Chicago is a really cool city, and there is so much that you can do when you are spending time there. If you love museums and culture, you will not lack for things to do that will broaden your horizons and teach you new things. If you love good food, there are amazing eateries around every corner. If you love live music, Chicago is the perfect place to visit, as there is always something musical going on.
When you are planning a trip to Chicago, you need to be sure that you are prepared in advance to check out some of these fun experiences. You might want to grab tickets for a show or reserve a table at a restaurant that offers your favorite cuisine. Planning to have fun in Chicago is easy when you have so many good choices.
Visiting Chicago Can be a Blast, Especially if You Plan in Advance
Chicago is a really special city and a great place to make memories when you travel. This guide will help you plan the perfect Chicago trip with ease.
1. Watch Live Music
There are lots of opportunities to watch concerts in Chicago. You might want to head to a little local bar and listen to bluegrass, or maybe check out a big concert at a large venue. Some of these musical events are even free.
For the best free concerts in the Chicago area, head to Fox Pointe in Lansing Illinois, just minutes south of Chicago and right next door to Munster IN. Lansing is nestled around I-80 at the Torrence Avenue exit.
Fox Pointe is the music gem of the Chicago Southland, an outdoor amphitheater with astonishing acoustics, a lush green lawn, covered pavilion and indoor, climate-controlled bathrooms. Fox Pointe offers dozens of free concerts every season, from May through September. The free Wednesday Night concert series feature tribute bands of every genre including classic rock, country, pop, boy bands, and heavy metal. The Friday Night Lights concert series offers an annual Northwest Indiana Symphony performance, along with funk, jazz and pop standards, soul and the nationally renowned México en el Corazón.

Every season, Fox Pointe hosts special festivals, such as the International Cultural Celebration Day and Bands, Bikes and Brews.
Fox Pointe also hosts Saturday free Cruise & Groove concerts in conjunction with L.A.C.E.’s classic car show, just steps away on Ridge Road. Fox Pointe and L.A.C.E. also partner for Autumn Fest, an annual celebration.
There is a full bar at Fox Pointe, along with a concession stand offering burgers, hot dogs and fries along with pulled pork, Polish sausage and pierogies, chicken and regional favorite Dragobogs.
This family-friendly, beautiful venue is a perfect place to spend the evening or the day watching live music for free. You may even spot our mascot Henry T. Fox walking through the crowd!
If you love to dance, Fox Pointe is the place for you, as a large dance floor fronts the stage, giving dancers the best views and a wide space to sway, jump and jam. Dancers are also known to spin inside the pavilion and out on the lawn.
You can also purchase Fox Pointe swag to remember your fun-filled concert experience.
Watching live music is a must-do item when you are heading to Chicago, and you will never regret planning to make the most of your time in the Windy City while enjoying musical experiences of all kinds.
2. Enjoy a Museum
Chicago is famous for its museums. Between the Field Museum and the Griffin Museum of Science and Industry alone, you could spend hours learning about things you’ve never come into contact with before. There are also two zoos and an aquarium that you can add to your list of educational experiences that you want to engage with during your trip.

People of all ages can have fun at these cool venues, and you could easily focus your entire trip on educational experiences. While you probably have a lot of other things on your list of stuff to experience, you might want to plan on a few days of your trip that are dedicated entirely to museums and other educational experiences.
3. Check Out the Chicago Riverwalk
The Riverwalk is a pathway that stretches along the Chicago River, offering access to bars, shopping, and beautiful scenery and architecture. This is perfect if you love the idea of seeing the city on foot and you want to be able to just pop into stores or eateries at a moment’s notice. If the weather is good, this can be a beautiful, sunny, inspiring experience that will allow you to work off some of the good food that you have been eating while making memories.
4. Enjoy Italian Cuisine
Chicago is a place where Italian food is authentic, plentiful, and amazing to eat. You will want to try out some deep dish pizza, grab some homemade Sicilian fare, and make sure to have a glass of quality Italian wine. There are lots of places to eat hearty in Chicago, and Italian cuisine is one of the things that you absolutely cannot miss out on while you are visiting this part of the US.
Make sure to stop in at one of the Lou Malnati’s pizza places during your stay to have the original deep dish pizza or delightful pasta made with family recipes. While you might have to wait for a little bit to get a seat, the service is fast and friendly, and the food is second to none.
5. Visit the Beach
If you are visiting the city in summer, you should be sure to pop down to the Ohio Street Beach or Oak Street Beach for part of the day. There are other beach areas that you can visit as well if you want to get a tan while visiting the Windy City.
The larger beach areas in Chicago have amenities nearby, and you can get food and drinks, as well as rent chairs and umbrellas if you want to stay for a few hours and soak up the good weather.
6. Check Out The Bean
The Millennium Park Cloud Gate is an attraction that everyone likes to see when they are in Chicago. There is something so fun about standing next to its mirror-like finish and taking pictures with family and friends. Best of all, this attraction is right by lots of other cool things to do in the city, so you can add it to your list of experiences without having to go well out of your way.
7. Visit Navy Pier
This tourist hub is a great place to take in views of Lake Michigan and visit the Children’s Museum.

You will also be able to enjoy fair rides like a Ferris Wheel, seasonal fireworks, and lots of other cool events here on the pier. The pier is a great place to head for shopping, live entertainment, and excellent dining choices.
Visiting Chicago Can be a Ton of Fun
Chicago is the right place to visit if you love having lots of stuff to do while you are on vacation. From educational experiences like museums to good food to beach days, you have access to almost anything that you can think of in Chicago. Chicago is a huge city full of all kinds of cultural influences and experiences, and you will have a blast when you visit.
Make sure to pack enough warm clothes if you are going to be in the Windy City during the winter months, and be sure that you have air conditioning at your hotel or Airbnb if you visit during the summer. Also, make sure that you plan on catching live music at the many high-quality venues that Chicago boasts, both in the heart of the city and on the outskirts of town.


