10 Free Things to Do & See in Chicago

6. Watch the show at Buckingham Fountain

Buckingham Fountain is one of the city’s most interesting historical sights (it opened in 1927). This beautiful fountain is one of the largest in the world. At night, the fountain dazzles even more with the addition of a spirited music and light show. This can’t-miss gem, located in Grant Park, is even more beautiful on a clear day when you can clearly see the city’s stunning architecture in the background. I really love this picture-perfect spot.

It’s located within close proximity to most of the big downtown attractions, so the show can easily be incorporated into your trip. The fountain runs from 8:00am-11:00pm (April through October). The lighted night shows begin at dusk and run for 20 minutes (each shows starts on the hour).

Learn more about the fountain’s history

7. Attend free events at Grant Park

This large 300 acre park is home to many of Chicago’s hottest tourist attractions including the Museum Campus, Millennium Park, The Art Institute, and Buckingham Fountain. All of these touristy places are worth a visit on your trip. Check for free dates offered throughout the year at the 3 main museums (Shedd, Field & Adler). Millennium Park and Buckingham Fountain are both free of charge all the time.

Numerous large festivals are held at this park throughout the year, especially during the warmer summer events. Popular annual events with no charge include the Taste of Chicago and Summer Dance. The summer concert series is one to be on the lookout for. I recommend planning a summer trip to take advantage of all the entertainment. One of the biggest and best free events of the year is the Grant Park Music Festival where you can listen to The Grant Park Orchestra and concerts via The Great Lawn.

One of the biggest and best events I’ve ever attended here was the Bulls Championship Rally in 1998. This was one of the city’s most attended festivals according to this ABC article. I was really into the Bulls during their period of dominance in the 90’s (who wasn’t?), so this was a really memorable experience.

8. Relax at beautiful lakefront beaches

Oak Street & North Avenue are 2 very popular beaches located in the ritzy Gold Coast area. Oak Street, with the reputation of being the place “to see and be seen in the city,” is the more popular of the two. Both of these beaches are located directly on the lakefront trail I mentioned earlier and make for a nice summer break during your ride or walk.

I really love the skyline views at Oak Street – it’s such a gorgeous place to spend a day in the city. I also love swimming here – the waves are actually pretty big and it’s a great time. The water seems pretty clean to me, but you will want to check for any special warnings prior to your day out.

Spending the day at a clean, well-maintained beach with a fabulous skyline view; what better way to spend a hot, humid afternoon in the city? (there are many!). Add in beach volleyball and a beachfront restaurant and you have more than enough options to keep yourself cool & entertained! There is a beachside restaurant called Whispers at Oak street. I’ve never been here yet but tourists seem to like it.

You can read more about Chicago’s beach scene for a full list of options and special events.

9. Enjoy a stroll around Navy Pier

You can’t leave Chicago without taking a walk around historic Navy Pier. This fun boardwalk doubles as a photography hotspot. The lakefront bike path is adjacent to the pier so this is a great stop along the way. The best view of the pier can be seen along this path. Best of all, many free events are hosted here throughout the year, including a popular weekly summertime fireworks display and concerts.

For those looking to spend, you will find plenty of dining, shopping, & entertainment options on the pier. One affordable treat is the amazing rainbow cone (featuring 5 slices, not scoops of orange sherbet, pistachio, Palmer House, Strawberry, and Chocolate ice cream). As a native, I’ve enjoyed my fair share of rainbow cones and they never disappoint – any time I visit home during the summertime, getting a cone is on my list. There are also a few art exhibits you can browse for free and fishing is quite popular.

10. Ice skating & holiday fun

Many tourists mistakenly think of The Windy City as solely a summer destination. This is not the case! The holidays are my favorite time to explore the downtown in the country’s best Christmas city (in my opinion). During the winter season, Chitown is still very much alive despite the bleak, cold, and oftentimes snowy skies.

Numerous festivals, seasonal activities, and special attractions are held throughout this time. I find that there is so much to do this time of year that it is hard to fit it all in, especially around the holidays. It’s actually my favorite time being a big Christmas buff and regular ice skater. I love the ambiance, festive cheer, and beautiful ice rinks the city offers this time of year.

Admission to the Christkindlmarket, a seasonal German inspired shopping village in Daley Plaza, is free to browse around. If you feel like spending a few bucks, you can order cocoa in the cutest souvenir glass or treat yourself to some potato pancakes. Another can’t-miss attraction is seeing the iconic Christmas Tree. From here, take the short walk over to Macy’s on State Street to see the famous holiday window stories.

I also love that the rink is open all the way until March which is nice as it gives you something to do outside all winter. As I mentioned earlier, Lincoln Park Zoo Lights is also fantastic. I’ve also heard that the ribbon rink at Maggie Daley Park is amazing – I haven’t skated here and unfortunately, it is not free.

Address Info

• Lakefront Path: 7100 South/2560 East to 5800North/1000 West
• Lincoln Park Zoo: 2001 N. Clark St.
• Millennium Park: 201 E. Randolph St.
• The Art Institute: 111 S. Michigan Ave.
• Buckingham Fountain: 301 S. Columbus Drive
• Grant Park: 337 E. Randolph St.
• Oak Street Beach: 1000 N. Lakeshore Drive
• North Avenue Beach: 1600 N. Lakeshore Drive
• Navy Pier Address: 600 E. Grand Ave.
• Daley Plaza Address: 50 W. Washington St.
• Macy’s on State Street: 111 N. State Street

Looking for more fun? Check out my Illinois Travel Guide where you can find more bucket list attractions in both the city, suburbs, and surrounding rural areas.