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The Perfect Weekend Getaway: Pittsburgh From Chicago

Our new series on weekend road trips aims to inspire you for what's to come as we slowly return to travel.

Covid-19 Disclaimer: Make sure to check the status of the states, regions, and establishments in which you’re planning to visit prior to travel. Many regions continue to see high infection rates and deaths, while many states and counties remain under varying stay-at-home orders. Those traveling from areas with high rates of Covid-19 should consider avoiding travel for now in order to reduce spread.

A blue-collar town at first glance, one must only dig a little deeper to find that Pittsburgh is home to cutting edge art, incredible eats, and outdoor adventures aplenty. The only Platinum certified greenhouse in the world, The Phipps Conservatory, is in Pittsburgh, as well as more than 8,000 works of art by local boy Andy Warhol at the Warhol Museum. The city is also a master at rebirth, an expert at modernizing its industrial past with art galleries in old warehouses (The Mattress Factory) and restaurants built along rail lines and inside car dealerships (Eleven, Superior Motors). And of course, the original Mister Rogers neighborhood is Pittsburgh’s upscale Squirrel Hill, where Fred Rogers and his wife Joanne raised their two children while he started filming the award-winning television show. And there’s plenty for outdoor enthusiasts, too, with 24 miles of riverfront trails for walkers and cyclists alike.


To get to Pittsburgh, drive seven hours east on I-90 from Chicago. Listen to Positively Pittsburgh Live or the Pittsburgh City Paper podcast for all the details on what’s going down in Pittsburgh.


Leave Chicago early morning and arrive in Pittsburgh mid-afternoon for a late lunch at Federal Gallery, a pared-down food hall on the North Side where you can choose from burgers and banh mi at Provision PGH; tacos and tortas at El Lugar; pizza at Michigan and Trumbull; or farm-to-table seasonal eats at Supper. Order lunch and a local craft brew then grab a seat on the outdoor patio in summer.

After lunch, take a short stroll to the Mattress Factory, a four-story Stearns & Foster warehouse that became an art installation space in 1977. Walk through James Turrell’s light sculptures or immerse yourself in a sea of Japanese artist Yoyoi Kusama’s red dots.

Top off your afternoon with a visit to The Andy Warhol Museum a short walk away. Seven floors of the Prince of Pop Art are on display here, in the artist’s hometown, including drawings, prints, paintings, sculptures, videos, and film. If you’re lucky, there might be a Sound Series concert taking place in the museum’s theatre. These live performances from bands around the world were inspired by Warhol’s role as a record producer and manager of the Velvet Underground.

Once you’ve had your fill of culture, call a cab from the museum and cross over the Allegheny River by way of the Andy Warhol Bridge to arrive at Eleven, an elegant farm-to-table restaurant in a rehabilitated warehouse along the old Pennsylvania rail lines. Entrees include Elysian Fields Farm Lamb Loin with cherry-Marcona almond salsa and Gerber Farms chicken with thyme jus.

For a more casual dinner, head to Tako, a gourmet Mexican street food spot that’s garnering buzz with its unique preparations like grilled octopus tacos.


Start your day with a hearty breakfast at Pamela’s, a retro diner in the Strip District serving hearty basics and a favorite of Barack Obama, who shared an order of pancakes here with Michelle during his presidential campaign. For an on-the-go breakfast, grab a coffee and pastry at Allegro Hearth Bakery instead.

Make your way on foot to Phipps Conservatory and Botanical Gardens and absorb the blossoming eye candy: tropical bonsai, desert plants, ferns, orchids, and palms. Opened in 1893, the conservatory was a gift to the city from philanthropist Henry W. Phipps and makes an excellent year-round excursion, especially for kids.

Leave the confines of the conservatory and explore Schenley Park itself. Listed on the National Register of Historic Places as a historic district, the 456-acre wooded park in Pittsburgh’s Oakland community offers hiking trails, a swimming pool, a disc golf course, ice skating, and even film screenings. The main trails that run through the park are in Panther Hollow.

For a healthy lunch, no need to go far since Café Phipps has been rated by Food & Wine as one of the “Best Museum Restaurants in the U.S.” The light, airy café at the entrance to the conservatory serves dishes like organic Waldorf Salad and grilled tempeh Rueben. If you’re hankering for something more filling, head to The Porch at Schenley where you can sit on the patio and enjoy their famous burger on brioche with giardiniera pickles.

Now that you’ve sampled Pittsburgh’s culinary landscape, hop on a bicycle and burn it off. One of the best ways to see and experience any city is by bike, and Pittsburgh is no different. Rent bikes for a guided, two-and-a-half-hour tour of the Steel City with Golden Triangle Bike Rentals. The tour takes advantage of the city’s 24 miles of riverfront trails while highlighting landmarks, public art, bridges, and beyond.

For dinner, shift from two wheels to four as you descend upon Pittsburgh’s most talked-about restaurant of the decade, Superior Motors, opened in 2017 in an old Chevy dealership after a record-setting $310,225 Kickstarter campaign. The eclectic, seasonal fare here includes everything from beef tartar to gnocchi with swiss chard and cashews to scallops with turnip, pomegranate, and kimchi. Visit Carmi Soul Food for shrimp and grits in a 1900s Victorian Row House on the South Side for an alternative.

After dinner, head to Arcade Comedy Theatre in downtown Pittsburgh where they keep the laughs coming with the best local talents and national touring acts who perform stand-up, sketch, and improv on the theatre’s open stage. It’s BYOB, and the theater offers children’s comedy shows on a monthly basis.


For breakfast, stop into Bluebird Kitchen in downtown Pittsburg for the house-made granola served with Greek yogurt, honey, and fruit.  Or, pop by Geppetto’s Café for a savory crepe and a cup of the house coffee.

You can’t visit Pittsburgh without paying tribute to Pittsburgh native Fred Rogers, whose critically-acclaimed Mister Roger’s Neighborhood ran for 33 years. At the Heinz History Center in the Strip District, you can visit the Land of Make-Believe by checking out the display of the original set and items from the show, including the entryway and living room where Mister Rogers would lace his sneakers, King Friday’s Castle, and the Great Oak Tree where Henrietta Pussycat and X the Owl live.

For lunch, head to the achingly hip Ace Hotel in an old YMCA building in the East Liberty neighborhood and experience Whitfield, the hotel restaurant, run by James Beard Award-nominated chef Bethany Zozula, which claims a dining experience “with influences culled from the culinary traditions of the region’s Polish, German, Eastern European, Italian and Jewish settlers.” Lunch includes entrees like steak and eggs with fries and bearnaise and a trout niçoise with lemon caper vinaigrette. At Fireside Public House nearby, craft beer and wood-grilled burgers are the specialties.

With a full stomach, explore the neighborhood on foot. Formerly scrappy Lawrenceville, along the Allegheny northeast of the Strip District, has become one of the city’s hippest hangouts. Butler Street from 34th to 54th Streets is an eclectic strand of shops, galleries, bars, and eateries on every cool kid’s radar. East of Allegheny Cemetery, you’ll find the Garfield and Bloomfield neighborhoods, both Polish and Italian strongholds. Due east is the gentrified East Liberty enclave, now home to a Google office.

Hit the road around mid-afternoon to return to Chicago by bedtime.


Once the home of industrialist Henry Clary Frick’s lawyer, Willis McCook, the 20,000 square-foot, 1906-built Mansions on Fifth were designed in the Tudor and Elizabethan Revivalist styles on “Millionaire’s Row” in Pittsburgh’s posh Shadyside neighborhood. Return to the Gilded Age at this impeccably-restored hotel (a main house and smaller, adjoining home), which offers 22 individually-decorated guest rooms, a dining room, Oak Room pub, chapel, library and wine cellar with butlers on call from 7 a.m. to 11 p.m., seven days a week. Centrally-located and dog-friendly, the boutique Shadyside Inn All Suites Hotel has studio, one-bedroom, or two-bedroom suites, each with a clean, contemporary look. Amenities include kitchenettes, a complimentary local shuttle, and the hotel’s own dog park. Fido will feel positively pampered!

A former Benedictine monastery on Pittsburgh’s North Shore in the historic Deutschtown neighborhood, The Priory has a parlor scattered with Edwardian antiques and a cozy fireplace.  Rooms are spacious with high ceilings, and the minuscule Monk’s Bar just off the lobby is open 5 p.m. to 11 p.m. daily. There’s a highway nearby, so request a room facing the inner courtyard, where a spewing fountain provides white noise.


Pittsburgh weather is similar to that of New York, only with more humidity. The weather is changeable, with heatwaves in the summer and cool weather in the fall and spring. Winter can be brutally cold. Late spring and early fall are the best times for visiting Pittsburgh, weather-wise.