How to Plan the Perfect Trip to Chicago in 2025

Looking for the greatest Girls' Weekend in Chicago? This is the planning guide for you!

Chicago offers a plethora of exciting activities for a girls' weekend.

The massive, urban city offers something for everyone. I visit Chicago and enjoy its laid-back neighborhoods, panoramic skylines, and outdoor attractions.

This detailed itinerary outlines all of the greatest things to do during your weekend in Chicago.

These activities include well-known attractions. Such as the Chicago Architecture Cruise and Millennium Park. As well as unique experiences such as the 2D Cafe.

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Chicago Architecture Cruise

Begin your weekend with a cruise!

The Chicago Architecture Cruise is one of Chicago's most popular tours. Both residents as well as visitors appreciate it.

While cruising the Chicago River, you will witness prominent landmarks. Such as the Willis Tower, the Wrigley Building, and historic bridges. Wwhile hearing about their history and design.

It's a pleasant and entertaining way to kick off your girls' weekend!

Chicago Riverwalk

After your cruise, go around the Chicago Riverwalk. This approximately one-mile route runs along the Chicago River. It is stunning.

There are many eateries to grab a bite while wandering.

Tip: There are seasonal photo opportunities along the path. In October, Chicago has pumpkins and hay barrels, as well as fall festival events!

2D Cafe is a top Instagram destination in Chicago. The Lakeview Neighborhood is where the cafe is situated.

. Makes you feel like you've stepped into a Paris-themed comic book

A magnificent comic book painting spans from floor to ceiling.

The Crembrule Coffee and Mochi Donuts are my favorites.

Deep Dish Pizza Dinner 

Deep-dish pizza is a must-have on every vacation to Chicago.

A Chicago mainstay, deep dish pizza is renowned for its numerous toppings, thick tomato sauce, and layers of cheese.

It's known for its rich flavors and pleasing texture. To savor this culinary delicacy. Visit renowned pizzerias such as Lou Malnati's or Giordano's.

Laugh Factory

One of Chicago's most recognized standup comedy venues offers nightly weekend shows at 7:00 pm, 9:00 pm, and 11:00 pm. Making it easy to fit into your ladies' weekend.

I laughed out loud throughout every performance that night.

Tickets are roughly $35 per concert. And the venue asks each ticket holder to pay for two beverages (which can be non-alcoholic). You may buy Laugh Factory tickets here.

Millennium Park 

Millennium Park is a well-known urban park located in downtown Chicago.

It's a hotspot of art, music, architecture, and lively events that attract both locals and tourists.

People appreciate visiting because of its stunning installations. Including the famed Cloud Gate sculpture, fondly known as "The Bean."

Visitors can explore the verdant Lurie Garden, and attend concerts in the Jay Pritzker Pavilion. Or relax in the peaceful surroundings.

Entrance is free.

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Interactive Museum

Consider visiting an interactive museum, such as the Color Factory or Wonder Museum.

Visitors at Color Factory can explore themed rooms with color-based art. And interactive elements such as ball pits and color palettes.

My friends and I enjoyed the many surprises on each floor of the museum. These included multicolored macaroons, jelly beans, and a little ice cream cone!

The WNDR Museum features dynamic exhibitions that highlight creativity and imagination. Encouraging visitors to take part in art installations, optical illusions, and other interactive displays.

Both museums are very expensive. But they provide an opportunity to spruce up your Instagram and shoot hundreds of images.