17 Spots for Dinner and a Show Around Chicago (Date Night, Sorted!)

Date Night: DINNERSHOW_Petterino's interior

The holidays may be over, but the party has just begun.

Winter has come to Chicago (brrrrrr!) and that’s the perfect time to seek out places where you can plop yourself in one spot for the whole evening. Who wants to pay to park (or ride share, or take the El or Metra) more than once? Who in their right mind wants to spend any more time outside than is absolutely necessary? Hint: These are rhetorical questions. The answer is NOBODY.

Chicago is a music and theater town; there is no shortage of performers, starting with your restaurant’s front staff — every artist needs to pay rent. So it’s no surprise that we’ve got a plethora of places from which to choose, including stalwarts like Kingston Mines, SPACE/Union Pizzeria, Schubas Tavern, Andy’s Jazz Club, and Thalia Hall/Dusek’s, all of which you can read about here.

But, some new venues have popped up that are worth a try, and equally as toasty on a cold January night.

Wise up, people! Find a good restaurant, and then stay to be entertained afterward, be it theater, comedy, film, or music. We’ve got just the list for you.

Dinner and Drama

Drury Lane Theatre/Lucille Restaurant

The Drury Lane Theatre is known for their outstanding musical productions, and “Joseph and the Amazing Technicolor Dreamcoat” (running through March 25), their final show of the 2017-18 theatrical season, is sure to be a stunner. Conveniently, Lucille Restaurant, located inside the Drury Lane complex, offers both a la carte and pre-theater menus, including favorites such as Baked French Onion Soup ($7); Burrata with Roasted Tomato Bruschetta ($8); Slow Roasted Chicken ($19) with potatoes and shallots; or Seared Jumbo Sea Scallops ($27) with leeks, pancetta jam, wilted arugula, and a white wine cream sauce. Full stomachs, open minds, and great theater … can’t lose! 

Goodman Theatre/Petterino’s

date night: Petterino's Chicken Pot Pie
Petterino’s Chicken Pot Pie (Photo courtesy of Petterino’s.)

This one’s a two-fer, because not only can you have pre- or post-theater dinner (or matinee lunch!) at Petterino’s before you go see “Blind Date” (through Feb. 25) or “The Wolves” (Feb. 9 to March 11) at the Goodman, but on Mondays, when the theater is dark, there’s Monday Night Live! This weekly open-mic cabaret showcase has been going strong for a decade, hosted by Denise McGowan Tracy and Beckie Menzie. You never know whom you’ll see — often cast members from nearby musicals (yes, even “Hamilton”!) will drop in for a night of fun. Petterino’s makes a mean cocktail, and the three-course, prix-fixe theater menu is a bargain at $36. Ordering a la carte? The Maryland-Style Crab Cakes ($29) and the Chicken Pot Pie ($19) are especially delish, and save space for the rich Tiramisu ($8).

Steppenwolf/Front Bar

date night: Front Bar
Front Bar (Photo by Neil Burger.)

Everyone knows the world-famous Steppenwolf Theatre, of course, but did you know about their very own Front Bar, opened in April 2016? So, if you’re off to see “BLKS” (running through Jan. 28), or “You Got Older” (Jan. 25 to March 11), stop in and order a cocktail (I’m partial to the Solstice, $11, a winning combination of CH gin, Rubin grapefruit liqueur, elderflower, and Lambrusco) and share a Sausage, Goat Cheese & Pear Flatbread ($12), Short Rib Grilled Cheese Sandwich ($12), and a slice of Goddess Rainbow Cake ($7) with someone you love, then go forth and experience the magic of live theater. You’re up to the challenge.

Theater on the Lake/The Lakefront Restaurant

This historic Chicago Park District venue in Lincoln Park started out as a tuberculosis sanitarium in 1920, and then became a theater in 1953. Before a 2017 renovation, it was solely a summer performance venue, but now operates year round, hosting festivals, concerts, movies, and plays. Also new is the Lakefront Restaurant, helmed by chef Cleetus Friedman, known for his love of craft beers and full-flavored, updated pub food. Brunch here means an obligatory Cleetus Heatus Bloody Mary ($12) and a platter of Chicken-Fried Chicken ($18) or Cereal Milk French Toast ($11); at lunch, opt for the Whiskey Bacon BLT ($14) or the Chimichurri Chicken ($17). Dinner brings Griddled Corn Cakes ($10) with tomato jam, Smoked Trout Nicoise ($13), and the Slow-Cooked Brisket ($24) with sweet potato mash and apple cider drizzle. Now you know why traffic is always backed up at the Fullerton exit. 

Comedy and Cuisine

Second City

Whether you’re at the Mainstage or E.T.C. Theater or the Up Comedy Club, you’ve come for the funny. Laughter may be the best medicine, but it also makes you ravenous. You’re in luck! Dishes like Kale Caesar Salad ($10), Grilled Chicken Sliders ($12), or the UP Burger ($14) with BBQ Sweet Potato Fries ($6) will tickle your fancy, while specialty drinks (the Old Town Paloma hits the mark) come by the glass ($13), the huge souvenir glass ($29) or the 60-ounce pitcher ($59). Happily, there’s no drink minimum!

Menus and Music

210 Live

This Highwood hotspot brings in live bands Wednesday through Sunday evenings. The menu is glamorized bar food, and we’re OK with that, especially when there’s Yellowfin Tuna Poke ($13) with toasted sesame oil and guava juice, a bounteous Vegan Israeli Platter ($10), Jambalaya ($10), and a serious Brisket Sandwich ($16). The Fries ($7) are hand-cut and crispy, and local products are featured whenever possible.

Artango Bar and Steakhouse

date night: Artango (Flamenco)
Artango’s Flamenco night (Photo courtesy of Artango.)

If you’re a fan of Argentine Malbec, steak, and tango, you are in just the right place. In the heart of Lincoln Square lies a restaurant that wouldn’t be out of place in Buenos Aires. You’ll find empanadas ($4, 3 for $11, 5 for $15); smoky Provoleta ($12) with tomatoes and chimichurri; Paella del Sur ($34/$51) with plump fresh prawns, scallops, calamari and more; and some truly tasty, locally raised Black Angus beef grilled gaucho-style, among other delicacies. The San Telmo Flan with cardamom and cinnamon is insane. All this, and tango, too! Check the online schedule to see if you’ll be listening to Latin jazz guitar, watching a tango show, or learning how to dance it yourself!

date night: Artango
Artango’s Grilled Duck with Cherry Malbec Sauce (Photo courtesy of Artango.)

Benny’s Chophouse

Benny’s hits the sweet spot of food and entertainment with a versatile steakhouse menu ranging from Grilled Caesar ($11) and Oysters Rockefeller ($17) to Whole Dover Sole ($50) or high-quality beef. The side dish game here is strong — I could make an adult happy meal from the Mac & Cheese with Lobster ($25) and the Crisped Kale ($10) and garlic-laced Broccolini ($14) — and the cocktails and wine list outstanding. All this, and jazz, too! Every Wednesday through Saturday evening, you’ll find acclaimed artists playing a diverse blend of jazz, from classic to fusion. Just listening to it will make you infinitely cooler.

date night: Benny's Chophouse
Photo courtesy of Benny’s Chophouse.

Bub City

With two locations — Chicago and Rosemont — Lettuce Entertain You’s reincarnation of the original Bub City offers many options, from Live Band Karaoke and Whiskey Wednesdays to nationally known visiting music acts. Millennials flock here for the Fried Pickles ($10); TNT Taquitos ($12) stuffed with spicy smoked brisket; Southern Fried Chicken ($10-$16); and Chicago-Style Ribs ($19/$29). Come for the BBQ, stay for the country music.

date night: Bub City
Photo courtesy of Bub City.

Buddy Guy’s Legends

Blues aficionados from around the world descend on this South Loop joint, hoping to get a glimpse of the legend himself. At 81, Buddy Guy is still at it, performing with various local and national artists. Louisiana-style Cajun and soul food are the name of the game here, with Gumbo ($5/$8), cornmeal-breaded Fried Oysters ($12), Catfish Po-Boy ($12), and a Soul Combo ($20) of ribs, BBQ chicken, fries, and cole slaw setting the tone. How can you have the blues when you’re eating something so soul satisfying?

City Winery

If you’re looking to combine wine, food, and great music, City Winery should be on your short list. They offer everything from concerts and private events to food and wine classes, and they’re a functioning winery to boot. If you’d like to dine before a show, they start taking reservations two hours before show time, and you can enjoy dishes such as their Wild Mushroom Flatbread ($16) with rosemary goat cheese, arugula, and caramelized onions; Moroccan-Spiced Burger ($15) with pickled red onion, harissa aioli, and herb and feta cheese spread on a house-made roll; or perhaps the Braised Duck Tacos ($16) with “guacamatillo” salsa and cabbage salad. Become a Vinofile member for special discounts and advanced ticket sales so you don’t miss out on some of their big shows, which sell out quickly.

Pete Miller’s

When your tag line is, “Chew with your ears open,” it’s obvious you’re as committed to your food as your entertainment. They’re bringing in some terrific jazz artists — seven days a week — to entertain you while you consume fine wine and aged beef. You can choose to sit in one of the back rooms, where the music is in the background, or up close and personal in the front lounge. Menu favorites include the Lamb Lollichop ($16) with merlot reduction; the classic Wedge Salad ($11); Tuna Yuzu Tataki ($35); and the 20-ounce Pete’s Cut Bone-In Ribeye ($52).

The Promontory

This “Hearth to Table” restaurant/bar/music venue spot is brought to you by the same group that gave us Thalia Hall/Dusek’s and SPACE/Union Pizzeria, so you know you’re in good hands. The music acts are an eclectic mix here, from Rap and Hip Hop to Classical and Blues. Downstairs, you’ll enjoy dishes such as Pierogi Ravioli ($14) with shishito peppers and lemon butter; Kalbi Short Ribs ($16) with soy caramel and cashew; Hearth-Grilled Oysters ($9); and a generous Slagel Farms Cheeseburger ($15) with fries. The craft cocktails are a thing of beauty, from the Smoked Sazerac ($10) to the Promontory Cognac Sour ($10). Coolness factor here is high.

date night: The Promontory
Photo courtesy of The Promontory.

Untitled Supper Club

Chicago hasn’t seen the likes of this since the Prohibition Era. This five-time Michelin Bib Gourmand recipient is firing on all cylinders, from the kitchen to the live entertainment on stage, be it burlesque, funk music, vintage soul, or the occasional contortionist. Cheese and Charcuterie Boards ($15) are a good entry point, especially accompanied by one of their many craft whiskeys, as they purportedly have the largest selection of American Whiskey anywhere in the world. Burrata and Duck Confit ($15) or Steak Tartare ($16) with preserved lemon aioli are lovely small plates, and you might think of sharing the Sea Scallops ($28) with sunchokes and lemon broth, or perhaps the Rack of Lamb ($38) with whipped feta and chickpeas. Tastiness will ensue.

Food and a Flick

AMC Dine-in Theatres at Block 37

Head up to the fourth floor of the Loop’s Block 37 shopping complex to discover 11 movie screens and a dine-in menu that runs the gamut from a Crab & Avocado Sushi Roll ($10) to a Shrimp Carbonara Flatbread ($13). Want a bowl of Traditional mac ($12.50) with bacon and chicken? They’ll deliver it to your lounge-like seat, along with a bottle of wine. Ultimate Nachos, laden with black beans, guacamole, cheddar cheese sauce, and chicken, will set you back $14 — and 1,840 calories. You might want to plan on sharing.

AMC Dine-In Theaters at Northbrook Court 

Much of what I said above rings true in this location, but the shopping is better! New menu items include Korean BBQ Bacon Buns ($10.89), Loaded Brisket Fries ($10.29), and Molten Chocolate Churros ($5.99), all with Dine-In Delivery direct to your seat. On second thought, you might want to hold off on buying new jeans if you order any of these.

Davis Theater/Carbon Arc Bar & Board

Formerly known as the Pershing Theater, the Davis was renovated in 2016, with gorgeous Art Deco-inspired bathrooms, plush and comfy theater seats that gently rock (comforting in scary movies, y’all), and the Carbon Arc Bar. The menu goes beyond basic bar food with items like the Beet & Goat Cheese Salad ($12.95) with pear, mint, and togarashi spice; Fried Chicken ($17.95) with sausage gravy, potatoes, and slaw; and Baja Fish Tacos ($12.95). Pizzas, burgers, and more are also available. Grab a Sazerac or Peach Frozé (all cocktails are $10) and enjoy your dinner in the bar, or bring it into the theater. Of course, popcorn is freshly made in-house.


Julie Chernoff, Make It Better’s dining editor since its inception in 2007, graduated from Yale University with a degree in English — which she speaks fluently — and added a professional chef’s degree from the California Culinary Academy. She has worked for Boz ScaggsRick Bayless and Wolfgang Puck (not all at the same time); and sits on the boards of Les Dames d’Escoffier International and Northlight Theatre. She and husband Josh are empty nesters since adult kids Adam and Leah have flown the coop. Rosie the Cockapoo relishes the extra attention.





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