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Celebrate 100 years of Route 66 with a scenic 301-mile road trip from Chicago to Madison, filled with historic sites, local eats, and small-town charm in Illinois.

From shopping and sailing to Michelin stars and spas, the Midwest’s biggest city has it all.

Blues music came from Mississippi to Chicago during the Great Migration, as praised in the new Michael B. Jordan film and throughout the city today.

Diners and cafés along the Mother Road dish out nostalgic sweet treats, good enough to stay on menus for nearly 100 years.

Escape Chicago for a few days with one of these 10 weekend trips, all within easy driving distance or by train.

State parks and expansive forests serve as the perfect backdrop for stargazing in the Prairie State.

To do: Meet the dinosaurs. Swim in the river. Gorge on ice cream.

The St. Regis Chicago is big on indulgence—but tucked in a corner most tourists never reach.

Here’s how to spend a day in the city as the former president would, from legendary restaurants to the new Barack Obama Presidential Library opening in June 2026.

The famous French restaurant guide is rating hotels now with a new key-rating system, similar to its star ratings for restaurants. Only a handful of hotels in New York and California received three keys.

Find the retreat that best matches your taste in the Windy City.

Amtrak predicts the new train will welcome more than 200,000 passengers aboard within its first year of service, and it’s expected to greatly reduce car use along the Midwestern route.

For those willing to slow down and experience a taste of America that largely goes unseen, these small towns are well worth the detour.

United Airlines loyalists who fly from or through the Midwest’s busiest hub are sure to be pleased with this major upgrade.