Southwest® flights from Sarasota/Bradenton to Chicago-Midway from $159

A city of neighborhoods offers a nearly endless number of opportunities to get lost in new cultures, cuisines, and curiosities. The Loop, the central downtown area of the city, is a great place to start if you’re a first-time visitor. If the weather is agreeable, one of the best ways to enjoy the Loop is to take an architectural tour along the Chicago River. Experts on the stunning and iconic buildings will bring you up to speed quickly on the most important landmarks along the riverfront. If you visit during a colder part of the year, the downtown and River North neighborhoods are easily accessible by public transit. The Chicago ‘L’ train offers some stunning views as you cruise around above street level.

If you’d prefer to travel by land, start your adventure on the Chicago Museum Campus, home to the Field Museum, Adler Planetarium, and more. You’ll easily find the Chicago Lakefront Trail while you’re there. Rent a bike and follow it south to scenic Promontory Point or the Museum of Science and Industry. You can even stroll the main fairgrounds of the 1893 World’s Fair at the lakefront Jackson Park. Traveling north will give you easy access to a number of beaches and popular neighborhoods like Lincoln Park, Lakeview, and Edgewater. There’s no telling where your day might go when you start to explore the vibrant sights, sounds, and delicious smells of these historic neighborhoods.