The Perfect Itinerary for a Mother-Daughter Day Trip to Chicago

mother-daughter day trip to Chicago

Mother’s Day is around the corner, and it wasn’t too long ago I showed my Mom around Chicago for the first time. I moved to Chicago in 2020. Ever since then she comes to visit from out of town and we explore the city together. I show her all the main attractions and everything you cannot miss when visiting Chicago. Last year was the second visit and I have found the ideal itinerary for a mother-daughter day trip to Chicago. We took the train to the city for the day, looked at Monet’s painting, ate deep-dish pizza, and she got to experience this city I love with me. Here is how to treat your mom to a fun mother-daughter day trip in Chicago.

mother-daughter day trip Chicago

Take the Train 

Taking the train down to the city is a must as you embark on your mother-daughter day trip to Chicago. Most rural towns in the United States don’t have excellent public transportation like trains, the city my mother lived in being one of them. If you are a regular Chicago commuter, you might think the train is a drag, but it’s an exciting new adventure for a visitor. The bonus of taking the train is that you do not have to worry about parking. The last I thing want is my sweet southern momma trying to figure out how to park in downtown Chicago. Taking the train is avoiding that disaster.

Chicago Art Institute 

When we first arrive in town, we walk the twenty-minute walk to the Chicago Art Institute. I was around five years old the last time my mom was here. She loves the impressionists at the Institute like Renoir, Van Gogh, and Monet- all the classics. Her favorite is a painting by Georges Seurat called Sunday Afternoon that was above her bed for many years. I remember staring at it as a child, but now seeing the real thing is something to marvel at. His painting technique is rather unique. Seurat paints using small dots with a technique called pointillism. When you look closely to the painting you can see all the small dots, but step away and they all disapear and melt into the larger image.

My best advice for taking your mother to the Chicago art institute is to know what she’s like before heading in and seeing that first. There is too much to see to take it all in at once, but I know my mom doesn’t care for modern art, so we skipped that wing. After seeing all the exhibits, you want to remember to stop by the garden outside and the city views on the rooftop on your way out.

Chicago Art Institute on a mother-daughter day trip
Chicago Institute of Art mother-daughter day trip to Chicago

The Bean 

If your mother is from out of town like mine, she has heard of “The Bean” for years but has never been. The first time she saw it I couldn’t wait to show her the iconic bean. It has become the symbol of Chicago and I take all of my out of town friends to see it. It’s a short walk from the Art Institute. While my mom had heard of the bean, she momentarily forgot its name and blurted out, “Are we going to that egg-looking thing”. Ever since then, I refer to The Bean as ‘That egg-looking thing’ when in my mom’s presence.

Hot Chocolate at Nutella Cafe or Coffee at Intelligentsia

My mom is not a coffee drinker but loves participating in coffee culture by having a hot chocolate every morning and pretending it’s coffee. This morning is no different, except we stop by the Nutella Cafe to get a hot chocolate. The line is wrapped around the door and outside but we are willing to wait. It’s nuetella after all. If your mom doesn’t care for hot chocolate there is a great coffee shop a couple blocks over. I recommend the honey oatmilk latte. 

Cultural Center 

Still close by the Cultural Center is a great place to stop by to see the stunning interior architecture and exhibits. While the architecture remains for guests to view the exhibits change throughout the year. When we went, they had an exhibit about print journalism. My mom loves museums and enjoyed reading all of the information in the exhibitions and at the Cultural Center.

Shopping on Michigan Ave 

It wouldn’t be the perfect mother-daughter day trip to Chicago without a little bit of shopping. My mom is from a small town where the shopping consists of Walmart and Belk. We would drive an hour to Wilmington just to hit the mall for a girls trip. I loved having shopping trips with my mom. While there are few options in her hometown, on Michigan Ave, you can find just about anything you want. There’s Sephora, Burberry, Nike, and Zara, to name a few. If you can’t find anything there, go to the giant Macy’s off of Michigan. It’s eight floors of a shopper’s paradise.

Starbucks Reserve Roastery 

Not too far from the Macy’s is the Starbucks Roastery, currently known as the largest Starbucks in the world. The Starbucks Reserve Roastery in Chicago is truly a unique space. It’s four levels. Each level is something new. The first floor is the coffee bar. The second floor is the Princi Bakery and Cafe menus. The third floor is the experiential coffee bar menu, with extravagant latte options. Finally, the fourth floor is the Arrivamo bar menu, this is the spot to get the golden foam espresso martinis and other coffee cocktails. Even if your mom is not in the mood for coffee, or my case, hot chocolate, the roastery is fun to see . Or it might be time for an afternoon pick-me-up, including a pastry. The Starbucks Roastery has fresh pastries made every day, and the raspberry jam pastry is divine. 

Deep Dish Pizza Labriola 

Labriola is where I take all of my out-of-town friends to get deep-dish pizza, and my mom is no exception. Located just off Michigan Ave, there is rarely a wait at Labriola, and it has the best deep-dish pizza in town. We order the garlic knots and the basil and mozzarella deep dish pizza. The garlic knots come to the table warm and buttery. I have to stop myself from eating too many and getting full before the pizza arrives. The deep dish pizza arrives with the cheese still steaming as we put a slice on our plate. If you are looking for the best place to try Chicago deep dish, try Labriola.

Deep Dish Pizza
Chicago Food
Chicago Deep Dish Pizza

Wine by the River 

End the day by sipping on wine by the river. The Riverwalk at sunset is the place to be. People are running, walking dogs, going out for the evening, or ending the night like us. The Riverwalk overlooks some of Chicago’s grand architecture. This is the perfect spot to see the sun going down over the Michigan River and relax before getting on the train, uber, or be adventurous and take her on the water taxi before calling it a day. The water taxi is an inexpensive way to get from one part of the city to the next without making your mom walk the whole way. 

Chicago Water Taxi
Chicago Riverwalk

The last time I lived in my hometown in North Carolina was when I graduated high school, but I love showing my mom around the new places I call home. This was the perfect mother-daughter day trip to Chicago. It’s so fun to take her around all my favorite spots for food and things to do around the city to become part of my new life. If you still live in the same town as your mom, give her a big hug today. 

Happy Mother’s Day! 


Morgan & Jolene mother-daughter day trip to Chicago

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