Looking for the best girls’ weekend in Chicago? This is the planning guide for you!
Chicago has so many amazing activities that you can enjoy for a girls’ weekend.
The giant, metropolitan city has something for everyone. I go to Chicago all the time and love the laidback neighborhoods, sweeping skylines, and outdoor things to do.
This detailed itinerary plans all of the best things to do on your girls weekend in Chicago.
These activities include famous activities like the Chicago Architecture Cruise and Millennium Park, as well as less common things to do like the 2D Cafe.
I collaborated with Color Factor, WNDR Museum, and Laugh Factory for this post. All thoughts and opinions provided are my own.
Day 1:
Chicago Architecture Cruise
Begin your girls’ weekend on a cruise!
The Chicago architecture cruise is one of the most popular tours in Chicago. Locals and tourists recommend it.
While you cruise the Chicago River, you will see iconic buildings like the Willis Tower, the Wrigley Building, and historic bridges while learning about their design and significance.
It’s both a relaxing and exciting way to start your girls’ weekend!
Popular Chicago Tours:
Chicago Riverwalk
After your cruise, walk the Chicago Riverwalk. This approximately 1 mile path is located along the Chicago River. It is absolutely beautiful.
There are many cafes to grab a snack while walking.
Tip: There are seasonal photo spots along the walk. In October in Chicago, there are pumpkins and hay barrels, along with fall fest events!
2D Cafe
2D Cafe is one of the best Instagram spots in Chicago. Located in the Lakeview Neighborhood, the cafe makes you feel like you just stepped into a comic book about Paris.
Floor-to-ceiling is an incredible comic book painting.
My favorite part is the Mochi Donuts and Crembrule coffee!
Deep Dish Pizza Dinner
No trip to Chicago is complete without deep dish pizza.
Deep dish pizza is a Chicago staple known for its fillings of layered of cheese, thick tomato sauce, and various toppings.
It’s famous for its rich flavors and satisfying texture. Head to renowned pizzerias like Lou Malnati’s or Giordano’s to experience this culinary delight.
Laugh Factory
One of Chicago’s most highly acclaimed standup comedy venues has nightly weekend shows at 7:00pm, 9:00pm, and 11:00pm making it easy to fit into your girls weekend.
I LITERALLY laughed out loud during almost EVERY performance of the night.
Tickets cost approximately $35 per show and the venue requires every ticket holder to purchase two drinks (can be non-alcoholic). Laugh Factory tickets can be purchased here.
Rooftop
Top off your evening at a rooftop. Rooftop bars and lounges in Chicago are popular for their stunning skyline views and vibrant atmosphere.
Some popular rooftops in Chicago are:
- Cyndy’s
- Godfrey
- LH Rooftop
My friends and I enjoyed the Geodfrey Rooftop when we spent a night staying at the Godfrey Hotel.
Day 2:
Brunch
Begin your day with brunch in the heart of Downtown Chicago.
Popular Brunch spots include:
- Wildberry Cafe
- Nutella Cafe
- Hampton Social
Nutella Cafe is known to be touristy but people love it. There are long lines on the weekend so I recommend making a reservation. Wildberry is pricey but classic, good brunch.
Millennium Park
Millennium Park is one of the most famous urban parks in the heart of downtown Chicago.
It’s a hub of art, music, architecture, and vibrant events, attracting locals and tourists alike.
People enjoy visiting for its impressive installations, such as the iconic Cloud Gate sculpture, affectionately known as “The Bean.”
Visitors can explore the lush Lurie Garden, enjoy concerts at the Jay Pritzker Pavilion, or simply relax in serene surroundings.
Entrance is free.
Tip: If you go in the winter, I recommend following a Chicago Packing List to bundle up in the cold weather!
Interactive Museum
Consider checking out an interactive museum like Color Factory or Wonder Museum.
At Color Factory, visitors can explore themed rooms filled with color-based art and interactive elements like ball pits and color palettes.
My friends and I loved the various surprises in each room of the museum like colorful macaroons, jelly beans, and a mini ice cream cone!
Tickets cost $40 per person and can be purchased here.
WNDR Museum offers dynamic exhibits that highlight creativity and imagination, inviting visitors to participate in art installations, optical illusions, and other interactive displays.
Both museums are pretty expensive but provide an opportunity to splash up your Instagram and take tons of photos.
Spa
Top off your girls’ weekend in Chicago with a relaxing spa visit.
AIRE Ancient Baths in West Loop are known for a unique experience
The LH Rooftop is a luxury spa with skyline views. This comes with a huge price tag. I haven’t tried either spa yet, but AIRE is on my list!
Dinner at Time Out Market
I LOVE visiting Time Out Markets in each city I visit.
Think of it as a one-stop hub to get a taste of the city’s best restaurants. Chicago’s Time Out is located in Fulton Market and features Chicago staples like Jojo’s Shake Bar and more.
I recommend spending a few hours in Fulton Market to explore Chicago’s West Loop! It is considered one of the best neighborhoods in the city.
Tip: Chicago’s Time Out Market can double as your rooftop outing!
⭐Alternate Girls Weekend Activities:
Conclusion
To wrap up your unforgettable girls’ weekend in Chicago, explore the vibrant culture and diverse experiences this city offers.
From the artistic atmosphere of Millennium Park and interactive museums to a relaxing spa, there is something for everyone.
Top it off with an eclectic dining experience at the Time Out Market. Chicago caters to every taste and interest, ensuring memorable adventures all around.
Gather your girls, plan your itinerary, and set off on a delightful weekend getaway in the Windy City!
