornbread topped with cajun honey butter. There’s live music daily — sometimes free and for all ages — ranging from blues to alt rock.

Babygold BBQ is part of FitzGerald’s.
Barry Brecheisen/Eater Chicago

Pier 31 Restaurant

Summertime is when this South Side venue reigns for its lineup of jammin’ bands and deejays on its festive back deck facing Margaret Taylor Burroughs Beach. There’s reggae every Saturday afternoon, and guests are also treated to salsa, old school R&B, jazz, and more. There is excessive dancing, too, so it can get a little intimidating, but it’s also fun to watch the action from your table. Sustenance includes grilled burgers, a Chicago-style hot dog, salmon burger, and chipotle black bean burger.

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