How to Spend a Girls Weekend in Chicago

With its amazing architecture, good food and wonderful people, a girls weekend in Chicago is the perfect way to spend three days, especially during the summer. I was looking back through previous blog posts recently and I realized that I don’t blog about my favorite city often. I suppose since I live here, I get caught up in the day to day grind and forget how much fun it can be.

So I made a decision – from here forward, I am going to make a conscious effort to post about all of the great things there are to see, do and eat in Chicago. I hope it inspires you to visit and that once you’re here, you will love it as much as I do!

I recently had an opportunity to be a tourist in my own city when my cousin Brittany came to visit. Brittany had been to Chicago before but only briefly so I figured this would be a great chance for me to put my plan into action.



How to Spend a Girls Weekend in Chicago

Friday evening

No girls weekend in Chicago can be complete without checking out some of its amazing restaurants.

On Friday night, we headed to a restaurant I hadn’t been to in a long but really like. We went to Mia Francesca’s, a small Italian restaurant on the north side of the city. The restaurant is usually packed so I recommend getting a reservation if you don’t like long waits. We were able to get right in with our reservation and really enjoyed our meal. One of my favorite parts about Mia Francesca’s is that they don’t rush their diners. We were allowed to relax and catch up while finish our wine over dinner.

Saturday morning

On Saturday morning, we boarded the Red line (the Chicago transit system is known as the CTA and the trains are referred to as the “El”) and headed downtown to the River North neighborhood. I highly recommend taking public transportation when visiting Chicago. Traffic is bad and parking is expensive. The easiest and more economical way to get around town is by taking the train or a bus. The regular fare for the train is $2.50 while the fare for a bus ride is $2.25. They also have bulk passes that you can buy as well. You can find out more here.


Our first stop was to find some food. We chose to have brunch at Beatrix. I had been wanting to Beatrix for a while because I had heard lots of good things. I had the steak and eggs with chimichurri sauce…yum!

Architectural Boat Tour

After filling our bellies, we set out for one of my favorite “touristy” things to do in Chicago – an Architectural Boat Tour. This is a great activity for a girls’ weekend in Chicago as well as for a family weekend or a solo trip.

The architecture in Chicago is world class and there is no better way to see it and learn about it than aboard a boat. There are several companies that do these tours. I recommend going with the Chicago Architecture Foundation or Wendella. Go on a tour that goes up and down the river as well as out onto the lake. It takes a bit of time to get through the locks between the river and lake but on the lake is where you will get great skyline views of the city.

Girls Weekend in Chicago
The beautiful Chicago skyline.
Girls Weekend in Chicago
Brittany, me and the Chicago skyline

Admire the Amazing Views

After the architectural boat tour, we stopped by Cindy’s Rooftop to admire the views of Michigan Avenue and Millennium Park….and maybe to get a drink and bathroom break too!

Cindy’s is located on Michigan Avenue across from Millennium Park. The bar is on the 13th floor and has an outdoor patio with amazing views of the park and Lake Michigan. I have been to Cindy’s several times and can attest that the views are spectacular in both the daytime and at night.

There tends to be a line so if you can plan ahead and snag a reservation, I highly recommend it. There was a line when we arrived without a reservation but it went pretty quickly.  The good thing about the line and the crowd control was that the restaurant and patio were not overly crowded. We could stand along the patio railing and admire the views without be shoved or feeling pressured to move on so someone else could take our place.

A view of Millennium Park and "the Bean" from Cindy's Rooftop in downtown Chicago.
A view of Millennium Park and “the Bean” from Cindy’s Rooftop in downtown Chicago.

A Walk in the Park

A quick stop in Millennium Park was next on our agenda. Millennium Park is located along Michigan Avenue on the east side of the loop downtown. It opened in 2004 and covers 24.5 acres. It is the most popular tourist destination in the Midwest USA!

Millennium Park is home to the famous Cloud Gate sculpture (also known as “The Bean”) and the fountains with the faces on it. It also features the Pritzker Pavilion, which hosts free concerts and events throughout the summer (I highly recommend!).

In the winter, the park is home to a couple of ice skating rinks so you can skate while admiring the beautiful city views.

As I expected, the park was VERY crowded but we were able to weave our way through the crowds, see what we wanted to see and snap some photos.

Visit a Museum

To escape the heat and the crowds, we decided to finish our time downtown by exploring the Art Institute of Chicago. The Art Institute of Chicago located just south of Millennium park. It was founded in 1879 and is one of the oldest and largest art museums in the United States. The museum hosts approximately 1.5 million people annually. Its permanent collection has nearly 300,000 works of art and is augmented by more than 30 special exhibitions yearly. In layman terms, it is huge!

We only had an hour and a half or so to explore it before it closed so we only saw a few wings of the museum. We saw lots of interesting and famous art while concurrently enjoying the air conditioning and benches that allowed us to rest our feet when needed (my feet were barking pretty loud by this point in the day!).

Girls Weekend in Chicago
Seen at the Art Institute – Yellow Hickory Leaves with Daisy by Georgia O’Keeffe. This is one of my favorite paintings of the ones we saw. It is so bright and colorful.


After dinner on Saturday evening, we went to one of my favorite ice cream parlors in Chicago, Lickity Split. There are two locations – one of the far north side of the city and one on the northwest side of the city. They have great ice cream and lots of candy and sweet treats to choose from. The Tasty Turtle sundae is my favorite thing on their menu.


On Sunday, we grabbed a quick breakfast at home and then decided to give our feet a break and spend the day hanging out by Lake Michigan. We walked to one of the beaches on the north side, set up some chairs and spend the rest of the morning and early afternoon enjoying the company, breeze and people watching.

There are beaches all along the lake in Chicago. You can check out the list of them here. The ones closest to downtown, particularly Oak Street Beach and North Avenue Beach, tend to be really crowded, particularly on the weekends. If you are looking for the “scene”, this is where you should go. If you want something quieter, head further north or south from downtown.

And with that, our girls weekend in Chicago came to an end

After spending a few hours at the lake and dipping our toes into the water, our girls weekend in Chicago was over. I had so much fun and was sad to see Brittany go. I hope she had fun too and that she comes back to visit us soon!

You can check out more of my Chicago adventures here.