A Mother-Daughter Girls Trip to Chicago: Tips for What To Do

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A mother/daughter getaway is about breaking free of routines to do something special with the most important person in your life. That’s why we decided it was time to take a girls trip to Chicago!

Craig and I decided that it would be a good bonding experience for us to go on separate trips with the girls to give them the one-on-one time they crave with either parent, and have the opportunity to create special memories together.

When the opportunity came to travel to Chicago, I jumped at the chance to take Kalyra as my guest.

Kalyra is a city girl, and I love cities that are laid back and beautiful, so Chicago was a perfect fit for both of us.

Chicago is glamorous and self-assured without being pretentious, and with its 24 beaches and 28 miles of lakefront shoreline, there is plenty of opportunity to unwind and connect with nature.

Chicago welcomes you in with the freedom to be yourself while you explore its vibrant neighborhoods, historical sites, arts and culture, magnificent shopping and architecture and natural beauty.

We visited for two seasonal events, The Chicago Flower and Garden Show and St Patrick’s Day, which were spectacular and worth planning your trip to Chicago around.

Things to Do on a Girls Trip to Chicago

If it’s your first time in the Windy City or if you’ve been here before and just looking for girlie things. todo, then you’ve come to the right place. Here’s what we did on our Mother/Daughter Chicago weekend getaway in March!

1. Visit the Chicago Flower and Garden Show

“Oh My God!!”

Kalyra squealed and bolted across the room the minute we walked into the Chicago Flower and>Garden Show

I chased after her looking up into the air to where she was pointing. High up in a whomping willow was a cutout of The Flying Ford Anglia.

“I love this place it’s the best,” she said as we walked through the rabbit hole, through the chamber of secrets, under the hanging white flowers and decks of cards, and past the mandrakes in secret garden created to showcase the secrets and mysteries of enchanted forests, wizards, mad hatters, witches and hobbits.

The theme of this year’s Flower and Garden Show was Flowertales, bringing the beauty of flowers and the joy of books together.

The entire show was themed around popular stories from The Wizard of Oz, Harry Potter, Alice in Wonderland and The Secret Garden.

It was creative, inspiring, beautiful and smelled so divine! It definitely had us longing to usher in Spring, and to one day have a delightful garden of our own.

Although I’m not too sure about my abilities to create something as pretty and vibrant.

The annual Tulip extravaganza is not to be missed for an explosion of color and glory. The show also has a kids’ activity garden, chef demonstrations and gardening speakers.

We often like to research places we are visiting before we go to help the girls connect and get excited. I am so glad we didn’t for the flower show. It gave Kalyra unexpected joy and she’ll always remember that now and walked out of the Flower Show saying,

“That was so awesome. I wasn’t expecting that. I can’t wait to tell Daddy.”

2. Visit The Centennial Wheel at Navy Pier

Navy Pier is home to the Chicago Children’s Museum, the Imax theatre and Centennial wheel, a year-round Ferris wheel offering views of the Chicago skyline and Lake Michigan.

It was another adventure Kalyra and I had together braving the fear of going high and spinning slowly.

Deep breaths were needed as we stopped atop letting passengers on and off below.

I loved it and was stoked we had three spins around giving us ample time to soak in the extraordinary Chicago skyline views and the aqua and teal waters of Lake Michigan.

3. Marvel at Prismatica

Another unexpected surprise was Prismatica, the kaleidoscopic art installation in Polk Bros Park just in front of the Children’s Museum.

There is nothing like artwork your children can interact with without fear that they will break something and be told off by the patrolling gallery guards.

The 25 pivoting prisms are more than six feet tall and perfect for spinning, taking in a psychedelic Chicago view, and capturing selfies with a difference.

4. See the river turn green on St Patrick’s Day

Chicago reminded me a lot of Dublin, Ireland so it was quite fitting that nearly a million people come to Chicago each year to celebrate this festival with the turning of the river green.

It’s probably one reason I felt so at home in Chicago, as Dublin was a place Craig and I lived in for a year.

The Chicago River is the central focus point of the city separating north and south, just like the Liffey in Dublin does.

And the atmosphere is the same – open, fun, friendly.

The tradition of dyeing the Chicago River green started by accident in the ’60s by the Chicago Plumbers Union.

They were dyeing the river to locate polluted parts of the river to clean it up. The dye just happened to be green and performed close to St Patrick’s Day.

Someone had the idea to do it every year and turn it into a celebration for the luck of the Irish.

It was incredible to watch the water turn highlighter green in front of our eyes. The dye is powdered vegetable based and environmentally safe.

We saw the river from various viewpoints throughout the weekend. It sure made the city even more vibrant and beautiful.

If you love celebrating St Patrick’s Day, Chicago is the place to do it in the US.

Bring your costumes and your patience – I saw some long queues to get into any of the many Irish bars around the city.

It certainly looked like great craic though!

In honor of my Irish friends, I did have a green cocktail to match the river during the dyeing ceremony.

5. Check Out Magnificent Mile Shopping

The Magnificent Mile is Chicago’s most famous shopping street, and one of the most famous in the USA.

It begins at the Chicago River and stretches 13 blocks north along Michigan Avenue to Oak Street. There are over 400 shops, over 200 restaurants and has some of the biggest names in retail.

I will remember this experience shopping with Kalyra as the day my baby girl was no longer a baby girl.

She took charge of the experience and the budget to select shops that would give her the most value for her spend. She chose all her own outfits and I could see her little fashionista spirit swell with independent pride.

We took care not to forget her sister back at home, picking up some great deals on clothes for her spring and summer wardrobe.

We’re not big shoppers, and the girls were in need of new clothes, so this was a lovely treat, and something Kalyra will always remember of Chicago.

I’m pretty sure that was her favorite part of the Chicago trip. Her only disappointment was that she had to wait until we returned to Raleigh to warmer weather so she could wear her new clothes.

However, she did jump into bed the night after shopping wearing her jumpsuit and new cardigan.

6. Have Lunch at the American Girl Doll Café

How long can you spend in a doll store?

At the American Girl Store it can stretch into the hours. I had to end the adventure after 90-minutes.

Kalyra was in heaven and it was fun watching her race from stall to stall, pointing out her favorites and choosing some clothes for her and Savannah’s dolls.

She had been jumping up and down with excitement over it as soon as she saw it on our itinerary.

The girls plan to visit all the American Girl Doll Stores in the US.

Our special treat at this one was to eat at the American Girl Doll Café – yes there is such a thing.

Gabriella, Kalyra’s beloved Girl Doll of the Year 2017, joined us at the table in a little seat given by the café. You can borrow a doll if you need to. I passed wanting to give all my attention to Gabriella instead.

It’s pink and flowery and the dolls get their own plastic meal to enjoy with you. It’s a cute experience and one I’m sure your children will love too.

The American Girl Doll Store and Cafe is located on the Magnificent Mile inside Water Tower Place, a shopping paradise with over 100 stores.

7. Check Out Art Installations by Walking the Streets

Chicago is one giant art gallery and lucky for the intrepid traveler, very walkable. We walked almost everywhere during our mother daughter Chicago getaway.

Kalyra was in charge of the budget and knew the fewer Ubers we took the more money we’d have for shopping. That’s one way to encourage your kids to keep walking!

There’s always something innovative and creative to look at on the streets of Chicago. The architecture of the city is unlike any other and makes it an exciting place to discover.

In the middle of unique and unusually designed skyscrapers, you’ll come across Gothic-style buildings, small limestone churches, or dive bars, or deep crimson red boutique with immense porthole windows (Ikram building) #dropthemic

You’ll come across art installations, murals and giant sculptures, one of which was donated to the city by Picasso.

Chicago is a city that embraces art and culture – you’ll feel inspired just walking the streets. Plus, there are beautiful parks and the giant lake to enjoy as well.

The skyscrapers aren’t really high at all and the streets are wide and sunny. Unlike other metropolis you feel you have personal space, which reminds me so much of home.

There’s something magical about a city that embraces, encourages, and celebrates art and innovation.

8. Visit Millennium Park

Who doesn’t want to get a selfie in the giant bean, officially known as Could Gate?

Kalyra had fun jumping up and down amongst the Chicago skyline and clouds reflecting in the stainless steel plates.

This elliptical sculpture, created by British artist Anish Kapoor has a concave chamber, which makes it fun to touch and take photos of yourself up close.

Cloud Gate is a hugely popular Chicago tourist attraction and is known as one of the best spots for selfies.

Cloud Gate is one of the main features of Millennium Park, a 24-acre public park in the heart of downtown Chicago.

The park has interactive public artworks, ice skating, play areas and the dazzling Pritzker Pavilion, which hosts outdoor concerts, and is a piece of art with its billowing “headdress” of brushed stainless steel ribbon.

Crown Fountain is another popular interactive artwork in Millennium Park, designed by Spanish artist Jaume Plensa.

Kalyra loved watching the faces in the two 50-foot glass block towers change.

They face each other at the end of a shallow reflecting pool (which was dry when we visited, but refreshing and playful in warmer months) and project video images from a broad social spectrum of Chicago citizens.

After you’re done admiring the art installations in the park, cross over the bridge from the Pritzker Pavilion to the Maggie Daley Park.

9. Visit Maggie Daley Park

The first thing Kalyra said when we arrived at the park was,

“I really miss Savannah. I wish she were here with me. She’d love this park.“

I realized then just how close the girls are and how lucky they are traveling together. They’re developing such a close bond.

I wasn’t the right person to fully appreciate the park with Kalyra, but she had a great time exploring the 3-acre Play Garden, whose design was inspired by Alice in Wonderland and Charlie and the Chocolate Factory.

Maggie Daley Park is a relatively new lakefront green space designed with several low hills to give you vistas of Chicago’s famed skyline and lakefront.

Once again, Chicago bringing an element of play, imagination and artistic innovation with the park’ s skating ribbon, play gardens, rock climbing and bouldering walls, picnic areas and even an 18-hole miniature golf course.

Again, Kalyra has penciled that in as a must do when we return in the warmer months promising to bring back her sister and convince her to go down the slide.” (we better start planning that trip!)

It’s a pretty spot to relax and the kids will absolutely love playing here.

10. Take a Big Bus Tour

The Big Bus Tour is an open top bus that looks around the north and south of the river taking in the main tourist attractions in Chicago.

It is a hop on hop off bus that runs every 20 – 30 minutes.

The Big Bus Tour is a good way to get an overview of the city so you know what you want to come back and explore more deeply.

I enjoy these tours as the commentary gives you insights on the history and local culture.

The guides often point out insider secrets on cool things to see and do. We learned about Chicago’s various nicknames, the history of the Great Fire and the story behind some of the design features on some buildings.

It was also a great chance to sit and rest and soak up the city from a different angle. After a day of walking around the city, we were grateful to sit down and let someone else take us around.

In big cities like Chicago, time your bus tour right so you miss the heavy traffic periods, otherwise the Big Bus Tour can end up taking a lot of time.

Download the Big Bus app which will tell you more about the attractions at each stop, plus it has a handy bus tracker so you know how far away the next bus is.

11. See The Views at 360 Chicago Observatory

Looking for a skyhigh observatory?

360 CHICAGO observation deck, in the John Hancock Center is located 1000 feet above the famed Magnificent Mile offers breathtaking 360 degrees views of the city skyline and Lake Michigan.

360 Chicago observation deck is also home of TILT – Chicago’s highest thrill ride – an enclosed moving platform that literally tilts you out over Michigan Ave from the 94th Floor.

Would you dare to do The Tilt?

Kalyra and I contemplated it until we stood and watched others do it. Our hearts leaped and we knew it would be a fear that we couldn’t quite handle.

I would like to brave up for our next visit to Chicago and give it a go.

We were happy to settle for the extraordinary views of Chicago in every direction instead. Kalyra refuses to believe Lake Michigan is a lake and not an ocean.

It is really cool looking out over a lake and not being able to see the other side.

With 360 Chicago’s bar program within 875 N. Michigan, I recommend aiming to get up here for sunset and enjoying a drink as day turns into night.

Craig did that on our visit in 2004 and it was a highlight of our trip to Chicago.

12. See More Views at Skydeck Chicago and The Ledge, Willis Tower

Let’s keep those Chicago views going.

This time from the 103rd floor of the Willis Tower, formerly the Sears Tower.

Skydeck in the Willis Tower is the home of The Ledge, the all glass balcony providing you with your ultimate thrill walking on air.

At 1,353 feet up, The Ledge’s glass boxes extend out 4.3 feet from the skyscraper’s Skydeck providing never-before-seen views of the city.

We waited some time to get up to the observatory level and then to get onto the ledge. But it was worth it. You think it’s going to be a breeze and then you step onto the platform and look down and freeze.

We shuffled slowly out to the ledge and did our best to love the experience.

It was fantastic, but I was glad it only lasted 2 minutes.

It’s funny how much that scares you, yet you’d easily walk out there if the floor was concrete and not worry!

The Willis Tower was once the tallest building in the world; it is now the second tallest building in the Western Hemisphere. I loved the view from here out over to the 360 Observatory building (875 N. Michigan, formerly the John Hancock).

The afternoon is the best time to come as the sun will be behind you.

13. Check Out Lincoln Park

Lincoln Park is one of the most desirable neighborhoods in Chicago. It’s pretty tree lined streets have great dining and music venue options and it’s only a mile from downtown.

Most attractive about it however is its namesake, Lincoln Park, a sprawling 1,208 acres of green space right near the Chicago lakefront.

Within the park is a free zoo open year-round, a nature museum and conservatory.

We took in the neighborhood with a walk from our breakfast spot at Batter and Berries to the Lincoln Park Zoo, where we wandered around watching lions, penguins and polar bears playing.

The zoo is one of the oldest in North America and one of the few free admission zoos in the US.

We then finished the morning with a stroll along the lakefront to get back into the city. It’s the perfect place in Chicago to reconnect with nature, yet still have that pretty skyline in the distance.

We have already penciled in a bike ride along here and a stand up paddle boarding session for our return in the warmer months.

Chicago offers so much for families. I love this city.

14. See a Cubs Game at Wrigley Field

Who said all girls weekends had to be girlie? If you and your girl friends are into sports, then be sure to try and catch a Cubs game at Wrigley Field, one of the most historic baseball fields in Chicago that has been open since 1914.

Grab yourselves a corn dog and some wine and enjoy the festivities.

Be sure to check out the timetable before visiting to see when game days are on.

15. Enjoy Brunch at Hampton Social

Brunch dates are one of the best things to do on a girls trip to Chicago, so be sure to do it with class and style at the Hampton Social.

Enjoy a refreshing glass of rose with a view of the river at the Hampton Social. Located in River North, it’s ideal for enjoying drinks out in the beer garden, and dining on delicious seafood dishes.

The atmosphere is relaxed and friendly, but also elegant, so you can dress up or dress down, whatever fits your groups style.

16. Take a River Cruise

Check out the art murals along Chicago Riverwalk before heading out to see the city skyline on a river cruise.

If you’re only on a girlie weekend in Chicago, then this is a great way to take in all the sights whilst also spending quality time together.

You’ll sail past the architectural highlights of the city, such as the historic early skyscrapers of the Wrigley Building and the Tribune Tower, as well as see iconic works of engineering such as the circular Marina City Towers, Aqua, Trump Tower, and the Vista Tower.

Whilst you take in the sights, you can enjoy refreshments from the boats onboard bar.

17. Have a Spa Day

What’s a girls’ weekend with a spa day? One of my top recommendations for things to do with your girlfriends in Chicago is relax in a spa.

You will find relaxation at the Aire Ancient Baths spa, which is located close to the West Loop.

It’s set inside a restored 1902 factory, and offers a relaxing thermal bath, similar to what you would find in the Roman, Greek and Ottoman times.

You and your girls can sit back in the warm waters and let life’s stresses float away. They also offer hot stone massages and other wellness treatments.

Places to Eat in Chicago

Chicago is most famous for its deep-dish pizza, a particular style of hot dog, and Garret popcorn.

There are plenty more great meals to be had in the city. Here are the places we ate on our mother daughter getaway to Chicago.

It was especially lovely to sit down with my eldest daughter for meals and uninterrupted conversation and giggles. It’s something your children crave and appreciate so much.

Breakfast: Wildberry Pancakes

We arrived at 7:35 am, 5 minutes after opening and the restaurant was already full!

That’s how well known and popular Wildberry Pancakes is.

It is located next to Millennium Park and offers an extensive menu of pancakes in a variety of styles and flavors as well as some more traditional breakfasts.

Kalyra dove into a plate of silver dollar chocolate chip pancakes, and I stuck with smashed avocado on toast.

Breakfast: Batter and Berries

Located in Lincoln Park Neighborhood, Batter & Berries is famous for the French Toast Flight. Its a combination of four signature flavors of batter dipped Brioche.

Kalyra relished the Flight and rates the blueberry French toast as her favorite. The lemon one looked the best to me.

I settled their other famous dish, the hand shredded B&B cheese crusted hash. I saw a plate of it on almost every table.

Yes. It was delicious.

I had mine with the equally delicious special of the day: jambalaya omelet with shrimp and chorizo.

Lunch: Beatrix Café

You know a place is good when your 10 year old asks to go back there to eat. The Beatrix Café in Streeterville is a coffeehouse, restaurant and meeting place.

Our meals were simple, yet bursting with flavor.

I had the roasted cauliflower salad and Kalyra a simple pasta dish that she devoured. Both went well with our freshly squeezed juices.

We arrived early after our flight so sat in the small lounge area with a hot chocolate, latte and delicious pastries. I don’t usually eat desserts, but due to a rumbling stomach decided to have a grape coconut macaroon.

It was sensational. And Kalyra loved her cookie stuffed with oozing Nutella.

Dinner: Lou Malnati’s

So Chicago is famous for inventing deep dish pizza. It’s definitely a must when you visit Chicago.

Lou Malnati’s Pizzeria is known as one of the best in the city and it has stayed true to Lou’s traditional recipe for over 40 years.

Make a reservation if you can because everyone in Chicago likes to eat this pizza. It’s in the charming Gold Coast neighborhood.

I loved deep dish pizza last time we visited Chicago in 2004. This time due to my gluten intolerance, I couldn’t eat it, but I happily watched Kalyra stretching out her mozzarella cheese.

I had a delicious gluten free pizza packed with anchovies, olives and mushrooms!

Sweets: Nutella Café, Eataly

Eataly is an Italian lovers dream: two floors of food, drinks and products to sample in Chicago’s River North neighborhood.

We stopped in for crepes slathered in hazelnut spread and a topping of your choice.

Kalyra went for banana, and it reminded me of my days living in Bangkok sneaking down to the streets for 10c banana pancakes. It was the perfect end to our first day in Chicago for Kalyra.

Don’t fear if Nutella is not your thing, Eataly has plenty more choices for sweets: gelato, cannoli, pastries and tiramisu and even wine and cheese if you prefer something a little more savory and strong!

Drinks: Cindy’s Rooftop

Make the occasion magical with drinks and a view at one of the best rooftop bars in Chicago. Not only is Cindy’s Rooftop a sophisticated and elegant bar to enjoy evening drinks, but it also has a delicious seasonal menu.

With award-winning cocktails and freshly sourced ingredients, this is the place to be if you want to wine and dine with your girls.

The ambiance is relaxed and welcoming, with excellent views of Millennium Park, Lake Michigan and the Art Institute of Chicago.

Where to Stay in Chicago on a Girls Trip

We stayed at the Cambria Hotel and Suites (the Magnificent Mile location), and the location was excellent.

We were a couple of blocks south of the river and only a five-minute walk to Millennium Park. It’s also right near public transportation, such as the “L” train line.

The rooms were comfortable and quiet and the bathroom large and the shower good – priorities. Kalyra commented several times how much she liked the hotel.

We were so busy we didn’t use any of the facilities but they also have fitness center, a bar and a restaurant.

Final Thoughts on A Girls Trip to Chicago

Kalyra and I had a lovely weekend together and I am so glad we decided to spend this precious one on one time with our daughters on special getaways.

Chicago is special and one of my favorite cities in the US and ranks highly as a favorite in the world.

It’s a city I see myself coming back to again and again to explore a little deeper.

Check out these popular tours of Chicago

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