Road trips through
Illinois
23 road-trip plans across 3 cities.
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Cities travelers visit in Illinois
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Trips through Illinois
Utah's Mighty 5 & Beyond: A 30-Day Dog-Friendly Road Trip from Vermont
Arches to Zion, red rock canyons to alpine meadows — the whole magnificent show, done right, at a pace that lets it sink in
Route 66 End-to-End: Chicago to Santa Monica on Two Harleys
2,400 Miles of Asphalt, Americana, and a Las Vegas Detour
Toronto to Prince George: The Great Trans-American Road Trip
6 Days · ~3,800 Miles · Two Guys, One Tiguan, One Trailer, Zero Regrets
Rochester to Zion: The Great American Backroads Run
10 Days of Hidden Gems, Scenic Byways & Authentic Americana — Two-Up on Two Wheels
Plainfield to VOA: A Midwest Music & Eats Road Trip
5 Days from Chicagoland to West Chester, Ohio for the VOA Music Festival
Route 66: Chicago to Los Angeles — The Real American Road
10 Days, 2,400 Miles, One Legendary Highway — Two Europeans Go Full American
Route 66: Chicago to Los Angeles — The Real American Road
15 Days of Diners, Honky Tonks, Open Highways & Genuine American Life in a Classic Convertible
Toronto to Prince George: The Great American Heartland Haul
6 Days · Toronto → Chicago → Twin Cities → Badlands → Billings → Spokane → Osoyoos → Prince George
NY to Vegas the Long Way: Chicago Jazz, Montana Big Sky & Canyon Country
A slow-paced 10-day cross-country adventure — road tripping to Chicago, flying into Montana's dude ranch country, then cruising through Wyoming, Utah, and the desert to a Vegas finale
Coast to Coast USA: LA to Illinois, New England, Miami & Back
10 Days of Heartland Highways, Atlantic Shores & Southern Soul for Two
Rialto to Kentwood: Route 66, the Greenwood District & the Great American Midwest
A 10-Day Solo History-Chaser's Road Trip from Southern California to West Michigan
New York to Vegas: Chicago Jazz, Montana Wild, and the Wyoming-Utah Run
A slow-paced couple's road trip through Rust Belt diners, Chicago blues clubs, Montana dude ranches, and red-rock desert on the way to a Vegas finale
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