• Booze Box

Head to the alley just south of Sushi Dokku, find the door with the Booze Box sticker near its handle, and enter one of city’s finest secret bars whose dark, sexy vibes immediately immerse you in a subterranean cellar of cool. Sake flights are a thing. As are sakeritas. And saketinis. Sensing a theme here? Besides sake, it's throwing down Japanese-style wings, Japanese trail mix, rice bowls, and oyster shooters as DJs spin hip-hop amidst cedar sauna-like walls and the romantic glow of handcrafted red lanterns. If you can’t seal the deal on a date, something has gone seriously awry.

• STK

Toeing the line between steakhouse and nightclub, this self-proclaimed “sexy” new spot promises to be a see-and-be-seen destination for Chicago’s stylish set. The space flaunts a massive bar, curved booth seating, and an elevated DJ platform. Menu standouts include seared foie with huckleberry pancakes, orange marmalade, gingersnap crumbs, and a spiced rum reduction as well as an assortment of steaks organized by “small,” “medium,” and “large” cuts.

• The Jibarito Stop

This popular Puerto Rican food truck now lays claim to its first brick-and-mortar digs: a small counter-service storefront on W 18th St. The fast-casual eatery specializes in jibaritos, sandwiches that come stacked with proteins like seared steak or chicken, lettuce, tomato, and American cheese between a fried plantain “bun,” but you can also score empanada baskets, slow-roasted pork platters with rice and sweet plantains, and more.

• Swift & Sons

Two and a half years in the making and one name change later, the latest project from Boka Restaurant Group and B. Hospitality Co. has finally arrived. The massive modern steakhouse concept features a seafood restaurant within the restaurant, a stylish design with pastoral Midwestern touches, and a menu crafted by Chris Pandel (Bristol, Balena) that ranges from classic steaks and chilled king crab legs to creative dishes, like celery root agnolotti and Skuna Bay salmon with “borscht” pumpernickel crumble.

• Maple & Ash

Also contributing to the steakhouse boom is the long-awaited Maple & Ash, a dimly lit house of carnivory that harkens back to Chicago’s heyday as the Midwest’s steakhouse epicenter. The menu centers around items grilled on a wood-burning hearth, such as a 40oz porterhouse and a 28-day dry-aged strip. Also of note? An Anchorman-inspired cocktail called the “Scotchy, Scotch, Scotch” that promises to be, well, exceptionally Scotch-y.

• Piggyback BBQ

Add this spinoff barbecue joint to the Loop’s ever-expanding roster of fast-casual options. It’s the latest from Tavern Collective (Tapworks Tavern & Grill, Jackson Tavern) and offers a customizable experience for Downtown lunch-goers; options include hardwood slow-cooked beef brisket and pulled pork served as a sandwich, bowl, plate, or salad and a host of sides, like collard greens and jalapeno-cheddar cornbread.

• Corridor Brewery & Provisions

For those looking to get a craft brew buzz on in the Southport Corridor, this one’s for you: the same folks that brought you DryHop now bring you a part-brewery, part-kitchen concept flush with beer offerings, chorizo Brussels sprouts with aged manchego and caramelized onions, beer-steamed Belgian-style mussels, and more. Want some suds to go? The brewery also sells 32oz crowlers (can growlers) for your sipping pleasure.

• The Coffee Studio

Looking immaculate amidst exposed bricks and pretty wood, this no-frills modern espresso bar plays music by everyone (from Panda Bear to Beastie Boys), while packing a massive punch with its Double Strength Cold-Brew coffee. Stop shaking long enough for a Brie/apple/walnut flatbread followed by Miko’s Italian Ice and shots. Of booze. Or espresso. Or... both?

• Brew Brew Coffee Lounge

For most of us, the house Brew Brew Blend is more than enough to pry our eyelids open in the morning. Fancy types can also go with the Burundi Kirema or Colombia Los Naranjos single origin espresso, but it would take a fool of momentous proportions to skip out on the Dirty Mexican Hot Chocolate -- a seductive blend of Mexican chocolate and espresso shooters. Also stop by for the occasional live jazz and art exhibitions.

• Metropolis Coffee Company

One of Chicago’s most popular coffee shops ain’t exactly cheap ($8 for a bagel lox sandwich?), but it has pretty much everything you need in a coffee shop: cool vibes, comfy seating, and a variety of standout roasts including the famous Kyoto-style cold-brew iced coffee. It even has 96oz urns of coffee to go, depending on how deep your coffee crush lies on the addiction scale.

• Whispers Café

This little coffee stand in the heart of the Viagra Triangle’s Mariano Park is a peaceful oasis surrounded by a desert of douche. Besides excellent coffee, it is known for its gelato, which brings in the tourists as well as regulars -- all of whom peacefully coexist in the European-style outdoor setting that forms one of Downtown’s finest hidden gems.

• Star Lounge Coffee Bar

This place is just… cool. You know it from the moment you walk in. With an old-school neon sign hanging over burnt-orange walls, it feels like the kind of place rock stars go for coffee. If they drank coffee. They drink coffee, right? For you, it has Wake & Bake espresso with maple syrup, and Unicorn Blood lattes (which you should also probably add maple syrup to).

• City News Café

Few things go better together than coffee and some weird magazine you can only find amongst the stacks at City News. It also has live music and an inviting space tailor-made for wasting days in the most enjoyable of ways. The matcha green tea latte and homemade truffles are significant draw cards as well.

• Osmium

This one-year-old sister shop of Star Lounge could not have had a more successful debut year, establishing itself as THE coffee scene in a neighborhood packed with coffee shops. The spicy Mayan mocha is a fan favorite and, with everything from steampunk art to weekend DJs, the café is clearly a popular space for first dates. Bonus points for the cool back patio with graffiti-covered picnic tables.

• Café Mustache

Yes, it’s true: hipsters drink coffee, too. Discover this fact when ordering a Black Pepper & Vanilla Fig Latte while you listen to indie jams culled from a 1,200+ vinyl album collection. Also: live bands, vegan chili, and even house cocktails like the Mayor Daley (bourbon, iced tea, lemonade) and craft brews including Two Brothers' Outlaw IPA.

• Eva’s Café

Eva’s Café is the perfect place to pony up near the big picture and watch the world (OK, Sedgwick) go by. It also has a little fireplace section surrounded by leather sofas, a nice antique living room vibe with bookshelves and, of course, hazelnut latte served in owl mugs.

• The Perfect Cup

Sometimes it’s good to go back to the basics: good coffee, good sandwiches, and a quiet place to get some work done. Also if you love coffee-centric quotes like “My Blood Type Is Coffee” and “Coffee in Styrofoam Is Against My Religion,” this quaint little Parisian-inspired spot is calling your name.

• Heritage Outpost

Is it a bike shop? Is it a coffee shop? It’s a bit of both and, combined with a gorgeous open space of sofas and exposed brick in the lobby of an apartment building, it's one of the most legitimately cool places for your coffee fix in all of Chicago. The Lavender Latte is worth the trip in itself and, if you’re in the market for a bike, it has those too.

• The Wormhole Coffee

If you’re a sucker for full-scale Back to the Future DeLoreans, Teenage Mutant Ninja Turtles dolls, and framed Ghostbusters posters, this funky locals’ favorite is calling your name. Your ‘80s revival comes complete with Nintendo, Star Wars Trivial Pursuit, and coffee drinks that have no business being this good... specifically, the Peanut Butter Koopa Troopa.

• Pick Me Up Cafe

If Chicago had ridiculous coffee challenges on par with its ridiculous eating challenges, the Zombie at Pick Me Up Café -- three shots of espresso, two cups of coffee, steamed milk, and a massive serving of whipped cream drizzled with chocolate and caramel sauce -- would surely top the list. The café’s friendly, unpretentious vibes make this place stand out from the hipster-dominated coffee.

• Beauty Bar

Theme: ‘60s beauty salon Beauty Bar is well known as the place to grab “Martinis and Manicures” while seated in vintage beauty-salon chairs sipping drinks like the Deep Condition, Bed Head, and Platinum Blonde. Yet, unlike most salons, it’s even more well known as one of the best places to dance in the city with an expertly curated rotation of DJ nights from ‘80s nights, to Y2K parties, to the indie-centric Indie-pendant dance party the first Saturday of the month. Stop by on Monday nights for $1 beer and free Pie-Eyed pizza, or Thurs/Fri happy hour for 32oz pitchers of Old Style and two shots of Malort for $10. Hey, you’ll have plenty of money left over for that manicure.

• Monk’s Pub

Theme: Trappist Belgian monastery Named after a monastery where the owner once spent a childhood summer, Monk’s Pub nails the monastic theme right down to the font and cheerful beer-hoisting monk on the ancient-European-looking sign out front. Inside you’ll worship in a den of aged woods, dusty old barrels, and Trappist beer banners as Monk’s uncorks a divine selection of Trappist ales from the likes of Westmalle, Orval, and La Trappe. But the real holy trinity might be the bar’s decadent trio of burgers from chili cheese burgers, to poutine burgers, to maple bacon brisket burgers. Either way, you’re going to confession after.

• Boeufhaus

Tiny though it may be, this 34-seat meat-focused French and German brasserie is just the ballsy departure from the Downtown steakhouse cliché the Windy City has needed. The interior is noticeably devoid of opulent, high-end accents common to steakhouses and the location is far removed from glossy River North. With the exception of a few outliers, lunch is stacked with offerings that hover around the $10 mark, like the truly exceptional Reuben sandwich and short-rib beignets. Dinner also excels with its perfectly cooked-to-order steaks and attentive service.

• Prime & Provisions

Live out the classic steakhouse fantasy at this 12,000sqft spot on LaSalle, where the royal treatment extends far beyond the marble bars and cigar patio. Begin your meal with a stiff cocktail, a shellfish tower, and house-flared thick-cut bacon cooked with black pepper, Michigan maple syrup, and dark chocolate for a flavor experience that spans from fresh and briny to bold, smoky, and luxurious. After some thorough taste-bud indulgence, it’s time to treat yourself to what you really came here for: USDA Prime Creekstone Farms beef just about any way you could ever want it.

• Toast to Hollywood at Brew and View

Brew & View’s been doing the whole “drinking and a movie” thing likely since before you had your first taste of either. Most movies are still only $5 screened at The Vic, still one of Chicago’s finest live music venues. And you’re gonna need the extra laugh potion to make it to hour No. 3 of Trainwreck.

• Enjoy one of the city’s best lunches under $10 at Sultan’s Market

For under $9, the lamb shawarma dinner at Sultan’s Market is one of the best deals to be had in Chicago. Go crazy and splurge for the extra falafel on the side for an additional 50 cents.

• Scour Hot Tix for cheap theatre tickets

Second City is great, but not cheap. There are, however, MANY cheap theatre options out there… which you may handily peruse all in one place thanks to Hot Tix.

• Plan a boozy brunch

The best way to make it through brunch with the parents? Plan a boozy brunch at a place like F. O'Mahony's, where you pay $20 for all-you-can-drink mimosas and your choice of brunch entree, Sundays, 10:30am-3pm.

• Best new burger

Johnny’s Grill

Forget exotic cheeses and other gourmet accoutrements, 2015 was the year of back-to-basic burgers in Chicago, and the simple, expertly executed number at Johnny’s led the pack. Two juicy patties provide just enough meaty resistance with each bite, while melted sharp cheddar, tangy Dijonnaise, pickles, and onion amp up the flavor factor.

• Best new lunch spot

Wyler Road

From "Fernet Cows" (Letherbee fernet, mint, house-made fernet ice cream, and Coke) and a predominantly Midwestern draft beer list to the Sunbutter Sandwich (sunflower seed butter, honey jam, and toasted sunflower seeds on whole wheat) and a veal heart Philly with Cheez Whiz mayo and sautéed onions, this hipster-approved concept has the answer to all your lunchtime needs.

• Best new cool treat

Good Stuff Eatery

It’s no secret that celebrity chef Spike Mendelsohn’s sustainability driven burgers are great, but when it comes to milkshakes, let’s just say his burger joint’s toasted marshmallow confection is bringing everyone to the yard (sorry, we had to). The hand-spun shake is a veritable campfire in a cup, and is one of the best drinkable treats we’ve ever had in Chicago, let alone this year.

• Best new taco

El Carrito

Eat great on the cheap at this Mexican street food purveyor on the Northwest side, where the taco offerings range from al pastor with onions, cilantro, and grilled pineapple to a surprisingly satisfying veggie number bursting with fresh herbs, squash, zucchini, carrots, and more. And no outside-sourced tortillas here: each taco comes swaddled in a fresh tortilla made in-house.

• Bring Your Own Theater Productions

Second City and the Chicago Theatre are justifiably famous, but Bring Your Own Theater Productions is a new type of performance in the city that's making waves. "It's a bit different from any other live show I have seen or been a part of before," says Greg Torbeck, a performer with the company. "We go from concept to performance in 24 hours. Each month features a theme, voted on by attendees of the previous month's show, that isn't revealed to the performers until a Friday night pre-show meeting. After it's announced, writers and directors and actors are paired together, and the entire show—from writing to performance—is turned around by showtime on Saturday night at 8 p.m.

• Ethnic Museums

This is the melting pot of the Midwest, and what better way to celebrate the local culture than by learning about the ones that formed it? Sure, Museum Campus is great, but wrap your mind around the background of local immigrants at places like the National Hellenic Museum, the Chinese American Museum of Chicago, the Swedish American Museum Center, and more.

• Chop Shop

A cute patio, huge space, and a menu that will leave every carnivore drooling. Brunch at Chop Shop is nothing short of hearty meats (lobster polenta cake benedict!), flavorful cheeses, and original cocktails that’ll have you coming back for more.

• Kanela Breakfast Club

Kanela Breakfast Club has several locations in Chicago and has become a brunch go-to spot since opening the Lakeview location in 2010. The restaurant revamped its menu this year adding new items like chicken and waffles with a Sriracha honey sauce, a Nutella s'mores waffle, to complement the amazing staples like the bacon-infused waffles and spicy feta omelette. Worth going back to, unless you have been, which, shame on you.

• BOKA

Romantic enough for a date night and inventive enough to surprise even the most jaded of palates, this time-tested favorite promises a great atmosphere (including a breathtaking “living wall” punctuated with anthropomorphized animal paintings) and even greater food. Crafted by visionary Lee Wolen, the Michelin-starred menu is an exercise in mixing complementary flavors and textures; no dish better exemplifies this than Wolen’s heirloom carrots, which come to life with pistachio crumbles, bulgur, and smoked goat cheese. And by all means, save room for one of pastry chef Meg Galus’ equally whimsical desserts.

• Smoque BBQ

This Texas-style barbecue joint has been slingin’ its signature brisket and ribs for the better part of a decade, and remains steadfast as the North Side’s top dog for smoked meats. It’s BYOB, so arrive hungry and with a frosty six-pack of your favorite local brew in tow to fend off the inevitable meat sweats.

• Swift & Sons/Cold Storage

Although they occupy the same space on Fulton Market, this upscale steakhouse and casual seafood concept duo from Boka Restaurant Group and B. Hospitality deliver two very separate dining experiences. Indulge in colossal steaks and gold leaf-flecked sundaes at the former, or get a finger-food fix by way of beer-battered smelt, smoked whitefish dip, and seafood towers decked with oceanic delicacies at the latter.

• Avec

After over a decade in operation, this narrow, all-wood-everything restaurant still draws crowds of devoted regulars, first-time tourists, and everyone in between. The chorizo-stuffed bacon-wrapped dates -- which earned a spot on our list of the 50 Things to Eat in Chicago Before You Die -- are a perennial crowd favorite, and the slow-roasted pork shoulder with piri piri broth, cracked wheat, snow peas, smoked yogurt, and clams, is a tender, flavor-packed masterpiece that's prime for sharing.

• Coalfire

Thin-crust pizza joints often take the backseat in a city where deep dish is much more debatable, but this rebel pizzeria refuses to back down. Coalfire, which recently opened a second location on Southport, torches its pies in an 800-degree coal-burning oven that yields a thin, blistered, and bubbly crust. The choice of toppings is yours, but if you won’t get down with cloud-like dollops of whipped ricotta and thick-cut pepperoni, we’re not sure we can be friends.

• Small Cheval

Au Cheval’s pared-down little sister still slings the same superlative burgers and fries as its West Loop counterpart and has managed to keep wait times to a comparative minimum so far. The space is now open seven days a week until midnight and has just added a "boozy iced chocolate" to the drink menu. Weather permitting, snag a seat on the back patio and settle in for a bacon-topped cheeseburger and a killer malted vanilla milkshake.

• Parachute

Husband-and-wife team Johnny Clark and Beverly Kim have created a cuisine fusion all their own: American-Korean, wherein authentic Korean flavors collide with familiar, comforting forms. Don’t even think about visiting without ordering the famous baked potato bing bread studded with bacon and scallions and served with sour cream butter.

• Dusek's Board & Beer

Equipped with iron-roasted P.E.I. mussels, saffron-poached squid, Dutch baby pancakes -- topped with spiced apples, candied bacon, cinnamon sugar, and bourbon maple syrup -- and a swath of on-point alcoholic beverages, Dusek’s proves that Pilsen is a culinary force to be reckoned with.

• The Warehouse Bar & Pizzeria

Makes bloody mary's with slices of pizza on top.

• The Commons Club

Has an upside down tea party.

• Koval Distillery

In 2008, Dr. Robert Birnecker and his wife were living in Washington, DC when they decided to work together to bring his Austrian grandfather’s distilling traditions to America with from-scratch spirits. “I like getting my customers to push their boundaries by trying new things, and ultimately providing a new experience for them,” says Wagner. “The ones I'm pouring the most right now are Hanson, Spirit Works, and Koval.”

• Bordel

If you walk in here not knowing what the hell a porron or copita is, don't worry, you’re not alone. By the time you leave you will, or at least you’ll have the chance to hit upstairs lounge Bordel, one of Chicago’s finest secret bars. Scotty says: "Black Bull is an authentic Spanish restaurant with a focus on sherry and Spanish wines. The staff treats you like family and the cocktails are constantly evolving, while never straying far from their Spanish roots. I like to enjoy a glass (or entire porron) of cider with a copita of sherry on the side."

• Bob Inn

You bob in, you bob out. That's the way it's done at Bob Inn. That's the way it's always been done. Sean says: "Great place to get a low-key drink and a pool table that's almost always open."

• Dimo's Pizza
• Batter and Berries
• Breakfast House
• Chicago's Home of Chicken and Waffles
• GT Fish and Oyster
• Jam
• Luella's Southern Chicken
• Mother Cluckers Chicken
• Kitsch'n on Roscoe
• Hutch Bistro
• The Hideout

String lights, hurricane candles, a disco ball, exposed wood beams—and some great live music. This is one of Chicago's oldest music venues, decked out with posters from past shows, brewery signs, and band flyers soliciting new members. Don't expect so much as a garnish here. The Hideout is a shot-and-beer joint—and they sell a lot of PBR and Jameson. You're here for up-and-coming acts, as well as some national headliners, poetry slams, podcast tapings, and even political panels—but at the end of it all, this is an old-school dive serving ice-cold beer.

• Ada Street

Candlelight, vinyl, and solid cocktails: This is Chicago's go-to spot for a romantic night out, set rather incongruously in a still-industrial corner of town just northwest of Goose Island. Cocktails are inventive, verging on geeky. The rotating menu features mostly brown spirits in drinks like the 50 Ways to Leave Your Lover, a bottled cocktail of Flor de Cana rum and Laphroig single malt with pumpkin chai and oleo-saccharum (citrusy sugar syrup).

• Lucky Dorr

It's probably the best beer bar in otherwise unremarkable Wrigleyville and worth seeking out when you're catching the Cubs. It's a tight fit inside, so try to snag a seat on the patio overlooking the Park at Wrigley, the newly-designed plaza located in the shadow of historic Wrigley Field. Custom beers made specifically for the bar by local outfits like Burnt City, Dovetail, Right Bee Cider, and Maplewood. Easy-sipping draft cocktails are crafted by Lucky Dorr's sister bar, Billy Sunday.

• Kingston Mines

This is one of Chicago's greatest blues bars, with two performances on two stages every night of the year. There's a full bar, but most people are ordering stiff well drinks and foamy pints. There's not much to look at, just long four-top tables and stools, beer signs, and colored lights, but music lovers of all kinds, young and old, local and international flock here, especially on weekends.

• The Press Room

The secret's starting to get out: This still under-ther-radar wine bar is the perfect place for a low-key date or a chill night out with friends who dig esoteric bottles. Owner George Saldez is a hospitality industry veteran, and he's pulled together a list of 80-something wines, with a focus on his native Australia. Executive chef Jeff Williams, formerly of Sable in River North, does shareable plates inspired by Spanish and Italian bar bites.

• Maison Marcel
• Nick's Pizza and Pub
• Forno Rosso Randolph
• Barrio
• Big and Little's
• Daisies
• G & O
• Cold Storage

$1 oysters from 3-6pm

• The Allis at Soho House

The British-inspired ambiance, tall ceilings and beautiful glass chandeliers are reason enough to visit The Allis at Soho House. This classy restaurant is known for its popular tea-time and brunch special. The rest of the club is members only, but this ground-floor hangout spot welcomes all.

• ZIA’S LAGO VISTA

Craving Italian? Head to Zia’s Lago Vista for a truly unique boozy brunch experience. Though this Lakeview spot does serve up a few traditional breakfast items like omelette’s and French Toast, the true star of their menu is the breakfast pizza. With $12 unlimited mimosas or Bloody Marys to boot, a weekend brunch at Zia’s is sure to be a hit!

• HUTCH

With locations in both Lakeview and River North, this American Bistro has got the brunch game on lock. And though the food at Hutch is undeniably delicious, it’s their drink menu that really rakes in the fans. From stunning cocktails, to tall boys and everything in between, Hutch has got you covered no matter your tastes. Personally, I’d suggest going for the Spicy Sunset carafe: a tequila based drink with jalapeno, pineapple, orange juice and fresh strawberry puree. Though Hutch’s drinks aren’t strictly unlimited, they do offer $2 mimosa pours on weekdays and $4 pours on weekends, and kindly ask that you limit your meal to 90 minutes max.

• EL MARIACHI TEQUILA BAR & GRILL

Swing by El Mariachi on a Sunday morning to get a breakfast entree and bottomless mimosas for just $24 total. With Mexican inspired options like Pina Colada French Toast, Torta de Pollo, Huevos Rancheros and more, you simply cannot go wrong with this boozy brunch option.

• SUNDA

If you’re thirsty and hungry, order the Sumo Mary – it comes with a grilled cheese, steamed duck bao bun, crab handroll, crispy pork belly, wok fired shishito peppers, applewood bacon, sunda potatoes, lumpia, takuan, and kai-lan. Might as order a bowl of ramen, more duck bao, and dumplings while you’re at it. What to order: duck buns, Sumo Mary, and ramen.110 W Illinois St, sundachicago.com

• Fulton Market Kitchen

Located in Chicago’s West Loop, Fulton Market Kitchen menu’s is rustic with a touch of artistry. The foie mousse is served in a mandarin orange jelly mold in the shape of a mandarin with toasted sourdough. It’s a great place to hang out and enjoy cocktails and food while taking in all the local art in this cool warehouse space. What to order: foie mousse, chili garlic Brussels sprouts, and lamb shank.311 N Sangamon St, fultonmarketkitchen.com

• Kim's Corner Food

1371 W. Estes Ave. - Rogers Park (image 8384) “Be happy,” commands a Rogers Park mural featuring a hot dog. The mural’s abstract shapes are inspired by the work of Thomas Kong, owner of nearby Kim’s Corner Food. Inside the convenience store, Kong recycles merchandise packing materials by turning them into collages. Thousands of Kong's joyful artworks cover the store's walls, shelves, coolers, and even the stuff for sale. An adjacent space called the Back Room exhibits artists responding to Kong's work, truly turning the everyday into art.

• Skyspace

803 W. Roosevelt Rd. - University Village We can’t blame you if you mistook this as a water tower and kept walking, but you're missing out. It's actually a "skyspace," an observatory for viewing a slice of the sky as art. Artist James Turrell has installed more than eighty skyspaces around the world, and Chicago's is the first that's fully public. Experience the skyspace at sunrise or sunset, when the changing atmosphere plays off the colored lights inside.

• Jim Bachor's Pothole Art

See bachor.com for locations When the potholes on mosaic artist Jim Bachor's block never got filled, he took to the streets. Bachor uses the ancient methods of mosaic art to fill the modern problem of potholes. Look down and you might stumble on his mosaic series of ice cream treats or luxury fashion logos. Bachor's work inevitably gets damaged or replaced, so visit the map on his website to catch his installations while you can.

• Vanderpoel Art Collection

9625 S. Longwood Dr. - Beverly Where can you see priceless works by Maxfield Parrish, Mary Cassatt, Grant Wood, and over 100 Chicago artists for free? Try the Chicago Park District. After Beverly artist and teacher John Vanderpoel died in 1911, his friends and admirers began donating works in his name. The Vanderpoel Art Association now resides in a quiet gallery tucked in the Ridge Park Field House, where about 200 pieces are on view.

• Henry Darger Room Collection

756 N. Milwaukee Ave. - River West

Want to see “where the magic happens?” It might not look like you think. The room of reclusive Chicago artist Henry Darger is recreated at Intuit: The Center for Intuitive and Outsider Art. Stacks of old magazines and paint are piled on Darger’s furniture and religious statues line his mantle. It’s a fascinating look inside the life of a prolific and mysterious outsider artist.

• Lakeview Post Office

1343 W. Irving Park Rd. - Buena Park Encountering historic art can be as easy as sending a letter IRL. Several Chicago post offices are still rocking Depression-era works created as part of the Federal Art Project. The Lakeview Post Office gives you plenty to look at while you wait in line - a twenty-four-foot-long mural depicting Chicago’s perseverance. See if you can spot other FAP works at post offices in Logan Square, Uptown, and Morgan Park.

• The Palm
• Scooter’s Frozen Custard

Walk into Scooter’s and disregard the hot dogs, Italian ice and anything else that doesn’t contain the words frozen and custard. Purists should order a cone of vanilla or chocolate and savor every last lick of the cream-laden treat. If you're hankering for something a bit more involved, opt for the banana splice: vanilla custard, banana, chocolate, strawberries, pineapple and nuts. It's big enough to split, but we won't judge if you're selfish.

• Black Dog Gelato

After peddling her gelato all over town to the city's best chefs and markets, Jessica Oloroso found a fitting home for her first storefront in Ukrainian Village. There, she lures folks with boundary-pushing scoops of gelato such as avocado-cinnamon and sesame-fig-chocolate chip. If you're downtown, check out her stall inside Revival Food Hall for a quick fix over the lunch hour.

• George’s Ice Cream & Sweets

Sweet Occasions fans can stop their mourning: The ice-cream slinger that took over this space is practically identical to the previous tenant—only upgraded. The walls are decked out in grays and dark blues, and the food menu now includes hot panini, crêpes and waffles. Most important, the ice cream is the same (Chocolate Shoppe from Madison, Wisconsin). The scoops are now offered in over-the-top sundaes, but save the cash and the sugar overload—this ice cream holds up well enough on its own.

• Caffe Gelato

You’ll feel as though you stepped into a Sicilian gelato bar at this little spot, where everything (from the chocolate and nuts to the furniture and gelato machines) is imported from Italy. All flavors are made in fresh batches daily, including rich, creamy hazelnut, Stracciatella, peanut butter with brownie, pistachio and Bacio (a chocolate and hazelnut blend named for Baci candies). Seasonal fruit gelati and sorbets also fill the menu, as do a couple of panini and expertly made Illy coffee drinks.

• Scoops

The aroma of fresh waffles pervades the air of this Bridgeport parlor, evidence of the signature house-made waffle cones. Dipped in chocolate and adorned with brightly colored candies, these deep cones are indulgent carriers for both types of chocolate ice cream on offer (though our preference is for the darker variety). Should the ice cream be too rich, you’re in luck: Like all good Italians, these guys focus on espresso, the perfect antidote to your forthcoming sugar crash.

• Paciugo

The Lakeview location of the Texas-based franchise is basically Baskin-Robbins: Italian Edition, but aside from the color palette—faded pastels and the incumbent sterility—that’s not necessarily a bad thing. Yes, the gelato lacks the thick consistency of the authentic stuff, but it’s creamy, melty and comes in some 300 flavors (pistachio and sea-salt caramel are both worth trying). The frequently rotating selection of 32 at a time means more adventurous flavors like black-pepper olive oil keep regulars on their toes.

• Joe's Imports Wine Bar
• Innjoy

Good for dancing

• Smart Bar

Good for dancing