Southwest® flights from San Diego to Chicago (O'Hare) from $100

Year-round, Chicago is a wonderful place to visit. Midwesterners have a keen way to adapt to the long winters. In Chicago, that means eating lots of deep-dish pizza and other delicious foods available around the city as well as enjoying brewery tours and live shows. Summertime in Chicago makes the cold winters worth it: outdoor festivals and block parties fill up nearly every week and weekend in every neighborhood in the city. Consider one of the neighborhood festivals where local restaurants can share their delicious cuisine, artisans share jewelry and other works of art, and musicians come from around the world to spread happiness to Chicagoans and its visitors. Some of the most famous music festivals occur during the warmer months, including the Chicago Jazz Festival, which takes place in Millennium Park and features world-renown musicians from around the globe.

In addition to music festivals, Chicago is home to a number of famous music venues. The city is the birthplace of its own form of Blues, thanks to musicians like Muddy Waters who emigrated from the South and brought the Delta Blues to the City of Big Shoulders. Today, you can find a few great Blues clubs in the city where local and national musicians play. There are great opportunities to find a range of other genres of music, too, at places like the Vic Theatre, the Aragon Ballroom, the Riviera Theatre, and the Chicago Theatre, to name a few.