Southwest® flights from Houston (Hobby) to Chicago (Midway) from $46

Everything may be bigger in Texas, but Texans will feel right at home when they trade Houston for Chicago—both are their respective states’ largest cities. Go big when you get to the City of the Big Shoulders and visit the tallest building in the Western hemisphere. The Willis Tower (locals still call it the Sears Tower) features the famous Skydeck Chicago Ledge, a glass outcropping 1,353 feet above the street below that’s sure to thrill (and make for some great selfies). Want to stay closer to terra firma? Grab a stuffed pizza from one of the big names in tourist cuisine, or chow down like a Chi-Town local and order yourself a thin-crust pie.

Depending on the time of year, Chicago has a range of indoor and outdoor activities, sights, and sounds to enjoy. Flora and fauna fans can visit the Lincoln Park Zoo, take a Metra train to the western suburbs to check out Brookfield Zoo, or take a different Metra line north of the city to the Chicago Botanic Garden. Chicago is lucky to experience each of the four seasons distinctly (sometimes all four in one day!), which means the foliage of the residential neighborhoods is a changing display year round. Neighborhoods throughout the city have thick canopies of trees over expansive parks and residential streets; be sure to take a stroll if you find yourself in Chi-Town in the fall to see the rainbow of foliage colors.