15 Things you can’t Miss in Chicago!


1. Wrigley Field

Wrigley Field opened in 1914 and is the home of the Chicago Cubs. If you’re lucky and here during baseball season, you can attend a game here! But even if you are visiting during offseason, you can still take a guided tour of the park for $30. If baseball is not much your forte, it is still worth coming to check out the neighborhood. The surrounding area is dubbed as “Wriglleyville,” and has become a popular tourist hub. There are a ton of fun sports bars, gift shops, eccentric pubs, stereotypical hot dog stands, and cool rooftops you can even get a view of the field from! 

2. Chicago Bean

The Chicago bean is iconic to say the least, and by the picture you can tell it’s a popular tourist destination. We went during the middle of the day on a weekend – so if you want less of a crowd I recommend avoiding peak hours! It was designed by Anish Kapoor (gotta give credit to the artist y’all!) and is one of the largest outdoor art installations in the world.

Why is it known as “The Bean,”? 

I actually only recently discovered the official name of this art piece is “Cloud Gate.” I was curious why I had only ever heard of it referred to as “The Bean,” and upon research, found that the artist does not ever name his pieces until they are entirely complete. Thus, in the midst of his creation, passerby’s had already dubbed the piece “The Bean,” and it has stuck ever since. The piece is made entirely out of stainless steel, and weighs the equivalent of 15 elephants! 

Where is it located?

It is located in the heart of Millenium Park, you can’t miss it. In fact, you could easily spend all day Millennium Park alone. Although the Bean is one of the more well known landmarks of the park, there are several other noteworthy spots in the area including the Crown Fountain, rock climbing at Maggie Daley, Lurie Garden, Plaza at Park Grill, and the Jay Pritzker Pavilion which features a summer music and film series every year!

3. Rainbow Ice Cream at Navy Pier

Anyone who knows me knows that I am an ice cream fanatic, so of course I would never pass up a chance for a FIVE scoop ice cream cone. The flavors on the Original Rainbow Cone are Chocolate,  Strawberry,  Palmer House,  Pistachio, and Orange Sherbet. I am honestly not the biggest fan of pistachio, but all the others were amazing and you can bet that I ate the whole thing! They do have other flavors but chances are if you are coming here, you are coming to get the Rainbow Cone. 

Is there a story behind The Rainbow Cone?

Why yes there is, I am so glad you asked. It is a family business that was established way back almost a century ago, in 1926. Joseph Sapp is the mastermind behind the creation. He grew up an orphan on a dairy farm and was a lover of ice cream, but could never decide on just one flavor. At the time, there weren’t many ice cream shops offering multiple flavors in one cone – much less 5! Thus, the Rainbow Cone was born. They use the same 5 flavors today that were established by Joseph Sapp in the twenties.

What else is there to do at Navy Pier?

Navy Pier is 3,000 feet long and there is an abundance to explore. The Navy Pier Park features a ferris wheel and other fun carnival rides. Fun fact: I love carnival rides. I feel like some people find them unsafe or it just isn’t their thing but I have always loved them! 

4. Art Institute of Chicago

The Art Institute of Chicago holds around 300,000 works from all around the world, making it one of the largest art museums in the United States. Admission is $25, which might seem a little steep for a museum but is well worth the price. (And quite honestly not far off from the price of some cocktails in the city. Choose wisely!) They hold works from artists including Monet, Picasso, Grant Wood, Vincent van Gogh, Andy Warhol, and Mary Cassatt, just to name a few.

How much time do you need here?

You can spend as little or as much time as you’d like – but ideally you will need at least 2-3 hours to explore . Some of my personal favorite paintings at the museum are A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat (If you’ve seen Ferris Bueller’s Day off – then you know), Sky Above the Clouds by Georgia O’Keeffe, and Cliff Walk Claude Monet.

5. Lunch at the Hampton Social

If I were to recommend one restaurant for you to go to in Chicago, this would be the one. I loved everything about it – the ambience, coastal atmosphere, the cocktail selection, food variety – it is all a win/win for me. I had heard this restaurant can be quite popular so I made reservations, and was surprised when the place was almost empty when we arrived. We went for a late lunch so maybe it was just the timing, because I was convinced it was going to be packed. This is the perfect afternoon hangout spot, and of course has many instagram worthy opportunities! 

6. Chicago Theatre

A well known landmark in the loop area of Chicago is the Chicago Theatre. We didn’t get the chance to go to a show on this trip, but I am definitely adding it to my list for my next trip to Chicago. I hear that the interior is stunning and is well worth a visit!

7. Skydeck Chicago

The Skydeck Chicago is located on the 103rd floor of the Sears/Willis Tower (big debate on the changing name – you call it what you want I know this can be touchy for Chicago natives.)  This was one of more crowded/touristy attractions we did but I honestly think it was worth the experience. You can’t really tell from my picture but you stand in a glass box on ledge overlooking the city. You have to be pretty quick with your photos since there is usually a long line waiting, but it’s kinda cool just checking out the view and getting that adrenaline rush! 

8. John Hancock Center Skyscraper 

The Signature Lounge at 95th is a snazzy cocktail lounge on the 95th floor of the Hancock building. This is the perfect place to unwind after a long day and enjoy the beautiful sunset! 

Thrill seeker? Check out the 360 Chicago TILT!

360 Chicago is similar to the Skydeck in that it is a glass platform looking over the city. However, this time, you stand on the platform and it actually tilts downward towards the ground while you are over 1,000 high! You can see the beautiful Chicago Skyline and Magnificent Mile below you.  Subsequently, this is not for the faint of heart. I am mildly afraid of heights and almost didn’t go through with doing it – but I paid the $22 and also hate backing out of things so I pushed through. My knees were shaking uncontrollably the whole time but I have to say the view was pretty unbeatable! I also just love the satisfaction of conquering something, even as silly as not passing out on an attraction lol. 

360 Chicago is located on the 94th floor of the John Hancock building. 

9. River Cruise 

Chicago Architecture Foundation Center River Cruise

Taking a river cruise is a great way to get a glimpse of the city. I recommend doing this at the beginning of your trip – so you can learn a little bit about the city and plan ahead for anything you may want to add to your to-do list! There are many boat companies to choose from, but we chose the Chicago Architecture Foundation Center River Cruise, which is rated #1 on Trip Advisor for boat cruises in Chicago. The cruise is 90 minutes long and gives you an overview of Chicago History as well as informs you on some of the monumental buildings and architecture along the way. 

10. Chicago Riverwalk

I live in San Antonio, and we are known for our Riverwalk, – so I had some high expectations for the Chicago Riverwalk! My standards may be set a little high, but I was honestly very impressed by the riverwalk in Chicago and it ended up being one of my favorite areas of the city. We were lucky to be visiting in July and had beautiful weather in the mid seventies. There were people lounging in chairs by the water, enjoying a meal at a nice riverside restaurant, or listening to some live music.

11. London House Rooftop Bar

When you look up ‘best rooftop bar Chicago,” this is one of the first to come up. I spent my 22nd birthday in Chicago, so knew I wanted to go to a fun rooftop at night to celebrate! London House has breathtaking views of the Chicago River, Magnificent Mile, and Lake Michigan. We didn’t eat here, but they have an impressive cocktail menu! My personal favorite was the French 75. 

12. Legend Tasty House in Chinatown

Legend Tasty House is a highly rated ice cream shop located in Chinatown. Ironically, this is actually Thai style rolled ice cream, and boy it is heavenly! The aesthetics of this shop are super bright and cheerful. Ice Cream aside, Chinatown is a great area to explore. We enjoyed some excellent Chinese food and bought some fun souvenirs in this area!

13. Shopping in the Magnificent Mile

The Magnificent Mile is known as the premier shopping district in Chicago. This area encompasses a 13 block stretch of shopping, dining, and hotels on Michigan Avenue. If your looking for where to stay when visiting Chicago, this is a great area to be in if you want to be in the heart of downtown Chicago! 

Things to do on the Mag Mille:

  • Enjoy drinks at the famous Sugar Factory, which is just off the Magnificent Mile. The Sugar Factory is well known for their over the top, massive, candy cocktails! (And might I add very expensive.) The Kardashians were seen at one of their locations, adding to the craze!
  • Enjoy some Chicago PIZZA! Don’t think I would miss out on adding this to the list! Chicago is famous for their deep dish pizza, and it is sure to not disappoint. Some well known pizza in the area are Giordano’s, Gino’s East, and Labriola Chicago.
  • Stop by the famous Wrigley Tower, John Hancock Center, or Chicago Water Tower! 

14. Fannie May Chocolate

I am starting to realize how much of a foodie, or I guess more-so sweet tooth I am due to how many food related things I have on this post. But no joke, Fannie May is the real deal y’all. I literally ship these chocolate to Texas whenever I can because it is THAT good and I can’t find anything like it here in the South. (shipping is only available to TX in the cooler months) My #1 ride or die recommendation is the dark chocolate buttercreams. Just thinking about them right now is making me salivate.  Pixies (filled with caramel and crunchy pecans) and Mint Meltaways are my other favorites.

We bought several pounds of chocolate during our last trip here – next time I go back I will probably by the whole store. Also *pro tip,* when you are curating a chocolate box they will usually let you try flavors to see what you like best!

(There are like 80 stores in Chicago so really no excuse to not go)

15. Explore downtown Chicago!

This photo is not great quality and that is because it is derived from my facebook. Actually all of these photos are from facebook because my phone was stolen after this trip so I have none of the originals. (I don’t have a good track record with phones, but that’s a story for another time.)

There are many things to see when exploring in Downtown Chicago! CIBC Theatre is located in the loop area and features Broadway shoes. My Grandmother actually used to work at this theatre, so I would love to see a play here one day! Hamilton was playing when we were in town, but was of course sold out! 


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