Chicago is paradise for people who know how to enjoy themselves. Great food, all-night spots, the capital of House music, festivals every night…the fun never ends! One of the coolest things about it is that you don’t have to make plans, not even a day ahead of time. There’s so much to do on any given day, you have the freedom to wake up and do as you please. Ahhh, the beauty of living in a world-class city. But that doesn’t mean there are some things that you should plan for. Planning can make sure you get a ticket, get in early, or even just maximize the amount of fun that you have. Here’s a few things going on in Chicago in the upcoming months that you are definitely going to want to plan for.


Lollapalooza IconLollapalooza is annual music festival that makes a stop in Grant Park this year from August 1st – 4th. This is one of the biggest music festivals in the United States and typically tickets sell out fast. With past musical performances by superstars like: The Weekend, Bruno Mars, Travis Scott, Artic Monkeys, Chance the Rapper, Kanye West etc. it’s easy to see why. If you’re looking to buy an Every-Day Pass, you’ll be ok. Those don’t sell out in the first 10 minutes, so you shouldn’t have any trouble buying one when it’s convenient for you. But if you’re looking to only buy a ticket to a specific performance…that’s a different story. You may want to have an alarm set for the time the tickets go on sale so you can log in and order them. It sounds crazy, but that’s how fast they sell out. The shows are amazing and the atmosphere is electric with energy. If you’re a fan of live performances, you can’t miss Lollapalooza.

Cirque Du Soleil Volta

Icon for Cirque Du SoleilCirque Du Soleil brings their latest production, Volta, to Chicago in May. They are the famous group that performs live shows around the world. It’s a little hard to classify them; they do gymnastics, dancing, there’s music and pyrotechnics, the list goes on and on. The only way to truly sum it up and capture what goes on is to call is a “show”. The only problem with that is that it sells them short. This isn’t just a “show”, this is the show. This is the type of performance against which other performances get measured. Volta is their latest who and it is a big top show that centers around the theme of extreme sports. The show story-line is about a game show contestant named Waz, who has lost touch with himself, but starts a personal quest to find again his true self by going through his memories, after discovering a group of free spirits who encourage him during this process.

Chicago Blues Festival

Chicago Blues Festival IconEveryone knows Chicago is the home of the Blues. Well, not the home in the sense of this is where it all started, that honor belongs in Mississippi, but Chicago definitely took it and ran with it! Three days of performances by some of the best Blues musicians in the world come to Chicago this June. Past shows have included names like Bonnie Raitt, Ray Charles, B.B. King, Buddy Guy and more. You won’t have to worry about tickets selling out, but it’s only three days long and you don’t want to miss it. If you double book yourself and end up spending the weekend picking out table linens instead of being here, you’re going to regret it. Numerous Blues musicians of this caliber don’t get together very often, make sure to check it out.

Chicago Cubs Home Opener

Wrigley Field sign in front of fieldIt only happens once a year! The Cubs used to be everyone’s favorite Lovable Losers, but those days are no more. Only a couple years removed from winning the big show, the Cubs have put the past in the rearview mirror. These days they consistently turn in winning seasons and thrill crowds that show up to Wrigley Field. Unless you want to sit behind a massive steel beam in the outfield, I suggest you get your tickets early. Cubs games are the type of experiences that people drive in from out of town to see. The type of event that people plan into their vacation, and when you get here, you’ll see why. Cubs fans know how to party. Whether it’s shutting the city down after winning the World Series or just making a regular game the highlight of your weekend, they know how to do it right.

There’s always something going on, but if you have your heart set on any of these events, you’re probably going to want to plan ahead. The best ones are in high demand! Chicago has so many things going on, way more than we could ever fit on a single list. You can either stick with your tried and true favorites, or you can expand your horizons. Either way…you can’t lose. Check out our calendar for more things to do.