Plan a Memorable Girls Weekend in Chicago
What do you get when you combine the best of Chicago with a group of amazing women? A girls weekend in Chicago that’s just as much fun as it is relaxing. I’ve visited Chicago three different times with my sisters, and each time is equally amazing.
Chicago is the perfect city for a girls’ getaway. It offers the best of everything, from rooftop bars, shopping, and great food to seeing a game at Wrigley Field.
You wouldn’t know it’s the largest city in the Midwestern United States since Chicago is extremely walkable and exciting to explore.
These travel tips will help you plan the perfect Chicago girls weekend in one of my favorite cities in North America to visit. I can’t wait to share all the fun things to do on your girls getaway to Chicago.
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Where to Stay for Your Girls Weekend in Chicago
Chicago is a fantastic city, and it’s especially fun when you’re there with your friends. Luckily, planning a girls’ trip to Chicago is a cinch since there are some great places to stay.
These are all hotels that I personally recommend for your Chicago girls weekend or getaway.
DoubleTree by Hilton Hotel Chicago – Magnificent Mile
DoubleTree is within walking distance to the Magnificent Mile, Chicago’s premier shopping district, Navy Pier, and other famous Chicago attractions. It’s a comfortable hotel in a perfect location to see the best of Chicago.
Swissotel Chicago
For a hotel with all the bells and whistles, consider the Swissotel Chicago.
This luxurious all-glass hotel located directly opposite the Chicago River overlooks Lake Michigan. The large rooms are well-appointed, with fantastic views of the Chicago skyline. The hotel has a penthouse fitness center with unbelievable panoramic views from the 42nd floor.
Royal Sonesta Chicago
The Royal Sonesta Chicago River North is a chic oasis in the heart of the Windy City, making it an impeccable choice for a Chicago girls weekend.
This hotel boasts an unbeatable location in River North within walking distance to iconic attractions like the Magnificent Mile, Navy Pier, and the Chicago Riverwalk.
Its spacious rooms offer a luxurious retreat with expansive city views, allowing ample space for you and your friends to unwind.
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The Palmer House
For something with a little bit more character, check out The Palmer House. It is the nation’s longest continually operating hotel. When the Great Chicago Fire burned down the building after only being in operation for thirteen days, it was rebuilt in 1873. Even though The Palmer House has a rich history, its rooms are large and modern.
Book a room with two queen beds, a large living area, and two bathrooms, perfect for everyone getting dressed in the morning.
Fun Fact About The Palmer House
The Palmer House is known as the place where the brownie originated. How could you not want to stay here?
You will love the location of The Palmer House. It is close to Lake Michigan, Buckingham Park, and Millennium Park.
Trip Tip: You can buy The Palmer House brownie cutely packaged for $5. It makes a great souvenir treat for someone back home.
Use Vrbo to rent a cute apartment
Chicago is big enough to feel like a real adventure but small enough that you’re never too far from a place to hang out with friends. And while there are plenty of hotels in the city, I love the idea of renting an apartment. It’s more laid-back, less formal, and lets you make yourself home in the city.
There are many great options if you plan to stay in downtown Chicago. Use the search bar to find your perfect rental.
How to Get Around Chicago
You do not need a car in Chicago. Plus, parking is expensive. Use rideshare from the airport, and then walk or use public transportation throughout your stay.
Where to Eat in Chicago
Chicago is a foodie experience waiting to happen!
Picture this: you start your day with a scrumptious brunch in Lincoln Park, chatting away with your besties over mimosas and delectable dishes. Then, after a day of shopping, you load up on Chicago’s classic deep-dish pizza. Finally, you end the day at one of the many restaurants in the trendy vibes of West Loop.
Your possibilities are endless. Here are some of my favorite Chicago spots you must check out.
For one of the best brunch spots in Chicago, head to Egg Harbor Cafe. The views are amazing, and the food is scrumptious.
The first stop on your itinerary should be Lou Malnati’s Pizza. This is the place to go in Chicago if you’re craving deep-dish pizza. They offer all different types of pizzas—you can choose from their classic favorites or try something new.
For one of the best Italian beef sandwiches you will ever eat, visit Portillo’s Italian at one of their several locations in Chicago, including a stop right off the Hop-On, Hop-Off bus.
Italian Village: Chicago’s Oldest Italian Restaurant is Chicago’s oldest Italian restaurant, and it is delicious. The pistachio chocolate cannoli is fabulous.
If you go for dinner, ask about the pre-fixe menu, especially if you have a big group.
If you haven’t had your fill of classic deep-dish pizza, look no further than Giordano’s. Be prepared to wait for an order. These deep-dish pizzas take some time to cook.
The Signature Room is located on the 95th floor of the John Hancock building. The food is good, but the view is fantastic.
I love to try donut shops whenever I am on vacation. If you do too, then stop at Stan’s Donuts & Coffee. There are several locations, including one by Millennium Park and one on the Magnificent Mile. My favorite flavor is the Buttercream Bismark.
The food at The Capital Grille is fantastic. Try the parmesan truffle fries.
Finally, make sure to visit Goddess and the Baker. The sandwiches are fresh and delicious.
Rooftop Bars
Chicago has so much to offer in terms of art and culture, but it also has some of the best rooftop bars around. That’s right, I said ROOFTOP BARS.
And they’re not just any rooftops either. They’re bars with some of the most stunning views in the entire city.
The rooftop bars are an amazing way to wind down from the day and see the sunset in the spring and summer.
These also make great places to start the evening if you are in Chicago for a bachelorette party.
These are some of my favorite rooftop bars in Chicago.
Cindy’s
Cindy’s is located in the Chicago Athletic Association Hotel and has fantastic views of Millennium Park, The Bean, and Lake Michigan. Plus, the drinks are extraordinary.
Z Bar at The Peninsula Hotel
Chicago’s Z Bar at The Peninsula combines chic and chill in one rooftop bar.
It is located on Michigan Avenue and offers views of the city and delicious cocktails.
Its unique atmosphere makes for a perfect place to hang out!
LH Rooftop
This LH Rooftop bar is located on the 21st floor of the London House Chicago.
I love this bar because of the fantastic Chicago River and Michigan Avenue views.
The drinks here are expensive, so don’t expect to stay too long unless you want a huge tab. Check out the bathrooms here. They are pretty cool.
What to Do for a Girls’ Weekend in Chicago
You’re going to love your weekend in Chicago.
Chicago is a city of endless possibilities, and there’s no better way to experience it than with your besties.
With so many fun things to do in Chicago, you can’t go wrong. Whether you’re looking for a quiet day of museums or a raucous night out on the town, you’ll find whatever suits your mood at one of the city’s many attractions.
It’s impossible to do everything in Chicago in one day, so hopefully, you can spend a few days here.
Millennium Park
Millenium Park is home to Cloud Gate, also known as The Bean.
The Bean is a giant outdoor stainless steel art sculpture created by Anish Kapoor that reflects the city skyline around it. It’s just one of the many Chicago Instagram spots and makes for some amazing photos.
Millennium Park is also home to Lurie Gardens, a not so “secret garden” in the middle of the city.
Lurie Gardens is full of lush plant life and beautiful architecture.
If you visit in the spring or summer, there are even more reasons to visit, as you’ll be able to see their butterfly house and floral displays.
We happened upon the gardens by chance after exploring the park. This was an awesome find for someone who loves to garden like me.
Another unique art installation found in Millennium Park is the Crown Fountain.
The Crown Fountain is a 50-foot glass structure with images projected onto LED screens. The interactive water feature sits above reflecting pools of water.
The LED screens show the faces of native Chicagoans with a fountain of water appearing to spit out of their mouths into the collections below. It is pretty impressive to see in person.
It’s a great place to take pictures or relax by the fountain after exploring downtown Chicago all day.
Trip Tip: For a guided art tour through the park, you can arrange for a free walking tour with chicagogreeter.com. You need to make arrangements at least ten days in advance.
Navy Pier Activities
Navy Pier is located on Lake Michigan, one of the city’s most popular tourist attractions.
It has restaurants, shops, and other fun activities like the iconic Navy Pier Centennial Wheel, an enclosed gondola-like Ferris wheel with magnificent city views.
There is a hub of activity in and around Navy Pier, especially in the spring and summer.
Here, you can jump on a City Sightseeing Hop-On, Hop-Off bus tour of the city. These tours are delightful in the Chicago summer weather.
Navy Pier is also where you can board a boat to cruise Lake Michigan. If you have time, book this cruise that includes fireworks at the end of the night. It’s an experience you’ll never forget.
Seeing the fireworks from the water with the city skyscrapers in the background is amazing. It is cool on the water in the summer, so bring a sweater or jacket.
Navy Pier Places to Eat
There are many places to eat at Navy Pier.
You can pick up a quick bite to eat or a light snack, or if you want a taste of deep-dish pizza, you can have your first experience here at Giordano’s.
Make sure to give yourself enough time. The pizza can take up to an hour to prepare.
For the sweet tooth in your group, head over to It’sSugar. It is the largest candy retailer in the world. Browse their extensive selection, and get a picture for your Instagram here.
While you’re there, don’t miss out on the best of Chicago. Stop at Garrett’s Popcorn. The smell of the popcorn will entice you to find its location in Navy Pier. As we’ve visited, there’s always been a line, but it moves quickly.
The Chicago blend is one you want to taste. It is a mix of cheese and caramel, and it is delicious. Take a bag for your day on the Hop-On, Hop-Off bus tour or a boat trip on Lake Michigan.
Chicago River Architecture Boat Tour
Whether you’re looking for a fun adventure or want to see the city from a different angle, check out the Chicago River Boat Architecture tour.
The 90-minute tour along the Chicago River is narrated by an architect or an architect student.
Their expertise about the buildings along the river provides a unique perspective. It is a fascinating trip that takes you on a scenic journey along the Chicago River, while learning about one of the most iconic cities in America.
City-Sightseeing Hop-On, Hop-Off bus tour
Use the City-Sightseeing hop-on, hop-off bus tour on the first day of your trip. You get an idea of where things are in the city and which places you may want to visit on the following days.
If you are with a group for your girls’ weekend in Chicago, the hop-on, hop-off bus allows you all to get around the city without relying on public transportation or ride-shares.
The City-Sightseeing tour also offers a night tour. You can’t hop off on the night tour, but it is an excellent way to see the city in a new way.
Take Advantage of The Chicago CityPASS
There are so many things to see in Chicago, and with the Chicago CityPASS, you can save a ton of money while seeing them all!
The CityPASS lets you skip the ticket lines at some of Chicago’s most popular attractions, including the Field Museum, Shedd Aquarium, Adler Planetarium, Skydeck Chicago, and more. You can explore everything from the natural world to outer space without waiting in line.
The Chicago CityPASS is an excellent option if your group wants to see all the major sights in Chicago. It’s a fun way to get a taste of what this city offers and saves you money.
Plus, there are many great restaurants, bars, and shops near each attraction, so you can stop for lunch or browse around before returning.
See a Cubs Game
If you’re looking for a fun girls weekend in Chicago, there’s no shortage of things to do.
From shopping on Michigan Avenue to exploring the city’s museums, plenty of options won’t break the bank. But if you’d like to take it up a notch, I’ve got one suggestion: go see a Cubs game!
After all, what better way to celebrate being in Chicago than seeing a baseball game in one of America’s most historic ballparks?
There are several ways to get from your hotel to Wrigley Field. The best option is public transportation.
Chicago’s trains to the game are easy to navigate to Wrigley Field. A direct train runs from downtown to the field on game days. Your hotel can tell you which one to get on.
For the foodie in your group, the food at Wrigley Field is amazing. The Cubs partner with local chefs to offer specially curated game menus. It is a fabulous way to spend the afternoon.
Thankfully, the Cubs won when we went. I promise you will sing the Go Cubs Go song long after leaving. It is one of the most infectiously catchy songs you’ll hear all year.
Chicago at Night
Experience the pulse of Chicago at night as the city truly comes alive with endless possibilities.
From the glittering skyline views atop rooftop bars to the sultry beats of jazz clubs in historic neighborhoods like Wicker Park, each corner of the city offers a unique nocturnal adventure.
Stroll along the illuminated Riverwalk, indulge in a spa experience overlooking the city or snack on gourmet delights at late-night eateries. These are my favorite ways to create memories that sparkle against the backdrop of Chicago’s charm.
See Chicago from The John Hancock Building
One of the best ways to see Chicago is from the sky during a visit to 360 Chicago.
This rotating observation deck offers views of the city that are just as stunning as the skyline.
Another fun activity is spending an evening at the Signature Room at the John Hancock Center.
This restaurant and bar sits atop Chicago’s tallest skyscraper and provides stunning views of Lake Michigan. You’ll feel like floating on air while looking out over the city lights below.
If you want a seat by the window, go at off times, a.k.a not happy hour, and tip your hostess.
Trip Tip: Sorry, guys, but the ladies’ restroom view is even more impressive. Take all the silly pictures you want in front of the floor-to-ceiling windows without an audience.
Chicago Gangster and Ghost Tour
If you’re looking for a fun way to see the sights in Chicago at night, look no further than the Chicago Gangster and Ghost Tour!
This tour takes through the best parts of the Windy City, including some stops at some of the most famous gangster hangouts.
You’ll hear stories about Al Capone and other notorious criminals who used to run the city’s underworld and stories about ghosts still haunting their old haunts.
The Chicago Gangster and Ghost Tour‘s guide tells real-life stories of Chicago’s events from the past.
This night tour is not as spooky as a New Orlean’s ghost tour, but it is pretty spooky.
Indulge in a Spa Experience
Enhance your girls weekend in Chicago with ultimate relaxation at one of the city’s top spa retreats.
Discover serenity at the Aire Ancient Baths Chicago, where ancient bathing traditions meet modern luxury, providing a tranquil escape for you and your girlfriends to unwind together.
Elevate your spa experience to new heights at The Peninsula 20th Floor Spa, boasting breathtaking skyline views and a range of rejuvenating treatments designed to pamper every inch of your body.
For a chic and intimate retreat, immerse yourself in the cozy ambiance of Cowshed Spa at SoHo House, where you can enjoy treatments tailored to your individual needs while savoring quality time with your closest friends.
With these exceptional spa options, your girls weekend in Chicago is sure to be filled with relaxation, rejuvenation, and unforgettable memories.
What’s a Chicago Girls Trip without Shopping?
If you’re taking a Chicago girls’ getaway, you must stroll down Michigan Avenue and shop at the city’s most famous shopping district: The Magnificent Mile.
The Magnificent Mile is a 13-block stretch of downtown Chicago stores, restaurants, and attractions along North Michigan Avenue.
There are many great stores to check out, including Saks Fifth Avenue and Nordstrom. You can also stop by the Apple Store or one of several other shops along the way if you’re looking for something specific.
There is sure to be a stop for everyone in your group.
You can pick up a few special items to remember your Chicago girls weekend or buy anything you might have forgotten to pack.
Or, use this women’s packing list to ensure you have everything you need for your trip to Chicago.
When is the best time to visit Chicago?
For the best experience, travel to Chicago in spring or summer. The weather is beautiful, the attractions are active, and the city is alive.
No matter when you go, you will have a fantastic time in this beautiful city on your Chicago girls’ getaway.
Plan Your Chicago Getaway Today
Chicago is truly a gem for a fabulous girls weekend!
Whether you’re exploring iconic attractions like Millennium Park and Navy Pier on a mother daughter weekend, or indulging in retail therapy with friends along the Magnificent Mile, Chicago never disappoints.
The memories made here, strolling along the lakeshore or enjoying drinks at one of its lively rooftop bars, are simply unforgettable.
Don’t wait any longer. Book your tickets, plan your itinerary, and let Chicago be the backdrop to your next amazing girls’ trip.
Trust me, the experiences awaiting you in this dynamic city will create bonds and stories that will last a lifetime. Start planning now using this travel guide and get ready to make memories that will have you smiling for years to come!
