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36 Hours in Chicago

Big city, little time? You can still pack a lot into a short Chicago visit, and get a feel for the city by mixing touristy sites and local hangouts. This itinerary includes photo ops at “The Bean” and Saturday Night Live’s “Wayne’s World” couch, plus stops at authentic Mexican restaurants, hipster basement bars—and, of course, a deep-dish pizza spot.

DAY ONE

Cool check-in @ 4 p.m.

At the Ace Hotel, a new industrial-style, hyper-cool hotel in the Fulton Market neighborhood, your room might even have a guitar or vinyl record player in it. Weather permitting, have a pre-dinner drink at the hotel’s 7th floor rooftop bar, Waydown. acehotel.com/chicago

ACE Hotel. Photo courtesy of ACE Hotel.

Photo courtesy of Ace Hotel

Pop over to Pilsen @ 6 p.m.

Grab a six-pack of your favorite Mexican beer and hail a ride to this up-and-coming Southwest side Latino neighborhood for a budget-friendly dinner at Canton Regio. The cash-only, BYOB spot serves delicious Mexican brochetas and shrimp skewers that arrive dangling from a little stand, plus authentic Mexican dishes like mollejas de res (charbroiled beef sweetbreads over grilled spring onions and fire roasted peppers). Canton Regio on Facebook For something more upscale, try the buzzy new S.K.Y, where chef Stephen Gillanders prepares fresh takes on American cuisine such as Maine lobster dumplings. skyrestaurantchicago.com

Catch a show @ 7:30 p.m.

Enjoy a concert or comedy show at historic Thalia Hall, a recently restored 125-year-old building reminiscent of a Prague opera house. Acts include up-and-coming bands, well-known musicians like Chris Robinson, comedians such as Ilana Glazer, or even an NPR podcast taping. thaliahallchicago.com

Get “punched” @ 10:30 p.m.

Below Thalia Hall, have a post-show drink at Punch House, the hipster basement bar with leather booths and wood paneling that will remind you of your grandparents’ basement, but with great music and craft cocktails. The house specialty: alcohol-infused punch, sold by the glass, in “sno cones,” carafes, or a $66 bowl. punchhousechicago.com

DAY TWO

Coffee break @ 9 a.m.

Grab a cup of Stumptown Roasters coffee in the Ace Hotel’s café, or walk around the corner for some strong drip coffee or a picture-worthy Military Latte (green tea, vanilla syrup, cocoa powder and a shot of espresso) at Sawada Coffee, 112 N. Green St., which also sells decadent, locally-made Doughnut Vault doughnuts. sawadacoffee.com

Exercise with a view @ 10 a.m.

Head downtown for a run or bike ride along Chicago’s lakefront, one of the country’s most beautiful urban paths. Lake Michigan sparkles on one side; the other is lined with skyscrapers and attractions such as Buckingham Fountain or Soldier Field.

More of a yoga person? Do a drop-in class at Studio Three, an upscale new downtown yoga/interval training/cycling studio (studiothree.com/studios). Or if it’s Saturday morning, try to snag a ticket to 360 Sky Yoga, on the top of the John Hancock Building (360chicago.com/360-sky-yoga/), or the Adler Planetarium’s Sun Salutations Yoga, inside the star theater (adlerplanetarium.org/events/sun-salutations). (Buy tickets well in advance for Adler!).  

The classic Chicago photo op @ noon

Stop at the iconic reflective sculpture Cloud Gate, better known as “The Bean,” for a quick selfie. Linger in Millennium Park if it's a pleasant day, or head into the nice-but-unpretentious MySpa, in the Fairmont Chicago Millennium Park hotel, for a shower and a reasonably priced and relaxing deep tissue massage. fairmont.com/chicago/spa

The Bean sculpture

Cloud Gate

Lunch in the hall @ 1 p.m.

Food halls are trendy in Chicago right now—groups of small, local restaurants serving a variety of freshly made foods. The centerpiece of the newest food hall, Forum 55, near Millennium Park, is the Community Garden salad bar with regionally grown produce. But it’s hard to pass up the slow-smoked BBQ from Pork & Mindy’s, the chain by Food Network star and Chicagoan Jeff Mauro. forum55chicago.com

Walk along the river @ 2 p.m.

Walk off your lunch along Chicago’s newly developed Riverwalk, lined with art (look for the giant deer sculpture by the Merchandise Mart, and the new Apple store near Michigan Avenue, a glass building with a laptop-styled roof). If the weather’s lousy, go up a level and pop into two new British game bars—Flight Club, a swanky place to play darts (us.flightclubdarts.com/chicago; opening in spring 2018), or AceBounce, the ping-pong bar next door (acebounce.com/chicago).  

Chicago riverwalk

Chicago Riverwalk

AceBounce Chicago

Grab a paddle and a drink at AceBounce. Photo courtesy of AceBounce

Live from New York! @ 3 p.m.

Head to the Museum of Broadcast Communications’ fun new Saturday Night Live: The Experience exhibit. Pose for photos on the Wayne’s World couch and learn about the process of making an SNL show while perusing the legendary comedy’s costumes and props. Advanced ticket purchase recommended. museum.tv

Dig in @ 7:30 p.m.

You can’t visit Chicago without indulging in a gooey cheesy deep-dish pizza. At Lou Malnati’s, consider adding the signature pork sausage (or, as the Chicago Bears Superfans say with their accent, “sah-sige”) to your pie. Even if you pre-order your pizza, which is a good idea, expect a wait, and a stuffed (but happy) feeling as you leave. loumalnatis.com

Lou Malnati's

Lou Malnati's

Dance on the ROOF @ 10 p.m.

Head back to your hotel to dress up for a night of dancing. The retractable roof on ROOF on theWit means you can dance indoors or out at the swanky, 27th floor club. Regardless of the weather, there’s a stunning nighttime skyline as your backdrop. roofonthewit.com

Sweet stuff @ 1 a.m.

Late-night sweet craving? Call Insomnia Cookies, which will deliver fresh cookies, brownies and cold milk to your door up until 3 a.m. insomniacookies.com

DAY 3

On a roll @ 9 a.m.

Dig into a honey-butter cinnamon roll and some fresh-squeezed juice at the modern coffee shop Beatrix, or try one of the restaurant’s creative dishes like quinoa cakes with poached eggs. beatrixrestaurants.com

Maggie moment @ 10 a.m.

Walk (or in the winter, rent ice skates and glide) along the “ribbon” path at Maggie Daley Park. maggiedaleypark.com If the weather isn’t cooperating, head north on Michigan Avenue to soak in the 360-degree views at the top of the John Hancock Building. Daredevils will want to pay the extra $5 to try “Tilt!” where you stand in a glass box and are tilted over the 94th floor of the skyscraper. 360chicago.com/tilt

Maggie Daley Park

Maggie Daley Park; photo courtesy of Choose Chicago/Abel Arciniega

 

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