top of page

Hi, we're Georgina and Nathan, college friends turned travel partners. We're coffee and animal-loving adventure enthusiasts here to share our favorite travel tips with you! Our goal is to inspire others to get out and explore this wild planet by camping, hiking, or wandering around a fun new city!

5 Apps & a Free Planner

Join our newsletter to receive the 5 apps I use to plan a trip, my go-to travel essentials list, and a free travel planner pdf!

Free Travel Planner Printable!

free travel planner printable pdf.jpg

Grab your FREE travel planner printable below and get planning your next trip with Alpacka My Bags!

  • Georgina D'Angelo

17 Best Things to do in Chicago

Updated: Jan 23

The Top Paid and FREE Activities to Enjoy in the Windy City

Best 15 Things to do in Chicago - Alpacka My Bags

Chicago, you have to go experience it for yourself. Each neighborhood has its own unique vibe. There is so much to see and do here, you are bound to love it.

From Andersonville to the Loop to Little Italy. Chicago is huge and it all deserves to be explored. Find locally owned bakeries, shop until you drop downtown, and walk more than you probably ever plan to.

If you haven't yet visited Chicago, this is your sign to go! You can eat all the delicious food you possibly can, learn about Midwestern history, admire architectural styles throughout the city, sip on coffee and devour fresh donuts.

Read Also: The Best Cafes in Chicago

If you want to visit multiple museums and attractions, save money and check out the Chicago City Pass! With a pretty limitless list of things to do, we've narrowed it down so you can see the best of the city in a short amount of time! Check out the best things to do in Chicago.

What to do in Chicago

1. Cloud Gate

You can't visit Chicago without seeing Cloud Gate, or The Bean, for yourself. This beloved, well-known sculpture sits in Millenium Park and is free to visit. Get your camera out and be ready to take fun selfies on the reflective surface of The Bean.

things to do in chicago - cloud gate

2. Navy Pier

While there are stores and restaurants, a children's museum, a Ferris wheel, and more to enjoy at Navy Pier, it is a fun, lively place to walk around and admire for free. If you'd like, stop for an ice cream or a hot slice of pizza at this true Chicago classic!

things to do in chicago - navy pier

3. Sky Deck

Get the best view of Chicago from the top of Willis Tower in the Sky Deck! Tickets are required to be purchased in advance, but this view is totally worth it. This is also included the Chicago City Pass!

4. Magnificent Mile

This is a great street to walk down and really get a feel for the bustling vibe of Chicago. With stores up stores on the Magnificent Mile, this is the perfect spot to go shopping all day. It's also really pretty during the holidays with tons of lights and decorations.

5. Lincoln Park Zoo

A free zoo?! Yes please, let's go! The Lincoln Park Zoo has FREE admission which is perfect if you want to squeeze in a quick stroll around to admire the animals. And next door is the Lincoln Park Conservatory which is a free botanical garden!

what to do in chicago - lincoln park zoo

6. Garfield Park Conservatory

If you enjoy the beauty of nature, you definitely need to head to the Garfield Park Conservatory! This is another free conservatory, although it is bigger and homes more plants than the Lincoln Park Conservatory.

what to do in chicago - garfield park conservatory

7. Water Tower Place

Along with lots of shopping and dining options, Water Tower Place is a classic Chicago building. Even if you don't want to spend money in the stores, it's a pretty area to walk around. Check out the City Gallery in the Historic Water Tower right next door!

8. Museums

There are so many incredible museums to visit in Chicago. From history to science to art and more, the options are endless. There really is a museum for everyone to enjoy in Chicago. Check out the best museums in Chicago here!

9. Buckingham Fountain

A beautiful, and free, sight to see in Chicago is Buckingham Fountain. Located in Grant Park, this is one of the biggest fountains in the world. The details are gorgeous and it is a Chicago must-see classic.

things to do in chicago - buckingham fountain

10. Architecture River Tour

Cruise down the Chicago River, sip on cocktails, and learn all about the interesting architectural styles found throughout the city. The Architecture River Tour is a very fun way to see lots of the downtown area and learn about some Chicago history as well!

chicago architecture river tour

11. Montrose Beach

You can't visit Chicago without a stroll on one of its "beaches." Because it is located right on Lake Michigan, Chicago boasts some pretty lakeshore beaches, one of the best being Montrose Beach. It is free to walk down and has some beautiful views! Another great option is Fullerton Beach.

12. Alfred Caldwell Lily Pond

You might be surprised by how much nature you can find in the bustling city of Chicago. With tons of parks, huge potted planters, and tree-lined streets, you can still get in your nature fix here. One of the BEST parks to visit is the Alfred Caldwell Lily Pond. This beautiful oasis is a must-visit in spring and summer but sadly closes in fall and winter.

13. Lincoln Park

Not only is Lincoln Park a gorgeous neighborhood in Chicago, but it is also a massive 1,200-acre park that follows the lakeshore of northern Chicago. If the weather is nice, you can spend a day exploring this park and stop by nearby attractions such as Lincoln Park Zoo and Peggy Notebaert Nature Museum.

14. Rooftop Bars

If you enjoy having a drink with a view, head to one of Chicago's many rooftop bars. One of the best in town is Cindy's Rooftop, located at the top of the Chicago Athletic Association Hotel. While quite expensive, it makes for a fun, memorable night in the city.

cindy's rooftop chicago

15. Harold Washington Library

Another free activity in Chicago is the Harold Washington Library. And I'm not telling you to go check out some books, although it houses more than 1 million books, but check out these cool things to do in Harold Washington Library. It is a seriously beautiful building.

harold washington library - what to do in chicago

16. Baseball Game

If you're a sports fan, head to Wrigleyville, where Wriglefield, the home of the Chicago Cubs, is located. You might be in town for a big game, but even if you're not, it's still a fun Chicago activity to check out. Or if you're not a fan, check out the White Sox.

17. Musical, Show, or Concert

Did you know you can catch a plethora of shows, musicals, and concerts in Chicago? With a variety of Chicago Broadway shows to choose from, see top performing musicals, or look in advance to see if your favorite artist will be performing!

what to do in chicago

If you haven't been to Chicago yet, this is your sign to book a trip now! With an incredible variety of things to do, the list could go on forever. But these are some of the best things to do in Chicago.

When you visit a new city, what is something you always try to do? Find a museum? Look for a botanical garden? Well lucky for you, Chicago has it all! This is a must-visit travel destination in the US.

Now you know what to do in Chicago, where will you be heading first? Let's chat about this wonderful US city in the comments below!

Post: Blog2_Post

Ready To Book Your Trip...

Planning a vacation can be time-consuming and a little overwhelming. To help smooth this process for you, we've compiled our favorite travel planning resources.

From finding the best flights and hotels to the essentials you need to make the most of your trip, check out the Alpacka My Bags travel resources page.

5 Apps & a Free Planner

Join our newsletter to receive the 5 apps I use to plan a trip, my go-to travel essentials list, and a free travel planner pdf!

Alpacka My Bags Travel Blog.jpg


We're Georgina and Nathan, two adventure enthusiasts and creators of Alpacka My Bags. We're here for all of your travel and adventure planning needs! 


We've been exploring this insane planet that we call home together for over 3 years now. After college, we knew the "traditional career path" was not for us, and honestly the "traditional life path", in general, just wasn't for us.


We needed to travel and explore what this world has to offer, it sounds cliché but you do only live once. So we made going on adventures a priority, and soon realized that we wanted to share them with others so they can enjoy them too! 

Our passion is spreading the travel bug and showing others that travel is attainable and so worth it. From itineraries to camping tips to packing lists, Alpacka My Bags has you covered!

Join us, and often our dog, JoJo, as we find exciting adventures and travel recommendations for you! If you've been bit by the travel bug just as we have, we hope you find our tips useful for any and all of your future travels.

bottom of page