Chicago Vacations: So Much to See For Free!

Vacationing in Chicago, (vacationing in general) can be costly, but it doesn't have to be! Chicago Guest House offers special savings on our vacation rental homes. Mid-week stays are  20% Off normal nightly rates  on SELECTED DATES  throughout the year! Each home is fully furnished and fully equipped with everything to make your stay enjoyable---fully equipped kitchens so you don't have to spend a lot of money dining out either!   Not only can you get special rates on lodging but below you will find a list activities and events you can do in Chicago without spending a dime! Attractions around every corner---art, music, history, architecture--the list goes on!  


Cloud Gate at Millennium Park Chicago


Check out the mind-bending reflections at Cloud Gate (aka the “Bean”) a gleaming steel mirror that bends the Chicago sky and skyline around its surface---now on of Chicago's top attractions. Take a selfie with the virtual reality wonder of Crowne Fountain an interactive work of public art and video sculpture--the kids will love playing in the water as it squirts out of the mouths of the images of thousand of Chicagoan's! Wander the breathtaking native plantings at Lurie Garden an urban oasis for city dwellers and wildlife alike. And marvel at the architectural splendor of the Jay Pritzker Pavilion, as you lay out on the lawn to watch a free outdoor film screening or concert. 

Crowne Fountain at Millennium Park Chicago
Lurie Garden Millennium Park Chicago
Maggie Daley Park Chicago
One of the highest ranking attractions in Chicago! Maggie Daley Park’s 20 acres signature attractions:
  • 19,000 sq.ft rock-climbing sculpture 
  • A 1/4 mile long skating ribbon (roller-blade in the spring/summer/fall and ice skating in the winter).
  • A three-acre play garden in the southeast section provides diverse opportunities for fun, adventure, exploration and learning for children of all ages. Up to 600 children can play in this feature at one time.​
maggie daley park in chicago ice skating ring
Roller Blade in the Spring/Summer/ Fall and Ice Skating in the Winter
BRING YOUR OWN BLADES OR RENT FOR $12 for a thirty-minute rental
Grant Park
Music Festival

pritzker pavilion in chicago
Wenesday Night Concert Series
PRITZKER PAVILION. Bring a picnic and a blanket and make yourself at home in Chicago's most spectacular setting to listed to a live outdoor concert. Any outside food or drink, including beer and wine, is welcome in the Pritzker Pavilion during Grant Park Music Festival concerts. Our orchestra and chorus can be heard to the back of the lawn, thanks to a sophisticated audio system that provides quality sound for all. NO SMOKING & NO PETS allowed. ​NOTE: Chicago Guest House Has Picnic baskets, coolers and blankets
chicago cultural center tiffany dome
Chicago Cultural
Drawn by its beauty and the fabulous free public events making it one of the most visited attractions in Chicago. The stunning landmark building is home to two magnificent stained-glass domes, as well as free music, dance and theater events, films, lectures, art exhibitions and family events  
Summer dance people dancing in open air dance floor in Grant Park Chicago
Grant Park
Summer Dance Festival
Sundays  4pm-7pm
​​Swing, waltz, cha-cha…​​​​
or simply enjoy the music! 
Dance to the sounds of 48 different live bands + DJs and get into step with dance lessons beforehand. Glide across the restored 4,900-square-foot, 100 percent recycled, open-air dance floor designed by Chicago artist Dan Peterman.
Movies in the the park at Wrigley field in Chicago
  • July 11 - HOME ALONE
  • July 18 - TWISTER
  • August 8 - GREASE
  • August 22 - SPACE JAM
  • September 5 - TOP GUN
  • September 19 - BACK TO THE FUTURE
Music Box Theatre  Presents Movies
Gallagher Way | Wrigley Park
Wednesdays 7:30pm
Gather your friends and family and come enjoy Gallagher Way's summer movie series brought to you by Chicago's premier venue for independent and classic films, the Music Box Theatre. 
Sundown Sessions 
Gallagher Way | Wrigley Park
Tuesdays | Friday | Saturdays
Bring a blanket and enjoy the sounds of live music from local jazz and blues artists select evenings at Gallagher Way. Musicians from the Jazz Links Education Program Alumni Ensembles perform select Tuesday evenings and musicians from Buddy Guy's Legends perform Friday and Saturday evenings throughout the summer
Chicago Greeter Logo
FREE Chicago Greeter Tours
Let a friendly, knowledgeable local give you an insider’s orientation to Chicago!  Register at least 10 business days in advance. Greeter visits are customized based on your choice of neighborhoods, language and interests.  We have over 200 enthusiastic volunteers waiting to share their expertise and passion about the city with you
Mercury & Music box theater in chicago
Experience headlining shows at half the price! The League of Chicago Theatres has launched its brand new  Hot Tix website , featuring a sleek new look, user-friendly search options, geo-locating to find nearby half-price performances, and the ability to buy your half-price tickets straight from your mobile device.
For Only $15 A Day
Divvy is a fun and affordable way to get around the city.
The Explorer Pass costs $15 and includes unlimited rides in a 24-hour period, up to 3 hours each. Use it to get to local attractions or take a bike out for a ride along the lakefront. It's just like renting a bike but with more flexibility – you don't have to return it to where you started, and you don't have to worry about finding a safe place to lock it up if you want to stop for lunch, go to a museum, or explore on foot.  The best way to buy a pass is through the  Transit app . Purchase your pass, unlock a bike using a mobile ride code, and be on your way in minutes! Download Bike Map
People riding down the chicago lakefront path
The centerpiece of Grant Park. Come see the light show after dark!
​​The center piece of Grant Park is Buckingham Fountain, one of the world's largest fountains. The fountain, in a rococo wedding cake style, was dedicated in 1927 as a gift to the city from Kate Sturges Buckingham in memory of her brother Clarence. April to October water displays every 20 minutes and a light and water display from 8:00 am to 11:00 pm.​​
Lincoln Park