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.
