Getaway: The New Obama Presidential Center, Plus 25 Other Reasons to Visit Chicago Now

The Chicago River / Photograph by Mlenny/Getty Images

If you, like me, are a person who loves Philly for its unpretentious but big-city vibe, then Chicago is a place you will treasure. The crown jewel of the Midwest is culinarily formidable, architecturally stunning, and highly walkable — and with new destinations to explore (Barack Obama’s presidential library), anniversaries to celebrate (Route 66), and music to seek out, now’s the time for a long weekend in the Second City.

TRAVEL TIME: 2.5-hour direct flight, PHL to O’Hare

Day One

Drop your bags at the recently renovated, circa 1927 Talbott hotel (rooms from $234), in the Gold Coast Historic District, then head out for an afternoon of sightseeing. For one flat rate ($109 for nine days), the digital CityPASS gets you entry at multiple major destinations, including the Art Institute of Chicago (which features a Mary Cassatt exhibition through January). Bop around the adjacent Millennium Park, with its iconic Bean, and — if you’re here September 3rd to the 6th — check out some of the free concerts there, part of the Chicago Jazz Festival. (By the way: Route 66, celebrating its 100th birthday this year, starts steps from the park at the intersection of East Adams Street and Michigan Avenue. The commemorative marker is highly Instagrammable.) Later, hop on a First Lady boat tour along the Chicago River — a beautiful, engaging way to see architectural marvels like the Gothic Revival Tribune Tower — and then cap things off with a gooey deep-dish pizza from Pequod’s. Touristy? Yes! But worth it.

The Barack Obama Presidential Center in Chicago / Photograph by Kamil Krzaczynski/Getty Images

Day Two

Chicago, like Philly, is a city of neighborhoods. You’ll see hints of Fishtown and NoLibs in Logan Square and Avondale, with horror movie–themed coffee shop The Brewed, thrift store and dive bar hybrid Consignment Lounge, and veggie-forward all-day cafe Daisies. Folks looking for Rittenhouse vibes will find them in Lincoln Park, where you can cycle along the northern chunk of the 18.5-mile Lakefront Trail. (There are various bike rental outfits in the area.) Or get your fill of outdoor pursuits at the Lincoln Park Zoo and the Peggy Notebaert Nature Museum, known for its butterfly sanctuary, which is home to more than 40 species. For a different slice of Chicago pizza excellence (thin, crispy tavern-style pies), there’s Dimmi Dimmi, opened last August. (Save room for their hand-pulled mozzarella sticks and life-changing tiramisu.) Finish the night with a beer-shot combo and a local band’s set at cozy bar aliveOne.

The pork belly at Crying Tiger / Photograph by Lindsay Eberly

Day Three

If you were smart enough to get tickets to the brand-new Barack Obama Presidential Center way in advance (the museum portion is sold out through November), good for you. Planners like you can explore the four floors of exhibits, an Oval Office replica, and views of Chicago’s South Side from the Sky Room. Didn’t have the foresight? That’s okay: The sprawling campus is free to visit and boasts a public library, a basketball court, and a lawn made for picnicking. Since you’re already there, explore the rest of the neighborhood. Osaka Garden, a scenic green space gifted by Japan for the 1893 Chicago World’s Fair, is across the lagoon. For lunch? Try Mahari, an award-winning restaurant serving African diasporic dishes like jollof rice and shrimp étouffée. And over on the University of Chicago’s campus is the Frederick C. Robie House, a Frank Lloyd Wright–designed museum. Finish the day back downtown at lauded chef Thai Dang’s year-old, lavishly designed Southeast Asian restaurant, Crying Tiger, which in April opened a swanky cocktail bar, Kitty’s Cosmopolitan Club, on the lower level. Upstairs, it’s all about the confit duck pan​ang curry. Downstairs? Order the Jap​anese whiskey old fashioned, and say cheers to an unforgettable trip.

Jazz at The Green Mill / Photograph by Kathleen Hinkel

A Guide to Chicago’s Iconic Jazz Clubs

The Standards

Andy’s Jazz Club and The Green Mill (the latter was allegedly a favorite of Al Capone’s) are perhaps the city’s most well-known jazz bars. Pop in any night of the week to catch performers of styles from big band to free jazz.

The Greats

Since 1947, Jazz Showcase has been highlighting giants such as Yusef Lateef, Dizzy Gillespie, and Ahmad Jamal, who recorded his album Chicago Revisited at this bar. Expect an old-school vibe.

The Avant-Garde

For fans of more cutting-edge jazz, Constellation’s programming focuses on experimental performers. Example: Philly’s own Sun Ra Arkestra is playing here on September 25th.

Something Different

Technically, this is a blues club, but we’d be remiss if we didn’t mention Buddy Guy’s Legends, owned by the eponymous Grammy winner. (If you’re lucky, he might make an appearance.)

Published as “High Fidelity” in the September 2026 issue of Philadelphia magazine.