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The Perfect Weekend Getaway: Cincinnati 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.

After a speaking engagement there in 1901, Winston Churchill called Cincinnati “the most beautiful of the inland cities of the union,” saying that “the city spreads far and wide, its pageant of crimson, purple and gold laced by silver streams that are great rivers.” Meanwhile, novelist Charles Dickens described it as, “cheerful, thriving, and animated.” Do these feted Brits flirt with hyperbole? Perhaps, but there’s no knocking Cincy’s charms.

While many dismiss Cincinnati as a sleepy Midwestern town, this southern Ohio hub exudes unique energy that can’t be ignored. The historic Over-the-Rhine (OTR) district has lively Findlay Market, which draws culinary enthusiasts by the carload on the weekends while recent renovations of downtown Cincy’s riverfront Great American Ballpark and Fountain Square also speak to Cincy’s renaissance. But the bustling municipality has its natural assets, too. There are more than 80 parks and 116,000 acres of protected greenspace in the Greater Cincinnati region and a walk through any one of them reveals the city’s outdoor appeal. So, it should come as no surprise that Churchill and Dickens sang Cincy’s praises. After a weekend getaway, you just might too!


To get to Cincinnati, drive about three hours south on I-64 from Chicago, then another hour and a half south on I-74. On the drive, check out the podcasts Around Cincinnati and The Cincinnati Edition.


Leave Chicago early morning and arrive in Cincinnati just in time for lunch at buzzy eatery Fausto inside the Contemporary Arts Center downtown. Order the tarragon chicken salad sandwich with pistachios and an iced coffee from the owner’s custom-label coffee blend, a collaboration with Cincinnati-based Deeper Roots Coffee. Nada, an upscale cantina with outdoor seating, is about five minutes away if you’re in the mood for Mexican instead.

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After lunch, browse through the Zaha Hadid-designed Contemporary Arts Center which The New York Times called “the best new building since the Cold War.” It was the late Hadid’s first American building, which of course increased the reputation of an already infamous museum. (The CAC made national headlines in 1990 when it was prosecuted for including sexually charged images in an exhibition of photographs by Robert Mapplethorpe, making it the first criminal trial in history of an art museum over the contents of an exhibition.) Browse the museum’s 11,000 square feet and see new developments in painting, sculpture, photography, architecture, performance art and new media.

If your caffeine buzz holds out, walk to the nearby 21C Museum Hotel and get lost in their galleries or visit the neighboring Cincinnati Arts Association’s Weston Art Gallery, a staging ground for emerging art by local, national, and international artists.

Settle in for a leisurely dinner at Soto, one of the Queen City’s most popular restaurants just across the street from CAC. The Italian fare here is raved about by everyone, especially the black kale Caesar salad and short rib cappellacci. In the mood for a nightcap? Hit the patio of new spot Night Drop for a Mezcal and root beer float or bring your own growlers and fill ‘em up with a selection of craft beers on top for a mere $15. (And if Italian isn’t your thing, you can skip Soto and grab a burger or cobb salad from Night Drop’s bar menu.)


Start the day with the lemon ricotta pancakes or one of many omelet choices at Maplewood Kitchen & Bar.  For breakfast all day, descend upon the shabby chic Cheapside Café for a chorizo egg sandwich or oatmeal brulee (steel-cut oats, golden raisins, maple cream.)

Now that you’re suitably fed, it’s time to walk off some of those calories. Cincinnati Nature Center in Milford, just minutes from downtown, CNC covers more than 1,700 acres, forests, fields, streams, and ponds with almost 20 miles of trails. Wear comfortable walking shoes and enjoy spring wildflowers or autumn foliage, depending on the season. The center is open year-round and admission is $9 for adults.

If you’re on a budget and fancy a free outing instead, mosey on over to French Park in Amberley Village, where a series of trails are hidden behind French House, a 1900s brick mansion set majestically on the hill. There are four trailheads that lead out of the parking lot. The outermost trail is about 3-miles long and is an intermediate trail, not for novice hikers. An endearing tidbit to note: the grave of the cherished dog of French Park’s original owner, Procter & Gamble executive Herbert Greer French, can be seen from one of the backwoods trails.

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For lunch, head to Senate, which serves gourmet hot dogs in Cincy’s hip Over the Rhine neighborhood. The space is rustic and sleek and the dogs are creative and tasty. Try the Shia LaBeouf hot dog with goat cheese, caramelized onions, bacon, arugula, and balsamic.  For healthier fare, hightail it over to Trio and order one of its specialty salads. The Scottish Salmon Salad with field greens is a local favorite.

This afternoon, sit back, relax, and enjoy a historic Cincinnati sightseeing cruise on the Ohio River. BB Riverboats offers an hour-and-a-half sightseeing tour on the Ohio River. Listen as the captain guides your adventure with commentary of the beautiful river city. For example, did you know that 1 out of every 4 steamboats that were built in the United States, were built in Cincinnati? That’s just one of the tidbits you’ll learn on this relaxing, informative afternoon cruise.

Continue the history thread and don your best travel dress for dinner at one of the most celebrated restaurants in Cincinnati, if not Ohio. The Orchids at Palm Court restaurant in the Art Deco, National Historic Landmark Hilton Cincinnati Netherland Plaza (where Churchill stayed), not only boasts towering ceilings and Romanesque murals but also a French-influenced, 10-course tasting menu at $120. Dishes change depending on what’s in season;  items might include squash blossoms with green tomato and soubise or seared scallops with lardo, dukkah, and sunflower seeds. End your evening with a tipple at the adjoining bar.

For a less formal affair, head to Over-the-Rhine and the casual Forty Thieves, a walk-up Middle Eastern street-food counter by the streetcar stop at Liberty and Race.

Before bedtime, make way to the Cincinnati Observatory, if it’s open. Saturdays from 10:30 to midnight the observatory hosts a date night under the stars event where you and your squeeze will be able to view astronomical objects not visible until late at night through the observatory’s giant telescope.


On your last day, head to Findlay Market, Cincinnati’s oldest covered public market selling unique foods at its many stalls including fresh produce and local baked goods. Occasionally there’s even live music.  Enjoy breakfast on the go with a pastry from Blue Oven or a Honey Puff Donut from Cherbourg Cyprus (their T-shirts make a great Cincy souvenir.) People watch and shop for everything from artisan goods to specialty food items to home-made dog biscuits for your canine.

Spend the rest of the morning walking across the John A. Roebling Suspension Bridge, named for the civil engineer who designed it and offering some of the most beautiful views of the Cincy skyline. When the Roebling opened on January 1, 1867, its 1,057-foot span made it the longest suspension bridge in the world. It remained so until 1883 when Roebling’s most famous project, the Brooklyn Bridge opened.

For lunch head to Commonwealth Bistro for modern American fare and reward yourself for your walk with a craft beer at the restaurant’s midcentury modern-style rooftop bar, Yonder. Or choose Frida 602 just up the road for a la carte tacos and other Mexican dishes in a stylish setting, reminiscent of its namesake Frida Kahlo.

Head back over the bridge to the Underground Railroad Freedom Center. Opened in 2004 on the banks of the Ohio River, the center displays relics from the era such as a shackle-filled pen that once held slaves going to auction. The museum also features The Rosa Parks virtual-reality exhibit whereby visitors don a headset and goggles and sit on a ‘bus’ as Parks did when she refused to give up her seat.

Before hitting the road, grab a pulled pork sandwich from Eli’s BBQ or the Reuben at Izzy’s. Both are Cincy favorites.


One of Cincinnati’s hippest hotels, Hotel Covington, isn’t actually in Cincy itself but a quick jaunt across the Ohio River in nearby Covington, Kentucky. Industrial chic meets time-honored tradition at this trendy hideaway where the property’s past as a department store is on display in everything from its high ceilings to its gigantic window displays. Partake in lawn games on the outdoor grounds, indulge in local comfort food at the hotel restaurant Coppins, or nurse a cocktail with neighborhood hipsters in the lobby bar

History buffs will want to stay at Six Acres, a B&B in the suburb of College Hill about fifteen minutes from downtown Cincinnati. Located on (surprise!) six acres, this historic home was built by Quaker abolitionist Zebulon Strong in the 1850s and was a stop on the Underground Railroad, housing fugitive slaves as they made their way north to freedom in Canada. Guestrooms have comfortable Queen-sized beds with private bathrooms.

21c’s restoration of the old Metropole Hotel in Cincinnati’s historic center helped spur the renaissance of downtown Cincy. Fittingly positioned next to the Contemporary Art Center and across from the Aronoff Center for the Arts, the hotel doubles as an art gallery with rotating exhibitions in the lobby, original art in every guest room, and regular, guided tours. Metropole, the hotel restaurant, offers farm-to-table fare and the hotel’s Cocktail Terrace is one of the city’s hottest rooftop bars.


Cincinnati’s summers are hot and humid, pulling in heat from the Ohio River, and yet there’s plenty on the city calendar in summer. One of the best times to visit Cincinnati is in the fall, when temperatures are ideal, in the 50s and 60s, and the trees show their autumn colors.