When going to Chicago, it’s best to visit your desired destinations during certain times of the year. Why would you visit Wrigley Field if there’s no Cubs’ game? Even if you weren’t a baseball fan and didn’t want to watch a game, it’s still worth it to see Wrigleyville full of buzz and excitement, which happens even if the Cubs are on a ten-game losing streak. There just needs to be a ball game going on.
However, as most Chicagoans also know, a good time in the city is largely dependent on how you’re dressed, which is why anyone who visits the city should first and foremost check their weather app or Google for up-to-date information. Not only can it be windy, but it can also be extremely cold or muggy and hot — and everywhere in between.
There’s still a lot that goes into the decision of what to do in Chicago, but if you’re prepped for the weather, I can almost guarantee that this wonderful city will offer you a good time.
Know before you go
Other than the weather, the thing you need to know before you visit Chicago is what major events are going on in the city. While most are harmless, there are a few that will completely take over the city.
For instance, if you go to Chicago during Lollapalooza but don’t plan on going to the festival, then your experience may be significantly tainted.
However, the fact that the city of Chicago enjoys festivals so much is actually a good thing. In fact, there will be a number of street festivals taking place throughout the summer.
One of the most famous is Taste of Chicago, which takes place in early July. However, there are dozens of other festivals, that can easily be found by visiting the Chicago Redeye.
Take it from a local
Chicago pretty much knocks it out of the park when it comes to any type of food you’re looking for.
This is why listing places where you must eat would be a mistake. Food is an emotional and visceral experience, and, while it can be helpful to give you recommendations, this is really something you should come up with yourself.
However, when it comes to deep-dish pizza, locals think it’s important to mention a Chicago staple that isn’t quite so mainstream.
“It’s hard to think about Chicago without thinking about the food scene,” explains Megan Scameheorn, a long-time Chicago resident. “Everyone can do their research and figure out where to eat and what they might like on their own, but if you’re going to have deep dish then I recommend Pequod’s.”
What Pequod’s has that other deep-dish places don’t is that it has the well-received reputation and has been a part of the community for years, without the notoriety or commercialization. It also does deep-dish with a slight twist by buttering the crust of each pizza before baking it. This creates a tasty caramelized crust that can’t be experienced anywhere else in Chicago.
The best Chicago tour is a must-see in late spring through early fall because it takes place on the river. I’m talking about the Seadog Chicago River and Lake Architecture tour, which takes you on a journey of the eclectic history of the city through its buildings.
Part of the magic of this tour is that even if you don’t know anything about architecture, it is still thoroughly fun.
Chicago has been at the epicenter of American culture and politics in the Midwest since the 1800s. It was the industrial backbone for much of the region, then it helped jumpstart the blues and jazz movements and was at the heart of political turmoil throughout the sixties and seventies. This rich history is shown through the city’s architecture in a variety of ways.
The tour also gives guests a unique vantage point from the Chicago River. The river is such an important part of the city that it has more drawbridges than any other city in the world, many of them running through downtown and the Magnificent Mile. It’s the city’s heart.
Need to try
When it comes to old-timey jazz and blues, what comes to most people’s minds is probably New Orleans or Memphis. African Americans came to Chicago looking for jobs after World War II, and the city has been a hotbed for jazz and blues music ever since.
That’s why, when you visit Chicago, you need to try a blues bar — and not just any blues bar but Kingston Mines.
The world-famous blues nightclub has been at the center of the Chicago music scene since it was founded in 1968. A steady collection of blues artists and bands can be seen playing there every night.
Typically they have three different music acts Monday through Sunday, often going from 8 p.m. until early the next morning. That way, whether you’re a night owl or you go to bed early, you have a chance to catch a quintessential Chicago show.
Make the most of your experience
The hustle of Chicago can be busy and exciting but, at the same time, getting away from all the noise can be difficult, but it can certainly be done. One of the best ways to do it may surprise you.
“You can literally walk from Fullerton Street all the way down to Oak Street Beach or all the way down to Navy Pier, and it’s all along the water,” explains Scameheorn. “It’s especially pretty at dusk when all the building lights turn on. Then when you look to the east you see Lake Michigan.”
This mile long hike will give you an easy to follow path along crashing waves and allow you to go at your own pace, while you take in the city. This way, you can see the beauty in the hustle of the metropolis, as you try to understand it all. Or you can just walk and not think at all as you let Lake Michigan give you a reason to put your phone down.
Chicago is a place where people know how to have fun — because how else could they survive long winters and hundred-year-long World Series droughts? But, through all of that, this is a place that knows how to make the most of its sunshine, Midwest friendliness, and all that a big city has to offer.