top of page
  • Writer's pictureMadeline Hill

The Ultimate Guide to Chicago

Updated: May 24, 2020

The Bean Chicago
Visit Cloudgate- otherwise known as the Bean!

Every time we are state side- we always manage a trip to Chicago! There is so much to see and do in the Windy City. Between visiting rooftop bars, botanical gardens, and shopping, you'll be stretched for time to do it all! Check out our guide on what to see and do in Chicago.

What to See:

the Bean Chicago
Make sure to get here early- as it does get very crowded!

The Bean- Millennium Park

No trip to Chicago is complete without seeing the iconic Cloud Gate- otherwise known as the Bean. Find your reflection in this stainless steel structure in Millennium park. The Bean is located above the Park Grill. Make sure to get here early as it does get crowded during the day!

Millennium Park is also a fun place to visit. We enjoyed wandering through the park admiring the Chicago skyline. Constructed above a parking garage, this is considered to be the world's largest rooftop garden. During the summer, there are concerts in the park at the Jay Pritzker Pavillion. Click here for upcoming events.

Lincoln Park

Spend a morning walking along the boardwalk at Lincoln Park and enjoy beautiful views of the Chicago skyline. Also, make sure to check out the Lincoln Park Zoo- one of the oldest zoos in America. It's also one of the last free zoos remaining in the world. It's a beautiful place to wander through and we loved seeing all of the animals.

Click here to view the exact location of the Honeycomb on Google Maps. If you walk along the bridge over South Pond, you'll be able to spot this structure (pictured above)!

London House

No trip to Chicago is complete without a rooftop bar experience! Many locals recommended London House. Located on the riverwalk, you take the elevator up to the 22nd floor and are treated with fantastic views of the riverwalk and some beautiful Chicago buildings. The drinks are a little pricey, but it completely makes up for the view! London House is open Monday-Friday from 11 AM-Midnight and Saturday-Sunday 10AM-Midnight. There is also a restaurant here.

The riverwalk Chicago

Architectural Tour

Chicago is known for its outstanding architecture. After the Great Chicago Fire in 1871, when most of Chicago burned down in a fire, the city was completely completely transformed into an architectural hub of skyscrapers and unique buildings. We took an architectural tour by kayak along the river and we highly recommend it! Do the 90 minute guided excursion along the riverwalk and learn about the history and fun facts about Chicago. Click here to book.

Garfield Park Conservatory

Another fun and FREE thing to do in Chicago- visit the Garfield Park Conservatory! Wander through this indoor botanical garden and enjoy all of the beautiful rooms of plants, waterfalls, and stunning palm tree walkways. There is also free parking available. Click here to visit.

Flamingo Wall in Chicago
The famous Flamingo Wall in Chicago

Flamingo Wall

For a great photo opportunity, visit this fun Flamingo Mural! I spent some time researching this address, but here it is: 601 N Wells St. Chicago, IL 60654. Click here to view in Google Maps!

The Chicago Theater

Chicago Theatre

Built in 1921, The Chicago Theatre is always a fun night out in the city. Click here to view their schedule, and perhaps you'll catch a show when you're in town.

Where to Eat

3 Arts Club Cafe Chicago
Isn't this restaurant beautiful!

3Arts Club Cafe

This restaurant has a beautiful interior. Located in Restoration Hardware, I wouldn't expect anything less than perfection. An indoor fountain, olive trees, and chandeliers everywhere, it's a fantastic spot for lunch! I would suggest arriving before opening to stand in line, as there are no reservations. The food is a little on the pricey side here, but it is a beautiful cafe! We enjoyed a brunch complete with eggs on toast and a smashed avocado. All the food was delicious! Click here to find the location!

Hampton Social

This restaurant is famous for the Rosé all Day sign! It's such a fun restaurant. Of course, we had some Rose to go with our meal! There are a couple of locations in Chicago- we visited the River North restaurant. You can easily make reservations online. Click here to view their website.


This was our favorite brunch spot in Chicago! Every dish we ordered here was so tasty. You must try the ham and cheese crepes and the homemade donuts! We even noticed that Eden had their own garden for some fruits and vegetables. The best part was the frosé! So yummy! Click here to view their menu and book your table!

Let me know! Have you been to Chicago? What are your go to spots?

Like this post? Pin it for later!

Visit Chicago: What to see and where to eat!

Recent Posts

See All
bottom of page