36 Hours in Chicago

You can't possibly see and taste everything in Chicago on one trip, but that's why we love it. You'll want to go back again and again to dive deeper into the city's culture and neighborhoods. This itinerary includes classics like photo ops at "The Bean" plus strolling along the Riverwalk, popping into hipster basement bars—and, of course, eating at a deep-dish pizza spot.

Day One

Cozy check-in @ 4 p.m.

Guests of The Publishing House Bed and Breakfast in the West Loop stay in one of 11 luxe rooms, but curling up with a book in a nook of the 1909 historic building is encouraged.

Pop over to Pilsen @ 6 p.m.

At the buzzy S.K.Y, chef Stephen Gillanders prepares fresh takes on American cuisine such as Maine lobster dumplings.

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.

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, carafes, or a $96 bowl.

Day Two

Coffee break @ 9 a.m.

Your Publishing House room comes with breakfast, but if you want a little something extra, walk a few blocks 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.

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.

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 spa in the Fairmont Chicago Millennium Park hotel for a shower and a reasonably priced and relaxing deep tissue massage.

Trendy lunch @ 1 p.m.

Food halls are trendy in Chicago right now—groups of small, local restaurants serving a variety of freshly made foods. Revival Food Hall (currently open Monday through Friday) features 15 fast-casual stalls like Lito's Empanadas and Smoque BBQ. If you're in Chicago on the weekend—or just want a different type of atmosphere—The Gage restaurant, only a short walk from Millennium Park, promises an elevated experience with lunch options like free-range Amish chicken, Thai coconut curry or Alaskan halibut.

Walk along the river @ 2 p.m.

Walk off your lunch along Chicago's recently developed Riverwalk, lined with art (look for the giant deer sculpture by the Merchandise Mart, and the 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 British game bars—Flight Club, a swanky place to play darts, or AceBounce, the ping-pong bar next door.

Museum stop @ 3 p.m.

Pick your passion: Art, science, communications, history....Chicago has a top-notch museum for just about any interest. Think about the American Writers Museum, the Field Museum, the Chicago History Museum, the Art Institute of Chicago, the National Museum of Mexican Art or the Museum of Science and Industry.

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.

Cocktails with a view @ 9:30 p.m.

The retractable roof on ROOF on theWit means you can be indoors or out at the swanky, 27th floor club. Regardless of the weather, there's a stunning nighttime skyline as your backdrop.

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.

Maggie moment @ 10 a.m.

Walk (or in the winter, rent ice skates and glide) along the "ribbon" path at Maggie Daley Park. If the weather isn't cooperating, head north on Michigan Avenue to soak in the views at 360 Chicago. Daredevils will want to pay extra to try "Tilt!" where you stand in a glass box and are tilted over the 94th floor of the skyscraper.