Southwest® flights from Tampa to Chicago (O'Hare) from $90

A city of neighborhoods such as Chicago offers a nearly endless number of opportunities to get lost in a new culture, cuisine, or curiosity. The Loop, the central downtown area of the city, is a great place to start if you’re a first-time visitor to Chicago. If the weather is agreeable, one of the best ways to explore 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.

Branching out into the neighborhoods is the best way to get a feel for the true character of Chicago. 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 a favorite spot great for picnics and photographs known as Promontory Point and beyond. 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.