Top Discounted & Free Places to Visit in Chicago

Many of us have heard of the famous windy city, but what makes it one of the most visited cities in the United States? Well, for starters… there is so much history here with so many discounted and free places to visit in Chicago! They have beautiful landscapes and is the home to the second-tallest freestanding building in the world!

The best part? You can enjoy the Chicago tourist attractions over a weekend getaway! That’s right… you do not need to spend a whole week here to enjoy the windy city (though there’s plenty to do if you did want to stay for the week).

Disclaimer: Please note this post may contain affiliate links. This means I may receive a commission if clicked at no extra cost to you. Though the opinions remain my own. All images were taken by Cheers to Travel Blog.

I was lucky to attend a 4-day convention here with my days being booked up but still managed to enjoy the top attractions below in my spare time. And no, I didn’t have to spend a lot of money to do it thanks to the amazing Chicago CityPass offer.

Ready to see why Chicago is a top tourist city?

See below for visiting tips, along with the discounted and free places to see in Chicago to plan to see during your visit! While many are discounted using this link, there are also others that are FREE!

All images taken by Cheers to Travel Blog.

Discounted Attractions in Chicago

Vacationing doesn’t have to be expensive. In fact, I prefer to travel on a budget whenever possible. So to help keep you pocket a bit more full during this getaway, here are some discounted attractions you can visit in Chicago.

Skydeck Chicago (Willis Tower)

The Skydeck at the Willis Tower has the most beautiful sights of the city! It is 1,353 feet high on the 103rd floor, making it the eighth tallest freestanding building in the world. At one point, it even used to hold the first place title!  

Skydeck view of Chicago
Skydeck view of Chicago
huge 103 orange sign while waiting to go up at chicago skydeck
The Famous Skydeck on the 103rd floor 😮
woman sitting on chicago skydeck ledge
Don’t let my face fool you, I was terrified! 😅

In 2009, the Skydeck opened its famous attraction – The Ledge. This is a clear glass box placed on the 103rd floor where Instagram perfect pictures can be captured! To get up here, you take an elevator which shoots you up to the top in just 60 seconds! I know, crazy right?

Unfortunately, this isn’t one of the free attractions but I do have a discount link you could use for your admissions here! Almost 2 million tourists visit here every year – you should be one of them!

CityPass Attractions in Chicago

Doesn’t this CityPass sound awesome?? It literally saves you over $100 per person each time you visit Chicago! Even with just the attractions already mentioned it is a huge money saver. But that’s definitely not all this Chicago CityPass deal includes.

Here’s the full list of what the Chicago CityPass Admission includes:

  • Shedd Aquarium – PRIORITY ENTRY
  • Skydeck Chicago – EXPEDITED ENTRY
  • Field Museum – ALL-ACCESS PASS
  • Adler Planetarium – ENTRY + 2 SKY SHOWS + ATWOOD SPHERE EXPERIENCE OR Art Institute of Chicago – FAST PASS
  • Museum of Science and Industry – ENTRY + 1 TICKETED EXPERIENCE OR 360 CHICAGO Observation Deck – EXPRESS ENTRY

All this at an extremely discounted price. Take a look at the full CityPass details here.

Related Post: Best Places to See in New York City

Free Places to Visit in Chicago

I did say I like traveling on a budget didn’t I? So of course that means taking full advantage of all the free attractions in Chicago! And lucky for us, Chicago has plenty.

Chicago Riverwalk

The Chicago Riverwalk is a 1.25 mile long pathway along the Chicago River and was completed back in 2016. Since then, it has grown to accommodate a handful of restaurants and activities for awesome enjoyment.

Chicago Riverwalk during the day
Along the breezy riverwalk
Chicago Riverwalk at night
The view is just as pretty at night ♥

It is a great walk with a variety of options and a beautiful view, regardless if visiting during the day or at night. Besides what you choose to visit along the Riverwalk – the experience on the Riverwalk is free! So go out and take a nice walk along this breezy river!

Millennium Park

Millennium Park is located in the heart of the Windy City. It is a very popular spot for both, locals and visitors, to hangout. This destination is considered “lively” and is also known for their free events that are posted in their events calendar.

Bright and blossomed flowers – a view in itself
Look at that architecture! Just amazing.
Such a beautiful park filled with architect and nature

Within this park alone, you will find also some of the most popular attractions that Chicago has to offer including Cloud Gate and Crown Fountain. You could definitely either spend anywhere from a few hours to a full day at this park – and it is worth it!

Cloud Gate (The Bean)

Now, this is one spot that you absolutely must visit before leaving Chicago! Cloud Gate or better known as “The Bean” is one of the most famous Chicago attractions located in the heart of Millennium Park.

The biggest “bean” I’ve ever seen! 🤣
Look at all those reflections!
Such a unique piece of art

I do recommend you try to get there early as it tends to fill up with tourists thoughout the day. I mean who can blame them for wanting to visit this famous, free attraction right?

This mirror-like sculpture reflects the Chicago skies which is almost always covered with white clouds, making the reflection beautiful! AND of course, you will also see your beautiful reflection when getting up close 😉 so makes for a great picture spot as well!

Crown Fountain

Now the Crown Fountain is a unique attraction you won’t find anywhere else (that I know of at least). This is a two glass-block tower fountain which is 50 ft tall and displays the faces of Chicago citizens. And yup, you guessed it – it’s also free of charge!

The faces of Chicago (seriously, that’s what it is)
Was lucky to experience the fountain turned on

Between the spring and fall seasons, the fountains operate in a way that gives an illusion that the faces having water spouting from their mouths. Though this may sound a bit weird, this is actually a symbol of life. Who would of known right?

Tips When Visiting

Convinced to visit yet? Remember, you can do all the above in a weekend getaway! However, every city is different and therefore it’s always good to do research before exploring a new place.

Although I was there a short while, I learned a few meaningful tips I feel would be good to share.

Invest in the Chicago CityPass – Trust me, it saves you money!

If you plan on staying in Chicago a few days, then it is extremely worth for you to get the Chicago CityPass! Why? Well, because it would save you a TON OF MONEY, that’s why!

No seriously, as I mentioned – there are a TON of attractions in Chicago (many that I unfortunately did not get a chance to experience). But don’t let the same happen to you! With my link here to the Chicago CityPass, you get to pick 5 different attractions for only $108 – that’s under $22 per attraction!

Know how much it would cost to buy each admission separately? 50% more!! That’s over $100 in savings simply for buying this bundle deal! And plus, that’s not including the other free attractions you get to visit while you’re there. It is definitely a bargain vacation deal!

Click here for more details on the Chicago CityPass offer.

It’s called “Windy City” – BRING A JACKET

The weather here is super nice! Coming from Houston, we learn to appreciate any little bit of breeze. However, even 60 degree weather may be enough for us to throw on a light jacket, especially in the mornings and evenings.

Columbia brand jackets are my absolute favorite! They are light enough yet warm enough so perfect for a windy city! Actually, I’m lying. They are not only perfect for the windy city – I wear mine ALL THE TIME! 😅 And don’t get me started on the comfort and softness… It is seriously one of the best jackets I own (if not the best) and I strongly recommend you AT LEAST give them a try (free returns via Amazon so it’s a win-win)

Lots of top sights are on ground – BRING WALKING SHOES

With so much to do in Chicago, you are bound to do a ton of walking. There is a lot of public transportation to help you get around, but you will want to take a walk around the city, trust me!

If you’re walking around during the Spring or Summer, these Sanuk sandals are amazinggggg! They are super lightweight and have a cushioned bottom for EXTREME comfort. Since the bottom is made out of a YOGA MAT (yeah, literally), it feels like you are walking barefoot on a yoga mat all day! The great thing is they come in a huge variety of colors to match all of your outfits. Honestly, my new favorite walking shoe and have taken them on every vacation ever since I bought them.

Tired of walking? – GET A LYFT / UBER

There are plenty of Uber’s and Lyft’s in the windy city of Chicago! It never took more than 5-10 minutes to get a ride when we visited, no matter the time of day. If needed, the drivers are also knowledgeable on their city and can also recommend you more spots to visit.

Are you a big picture taker? – BRAINSTORM / RESEARCH POSE IDEAS

Or get creatives and create your own poses! Though, if you are like me, and don’t take many pictures of yourself… getting on Pinterest to see what others have done is the way to go! Especially since Chicago has so many prime opportunities for great Instaworthy shots!

Get Your Coffee & Donut Fix Here

Lastly, Stan’s Donuts & Coffee is an absolutely great donuts and coffee shop recommendation! 🍩 This place is AMAZINGGGGGG! The donuts were freshly warm and had lots of unique options to pick from.

If you aren’t a fan of donuts – these may change your mind!
Seriously, these donuts were DELICIOUS!

Though, be warned that that their donuts are pretty big so one was plenty for me… but it did take me a while to decide on JUST ONE. 😅 Their coffee selection was also tasty and unique making this space great for anytime in the day!

The Weekend Getaway!

If you need a weekend getaway or are unsure of where to go for your next vacation, I definitely recommend considering Chicago! I hope these tourist attractions in Chicago list helped make your planning a bit easier.

Have you visited any places listed above or have any additional recommendations I should add? Please drop a comment below as I would love to hear from you!

And remember, there is always something to be happy for… Cheers to travel! What are you cheering to today?


39 thoughts on “Top Discounted & Free Places to Visit in Chicago

  1. I appreciate the section of free attractions and I love all of your pictures! The reflections on the Bean are really fun. Thanks for this list of tips!

  2. A weekend in Chicago is on my US travel list, maybe the next time a flight takes me through O’Hare, I may have to spend a couple days. I have to tell you the picture with you on the skywalk thing literally made my stomach drop, and that was just the picture – lol!

    1. LOL! I promise it is not as bad as it looks! The first few seconds are extremely scary but you only get 60 seconds on the ledge anyways so it goes by really quick!

  3. Growing up in Madison, WI, a mere hour and a half away I had plenty of opportunities to visit Chicago. Although I have lived plenty of places Chicago is one of my favorite places to visit. Thanks for your post!

  4. I live only about 1 hour North of Chicago. We used to live close to downtown when we first got married. You have beautiful pictures of everything! I do hope you had some Chicago pizza while you were there too. 🙂 You are brave to walk out on that ledge. I have been up there, but that was before the ledge was built. I don’t think I would be that brave.

    1. It is BEAUTIFUL up there! Make sure you get the CityPass and take advantage by visiting all the free spots as well! Hope you love it ♥

  5. Chicago is certainly a place I’d love to visit. I’ve passed through Ohare Airport many, many times, but I’ve never taken the time to visit the windy city. Your city attraction blog list sounds like something I need to stop and do the next time. Thanks for sharing!

  6. I need to get back to Chicago. I haven’t been since my youngest was born, and she’s ten now. We did the CityPass when we went, and it was perfect for us. Somehow we missed Millennium Park and the Bean, but we only had two nights, so we did as much as we could. Great post!

  7. Great tour of my city! We love going down there and usually spend little to nothing when we do! So much to see! The weather has been a bit odd lately – we were able to enjoy Millenium Park without jackets the day after Christmas! Must try Stan donuts next time I am down there – they are always so busy!

    1. Oh this is great! So glad that I was able to impress a local with my post ☺ and OMG yes, you MUST try Stan’s Donuts – it was delicious! The donuts are huge so I didn’t even finish mine lol

  8. This looks like a beautiful city to visit! I might have an opportunity to go In June! I hope I get to go! I’ll have to check out some of these spots if I do get to go

  9. I haven’t been to Chicago for several years and when I did visit, I didn’t have very much time to see things. I would love to visit again and will make sure to refer to your list! thanks!

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