Illinois

10 days

The Classic Illinois Loop

Route: A circular drive taking in Illinois's iconic landscapes, gateway towns, and signature stays.

Our most-requested itinerary for first-time visitors to Illinois — a balance of headline sights and quiet, off-grid retreats.

7 days

Illinois Hidden Corners

Route: Lesser-known back roads, working ranches, and locally-owned inns across Illinois.

Designed with our regional partners for travellers who have already seen the postcards and want the unfiltered version.

16 days · Chicago to Santa Monica

Historic Route 66 — Curios, Pit Stops & Diners

Route: Chicago → Springfield IL → St. Louis → Springfield MO → Tulsa → Oklahoma City → Amarillo → Tucumcari → Albuquerque → Holbrook → Flagstaff → Las Vegas → Santa Monica / Los Angeles

The definitive end-to-end Mother Road self-drive — eight states from Lake Michigan to the Pacific, threading neon-lit motels, retro diners, ghost towns and roadside Americana. Tailormade with our DriveAmerica partners with curated overnights including the Wigwam Motel, La Posada and the Blue Swallow.

• •Chicago — Lou Mitchell's, the 'Begin' sign on Adams Street & Joliet's Route 66 Museum
• •Springfield, IL — Lincoln Tomb, Litchfield's Ariston Cafe & the Chain of Rocks Bridge
• •St. Louis — Gateway Arch, Ted Drewes frozen custard & Meramec Caverns
• •Springfield, MO — Route 66 Car Museum, Wagon Wheel Motel & Galena's 'Cars' tribute
• •Tulsa & Oklahoma City — Buck Atom's, the Golden Driller, Pops 66 Soda Ranch & the Milk Bottle Grocery
• •Amarillo — Cadillac Ranch, the U-Drop Inn, Leaning Tower of Texas & Big Texan Steak Ranch
• •Tucumcari & Albuquerque — Blue Swallow Motel, Tee Pee Curios, KiMo Theater & the 66 Diner
• •Holbrook & Flagstaff — Petrified Forest, Wigwam Village #6, La Posada Winslow & the Grand Canyon South Rim
• •Las Vegas — Neon Museum, Mob Museum & the Strip
• •Santa Monica — Roy's Cafe in Amboy, the original McDonald's, Beverly Hills sign & the End of the Trail at the Pier

19 days · Chicago to New Orleans

Get Your Vibe On I-65

Route: Chicago → Indianapolis → Louisville → Nashville → Florence/Muscle Shoals → Huntsville → Birmingham → Montgomery → Orange Beach/Gulf Shores → Mobile → New Orleans

End-to-end on Interstate 65 from the Great Lakes to the Gulf — Chicago's skyline, Indy's Motor Speedway, Louisville bourbon, Nashville's Music City, the legendary Muscle Shoals studios, Huntsville's Space & Rocket Center, Birmingham's Civil Rights heritage, Montgomery's history, the white-sand Alabama Gulf Coast, historic Mobile and a New Orleans finale.

• •Chicago — Millennium Park, the Bean, Navy Pier & Magnificent Mile
• •Indianapolis — Motor Speedway, Eiteljorg Museum & the Cultural Trail
• •Louisville — Kentucky Derby Museum, Bourbon Trail, Muhammad Ali's home & Louisville Slugger Museum
• •Nashville — Ryman Auditorium, Country Music Hall of Fame, Grand Ole Opry & Printer's Alley
• •Florence/Muscle Shoals — Muscle Shoals Sound Studio, Alabama Music Hall of Fame, W.C. Handy's birthplace & Frank Lloyd Wright's Rosenbaum House
• •Huntsville — U.S. Space & Rocket Center, Botanical Garden, Burritt on the Mountain & The Orion amphitheater
• •Birmingham — Civil Rights District, Vulcan statue, Barber motorcycle museum & James Beard kitchens
• •Montgomery — Civil Rights Memorial Center, Rosa Parks Museum, Hank Williams Museum & State Capitol
• •Orange Beach & Gulf Shores — Gulf State Park, sugar-white beaches, Fort Morgan & The Wharf
• •Mobile — birthplace of Mardi Gras, USS Alabama Battleship, Bellingrath Gardens & Dauphin Island
• •New Orleans — French Quarter, Creole cuisine, jazz & riverboats on the Mississippi

15 days · Chicago loop

The Great Lakes

Route: Chicago → Milwaukee → Green Bay → Hiawatha National Forest → St. Ignace → Mackinac Island → Traverse City → Detroit → Toronto → Niagara Falls → Cleveland → Chicago

A grand circuit of four Great Lakes — Chicago's skyline, Milwaukee's brewing heritage, Lambeau Field, Michigan's Upper Peninsula, the timeless resort island of Mackinac, the Motor City, Toronto, the mighty Niagara Falls and Cleveland's rock 'n' roll waterfront, before returning to Chicago via Indiana Dunes.

• •Chicago — Willis Tower, 360 CHICAGO, Cloud Gate, the Lakefront & Navy Pier
• •Milwaukee — Harley-Davidson Museum, Milwaukee Art Museum & brewery tours
• •Green Bay — Lambeau Field, National Railroad Museum & Bay Beach Wildlife Sanctuary
• •Hiawatha National Forest & St. Ignace — Gateway to the Upper Peninsula on Lake Huron
• •Mackinac Island — Fort Mackinac, the Grand Hotel & 70 miles of car-free trails
• •Traverse City & Petoskey — Mackinac Bridge crossing & cherry country
• •Detroit — The Henry Ford, Ford Piquette Plant, Motown studio & the Riverwalk
• •Toronto — CN Tower, Royal Ontario Museum, Distillery District & Toronto Islands
• •Niagara Falls — Skylon Tower, Journey Behind the Falls & nightly illumination
• •Presque Isle State Park & Cleveland — Lake Erie shoreline, Rock & Roll Hall of Fame & Great Lakes Science Center
• •Indiana Dunes National Lakeshore en route back to Chicago