There is always something going on in Chicago, so even if you visit during the winter months, you will have no trouble tracking down a bunch of really cool things to see and experience. You might like hiking, musical shows, or craft fairs, and you can find any of these experiences in Chicago throughout most of the year. If you love to travel to new places to make memories that you cannot make at home, you will love Chicago.
Fox Pointe is just one of the many venues that offer cool things to do and enjoy in the Chicago area. You will want to check out what they have on offer before you start making your travel plans. There are so many parts of the city where activities are offered year-round that you might want to start with major events and work your way outward from that first selection.
Up and Coming Things to Do in Chicago in 2026
1. The Navy Pier
Visiting the Navy Pier can be a ton of fun during the warmer months in Chicago. There are summer fireworks shows on Wednesday and Saturday from Memorial Day through Labor Day at the pier, as well as fair rides, concerts, and shopping and dining. This is one of the most walkable and unique places in the city, and there is almost always something going on that visitors of all ages will love, especially when the weather is nice.
2. Concerts
There are so many amazing musical events that go on in Chicago each year! Fox Pointe in Lansing Illinois is just minutes from Chicago and a fantastic music venue to visit for musical performances in many genres including classic rock, punk, emo, dance music, yacht rock, heavy metal, Motown and blues, R&B, pop music, crooners and music from the 80’s, 90’s and more. You’ll enjoy cover bands that pay tribute to Taylor Swift, NSYNC, Backstreet Boys, Eric Church, Chicago, Santana, NKOTB, One Direction, Dave Matthews, Tom Petty, and much more. Don’t miss the Northwest Indiana Symphony Orchestra or Bands, Bikes & Brews featuring Danny “The Count” Koker from the History Channel’s “Counting Cars” judging a motorcycle show.
Fox Pointe is a premier music venue with FREE parking, safe and secure with clean, climate-controlled bathrooms, a full bar and concessions featuring delicious freshly-grilled and prepared sandwiches, chicken, sliders, pierogies and more. Bring chairs or blankets to enjoy the lush lawn or take a seat at a picnic table in the large covered pavilion. Either way, you’ll find astonishing acoustics in this beautifully landscaped, don’t-miss music venue.
There are also lots of smaller venues throughout Chicago and the surrounding suburbs that host music evenings and events throughout the course of each year. Headliners like Lily Allen, Cardi B, Bruno Mars, and Demi Lavato are slated to play at the United Center in 2026, and the Chicago Symphony Orchestra performs almost all year round.
3. Farmers Markets
There are many locations throughout Chicagoland that offer farmers’ markets during set periods of the year. These are almost always big, colorful, welcoming events that will offer you a chance to pick up handmade goods, fresh foods and produce, and get some steps in as you enjoy the more local side of Chicago.
One of the newest and most exciting Farmers Markets is at Fox Pointe in Lansing Illinois, just minutes from Chicago. Walk the open-air layout to visit dozens of vendors selling fresh produce, grass-fed locally farmed meats, baked goods and other homemade goodies sure to tempt your taste buds. Support regional growers and small businesses every Tuesday, June through September, 9 am to 1 pm while you enjoy live music, kids events and yoga lessons. Parking is always free!
4. Sightseeing Opportunities
You will want to make some time to stop in at places like the “Bean”, Buckingham Fountain, and Willis Tower while you are out and about. Being able to check out these iconic landmarks is a must, and they make great Instagram spots. The Magnificent Mile is also really beautiful and special, and you might want to make time to explore the Chicago Riverwalk area as well.
5. Check Out Sports Events
Make sure to consider going to the NCAA Men’s Basketball Midwest Regional if you like basketball. This event will be going on in March of 2026 at the United Center. There is also the WNBA All-Star Game 2026 in July, and the Under Armor Women’s Run of 2026 to see and experience. The Chicago Cubs and White Sox are also a great option if you love baseball. There are all kinds of sporting events that are hosted in the Windy City throughout each year, so you should be able to find your favorite sporting event and get tickets during your visit.
6. River North Fests Presents Saturday Night at the Zoo
On May 2nd, you can head to the Lincoln Park Zoo and enjoy karaoke, photo booths, pop-up bars, and more, all inside the park’s zoo. This is the best way to celebrate the end of winter and the rise of summer weather and to have a Saturday night of fun that you won’t be able to experience anywhere else. The zoo in Lincoln Park is one of the best anywhere in the US, and being able to enjoy beverages, music, and other fun will just make your visit that much more special.
7. Broadway
Broadway shows run all year long in Chicago, and you will have your pick from classics like Chicago, Monty Python’s Spamalot, and Hamilton to get tickets for. There are many more shows than just these running throughout 2026, so if you love musicals, Chicago is going to be the right place to visit. Chicago’s Broadway experiences are top-notch, and you will never forget your experience seeing a show while you are in town.
8. Taste of Chicago
Held in July, this is a huge annual food festival that is held in Grant Park. Food vendors, pop-up restaurants, and free live performances are the name of the game at this event. Admission is free as well, which makes this a top choice for visitors to Chicago during the summer.
9. Lollapalooza
Also hosted in Grant Park, this is a famous four-day music festival in August. This year, headliners are Sabrina Carpenter, Chappel Roan, and Lorde, among many others. Lolla festivals happen all over the world, and there are companion festivals in Brazil, Argentina, and Chile as well. Music festivals can be the best way to enjoy access to many gifted performers for the affordable cost of entrance to the event.
Chicago is the Right Place to Visit if You Love Events and Experiences
There is always something fun going on in and around Chicago. You will find that you can easily fill every day of your trip with fun things to see and do. Whether you like music, you want to go shopping, or you are looking for theme parks or fair rides, you can find events that include these things in Chicago.
The 2026 event calendar for Chicago is filled with special opportunities to make memories. You are not going to be limited in any way when it comes to finding your favorite things to do and experience in this city. This guide is a great starting point for planning out a trip that you will remember for years to come.
