The Ultimate Girls Weekend in Chicago

Breathtaking view of Chicago's skyline from the Willis Tower, showcasing the city's architectural beauty, a must-see on a girls weekend in Chicago.

You’ve rounded up the ladies for the ultimate girls weekend in Chicago!  Wooh!  Believe me, I KNOW all of the hard work that goes into finding a common weekend and a location that works for everyone, so brava to you.


Chicago is located in the Midwest United States.  Its beautiful views from epic skyscrapers surrounded by serene Lake Michigan paint postcard worthy views for an amazing weekend.  


I might be biased because I have explored the city dozens of times throughout my entire life.  But this means I’ll give you the local, inside scoop!  


Planning your girls weekend in Chicago can be easy. This guide covers the basics alongside comprehensive information so that you can make a girls weekend in Chicago all your own.  

Chicago Skyline views

This post contains collaboration partnerships.  All thoughts and opinions provided are my own.  

Chicago Planning Details

Taking a girls weekend trip to Chicago can be seamless with the basic planning details!  Be prepared for the weather any season and learn how to navigate the city like a pro.

Getting There

Chicago’s two international airports are O’Hare and Midway.  The city can be accessed via train, taxi, or ride share from both airports. 

Chicago Weather

Chicago weather varies greatly throughout the year due to its midwest location and proximity to the Great Lakes. Historically, weather changes drastically in Chicago across seasons so it’s important to check weather before your girls weekend trip. 


Summer is the most popular time to visit Chicago, and winter is the least popular.  Winter temperatures can be pretty extreme, but it’s also the least crowded time of year.  


Fall and spring are generally pleasant.  However, you will definitely need an umbrella and rain jacket in the spring.

Getting around Chicago

Chicago is a HUGE city, so how do you get from point A to point B? 

Public Transportation

Chicago has got some prime public transportation.  Purchase a Ventra card inside of the airport or at the train station.  You can find the local bus, subway, and train schedules posted inside of any of the bus or train stations.

Union Station and Ogilvie Transportation Center are Chicago’s two central train stations.  


Rideshare services like Lyft and Uber are HIGHLY available in Chicago.  Price surges are common during peak times in tourist parts of the city.  Peak times are usually on Friday and Saturday nights, or when there are big weekend events like a Chicago Cubs game.  


It’s difficult to find weekend street parking in Chicago.  I recommend the SpotHero app to book your parking space in advance.  

Alternatively, there are meters everywhere. You can pay for meter parking and refill your time using the Park Chicago App or simply returning to the meter.

Tip: You are most likely to find free street parking on Sundays.  However, this varies by each individual parking zone.  


Chicago is a very walkable city.  I recommend walking throughout safe neighborhoods during daylight hours.  I recommend taking public transportation or rideshare services in the evening.  

Rideshare safety tips:

  • Remove yourself from any situation you feel uncomfortable with.  Stop prioritizing being “polite” over your comfort and safety!
  • Virtually sharing your ride with someone you trust so they can follow the route, selecting a driver who has completed several rides and has high reviews. 
  •  Report safety problems directly through the rideshare app.  

Best Girls Weekend in Chicago Ideas

From taking a lovely Chicago photoshoot with your girlfriends to experiencing some of the best rooftop views, you can enjoy your girls weekend no matter what activities you choose!

Chicago Photoshoot Locations- free

There are SO many photo spots in Chicago for your girls weekend.  Like, I’m giddy thinking about it.   Consider checking out these top Chicago Instagram spots:

Chicago River

Chicago River

Consider a lovely riverwalk stroll with your friends, or walk above the river for aerial views.  Several bridges connect above the river for more unique inspiration to your Chicago photoshoot. 

Navy Pier

Explore Chicago’s famous ferris wheel along its boardwalk.  There are COUNTLESS photo locations on the Navy Pier.  Get lost exploring, and choose your favorites!

The Bean

The Bean at Millenium Park in Chicago

It’s called the “Cloud Gate” officially… but take a local tip, and just call it the Bean!  The Bean is located in Millenium Park, and is one of the most famously photographed locations in Chicago.  

Its shiny, mirrored surface is the ultimate spot for selfies.  

Millenium Park

Millenium Park Chicago

After snapping your photos at the Bean, continue strolling through Millenium Park for beautiful city views and architecture.  Its 24 acre park features numerous works of public art, green space for a picnic, and more.

Chicago Photoshoot Locations- Paid

Most indoor photo locations in Chicago are paid.  Take this into consideration if the following activities make sense for your budget.  Paid or unpaid, there are so many beautiful photography locations for your girls weekend.

Skydeck Chicago

Skydeck Chicago

Skydeck Chicago reveals some of the very best views in the city!  I LOVED my experience.  Timed entry tickets can be purchased through the Skydeck Website in advance.  I recommend this to skip the ticket line.  


Visitors are allotted 90 seconds to stand in the skybox.  You can rotate through the line as many times as you want for no additional cost.  Tickets cost $35 and you can purchase them here.  


Tip: It’s really crowded over the weekend, so plan at last 90 minutes for your visit.  

2D Restaurant

2D Restaurant in Lakeview, Chicago

Entering Chicago’s 2D Restaruant made me feel like I was stepping foot into a storybook.  Its Vietnamese and French cuisine create a sensational charm.  

Waiting in the lobby area for a table made me feel very dizzy, but I was totally fine once I sat down at a table!   

Color Factory

Color Factory Chicago

Color Factory is a fun, interactive way to spend a couple of hours with your girlfriends.  We 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

WNDR Museum Chicago

One of Chicago’s newest Instagram spots is its WNDR museum.  Uncover unique, interactive art while snapping photos with friends.  Exhibits are frequently updated with technology and theme changes.  Tickets cost $40 each and can be purchased here.  


I recommend the Color Factory and WNDR Museum for visitors looking to splash up their Instagram.  

Best Chicago Tours

There are so many tours to choose from whenever visiting a new city.  While taking a tour in Chicago certainly isn’t necessary, there are some HIGHLY rated options:


  • Chicago Architecture Tour
  •  Chicago Sunset Cruise
  •  Food and Walking Tour


I have not personally taken any of these tours, but look forward to adding the architecture tour to the top of my list.  

Chicago Shows

Chicago is HIGHLY known for its broadway shows and highly acclaimed performances.  I recommend checking out an evening show to experience Chicago nightlife, if you have the time and budget.  


Chicago Theater

Chicago’s Broadway is always featuring new shows throughout the year.  Hamilton is one of the city’s top shows in 2023.  


Fun fact- I have a hard time sitting still and haven’t been to a Broadway show in like 12 years!  But there is certainly something to be said about experiencing the arts in each person’s own way.  

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 schedule.  


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 purchase two drinks (can be non alcoholic).  Laugh Factory tickets can be purchased here.  

Candlelight Shows

Candlelight Concert in Chicago

One of my favorite parts of the new Candlelight series is the opportunity to experience local artists at local venues.  

I don’t know when I would have made it to the small Chopin Theatre in Chicago’s Wicker Park neighborhood before, but now I can’t wait to go back.  The quirky two floor venue with antique decor hosts small performances and has a first floor bar.  

If you are interested but can’t make it in Chicago, Fever’s Candlelight series are popping up in venues around the world.  Ticket prices range from $35-$70 and can be purchased on the Fever website.

Chicago Salons

If you’re looking to freshen up at a Chicago spa for a blowout, manicure, etc, there are some amazing options across the city:


  1. Blowout Junkie
  2. Good Beauty Hair Salon Chicago
  3. Sine Qua Non Salon


I have personally visited Blowout Junkie and they did an amazing job!

Best Chicago Hotels

Some of the most highly rated hotels in Chicago are The Drake, Godfrey Hotel, and Loews Hotel.  These hotels come with a price tag.   Budget options are more common outside of the city.  

Tip: You can also experience afternoon High Tea at the Drake Hotel Thursday – Sunday.  Make reservations in advance. 

Where to Eat in Chicago

Famous Chicago food is probably the BEST way to experience the city with the girls.  But what food IS Chicago known for?

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!


Ed Debevec’s

OK this is not famous Chicago food nor is it a Chicago Instagram spot but hear me out!  


I recommend Ed Debevec’s for the experience.  Debevec’s used to be a staple in major cities across the US but just this location in Chicago remains.  


Waiters are sassy and will tell you to “get out!!”.  It’s a theatrical experience- so if you’re like me and can’t always afford a Broadway ticket, consider a show at Ed’s!

Deep Dish

Last and certainly not least… you will be hard pressed to visit Chicago and NOT try its signature pizza.  Chicago has a long-standing rivalry of its best deep dish, so join the fun!  Top restaurants include: Peaquod’s, Lou Malnati’s, and Giordano’s.

Best Chicago Rooftops

  1. Cindy’s– Located inside of the Chicago Athletic Association building, Cindy’s is known as one of Chicago’s best rooftops for view over Millenium Park.
  2. Time Out Market– Some of Chicago’s best food is merged with rooftop delight at Time Out Market!  It is located in the West Loop neighborhood.
  3. LH Rooftop– This rooftop is expensive and reservations must be booked in advance.  It is known as one of the best rooftop views in the city.  
Color Factory Chicago

Chicago Girls Weekend Packing List

Here are a couple of can’t-miss items to toss in your suitcase for a girls weekend in Chicago:

Supportive Shoes– A lot of exploring means a lot of walking.  Comfort is key when exploring the windy city!  

Water bottle– I always recommend a water bottle for long days exploring.  Hydrate, hydrate, hydrate!

Packable backpack– if this is what you fancy!  Love it because it collapses/folds so easily into your travel suitcase or backpack.  It’s an ideal size for day exploring.  

For Winter weather…

Winter jacket– The freezing winter temperatures are no joke.  Pack the jacket!  This puffer jacket is collapsible and easily compresses into a backpack or suitcase. 

Boots– Bring a pair of comfortable walking boots so the snowy sidewalks do not limit your exploring!  I enjoy wearing waterproof hiking boots when exploring in snowy weather.  

In the spring…

Umbrella– Take a travel umbrella for sure!  Spring rain in Chicago is unpredictable.  

Rain Jacket– Keep a lightweight rain jacket handy because it the spring you just never know.  I wear the same rain jacket for city exploring that I use on my day hiking trips.  

Rain Boots– Or water resistant hiking boots (which I find so comfy!)


Sandals– Carry a pair of sandals or flip flops in your bag in case you decide to lounge at the beach in between exploring

Travel Towel– I recommend this too, for a random beach stop, if it fits in your bag!  It’s so light weight and easy to take on the plane.  


Fleece jacket– A warm fleece jacket is ideal this time of year.  

Layers– Layer up with some packable, light, long sleeve shirts in your bag.  

Winter jacket– Check the weather ahead of time.  There is an equally high probability you will need a winter jacket, and equally high that you will not.  

You can also use these ideas for a Chicago solo trip or Chicago family vacation.  Happy exploring, and enjoy your girls weekend in Chicago!

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As a full time employee who loves her job, learn how I honor my wanderlust while working a 9:00-5:00 (because I want to!) This blog welcomes all, and specifically provides resources for those seeking travel intertwined into a busy schedule (3 days to 5 weeks).