Our #1 goal is for you to enjoy your visit to Chicago. Let’s assume that includes a Free Chicago Walking Tour, what will you do with all the money you save? Sure you could go shopping, treat yourself to fine-dining experience or take one of the best tours in Chicago (that isn’t Free Chicago Walking Tours).
Don’t get us wrong, there are plenty of free things to do in Chicago other than our walking tours. We felt it’s only fair to rank the best tours in Chicago that are going to cost you a few bucks. All of these tours bring something different to the table and are well worth the price of admission.
Chicago Big Bus
For those spending a day in Chicago, one of the best ways to tour the city is to get a ticket for the Chicago Big Bus. This bus tour will take you all over the city so you can explore great landmarks with live tour guides. One of the coolest features of this attraction is the ‘hop on, hop off’ feature where you can get off and explore the city’s landmarks yourself, and then hop back on!
Honestly, when the weather is beautiful this is one of our go-to things to do in Chicago. Sit on the upper deck, soak in the sights and listen to the guide. So relaxing, so enjoyable. Even as a local we hop on at least once a year.
This one day pass is $40, but you can save 10% by pre-booking online, making the total per ticket $36. If you purchase a premium ticket for $10 more, you also get a ticket for Centennial Wheel! This is a great way to view the Chicago skyline and get some great views of the city.
Tip: Take 5 minutes to review their stops and see if you can plan out an entire day without having to use other modes of transportation. You might save half or more of the price of the ticket by not having to pay for cabs!
Chicago Helicopter Experience
With the Chicago Helicopter Experience, you can feel like a king for a day. You can book a tour over the city, a private charter, a group charter, or even a shuttle to O’Hare. With the Chicago Helicopter Experience, you can travel or view the city in style. The cost of a helicopter tour is $180 per person, but you can bring that down to $99 per person if you book in a group of 12 or more, or book an early bird flight.
Also, if you want an incredible experience as you are departing the city, let the Chicago Helicopter Experience be your own personal pilot on your way to the airport. You won’t regret it
Willis Tower Skydeck
Probably the most iconic building in Chicago is the Willis Tower, formerly called the Sears Tower. Until the Freedom One tower was built, this tower was the tallest building in the Western hemisphere. It was also once the tallest building in the world!
Tickets are $24, and $10 less for children. Sky Deck is included in the Chicago CityPASS which will save you a bunch of money and give you access to more attractions. They also offer a ‘Pie in the Sky’ deal, where you can enjoy a deep dish Chicago pizza while looking over the city. You can also visit ‘The Ledge’ where you can look over the entire city while standing out on a ledge!
Some of our guests have wondered out loud “is this too touristy?” That is such a hard question to answer. On one hand, sure – this the Wilis Tower Skydeck is very popular and sometimes the wait can be over an hour long on a clear day. But it’s so popular because honestly, it’s that cool. If you are in Chicago and you have the opportunity this is one of those things that you have to do, or should strongly consider. The views are absolutely breathtaking.
Tip: Weekends are the busiest if you can try going on a Tuesday or Wednesday.
Wendella Boat Tours
This is definitely one of the best tours in Chicago. How can you beat drinking an ice cold beer and relaxing on a boat during summer in Chicago?!
Their flagship tour is the Chicago Architecture tour. We’ve done. Several times. Just last year. The tour takes you up and down the main artery of the Chicago River, up the North branch and then out into Lake Michigan briefly for a view of the skyline you just can’t get from land.
Wendella offers their Chicago Architecture tours throughout the day, so pick the time that works best for you. If you love architecture and want a more intimate up-close look make sure to check out our Chicago Total Loop Tour.
Tip: Arrive 30-40 minutes before boarding to be one of the first in line and have your choice of seat. It’s first come, first serve.
The Lincoln Park Zoo is one of the only free zoos in the country. The Lincoln Park Zoo is also one of the oldest zoos in the country! It may not be as large as other zoos, but it has over 230 different species of animals on a 35 acre lot. A great place to spend an hour with your family, or take a walk on your lunch break. This zoo has monkeys, reptiles, polar bears, and even tigers!
Millennium is one of the largest public parks in Chicago. Its original intention was to celebrate the entrance into the third millennium. You can view exhibits, architecture, a beautiful garden, and even go ice skating! This park even offers concession stands. This is among one of the best places to go in Chicago, and admission is always free. Get an unclose and personal experience on our 
This place is so awesome we either stop in or talk about it on almost all our 
For those who love art, the National Museum of Mexican Art is a completely free attraction open to the public. The museum is divided into separate sections for each era of latin american art and culture! This approach also makes this museum appeal to lovers of history. Exhibits change frequently, so check out what they have before you make an appointment. If you have been before, chances are that you can go again and see some entirely new works of art!
Located on Columbus Drive, Buckingham Fountain is one of the largest fountains in the world! For those who want a fun experience in Chicago should come on by and check this fountain out. This is also a great place to spend your lunch break, or take your family to see the fountain go off! This is one of our favorite places to get a group picture after the 
If you are looking for a good laugh, look no further than the legendary Second City in Chicago. Stars like Stephen Colbert, Steve Carell. Alan Alda, Bill Murray, and John Candy got their starts right here. It’s not an ordinary comedy club. This is where some of the funniest and brightest comedians perform. There is a reason this is one of the most notorious comedy theaters in the United States!
The Cadillac Palace Theatre, part of the Theatre District in Chicago’s Loop, has roughly 2300 seats, the perfect size for Broadway shows! The performances are always changing, and there is always something you must see here. Parking is limited in this part of town, we recommend taking an 
The Broadway Playhouse is also part of Broadway in Chicago. New York is not the only place you can see Broadway shows! Chicago has some of the best shows available right here in the Windy City. This theater was originally closed and converted into a movie theater, but in 2004 it was restored to its original glory as a place to see some amazing live shows in Chicago. Events change frequently, so be sure to look at their calendar to find a show you might want to attend!
This legendary theater has everything from music to dance. You may come for the performance, but the architecture is like a show itself! This theater values culture and frequently runs donations to help folks who might not be able to afford to come and experience live shows in Chicago. How cool is that!? If you want to see a wonderful performance in Chicago, check the 
What makes this place so special is how 100% authentic and unique their productions are. There is a beauty of an intimate theatre that doesn’t have the production budget of the shows you will see in Chicago’s Theatre District. The performers have so much passion, the stories are fascinating to follow, the prices are reasonable and the variety can’t be matched anywhere. Tucked right inside the beautiful Lincoln Park neighborhood, this is a must-see attraction for anyone interested in getting a feel for what “real” Chicago theatre looks like.
The Chicago Symphony Center has some of the most beautiful musical performances in the world. All lovers of classical music must attend a show here if they get the chance, as it will be a once-in-a-lifetime experience. Their in house orchestra is world class, and they also bring in other guest performers and some of the most talented conductors in the world. The building is also known for its great acoustics, making it an even more memorable experience.
Quite possibly our favorite tour to take in Chicago when we aren’t taking one of our tours. How can you possibly beat being on a boat, in the sun, downtown Chicago, looking at all these beautiful buildings while drinking an ice-cold beer? The guides do an absolutely incredible job. The material comes at you really fast, so listen carefully. And if you like what you saw and what a slightly more intimate experience take a 
If we wrote this little piece 5 years ago we might have included seeing a Cubs game as part of our 
The Shedd Aquarium is an indoor aquarium located on Lake Shore Drive. To date, it contains over 30,000 different animals! There is a reason that this aquarium was the most visited aquarium in the United States for several years. There will not be many chances to see wildlife from all over the world, so take advantage of this while you are here. The Shedd Aquarium is also involved in conservation and the fair treatment of animals!
The Willis Tower (formerly the Sears Tower) is one of the top tourist attractions in Chicago due to its spectacular views of the city. There is no better way to see the city than from the Willis Tower Skydeck! It’s also a great spot to get some pictures of the Chicago skyline. If you have your family with you, there are discounts available, as well as cheap or free admission for children.
