Lakefront breezes made Chicago's reputation as the Windy City. But now Chicago is having a moment with celebrated West Loop restaurants and authentic Bridgeport ethnic eateries, Bucktown blues bars and Millennium Park concerts, downtown's awe-inspiring Art Institute and Wrigleyville's gut-busting Improv Olympics. White Sox, Cubs, Bulls, and Bears games are not far from President Obama's Hyde Park home.
Read more about Chicago on Hipmunk's Chicago City Guide.
Though its palm-lined pools and beachfront art deco hotels are legendary, Miami doesn't spend all its time working on its suntan. Decorators trawl for finds in the Design District, star chefs devour Cuban pulled pork sandwiches in Little Havana, artists work on creative breakthroughs for December's blockbuster Art Basel Miami fair, and no one sleeps in the NE 11th Street club district.
Read more about Miami on Hipmunk's Miami City Guide.
Tips for traveling through ORD
Tips for traveling through MIA
Hipmunk is the fastest, easiest way to plan travel. Hipmunk saves you time by comparing top airlines and travel sites to find the cheapest flights and the best deals on airline tickets. Our exclusive agony sort also takes into account price, flight duration, and the number of layovers to find you the flight with the least amount of agony.