Aerial view of the Chicago skyline
Route 66 sign in Illinois

Chicago, the Great Lakes & Route 66: Travel Inspiration & Expert Guides

Few regions in America pack in as much variety as this one — from Chicago's world-class food and architecture to the vast shoreline of the Great Lakes and the neon-lit roadside Americana of Route 66. The guides below draw on over two decades of American Sky expertise, covering the stops worth lingering at and the drives worth planning your whole trip around.

Jade Pearson
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Oklahoma City on Route 66: Top Attractions, Food & Expert Tips

Cowboy heritage, world-class museums, an Olympic whitewater facility and a food scene that has quietly become one of the best in the region: this is a city that consistently over-delivers.

Top 10 Things to See and Do in Missouri

Missouri is one of America's most rewarding and underrated road trip destinations. From the soaring Gateway Arch in St. Louis to the hickory-smoked barbecue joints of Kansas City, the state offers a remarkable range of experiences that punch well above its profile.

Top 10 things to do in Chicago

Aside from the vast stretches of freshwater, that comprise: Erie, Superior and Michigan, Chicago also offers visitors an eclectic and entertaining location from where to relax, party and discover the city’s infamous past.

Top 10 restaurants in Chicago

From bring your own booze BBQs and pop-up doughnut shops, to fine dining tasting menus and French-Mexican fusion restaurants, Chicago’s dynamic menu of eateries will be sure to excite any avid foodie.

A true taste of Chicago

There's no denying Chicago's pizzas and hotdogs are delicious, but what's their history? We even have a deep-dish pizza recipe to try...

Road tripping Route 66

Who could resist the iconic Route 66? From kooky roadside museums and old Cadillac cars planted in the ground, to classic American diners and an 80-foot long whale, Route 66 is famous for a reason.

A beginner's guide to Lake Michigan

The only member of North America's Great Lakes to completely lie within the United States' borders, Lake Michigan is an alluring lake paradise that also happens to be right smack in the middle of the American Midwest.

Jade Pearson
Call our travel experts now
01342 331798 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun