Chicago is an amazing place to visit for so many reasons. There are so many things to see and do in this city that you will almost certainly run out of time before getting to do all of them during your trip. If you are planning to visit Chicago, you need to have a plan in mind so that you can do the things you want to do the most.
From live music to museums to excellent food and drink, there is no shortage of reasons that the Windy City is one of the most popular places to visit in the US. When you are looking at traveling to this incredible city, you need to be sure to do your research so that you don’t miss out on anything really special that you might want to experience.
Ways to Have Fun in and Around Chicago
1. See Live Music
One of the best things to do during your trip is to see live music in Chicago. This is the right place to head for exposure to music of all kinds. There are so many venues that offer access to quality live music in this city that you can easily see a live performance every night. Fox Pointe in the Chicago area offers over 25 free concerts and events from June through September. These amazing musical experiences include International Cultural Celebration Day on June 21, 2025. Guests will enjoy Polka, Navajo Dance and Stories, Irish Music, Bolly Bhangra, Necalli Dance, Reggae, Dutch Dancing, and even learn to Tango! Kids activities and crafts run throughout the day. Learn cricket, lacrosse and rugby from professional coaches. Fox Pointe also presents Bikes, Bands and Brews on July 12 featuring a motorcycle show with Guest Judge Danny “The Count” Koker from the hit History Channel show, Counting Cars. Guests will be treated to five different bands, including Kik-N-Jimi, Grindstone, Fatal Order, Count’s 77 and Pat Travers Band. Bikes can be registered for the show and general admission tickets purchased at their website.
Live music is one of the best features of visiting this cool city, and you should have no trouble finding a wealth of different live music experiences to enjoy during your trip.
2. Check Out the Museums
There is no shortage of opportunities to learn and experience history and culture in Chicago. The Field Museum is the most well-known of the museum experiences in this city, and you will want to book a couple of days just to check out the various exhibits at this amazing cultural and historical location. The Field Museum is just the most well-known of the museum options in Chicago, however.
You can also check out The Art Institute of Chicago, The Griffin Museum of Science and Industry, or the Chicago History Museum. There are so many other places to check out art and specific cultural experiences as well, like the Museum of Ice Cream, the Medieval Torture Museum, and the Chicago Sports Museum.
Chicago is well-known for being a city that is full of culture, and if you love museum exploration, you will have more than enough to do when you visit Chicago to keep you busy for your whole trip.
3. Visit Navy Pier
Navy Pier is a great place to visit if you love boat rides, a Ferris Wheel, or fireworks. There are also shops and lots of great places to eat at the pier. You can wander for most of an afternoon in this part of the city with ease, finding fun things to do and shopping for souvenirs. Kids love coming down here to ride the fair rides, and the view of the city skyline is incredible.
This is a family-friendly and really enjoyable activity that is fun for all ages. If you are visiting during the heat of the summer, this is also an ideal place to visit to cool off and enjoy the breeze off the lake.
4. Enjoy Delicious Food and Drink
Chicago is a true melting pot city. That means that you will be able to sample cuisines from all over the world here. There are also plenty of places to enjoy a pint, discover a new wine that you’ve never tried, or enjoy a flight of whiskey or scotch. You might be overwhelmed with choices in the best way when it comes to food and drink in the Windy City.
5. Visit Lincoln Park Zoo
The zoo in Chicago is a ton of fun, and there are gorillas, lions, and zebras here. Informative exhibits abound, and kids will love to run around and engage with all of the kid-friendly exhibits and animals. There are food options within the zoo as well, so you will not have to leave just to find a snack during your adventures.
Best of all, this zoo is free, which means that you don’t even have to budget to be able to enjoy this fun attraction within the city of Chicago. This is rare for a zoo, and if you usually avoid these kinds of experiences to save money when you are traveling, you should add the zoo to your list of things to experience while you are in Chicago.
6. Visit Parks and Green Spaces
There are tons of really nice parks and green spaces in Chicago. Making it one of the most beautiful cities in the US. You will feel like you are miles away from the hustle and bustle when you visit the parks in town, and you will find fun activities like mini golf, play structures, and more at most of them.
Visiting parks and green spaces is usually a great way to ensure that kids can blow off some steam, but it can also be the perfect way to get out and go for a walk or cool off as an adult traveler.
Having Fun in Chicago is Easy!
There are so many ways to have fun in Chicago. You might need to plan multiple trips to get to all of the things that you want to see and do. You will be able to enjoy live music, check out museums and art exhibits, and eat like a king or queen while you visit. Be sure that you prepare for the weather during the time that you are planning to visit, as it can be quite warm and quite cold in Chicago.
Whether you are traveling with kids or have come to the Windy City as adults looking for grown-up things to do, there is no shortage of fun to be had in this amazing city.
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