Recently, I had the opportunity to take an all-girls trip to the windy city. It was a solo girls trip where I traveled by myself and met up with some additional ladies, also traveling to Chicago, for a few days of sightseeing, fun, and amazing food!

If you have never been to Chicago, these are some fun things to do in Chicago that you must check out. If you have been, you may be surprised to find a few hidden gems. There is always something new and fun to explore in the windy city!

fun things to do in chicago

Getting To Chicago

My three days of fun started by catching a train headed for Chicago.


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I do live within driving distance, but Chicago is a quick flight or train ride from many destinations so you can get there quite quickly and easily no matter where you are.

If you are within driving distance like I am, I highly recommend taking the train. Not only do you avoid those pesky Illinois toll roads, but you have a little more freedom to explore the area without worrying about traffic, parking, etc. Plus you can sit back and relax, enjoy the scenery, sleep, or even work if you’d like.

Where To Stay

Once I arrived at Union Station in downtown Chicago, it was a very quick Uber ride over to my hotel, The Claridge House. 

Image credit: Claridge House

The Claridge House is a new hotel in the Gold Coast neighborhood of Chicago and it is an absolutely gorgeous place to stay. You truly feel like you are in a neighborhood instead of just somewhere in the city. You can’t even begin to take it all in in one trip, but that’s just one more reason to head back another time!

Image Credit: Roman Boed- Flickr

This chic little hotel is a good place to stay when you are headed to the city without the kids. The bed was extremely comfortable, and the space was just enough for either a girl’s solo trip, or even a couple’s getaway.


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Fun Things To Do In Chicago


360 Chicago

The very first thing we did was to head to the John Hancock Building and experience TILT at 360 Chicago. Not only were the views from the top of the building absolutely amazing in every direction, but with TILT you get to actually tilt over 1,000 feet above the Magnificent Mile in an enclosed moving platform on the 94th floor.  

TILT - fun things to do in chicago

For those afraid of heights, don’t worry… you are not actually standing on any glass or pushing on the glass at any time. You hold onto metal bars and stand on a metal platform. :)

Just look at this amazing view!


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Chicago’s First Lady Cruises

Even though I’ve been to Chicago quite a few times, this was the first time I’ve taken a riverboat cruise. I was a little nervous that it was going to be too cold as it was quite a brisk day on the day of our tour, but I was pleasantly surprised at how comfortable we were.

Fun things to do in Chicago - river cruise

There was very little wind and even though the temps weren’t all that high, I didn’t feel like I was uncomfortable. A coat and some gloves are all you need to enjoy the beautiful fall day!

The boat also has a heated indoor cabin so if you do get cold you can go sit inside, grab a drink or a bite to eat, and still see all the beautiful sights.

The cruise we were on was the Architecture Cruise. It was an awesome way to see Chicago and the history behind all of the buildings on the tour was really interesting to hear. Here is a little snippet of the cruise, but you have to experience the whole thing for yourself as there is so much more to see and hear!

One thing I forgot to ask the tour guide was about the lifting of downtown. I had heard from a friend that all of the buildings in the downtown area were raised by several feet to alleviate flooding issues. I’ll have to make sure to ask this question the next time I go!

The Shops At North Bridge

If you need a place to shop, this is where you want to go. I can’t even begin to tell you how many amazing stores you’ll find at The Shops At North Bridge. A few we visited were Winky Lux, Peloton, Aesop Skincare, b8ta, and Coach!

I fell in love with the Winky Lux Flower Balm — it changes color according to your pH! I’ve been using mine every day since I got one.

And while at the Winky Lux store you can visit several themed rooms that all have a different product associated with them. We had way too much fun taking pictures and trying out all the samples in each room.


In addition to the fun we had at Winky Lux, if you want another fun experience you have to check out the Coach store. Did you know you can get a custom bag, wallet, or even sneakers — all done right in the store for you?! See how mine turned out in the video below:

Redhead Piano Bar

If you are looking for a fun night out, you have to make a stop at the Redhead Piano Bar. Chicago’s nightlife is happening all week long so you are sure to have a fantastic experience any day of the week. We went on a Tuesday night and the place was full of people, laughter, and so much fun! I highly recommend stopping in at least once. 

There is live music and the talent makes sure to get the audience involved in the action, which is way more fun than just sitting there and listening. I love to have an interactive experience and you definitely get that here!

While at the Redhead Piano Bar I had to get the signature drink… the redhead! I was not disappointed, it is something I’d drink again for sure. 

Driehaus Museum

I love learning about history and how people lived before modern times. I also like to hear about how historic buildings have changed and evolved over the years, especially when someone has taken the care and effort to restore a building to its original design. 

At Driehaus, you will learn about all of this and more. This beautiful mansion has been fully restored to its original glory and is alive with history! On the tour, you will learn about the history of the home, some local history of what was happening in Chicago at the time the home was built, and some fun facts about notable Chicago people of the era. 

I had fun taking pictures of all the fireplaces in the museum. There were at least eleven that I counted, but there were probably a few I missed.

The Richard H. Driehaus Museum explores the art, architecture, and design of the late 19th and early 20th centuries with a focus on the Gilded Age. The Museum is located just steps from the Magnificent Mile within the meticulously restored Nickerson Mansion, renowned as Gilded Age Chicago’s “Marble Palace.” 

Photo Credit: Driehaus Museum

This museum is truly a hidden gem in Chicago and is worth a visit the next time you are in the windy city!

Places To Eat

There are so many great places to eat in Chicago that it would be hard to visit them all in three days. You definitely need to visit more than once to experience all the food options this city has to offer. For our trip, we decided to visit a few truly ‘Chicago’ places, as well as a few unexpected gems. 

Lou Malnati’s

When you think of food and Chicago, the first thing that may come to mind is Deep Dish Pizza. We had to experience it for ourselves, and I can safely say that the pizza at Lou Malnati’s is the best deep dish I have had so far, and I’ve been to Chicago quite a few times. 

This is definitely not your pick it up and eat it with your hands type of food. A deep dish pie from Lou Malnati’s is a meal in itself, and you really do need a knife and fork to dive in!

This was so good!


Eataly could be considered both an attraction and a great place to find food to eat. If you are looking for fun things to do in Chicago, you have to add a visit to Eataly to your list! 

Inside you can shop, you can dine, you can even watch cheese being made right in front of your eyes. We had a chance to sample some of the salami and cheese after it was made fresh and… OMG! So good!


Have you ever heard of a vegetable butcher? Eataly has one of those too! You can grab the fresh produce that you want and the veggie (and fruit) butcher will cut it up any way you like so you don’t have to do any prep work at home. 

How amazing is that?!

After a tour through Eataly, we sat down for a bite to eat at La Pizza & La PastaThe food here was so amazing! We had a sampling of pizza, which was a thin and crispy crusted pie that I could have eaten by myself if I didn’t have to share, caprese, and a selection of pasta dishes that included my favorite… the ravioli de Zucca that was stuffed with butternut squash. 

STK Chicago

STK is a fantastic lounge style steakhouse that has a DJ most weeknights and weekends that really adds to the fun atmosphere. The food is absolutely delicious, and the experience the staff provides will make your night out even that much more fun.

Image Credit: STK Chicago

The servers will definitely make sure you have a fantastic time, whether you are out with friends, on a date, or celebrating an occasion (p.s. be sure to tell your server if you are celebrating something because the parade of sparklers they bring out for you with shots to follow… so awesome!).


Ramen-san would not be a place I’d normally choose to eat on my own, however, when you are taking a trip with other people sometimes you need to be accommodating to what everyone else wants to do as well.

I’m so glad we decided on this place as I got to experience some food that I wouldn’t have otherwise. The food was good and I couldn’t believe how much you get for the price. The hardest thing for me was learning how to use chopsticks for everything… even the soup! It was definitely fun, though, and added to the whole experience. 

The next time you are looking for some fun things to do in Chicago, be sure to keep these places on your list! If you have more fun activities that I haven’t mentioned, please be sure to leave a comment and let us know. There is so much to explore and do in Chicago that I couldn’t possibly fit it all into three days!

If you need more ideas on planning your own trip with loads more fun things to do in Chicago, be sure to visit The Magnificent Mile Website as they have a complete guide to help you out. Be sure to visit as well to plan your trip to Illinois!

This post on fun things to do in Chicago has been sponsored by The Mag Mile Association and Enjoy Illinois. Opinions are my own.