30 Activities
New York to Chicago: Wright's Falling Water, Pittsburgh, Chicago, and Cleveland
Starts from
New York
Transportation
By Car
Guidance
Self-Guided
Activities
30
Duration
4 days
Length
1639 mi
Guide details
Starts from
New York
Transportation
By Car
Guidance
Self-Guided
Duration
4 days
Length
1639 mi
- Unusual Locations
- Arts and Creativity
- Gastronomy
Kristan Schiller
Traveller
- Tour Frank Lloyd Wright's masterpiece in rural Pennsylvania, Falling Water.
- Dine at one of Pittsburgh's best new restaurants.
- Laugh until it hurts at Second City, where many SNL comedians started.
- Visit Cleveland's Rock and Roll Hall of Fame.
- Grab dinner where Dunder Mifflin staff dined in Scranton.
Drive west across Pennsylvania to Falling Water, architect Frank Lloyd Wright's most famous home, completed in 1937 for Pittsburgh retail mogul Edgar Kaufmann. Tour this iconic structure with a waterfall running through it—which adorned the cover of Time magazine a few months after it was finished—then enjoy a night on the town in Pittsburgh. In Chicago, see art, architecture, comedy, and high fashion, all while enjoying the incredible cuisine coming out of the city's plethora of innovative restaurant kitchens. Turn around and head back east, stopping in Cleveland for sleep at a historic mansion and a tour of the Rock & Roll Hall of Fame. End your road trip with dinner at Dunder Mifflin's favorite Scranton eatery before rolling into the city by evening.
Categories
- Unusual Locations
- Arts and Creativity
- Gastronomy
Drive west across Pennsylvania to Falling Water, architect Frank Lloyd Wright's most famous home, completed in 1937 for Pittsburgh retail mogul Edgar Kaufmann. Tour this iconic structure with a waterfall running through it—which adorned the cover of Time magazine a few months after it was finished—then enjoy a night on the town in Pittsburgh. In Chicago, see art, architecture, comedy, and high fashion, all while enjoying the incredible cuisine coming out of the city's plethora of innovative restaurant kitchens. Turn around and head back east, stopping in Cleveland for sleep at a historic mansion and a tour of the Rock & Roll Hall of Fame. End your road trip with dinner at Dunder Mifflin's favorite Scranton eatery before rolling into the city by evening.
Kristan Schiller
Traveller
- Tour Frank Lloyd Wright's masterpiece in rural Pennsylvania, Falling Water.
- Dine at one of Pittsburgh's best new restaurants.
- Laugh until it hurts at Second City, where many SNL comedians started.
- Visit Cleveland's Rock and Roll Hall of Fame.
- Grab dinner where Dunder Mifflin staff dined in Scranton.
Travel itinerary
9 Activities
Day 1
371 mi1 mi
Wright's Rural Pennsylvania Stunner, Posh Digs, and Pittsburgh's Pas de Deux
Head west towards southwestern Pennsylvania, where you'll tour architect Frank Lloyd Wright's most celebrated structure, Falling Water. Lunch at the café there, then head north to Pittsburgh, where you'll see the Pittsburgh Ballet perform in a restored 1920s movie palace. Stay at the stylish Kimpton Hotel Monaco, Pittsburgh and enjoy dinner at one of Pittsburgh's buzziest new restaurants.
8 Activities
Day 2
481 mi0.9 mi
Art Institute of Chicago, James Beard Award-Winning Eats, Kickass Comedy
Hightail it from Pittsburgh to Chicago across Ohio and Indiana, then hit the town running. Browse the galleries at the fabulous Art Institute of Chicago, stroll through downtown, and enjoy dinner at one of Chicago's hottest culinary destinations. End your night laughing out loud with the funny folks at Second City, a Midwest incubator for Saturday Night Live comedians.
7 Activities
Day 3
382 mi1 mi
Windy City Architecture Cruise, Michelle Obama's Dressmaker, and Cleveland Historic Hotel
Take a 90-minute cruise along the Chicago River narrated by an architecture expert, then head over to Ikram, where Ikram Goldman displays her fabulous finery. Enjoy lunch at the café at Ikram then take a turn or two through the shop. Hop in the car and head back east to Cleveland, where you'll stay at a French Gothic historic mansion-turned-boutique hotel and dine on creative Mexican fare.
6 Activities
Day 4
401 mi
Good Coffee and Gibson Guitars
Enjoy breakfast at an elegant cafe in Cleveland's eastern suburbs, then take a turn through Cleveland's Cultural Gardens as you drive downtown towards the Rock & Roll Hall of Fame. Tour this I.M. Pei-designed tribute to rock then hit the highway to head back to the Big Apple. But don't forget to stop in Scranton and have dinner at Michael Scott's favorite Scranton restaurant, Cooper's Seafood House.