Cheap Chicago Things You Should Enjoy This Summer

The “dog days” of summer are upon us here in the U.S.  Whether or not you have a lot of money to spend on fun, I’ve got a list of some cheap Chicago things you should enjoy before summer ends.  Guess what?  You can participate in some of these events and attractions for FREE!

I thought that would get your attention.  Ready?


Chicago Summer Dance – Spirit of Music Garden, Grant Park



This is, by far, my favorite cheap Chicago thing to do in the summer.  In fact, it is FREE!  That’s right.  I believe this might be one of the better kept secrets in the Windy City.  Every week from Friday through Sunday, you can experience the live bands, early dance lessons and outdoor party which is Chicago Summer Dance.




Cheap Chicago things Chicago Summer Dance in Grant Park




Each week a different genre of music is showcased.  Come early and let the danced instructors give you a lesson on the makeshift dance floor.  Then, stick around in the beautifully manicured garden, until the band takes the stage and the party gets in full swing.





Cheap Chicago things Chicago Summer Dance lessons




Bring your own picnic or buy some food and drink at the one concession stand in the park. Don’t worry about your dancing skills.  Just don your dancing shoes, grab a friend or make a new one there. 😉  Let the rhythm move you against the iconic Chicago skyline.




Cheap Chicago things Chicago summer dance Grant Park

Bring your own picnic or belly up to the tasty food and drink concession stand.




Jazzin’ at The Shedd – Shedd Aquarium




jazzin' at the shedd Cheap Chicago things



Every Wednesday night, Chicago’s Shedd Aquarium hosts live jazz bands on its 2-tier terrace. Another jazz band plays inside.  This is one fun and sexy way to break up your work week. Admission is $18.  It gets you into many of The Shedd’s exhibits and entrance to the terraces where the party is going on.




Cheap Chicago things jazzin' at the shedd chicago lakefront




In additIon to the a cash bar and happy crowd, there are stunning views of the Chicago skyline and Lake Michigan.  It’s a prime spot to catch the Wednesday night fireworks from Navy Pier which begin at 9:15pm.  So, stick around for a full evening of fun.




Cheap Chicago things jazzin' at the shedd cocktails




Cheap Chicago things jazzin' at the shedd chicago



Pro Tip:  If you find the $18 admission to be too expensive, you can always bring a blanket or chair and hang out on the lawn outside of The Shedd.  Bring your own picnic or snacks. You will still be able to hear the music and watch the fireworks from Navy Pier without paying a dime 🙂



Millennium Park Summer Workouts



Cheap Chicago things Millennium Park workouts

Yoga, Pilates, Tai Chi and Zumba classes are FREE in Millennium Park



Whether or not you can afford a gym membership, you can get a FREE workout at Chicago’s Millennium Park.  Every Saturday until Sept 3rd, you can grab a spot on the lawn from 7am – 11am and sweat your way through Tai Chi, yoga, Pilates and Zumba classes.  Stop by on Wednesdays at 7:30am for more yoga poses.




Millennium Park workouts cheap Chicago things

Get your free workouts on in Chicago!




Millennium Park Summer Film Series




Cheap Chicago Things movies in the park




You can grab a piece of grass on the lawn in front of Jay Pritzker Pavilion every Tuesday night until September 5th to watch a FREE movie.  Go early to spread out with your picnic blankets, chairs, and tables.




Millennium Park Summer Film Series cheap Chicago things



Movies in the park cheap Chicago things

Free movies in the park is one of the many cheap Chicago things you can enjoy before summer ends.




Jazz Festival in Millennium Park


Looking for some FREE fun over Labor Day weekend?  Head to Millennium Park’s Jay Pritzker Pavilion, Harris Theatre rooftop terrace, Von Freeman Pavilion and Jazz Heritage Pavilion.  The cool jazz is available between Sept. 1 – 4.


The 606 Bloomingdale Trail



If you are looking for some fun on Chicago’s northwest side, head over to The 606 Bloomingdale Trail.  



Runners and cyclist on The 606

The 606 Bloomingdale Trails is one the best cheap Chicago things to do in the city.



The city of Chicago has transformed this elevated and defunct train track into a new park and playground which connects the hip and cool neighborhoods of Logan Square, Wicker Park, Bucktown and Humboldt Park.  There are several FREE access points along The 606 for you to take a stroll, run, bike and skate.  There are benches along this park as well where you can take a load off for a while and enjoy the scenery and views of the Chicago skyline.  The Bloomingdale Trail is easily accessible along the CTA Blue Line, so you can leave your car at home.  Currently, there are no food stations on The 606, but I’ve got some tasty restaurant suggestions for you near the trail.  So, get fit, then get fed!




Cheap Chicago things Place to sit on The 606 Bloomingdale Trail




Milwaukee Avenue and Bloomingdale Avenue



CTA Blue Line over The 606

CTA Blue Line runs along The 606 Bloomingdale Trail on Chicago’s northwest side.



Chicago Riverwalk



Chicago Riverwalk steps

Taking a break and enjoying Chicago Riverwalk is another cheap Chicago thing to do in the summer.



One of the most iconic places in the midwest is the Chicago River.  It runs through the city and separates the north and south sides.  The Chicago river also adds a calm to this often hectic and colorful city.  It was only a matter of time before Chicago created this year old Riverwalk.  Here is where residents and visitors alike can enjoy the riverfront, bridges, and skyline while getting active and grabbing some great food.  I love dining at River Roast, especially during its Blues ‘n Brews brunch.


Pro tip:  On Sundays pack your own meal and eat it along the riverwalk.  You will still be able to hear the free blues bands which perform on River Roast’s outdoor patio : 



Solo water vacations Chicago Riverwalk



City Winery Chicago Riverwalk



Urban Kayaks Chicago

Urban Kayak has many different types of rentals and tours



Lakefront Trail


Chicago’s lakefront trail is 18 miles of wonderful beauty along Lake Michigan.  Department store hot-shot, Montgomery Ward, fought long and hard to have the lakefront be Chicago’s “front yard” for all to enjoy.  You can bike, run, walk and skate along the lakefront trail from Sheridan Road on the north side to 71st Street on the south side.  Visit the many harbors and beaches, watch the Navy Pier fireworks (Wednesdays and Saturdays), grab a water taxi, kayak, etc. However you choose to play here, Chicago’s lakefront trail is one of the best ways to spend a summer day.




Chicago lakefront

The Chicago lakefront is one of the most beautiful cheap Chicago things to enjoy in the summer.



FREE Museum Days



Cheap Chicago things Shedd Aquarium



If you are an Illinois state resident, then you can get your fill of culture at Chicago’s great museums for FREE on certain days of the week each month.  Whether you are interested in The Art Institute of Chicago, the Museum of Science and Industry or the Museum of Contemporary Art, you can save a ton of money by avoiding the usual admission fees.  Click here for more details.


Street Fairs



Printer's Row Lit Fest in Chicago

New York Times bestselling author, Adam Rubin, signs his latest children’s book, Big Bad Bubble at Printer’s Row Lit Fest in Chicago


Street fairs and festivals are the best bet for cheap Chicago things to do in the summer.  They allow you to explore the many neighborhoods of the city on a shoestring.  Whether you seek the loud, heart-pumping action of the Chicago Air & Water Show at North Avenue Beach (August 20-21) or the stomach expanding challenge of Chicago Hot Dog Fest in Lincoln Park (August 6-7), there is so much to entertain at Chicago’s plethora of street fairs.  Entry to many of the fairs and festivals are free but some do have a small fee or suggested donation.  Check out the full list here.


The annual Printer’s Row Lit Fest takes place in June and it’s the largest book fair in the midwest.


Cheap Chicago things

Printer’s Row Lit Fest takes place in Chicago’s South Loop every June.



You’re all set, now!  Grab your shoes, a few dollars and check out these fabulous cheap Chicago things before summer ends 🙂  No excuses!  If you can’t find a good, cheap time in Chicago during the summer, it’s really your own fault.















Labeled: Culture & Community · Tips, Etc. · Travel