Start in New York City and see some Jazz at Birdland, now on West 44th, but located on Broadway when featured in the novel. Head west towards Chicago with $50 in your wallet, just like protagonist Sal Paradise. You could also take a bus, like Sal did for this stretch, and you'll want to leave in the spring if you really want to emulate the book.
Listen to some blues in Chicago like Kerouac did, who visited the Windy City "somewhere between its Charlie Parker Ornithology period and another period that began with Miles Davis." Unfortunately, the YMCA doesn't take short-term lodging anymore as it did in the late '40s, so you'll have to find other lodging.
Head to New Orleans and make sure to hit some bars. Since Sal hung out for a spell with the character "Old Bull Lee" (supposedly William S. Burroughs), you might want to read a little Burroughs during your stay.
Next you're off to Cheyenne, Wyoming, where Sal Paradise was taken aback by the sight of businessmen trying to pose as Westerners in ten-gallon hats and cowboy boots. Hopefully your budget will allow better lodging than the bus station Sal slept in!
Point south towards Denver for your next stop, and make sure to do some bar-hopping on Larimer Street. Neal Cassady (known as Dean Moriarty in the book) "was generally brought up on Larimer Street," and Sal Paradise hangs out there a bit in "On the Road."
Now it's off to the coast, where Jack Kerouac spent plenty of time in San Francisco during his heyday. Enjoy a hearty meal at Alfred's Steakhouse on Merchant Street (where Sal dined with his friend Remi Boncoeur), a San Francisco institution since 1928.
Head for Los Angeles and take the time to chow down at the colorful Clifton's Cafeteria on South Broadway, with fake waterfalls and a staged redwood forest. It is likely that Kerouac was eating at the Clifton's branch on Olive Street, although that site closed decades ago.
Wrap up your trip in Mexico City, where Sal explored the meandering streets with best friend Dean Moriarty. They also dined at Sanborn's (a chain of Mexican family restaurants) in the historic Case de Azulejos, a branch that is still serving meals to this day.
