1. Chicago, Illinois
"Sweet Home Chicago" by Robert Johnson
Chicago's a huge scene for many different kinds of music. You could go with songs by Spoon, Sinatra, Tom Waits, Sufjan Stevens, or just about anything by Kanye West, but for a town this important to the blues, there's only one choice. Spend time checking out music wherever you can at night, but also check out Wrigley Field, Lincoln Park, and the view from Lake Michigan while you're there. Of course, if you're on a music-themed vacation, there's only one road you can take when you head out of the city.
2. Route 66 (Illinois to California)
"(Get Your Kicks on) Route 66" by Nat King Cole Trio
"Route 66" is a classic American standard. Written by Bobby Troup and recorded by Nat King Cole's trio, it's been sung by everyone from Bing Crosby to Depeche Mode to John Mayer. The actual Route 66 is a classic piece of Americana, as well. The road doesn't officially exist anymore, but much of it is still standing. There are plenty of sites to help you plan a route from Chicago to L.A. that squeezes as much of the old-fashioned highway as possible into the trip.
3. Amarillo, Texas
"Amarillo by Morning" by George Strait
Amarillo isn't the biggest city in Texas, but there sure are a ton of songs about it—most of them, unsurprisingly, of the country and Western varieties. Emmylou Harris, Don Cherry, Robert Earl Keene, and Jason Aldean are just a few of the artists who've paid homage in song to this Texas town. As for sights to see, there's no shortage. There's the famous-but-baffling roadside oddity "The Cadillac Ranch." The scenery out here is largely flat and dusty, but Palo Duro Canyon is gorgeous, making it a great place to stop as you head back out on Route 66.
4. Albuquerque, New Mexico
"Albuquerque" by "Weird Al" Yankovic
Yes, okay, the Weird Al song might not be the best example of what the city is about musically, but it's undeniably epic in scope and length, and on a trip this long, that counts for a lot. Albuquerque itself is a cool city. There's some great skiing nearby, and while you might not find the same art community vibe as Taos or Santa Fe, you won't be hurting for local culture. It's easy to find traditional American Indian groups playing around town, and Albuquerque is also the site of the annual Mariachi Spectacular.
5. Los Angeles, California
"I Love L.A." by Randy Newman
If you don't want to take travel tips from Randy Newman, that's understandable. But Los Angeles' huge music scene, especially that country/rock singer-songwriter scene of the 1970s, means there's no shortage of songs about the city. Warren Zevon's "Join Me In L.A." is another great one. From Venice Beach to Hollywood to the J. Paul Getty Museum Complex, there's no shortage of things to do.
6. Pacific Coast Highway (California)
"Pacific Coast Highway" by Burt Bacharach
This jaunty little instrumental is vintage Bacharach at his most whimsical. If Bacharach isn't your speed, Hole, Sonic Youth, and the Beach Boys have both also written songs about the stretch of road you're taking north. It's a day-long drive, but this gorgeous cliff-hugging highway is the best way to appreciate the scenic beauty of the West Coast.
7. San Jose, California
"Do You Know the Way to San Jose" by Dionne Warwick
Okay, yes, it's another Burt Bacharach song, but Burt Bacharach is amazing. San Jose is a nice place to stop on the drive. The weather's gorgeous, plus there are a couple of theme parks out here: the Rosicrucian Egyptian Museum and Planetarium and the Heritage Rose Garden.
8. San Francisco, California
"Mission Street" by Vienna Teng
We're in San Francisco now. Lots of people have used San Francisco as a muse (for both better or worse), and a few have even mentioned Mission Street by name. This dreamy ballad by Vienna Teng, however, makes it sound a lot nicer than Scott MacKenzie, Journey, or the Village People ever managed. And of course, there's no shortage of tourist attractions here, including cable cars, Pier 39 and its sea lions, the Disney Museum, the Museé Mechanique, and some of the best airport restaurants in the country. There are also stories of some kind of bridge in the area.
9. Portland, Oregon
"City of Roses" by Esperanza Spalding
There are a lot of musical odes to Portland, Oregon, and in keeping with the outré scene here, most of them are janglier than what America's favorite jazz prodigy whipped up. Check out Sleater-Kinney, Kela Parker, The Replacements, Eliot Smith, and The Decembrists for more songs about the city that gave the world Pink Martini, Stars of Track & Field, Portugal the Man, and Stephen Malkmus. Portland takes full advantage of its position between two rivers, so check out the Lan Su Chinese Garden, the massive technicolor maples at the Japanese garden, the International Rose Test Garden, and the waterfront. Or just see how many street scenes you recognize from the TV series Portlandia.
10. Seattle, Washington
"Spanish Castle Magic" by Jimi Hendrix
Hendrix's ode to a now-demolished club between Seattle and Tacoma is only a small part of the city's musical history. Seattle is still known as the birthplace of Nirvana and the huge grunge scene of the 1990s, but there's also a huge hip-hop scene that's been bubbling up for years, waiting for a chance to boil over. If you're an old-school rap fan, Sir Mix-a-Lot's "Posse on Broadway" can help you navigate parts of the city, and if you're looking for something newer, check out "The Town," from a pre-breakout Macklemore.
For a comprehensive list of all the songs mentioned, listen to the Spotify playlist.