My mom and I love traveling together. We’ve been all over the world on our infamous mother daughter trip and at the end of May, we headed to Chicago to take in the Windy City and all it has to offer over a long weekend for a girls getaway.
We packed a lot in our 3 and a half days there. We’ve been to Chicago a few times together so I wanted us to do a few things we’ve never done before while also truly relaxing and having fun. We did a few touristy things while I also scheduled one self-care/pampering service a day so we would come home feeling rejuvenated and fresh. I’m sharing all of the details below!
Everything We Did on Our Mother Daughter Weekend Getaway
Where to Stay:
The Cambria Hotel in the Theatre District – For a weekend trip the Cambria Hotel is the perfect place to lay your head at night. We were only about a 15 to 20 minute walk from the river walk and Magnificent Mile. We were also surrounded by restaurants and coffee shops so we could get our morning jolt.
Massages at Massage Envy – After walking as much as we did in Chicago, it was good getting a massage the day before we left. Our muscles were a little stiff and sore so a little relaxation was much needed.
Pedicures at Pure Rain Nail – You can’t start a girls trip without a pedicure! There was a salon right around the corner from our hotel and we got a good scrub and polish. A pedicure is the ultimate self care and can make you feel so much better about yourself.
Blowout at the Dry Bar – If possible I like starting a girl’s trip off with a blowout. That way your hair is a little more low maintenance and you have to fix it less on the trip. I also hate washing my hair so whenever someone does it for me I’m a happy campter!
Where to Eat:
Pink Taco – I’m a lover of Mexican food so we had to find tacos and tequila right after we landed. Pink Taco was a short 15-minute walk from our hotel and we got there right during happy hour. We enjoyed chips, queso, nachos tacos, and margaritas and sat on the patio to enjoy the beautiful weather.
Goddess & the Baker – Goddess & the Baker is a Chicago chain with multiple locations around the city. They have the cutest decor but also the yummiest pastries. We came here two days in a row to caffeinate and get ready for the day. I can’t recommend their croissants enough!
Afternoon Tea at Russian Tea Time – A mother daughter trip isn’t a mother daughter trip without high tea! We went to Russian Tea Time and had a lovely afternoon drinking tea and eating finger sandwiches. Dress up and put your phones away and enjoy having tea with your mom or girlfriends.
Hampton Social – There’s a Hampton Social in Nashville and it’s one of my favorite spots. The Chicago location has a great view as well as the famous Rosé All Day neon sign at the door. We had espresso martinis, frosé, burgers and lots of appetizers. I recommend everyone come here to hang out and enjoy the cool vibe.
Cocktails and Jazz Music at The Bassment – After you’re done with dinner and drinks at Hampton Social, head to The Bassment, the secret speakeasy bar. They had an amazing band perform and we drank our cocktails and enjoyed the music. Also, how cute is the little red telephone booth for photos?!
What to Do:
Chicago River Boat Cruise – The best way to see Chicago is a River Boat Cruise. Chicago’s 1st Lady is the #1 boat tour in Chicago. They offer evening river cruises, a photography cruise, and the architecture tour. I’ve done the architecture tour a few times and always enjoy sitting on the deck and seeing the city. You learn something new each time!
Shopping on the Magnificent Mile – Personally, I can’t go to Chicago and not do a little shopping. The Magnificent Mile has some of the best shopping in the country. It’s a good way to see Chicago, explore and support the local economy with a little shopping. There’s a good mix of designer and affordable fashion and something for everyone.
Wander Around Navy Pier and See Lake Michigan – Navy Pier is a must see in the Windy City. While you’re there ride the carousel or ferris wheel, do some shopping, get pizza at Giordano’s and enjoy Lake Michigan.
Take in the Chicago Skyline – The skyline in Chicago is incredible. It’s gorgeous during the day and breathtaking at night. You don’t have to go far to see the beauty, just walk the river walk and enjoy the breeze and phenomenal views.
Cooking Class at the Chopping Block in Lincoln Park – What’s more fun than a cooking class? The Chopping Block is a 30 minute car ride to Lincoln Park. They offer so many fun cooking and wine classes that are so hands on. Since we went in early June our class was focused on grilling. The instructor helped us make pizza, grilled peaches for ice cream, scallops and more. There’s wine to purchase to sip on during the class and you talk and get to know so many people during the class.
See the Bean at Millennium Park – Rated the #1 thing to do in Chicago, Millennium Park and the Bean are must sees. I go here everytime I’m in Chicago and take pictures with the bean. Arrive early, get a coffee and enjoy the park before the tourists.
Explore the WNDR Museum – A 20 minute Uber drive away was the oh-so-fun WNDR Museum! You sign up for a time before and so you have the place to yourself during your timed slot. It was such an interactive experience and the artist in me was so inspired with all the installations and exhibits. This is something we wouldn’t normally do on a mother daughter trip but we loved it.
Skydeck at Willis Tower – After completing an extensive redevelopment, Skydeck Chicago reopened to the public in April 2021. The revamped Skydeck Chicago provides a can’t-miss, one-stop attraction to discover and see all that the city of Chicago offers from an incomparable vantage point. The complete transformation encompasses the attraction’s lower level, delivering an interactive experience that celebrates the unique personality, history, neighborhoods, and sites of Chicago. The lower-level museum is complemented by a visit to the internationally recognized observation deck to take in the city from 103 floors up and step out on The Ledge; the four thrilling glass floor balconies extend from the Tower.
You have about 30 seconds to get the perfect photo (they time you). If you want an epic shot for Instagram, research poses beforehand and have your camera settings ready!
After a full and fun weekend, it was time to head home and see our family. We flew out of Midway Airport and it wasn’t too busy. My rule at airports is to show up two hours early. Enjoy a drink at the bar and read a book while you wait.
Three to four days is plenty of time to spend in Chicago!
Millennium Park! You have to walk around and see the shiny, silver bean.
Deep Dish Pizza!
I need some other mother daughter trip ideas! Should we go to New York City, California Wine Country to do wine tasting in Napa Valley or Sonoma County, take a road trip, chill at the beach or visit a national park? Share with me your favorite trip ideas and places in a comment below!
Check out some of my other Mother Daughter Getaways!
2 Days in Boston: the Best Things to do on Your Mother Daughter Vacation
Mother Daughter Vacations to Florida: A Complete Guide to Key West & Miami
Mother Daughter Weekend to Beautiful Charlottesville, VA: Top 5 Things to Do
The Ultimate Savannah & Charleston Guide: Mother Daughter Trip Ideas