The Inside Out Guide to Chicago

chicago city guide tattoo shops
Credit: Miguel Romero

As the Midwest’s major metropolis, Chicago packs some serious cultural, culinary, and sightseeing delights into its sprawling confines, located on a picturesque stretch of Lake Michigan. That lakefront location means its Windy City nickname is no joke in the frigid winter and early spring months, but there’s still plenty of indoor action to easily fill a long weekend with; come summer and fall, there’s a bounty of public parks, gorgeous architecture to explore by foot or boat, and even a beach right in the center of the city to enjoy in breezy, warmer temps.

As for where to stay? In a city where rents can be significantly cheaper than other metropolises like NYC, San Francisco, or L.A., the lodging options are thankfully on the relatively affordable side, too. Look for spacious Airbnb options in desirable areas like Lincoln Park, West Loop, and Wicker Park for a more locals vibe. For a more luxurious, bank account-depleting experience, take your pick of high-end hotels on Magnificent Mile (the toniest, retail-packed stretch of Michigan Ave.) or in the Loop or River North, like The Peninsula, or, go the boutique hotel route.

Choices abound on the dining front, too. Chicago has no shortage of excellent eating and drinking options—many of which are on the heartier, meat and cheese filled side, all the better for surviving those notoriously frigid winters, but also all the tougher to cram as many stellar meals into one trip as you’ll want to. Local specialties include the Chicago-style hot dog (piled high with yellow mustard, diced white onions, a dill pickle spear, electric greenish blue sweet pickle relish, tomato slices or wedges, pickled sport peppers, and a celery salt) at the likes of Superdawg, Wolfy’s, and Wiener Circle and the jus-drenched Italian beef sandwich at Portillo’s. There’s also incredible Mexican, whether at the array of taco joints in the Pilsen neighborhood or Rick Bayless’ late ’80s-born trailblazers, like Toplobampo and Frontera Grill, and a wealth of proper Polish fare throughout the city, too. A few highlights, both iconic (deep dish pizza, because obviously) and new to the Windy City’s dining scene, below. Bring your appetite.

From excellent music venues large and small, to Grant Park’s  natural beauty and large-scale art and sculptural structures to ogle (the Bean in Millennium Park and the futuristic, Frank Gehry-designed Pritzker Pavilion bandshell) to Lincoln Park’s pleasant greenery and topnotch zoo, there’s a wide array of activities to consider. Basically, you’ll need multiple visits to even scratch the surface, but here’s a cribsheet of where to stay, eat, drink, do, see, and get inked.

Where to Get Tattooed in Chicago

Deluxe Tattoo: This Lakeview studio was previously helmed by Hannah Aitchison of TLC ’s L.A. Ink fame; these days, the popular spot is run by tattoo artist Ben Wahhh, whose colorful designs tend to include skulls, eyes, and mesmerizing, multidimensional abstract graphics, often rendered in shades of blue and red. 1459 W. Irving Park Rd., Lakeview

MayDay Tattoo Co.: At MayDay, self-described “lady tattooer” Carolyn Elaine is popular for her vibrant watercolor-esque floral and wildlife motifs; you might’ve seen her work on season 8 of Ink Master. Looking for an exquisite portrait or realism for your next ink? Opt for MayDay’s co-founder Pony Lawson. 1610 W. Grand Ave., West Town

Pioneer Tattoo: Striking, highly detailed work is a big draw at Pioneer Tattoo, which opened in 2010, and has built up a small but mighty team since then, from co-founder Tim Biedron’s epic, action-packed aquatic scenes to Michelle Wanhala’s cheeky fleet of cartoon-like critters. Note that the place is tucked away on a second-floor space, and it’s by appointment only; contact each artist directly to schedule. 3513 N. Lincoln Ave., Lakeview

Where to Stay in Chicago

Chicago Athletic Association: Formerly a posh private sports club, the Chicago Athletic Association reopened in 2015 as a boutique hotel in a prime location in The Loop, across from Millennium Park and just a block from the Art Institute, the city’s crown jewel museum. The striking Venetian Gothic-style building dates back to 1893, and underwent a lavish two-year revamp by hip design firm Roman and Williams before its hotel unveil. Thankfully, its incredible historical details, like stained-glass windows, intricate carved ceilings, and stately, elaborately detailed fireplaces, were preserved in the redesign process. There’s a game room, should you want to unwind over some pool, bocce ball, or foosball, and don’t miss the cocktails and views from the property’s rooftop bar and restaurant, Cindy’s, either. There are also six other dining options on the premises, including beloved burger spot Shake Shack; the Cherry Circle Room, a mid-century steakhouse, and the Milk Room, a hidden eight-seat microbar that was previously a Prohibition-era speakeasy. 12 S. Michigan Ave., The Loop

Freehand Chicago: This River North property, housed in a 1927 building that was once the Tokyo Hotel, is a the second outpost of the stylish but unpretentious Miami-born hotel, which also has locations in NYC and L.A. The digs are akin to fellow hip hospital chainlet the Ace Hotel: both were designed by Roman and Williams, the rooms themselves are small (40% of the rooms at the Freehand Chicago are even shared, hostel-style digs, complete with bunk beds, for a truly communal–and cheaper–stay), but there are cool common spaces and on-site dining and drinks options to stretch out and hang in. Cafe Integral serves up Mesoamerican comfort food; as at the South Florida original, there are topnotch cocktails available here at lobby bar Broken Shaker. As for the ‘hood, it can get touristy, as a slew of other hotels are located in the area, but the Freehand is more affordable than nearby options; plus, there are lots of places to eat and drink, many tourist attractions are close by, and there’s easy access to the El, making a solid, centrally located homebase from which to explore the city. 19 E. Ohio St., River North

The Guesthouse Hotel: While Chicago’s downtown areas, like The Loop, River North, and Gold Coast, have plenty to offer, it’s also a sprawling city of homey-feeling neighborhoods, with  low-profile, architecturally varied housing in lieu of high-rises. (New Yorkers might find commonalities with the leafiest, brownstone and townhouse-dabbled Brooklyn ‘hoods and…much of Chicago’s areas). For more of a residential vibe and space for bigger groups, consider this Andersonville hotel, situated on the city’s northern edge. Its tasteful one-, two-, and three- bedroom suites kitted out with stocked kitchens, balconies, and some features rarely, if ever, found in hotels: a grill, plus washer and dryer. It’s basically the vibe of a nicely appointed, spacious Airbnb that lives up to the photos, without the hassle of coordinating your arrival time, dealing with an MIA host,  et al. Make use of that kitchen thanks to the option to order in ingredients or meals from local grocery stores, and lots of dining options further down N. Clark St. Long-term stays are possible here, too. 4872 N. Clark St., Andersonville

Where to Get Inspired in Chicago

Architectural Boat Tour: In addition to being situated on Lake Michigan, a body of water so vast, it truly looks like the ocean from most vantage points, Chicago’s namesake river is a must-visit. Why? For the Chicago Architecture Foundation’s river cruise. Operated spring, summer, and fall, the 1.5-hour tour aboard a Chicago First Lady river boat, is a leisurely ride narrated by a CAC-certified volunteer docents, who entertainingly delve into the histories of over 50 buildings and drawbridges along the river. Sure, a history-filled boat tour might sound like a snoozefest, but hear us out: the Windy City’s architectural heritage is truly incredible and punctuated by fascinating anecdotes that are about so much more than pretty facades, and it’s perhaps the greatest way to get oriented in the city soon after arriving. Grab a seat on the top deck. Tours depart from Chicago’s First Lady Cruises, 112 E. Wacker Dr

Art Institute of Chicago: One of the oldest, largest art museums nationally, the Art Institute is a powerhouse institution that boasts iconic works from big guns llke Vincent van Gogh, Pablo Picasso, Claude Monet, Henri Matisse, George Seurat, Marc Chagall, Diego Rivera, Jasper Johns, and Edward Hopper. In addition to the many, many halls worth of ancient treasures worth exploring, a quirky but amazing highlight can be found in the subterranean Thorne Miniature Rooms, a collection of truly teensy (1” to 1’ in scale, to be exact) models of American and European interiors spanning from the 13th century to 1930s. Former dollhouse adorers will absolutely lose it, and everyone else should delight in the remarkable intricacies and attention to detail in these miniscule glimpses into dozens of environs from back in the day. 111 S. Michigan Ave., Grant Park

What to Do in Chicago

The Green Mill: This historic jazz club in Uptown, its name an homage to Paris’ Moulin Rouge (which translates to “Red Mill”) dates back to the 1920s, has played host to the likes of Frank Sinatra, Al Capone, and Charlie Chaplin. The sultry space looks and feels delightfully untouched by time, particular during one of the venue’s frequent jazz or swing shows. But the calendar has thoroughly modern offerings, too: Don’t miss “The Paper Machete,” a Last Week Tonight-esque “live magazine” variety show of sorts held each Saturday from 3 to 5 p.m., which unpacks the previous week’s political and cultural happenings. 4802 N. Broadway, Uptown

Baha’i House of Worship: Visiting during (relatively) balmy temps? Venture to the city’s northern burbs for an afternoon to check out the Baha’i House of Worship, one of 10 temples globally devoted to the Baha’i faith, and the oldest surviving one. Surrounded by lush gardens, the ornate, fondant-esque structure is nestled in Willmette, one of the Gold Coast’s poshest enclaves (be sure to stroll or drive by the palatial homes in the area, too). Easily reachable by the purple line on the El, the Metra commuter rail, or a 30-45 minute drive, it’s a peaceful, relaxing respite from Chicago proper. Located just north of Evanston, the nearby equally picturesque ‘burb that’s home to Northwestern University, save room before or after the Baha’i for a pitstop at Al’s Deli, located on Noyes St. a 10-minute El ride or drive or picturesque 25-minute stroll south. The pint-sized, French sandwich shop is only open 11:15 a.m. to 4 p.m. daily and doesn’t take credit cards, but its creations are sublime: get the roast beef with a chunky, piquant homemade bleu cheese dressing, or turkey, swiss, and bernaise sauce on a croissant, and absolutely save room (or grab a to-go dessert for the ride back into Chicago) for one of the cakey, iced cookies. Another excellent food move nearby: the massive apple cinnamon pancake at the Wilmette outpost of local breakfast chainlet, Walker Bros. Original Pancake House, a cake-like creation so hefty and sweet, it’s definitely best when shared. Baha’i House of Worship, 100 Linden Ave, Wilmette; Walker Bros. Original Pancake House, 153 Green Bay Rd, Wilmette; Al’s Deli, 914 Noyes St., Evanston

Where to Eat and Drink in Chicago

Pequod’s: Dire lactose or gluten allergies notwithstanding, you truly shouldn’t spend any time in Chicago without indulging in a deep dish pie (or two). Pequod’s is technically does a thinner crust more akin to a pan pizza or Detroit-style pie than most of the gut-busting, cheese-smothered, casserole-like versions of the genre, but it’s got plenty of heft, lots of crunch to balance out the doughier insides, and a crispy cheese crust, technically called frico, extending to the pie’s edges. In addition to its Lincoln Park location, there’s a outpost in the ‘burb of Morton Grove.  Giordano’s, Gino’s East or and Lou Malnati’s—the latter of which has multiple locations, a relatively thinner crust, and lighter, sweeter tomato sauce, and far shorter (if any) lines—are also beloved Windy City deep dish pizza picks worth a try; Giordano’s makes a fine pie, too, but it’s often overly heavy, and the sauce is far inferior to Lou Malnati’s. 2207 N. Clybourne Ave.

Fat Rice: Inventive twists on Macau’s cuisine, which melds Chinese and Portuguese flavors, are served up at this James Beard Award-winning Logan Square hotspot. Expect a lengthy wait for walk-ins at Rice, which was started by in 2013 after its initial start as an underground supper club; half a dozen years later, it still remains a hard reservation to nab. Highlights include the piri piri chicken,  or, if you’re chowing down with a large group, opt for the large-format, namesake feast. Fat Rice’s team has expanded with The Ladies’ Room, a cocktail lounge next door, and a daytime bakery serving Portuguese-inflected Chinese sweet treats. 2957 W. Diversey Ave., Logan Square

Alinea: Internationally lauded Alinea, from chef Grant Achatz and business partner Nick Kokonas, has won basically every major restaurant accolade out there (Michelin, James Beard, et al) and is the kind of place that gourmands fly in from the world over just to have a (high) three-figure meal at Achatz’s acclaimed culinary temple. It’s a special-occasion or expense account experience for the books. The Lincoln Park tasting menu-only restaurant’s wildly inventive dishes (think: an edible helium balloon dessert made from dehydrated apples; a pristine rosette constructed from prosciutto, served with passionfruit) that look positively futuristic and are served with lots of theatrical touches, like wafts of steam, beds of hand-carved ice, and garden-like arrangements of edible greenery. For a relatively more affordable Achatz experience, head to Next, a slightly less pricey tasting menu spot; The Aviary, a cocktail lounge with a la carte bites; or The Office, a speakeasy serving solely drinks. 1723 N Halsted St., Lincoln Park

Au Cheval: One of the best burgers nationally can be found at Au Cheval, a fancified diner-ish spot in the West Loop neighborhood. First things first: Yes, the waits can be hours long, but you can put your name down, grab an iced coffee a couple doors down at The Little Goat, and mosey around the area to work up an appetite; or try coming for a very early weekday lunch (brunch, really) when the place opens at 10 a.m., if possible. Thin, incredibly juicy griddled patties (two in the single, three in the double) comprised of prime beef are layered with slices of American cheese, slicked with Dijonnaise sauce made from Dijon mustard, mayo, and lemon juice, topped with homemade pickles, packed between toasted bunds, and dramatically served with a steak knife holding the whole thing together. Optional thick cut, peppered bacon is a decadent touch that you should absolutely add; other rich garnish options are foie gras or A fried egg. While the burger’s pretty much a must-order, the bologna sandwich has a loyal following, too. A range of well-made cocktails are worth trying, too. 800 W. Randolph St., West Loop

Related: Check Out More of Inside Out‘s City Guides

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