Girls Weekend in Chicago: The Ultimate Getaway for Fun and Relaxation
What do you get when you combine the best of Chicago with a group of fabulous women? A girl’s weekend in Chicago that is just as much fun as it is relaxing.
I’ve visited Chicago three different times with my sisters and friends, and let me tell you—it’s the ultimate destination for a girls’ trip.
Chicago 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 highly walkable and easy 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.
He Works So I Travel content may contain affiliate links for products I use and love. If you make a purchase after clicking one of these links, I’ll earn a small commission at no additional cost to you. For full details, please read my full affiliate disclosure here.
Getting To Chicago
How to Get to Chicago – Flying into Chicago is a breeze. The city has two major airports: O’Hare International (ORD) and Midway (MDW).
Both airports offer plenty of direct flights. Depending on where you’re flying from, you can often find reasonable fares.
I usually fly into Midway for my trips because Southwest Airlines flies directly from my home airport.
Getting Around – Once you’re there, Chicago’s public transit makes getting around so easy.
Grab a Ventra card to hop on the “L” (Chicago’s subway system), buses, or even trains to the suburbs.
Ride-share services like Uber and Lyft are excellent for a more laid-back vibe, especially if you’re heading out at night or unfamiliar with public transportation.
Pro tip: If you’re staying downtown, you’ll rarely need a car. Everything’s walkable, and the sidewalks are so scenic you’ll want to take your time soaking in the sights.
Where to Stay for Your Girls’ Weekend in Chicago
Chicago knows how to do hotels, and I’ve stayed at some incredible spots. I personally recommend these hotels for your Chicago girls’ weekend.
DoubleTree by Hilton Magnificent Mile – A more budget-friendly option that doesn’t skimp on comfort or location. Plus, you get warm cookies at check-in. Win-win.
The Palmer House Hilton – Talk about history and glamour. This iconic hotel has a stunning lobby (get your Instagram ready!) and is steps away from Millennium Park. The Palmer House is known as the place where the brownie originated. How could you not want to stay here?
The Royal Sonesta Chicago River North – This is my pick for river views. Waking up to the Chicago River from your hotel room window? Chef’s kiss.
Swissôtel Chicago – The all-glass triangular design means floor-to-ceiling views of Lake Michigan and the river. It’s perfect if you’re all about the aesthetics.
Where to Eat in Chicago
You can’t talk about Chicago without talking about the food. Chicago is a foodie experience waiting to happen!
You can start your day with a scrumptious brunch in Lincoln Park, chatting 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.
- Egg Harbor Cafe – One of the best brunch spots with lovely views
- Stan’s Donuts & Coffee – One of the BEST donut shops with several locations, including one by Millennium Park and one on the Magnificent Mile.
- Lou Malnati’s or Giordano’s for deep-dish pizza. Yes, it’s touristy, but it’s a must. It’s like a pizza and pie had a baby—in the best way.
- Portillo’s Italian Beef – Grab an Italian beef sandwich and get it dipped. Messy? Yes. Worth it? 100%.
- Goddess and the Baker – Fabulous lunch spot with fresh and delicious sandwiches
- The Capital Grille – For a nice night out – So good – try the Parmesan truffle fries
- Italian Village – Chicago’s oldest Italian restaurant, and it is delicious. The pistachio chocolate cannoli is fabulous.
- It’sSugar – Visit the largest candy retailer in the world at Navy Pier.
- Garrett’s Popcorn—Taste Chicago’s best popcorn. The Chicago blend is a cheese and caramel mix, and it is delicious.
Things to Do on a Girls’ Weekend in Chicago
You’re going to love your weekend in Chicago.
Chicago has so much to offer, and I’ve tried it all. Here’s a breakdown of my must-dos:
#1. Explore Millennium Park
Millenium Park is home to Cloud Gate, also known as The Bean, a giant outdoor stainless steel art sculpture.
Snap a selfie with the reflection of the city skyline in your background. 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.
Another unique art installation found in Millennium Park is the Crown Fountain.
The Crown Fountain is a 50-foot interactive piece of art with towering glass structures that project digital images of Chicagoans onto LED screens.
On a warm day, you can cool off in the shallow reflecting pool.
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.
#2. Visit Navy Pier
Navy Pier is one of the city’s most popular tourist attractions on Lake Michigan.
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 hop on a City Sightseeing Hop-On, Hop-Off bus tour of the city, which is delightful in the Chicago summer weather.
Navy Pier is also where you can board a boat to cruise Lake Michigan. During the summer, you can book a cruise that includes fireworks at the end of the night. It’s an experience you’ll never forget.
#3. Take an Architecture River Tour
I didn’t expect to be blown away by an architecture tour, but it was fascinating.
You’ll glide down the Chicago River while learning about the city’s history and iconic buildings. Book one in the spring or summer for the best experience.
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.
#4. Go Sightseeing
Use the City-Sightseeing hop-on, hop-off bus tour to get an overview of Chicago.
You can hop off at attractions like the Field Museum, Shedd Aquarium, or Adler Planetarium. The City-Sightseeing tour even offers a night tour.
Combine this tour with the Chicago CityPASS, and you can save a ton of money while seeing them all!
#5. Catch a Cubs Game at Wrigley Field
Even if you’re not a huge baseball fan, go see a Cubs game! The vibe at Wrigley Field is electric for a fun girl’s weekend in Chicago.
After all, what better way to celebrate being in Chicago than seeing a baseball game in one of America’s most historic ballparks?
Take the “L” to Wrigley Field, grab a hot dog, and soak in the iconic atmosphere.
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 impressive.
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 you leave. It is one of the most infectiously catchy songs you’ll hear all year.
#6. Indulge in a Spa Day
After all the walking you will do, you deserve some pampering.
Many hotels, including the Swissôtel, have incredible spa services. Schedule a massage or facial, and thank me later.
Here are some of the city’s top spa retreats to enhance your girls’ weekend in Chicago with ultimate relaxation.
- Aire Ancient Baths Chicago – where ancient bathing traditions meet modern luxury
- The Peninsula 20th Floor Spa – breathtaking skyline views and a range of rejuvenating treatments
- Cowshed Spa at SoHo House – a chic and intimate retreat
#7. Shop the Magnificent Mile
Shopping enthusiasts rejoice. The Magnificent Mile is a shopaholic’s paradise.
The 13-block stretch of North Michigan Avenue includes downtown Chicago stores, restaurants, and attractions.
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.
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.
#8. See Chicago from The John Hancock Observatory
One of the best ways to see Chicago is from the sky during a visit to 360 Chicago.
For breathtaking city views, head to the John Hancock Center, Chicago’s tallest skyscraper.
If you’re feeling adventurous, try TILT, a glass platform that tilts you out over the edge of the building. It’s equally thrilling and terrifying—and totally worth it for the bragging rights.
Looking out over the city lights below, you’ll feel like you’re floating on air.
#9. 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 you to the best parts of the Windy City, including stops at some of the most famous gangster hangouts.
You’ll hear stories about Al Capone and other notorious criminals. Hear stories about ghosts still haunting their old haunts, too.
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.
#10. Enjoy Chicago’s 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 in Chicago are great places to start the evening and offer spectacular sunsets in the spring and summer.
These are some of my favorite rooftop bars in Chicago.
- Cindy’s Rooftop – Overlooking Millennium Park in the Chicago Athletic Association Hotel, this rooftop spot serves up creative cocktails and small plates. It’s perfect for an afternoon chill session with your girls.
- Z Bar at The Peninsula – Combines chic and chill in one place with unbeatable views of the city
- LH Rooftop on the 21st floor of LondonHouse – The views of the Chicago River are unbeatable, especially at sunset.
Best Time to Visit Chicago
For the best experience, travel to Chicago in the 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.
Ready to Plan Your Girls’ Trip to Chicago?
Chicago is truly a gem for a fabulous girls’ weekend!
Whether 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 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 using this travel guide now, and prepare to make memories that will have you smiling for years to come!
