We absolutely loved our Chicago family vacation and had a blast in the windy city. From views at the top of towering skyscrapers, endless shopping on the Magnificent Mile, to browsing through renowned museums, Chicago has so many experiences to offer visitors.
We embarked on a Chicago family vacation during spring break and had no idea what to expect. We haven’t traveled to the midwest much and were excited about the adventure.
As always, Nami reached out to the JOC community and many of you came back with great recommendations on restaurants and places to visit in Chicago. You guys are the best —THANK YOU! By the end of the trip, we all agreed it was one of the best family trips we’ve taken and we absolutely loved Chicago. Ready to join us for the quick tour? Let’s go!
Chicago Family Vacation and Travel Guide
Our family spent a week in Chicago and a day trip to Milwaukee. We thought it would be plenty of time to see the city but there were still so many parts we missed. Here’s what we’ve learned on our trip and I hope it’ll help you plan your visit to Chicago.
We used Go City Chicago for the attractions during our Chicago family vacation. We also used Go City when we visited Boston and found it a good value. Every location that requires a ticket we visited was covered by Go City Chicago except for the Art Institute.
Table of Contents
- 360 CHICAGO at John Hancock Building
- Magnificent Mile
- Chicago River Boat Architecture Tours
- Museum of Science and Industry, Chicago
- The University of Chicago
- Frederick C. Robie House
- Frank Lloyd Wright Home & Studio
- Ernest Hemingway Birthplace Museum
- The Art Institute of Chicago
- Chicago History Museum
- Skydeck at Willis Tower
- Shedd Aquarium
- Field Museum
- Walk Around Chicago
- Northwestern University
360 CHICAGO at John Hancock Building
We started our visit at 360 Chicago at the top of the John Hancock Building. It’s a great way to orient yourself with Chicago and have some thrilling fun. Besides the panoramic views of the city, 360 Chicago also has an exciting Tilt Ride. Visitors hold on to the railing while the glass wall tilts downwards towards the streets. The perspective on the Tilt gives the impression that you’re about to fall down the building. Nami and the kids were surprisingly unfazed by it, but the simulation definitely gives me a freight.
Magnificent Mile
Head south on Michigan Ave. and walk along the Magnificent Mile towards the Dusable Bridge and Chicago River. The Magnificent Mile is known for its many luxury stores, hotels, restaurants, and department stores. The street is very clean and there are plenty of walkways for pedestrians on both sides of the street.
In addition to the many shops on Mag Mile, the world’s largest Starbucks (5 floors) is also on there!
Don’t forget to pick up some famous Garrett Popcorn while walking on Mag Mile. Their Garrett Mix is so addicting and we couldn’t stop eating.
DuSable Bridge and buildings along the Chicago River
Chicago River Boat Architecture Tours
Near the DuSable Bridge, we boarded the boat for Chicago River Boat Architecture Tours. Several of our friends have highly recommended the tours, so we had to experience it for ourselves.
Not only did the tour live up to our expectations, it was also enjoyable and informative. Our tour guide was an architecture student and did an excellent job in presenting the history and background story of the buildings along the river. We learned about the design characteristics that made them unique as well as the firms that designed them. To top it off, our guide shared his often candid and personal views on the designs which kept us all entertained.
The boat tour got us acquainted with the signature Chicago buildings very quickly and it was fun to recognize them throughout our trip. The boat goes west on Chicago River and then its south branch before coming back in a loop. The tour lasts about one hour.
With a juxtaposition of buildings designed from the 1900s through the current time, the Wind City certainly has one of the most captivating skylines in the country. There is a signature look to each design period—from gothic to curved glass to postmodern—and they all blend together beautifully against the sky, defining the character of the city.
It was 35º F (1º C)when we were on the boat ride, and while it was enjoyable, we were desperate to defrost back in the hotel and regain the sensations of our limbs.
Museum of Science and Industry, Chicago
On the second day, we got a rental car since we wanted to visit locations that are further out of the downtown area and not as accessible by public transportation. The first stop was the Museum of Science and Industry.
What a fabulous museum! For those who love science, you can easily spend an entire day there. The exhibits are spread out through two enormous floors and we’ve never seen anything quite like it.
There are too many exhibits to mention here but one of the highlights is the U-505 submarine exhibit. It tells the story of how the WWII German sub was captured near Africa and brought all the way to Chicago. The submarine is so large they had to build an entire structure around it!
Their space exhibit is also extraordinary. How cool it is to have an up-close encounter with the actual Apollo 8 capsule that had been on the voyage to space and back!
However, the most memorable part for us in the museum is the Colleen Moore’s Fairy Castle! The details and the meticulous workmanship simply take your breath away. One can only be in awe by the details and the meticulous workmanship that went into the production of such phenomenal structure.
As we browse through the transportation gallery, there’s a 727 hanging in the sky. Perhaps that’ll help you understand how large these exhibit halls are.
In the transportation gallery, there is a giant train set (the largest we’ve seen) that depicts the railroad from Chicago to Seattle. Including are the replicas of downtown Chicago skyscrapers.
There are additional exhibits on energy, storms, mirror maze, and more.
The University of Chicago
Our next stop after the Museum of Science and Industry is the University of Chicago nearby. We are in the process of visiting college campuses as our son is heading to college in a few years. It’s been very interesting to visit campuses with our children and see the colleges through their eyes.
We love the beautiful gothic architecture and the grand buildings at The University of Chicago.
Frederick C. Robie House
Right near The University of Chicago campus is one of Frank Lloyd Wright’s masterpieces, the Frederick C. Robie House. A tour guide takes visitors through the house and explains Wright’s design elements, recounting details of each room, including the window design, the fireplace, and the intricate grills for the lights.
If you are interested in Frank Lloyd Wright’s design, do not miss the tour!
Frank Lloyd Wright Home & Studio
Our next stop after the Robie House is Frank Lloyd Wright Home & Studio which is a bit far way (17 miles) in Oak Park. It’s part of the reason we planned all the itinerary that requires a rental car on the same day.
The guided tour covers both Frank Lloyd Wright’s Home and his design studio and takes about 1 hour. The design elements really clicked with us after the Robie House tour as we noticed the similarities. It was revelatory to discover that Frank Lloyd Wright had adopted many Japanese architecture principles in his designs from years of attending World’s Columbian Exposition and visiting Japan.
We learned a lot about this “greatest American architect of all time” from the tour and how he designed his family’s home. Did you know Frank Lloyd Wright’s son (John Lloyd Wright) invented the Lincoln Logs?
After walking through his home, the tour continued to his studio. It was such an experience just to be in the same space as where Frank Lloyd Wright worked.
Our tour guide was very knowledgeable and did an amazing job of telling us behind-the-scenes stories about Frank Lloyd Wright’s work and personality.
Ernest Hemingway Birthplace Museum
Just a few blocks away from Frank Lloyd Wright Home & Studio is Ernest Hemingway Birthplace Museum. The famous author was born in this house which belonged to his maternal grandparents.
The tour is roughly one hour and covers Ernest Hemingway’s family history and their relationship to the house. The Queen Anne house has been restored to what it would have looked like in the 1890s.
It was fascinating to learn about Hemingway’s family history and dynamics. If you’re a fan of his work, stop by and learn more about how he grew up!
The Art Institute of Chicago
On day three of our Chicago family vacation, we toured museums in the downtown Chicago area. We started at The Art Institute of Chicago, which was our favorite museum on the trip and we actually visited twice!
There are simply too many things to see and we had to go back a second time. The Art Institute is not part of Go City’s list of included attractions (it is part of City Pass). We purchased an annual membership which allowed us to enter 1 hour before the general public and that was fantastic. We felt like we had the museum to ourselves. It also allowed us to go back to the museum multiple times during the trip.
The museum is really large with unbelievable collections. You can easily spend days there. If you love art, we would recommend allocating at least 5-6 hours to give yourself some time to walk through the museum.
Besides artworks by masters like Monet, Van Gough, Pollock, and many others, there are large collections of sculptures, medieval armor, and many other types of art.
I found it surreal to see how much art was housed in one museum as there’s nothing close to it on the west coast. Since each of us likes different types of art, we all had the opportunity to enjoy what we liked.
One section of the museum we all loved is the miniature rooms on the lower floor. There are reconstructed rooms from different time periods and the details are astonishing. Don’t miss it!
Chicago History Museum
The next museum we went to is completely different, and it was about the history of Chicago. One recurring story we keep hearing about on the trip is the Great Chicago Fire of 1871. Most parts of the city were burnt down with 17,000 buildings destroyed. The Chicago History Museum does a great job of explaining the fire, how quickly it spread throughout the night, and the displayed artifacts such as the melted metal from the fire put you closer to the scenes.
The museum is educational and most information is presented in a way even elementary children would be able to understand. Besides the Great Chicago Fire, there are exhibits on industries that had thrived in the city. Other exhibits include Chicago’s sports team, renowned buildings, and famous designers. Expect to spend at least 2-3 hours at the museum.
Skydeck at Willis Tower
At night, head to the Skydeck at Willis Tower and take in the colorful night view of the Chicago skyline. As you make your way to the elevator that takes you to the observation deck, there are a number of Chicago-related exhibits and info.
Shedd Aquarium
On day 4, we continued to explore various landmarks of Chicago. Shedd Aquarium is our first stop. It is over 100 years old and has a great collection of aquatic creatures, including a coral reef tank.
In general, the displays and the tanks feel a bit dated compared to Monterey Bay Aquarium. Regardless, our son who loves animals and biology enjoyed every minute we were there.
As we made our way through the aquarium, we discovered the gigantic indoor Oceanarium. Wow! It was spectacular to see such a large tank and the dolphins jumping and splashing indoors. Expect to spend at least 2 hours in Shedd Aquarium.
Field Museum
Our next stop is the Field Museum right next to the aquarium. It is a natural history museum and its vast collection is unbelievable. The exhibits are spread over three very large floors with many halls, and each hall seems to contain countless artifacts.
The lower floor has a large exhibition on Ancient Egypt and Underground Adventure.
In Underground Adventure, visitors are transported to an underground world where they’re shrunk to 1/100th of their size and learn about soil science.
The main floor captures all the visitors’ attention with Maximo the Titanosaur. The surrounding halls lead to displays of birds, nature, Africa, Jurassic Oceans, and more.
On the upper level, it contains a wide collection of gems, meteorites, items from the Pacific Islands, plants, and most importantly Sue the T. Rex!
If you have older kids and limited time, we would say skip the aquarium and spend more time in the Field Museum. We could have easily spent an entire day there if we had more time.
Walk Around Chicago
Apart from world-class museums, Chicago has amazing outdoor spaces and parks to explore. It was a bit cold when we visited, some days were 20F with the wind chill so we didn’t get as much opportunity to walk around. However, you can always plan your trip during the nice, warmer months from May to October.
We loved walking around the downtown area and felt safe exploring. If your legs get tired, you can always jump on the L and enjoy the elevated views!
Northwestern University
One of the side trips we took on the trip was to visit our former super-intern Kylie at Northwestern University! She gave us an awesome tour of the campus and even sneaked our kids into a classroom for a few minutes so they could see what college lectures are like. Thanks Kylie!
More Places to Visit in Chicago
We hope you’ve enjoyed our Chicago family vacation so far. The weather was too cold during our trip so we didn’t visit many seasonal attractions such as the Navy Pier. We’ll share where we ate and our short excursion to Milwaukee in the next post!
There are so many great places to visit in Chicago that we’d love to cover in our future trip. Let us know what we’ve missed and we’ll add it to our list. We’re definitely going back!
I grew up outside of Chicago and so know most of these sites, except for the Hemmingway home! I am amazed how much you covered. I have been back due to my daughter being a student at the University of Chicago and subsequently U of I Medical School. Our go to restaurant had been Momotaro, but you probably didn’t bother since you make gourmet Japanese cuisine at home. As a child, I wanted to move into the Museum of Science and Industry. My mother even donated to them a folio from the Chicago World Fair that showed the origins of all those museums which were built for the Fair.
Hi Judy! We wish we had more time to spend in each place but we only had a week. We can’t wait to go back and see more of the city including the surrounding areas.
Your daughter is so accomplished! You must be very proud of her.
MSI is super cool, we can spend hours looking at the train set and the dollhouse alone.
As someone who went from Oakland to Chicago in the 60s to attend Northwestern and University of Chicago, your post brought back great memories. One place you should try to go to is the largest Japanese store in the midwest, Mitsuwa in Arlington Heights. You will love the fresh sushi, the 8 restaurants in the food court and many many specialty stores. Love your cook book and recipes, As someone who also lived in Okinawa for 8 years and have traveled to Japan mainland many times, your recipes are very authentic. Best, Ben
After having been to the Mitsuwa in Edgewater, NJ multiple times, I was a little disappointed by the Chicagoland Mitsuwa. It’s probably not entirely their fault, but the shelves seemed a little bare.
Hi Ben, thank you so much for your kind comment! Oakland to Chicago to Okinawa! What an experience.
We have a Mitsuwa here in San Jose but we don’t go often. We are lucky there are a few Japanese markets near us so we can avoid the crowded ones.
Sugei ne? ^_^
So so happy you enjoyed my hometown. Chicago is a wonderful city for education, sights, food, architecture, shopping, theater, entertainment, music and different neighborhoods!…everything 😍 And you did it all on a first trip! TY for an enjoyable report❣️
Hi Deanna! It was such a great visit for our family and we left our heart there and missed it terribly after coming home. We can’t wait to go back.
I’m so glad you enjoyed your time in Chicago! Sorry about the weather… it doesn’t really stay warm here until late May-early June. The museums and architecture boat tour are great, locals like them as well! Weather permitting, I’d always recommend renting bicycles and taking them up and down the lakefront trail, it’s really beautiful (but be careful on the one big curve by the Drake Hotel). Summer has LOTS of street festivals as well, every single weekend.
We heard about the amazing summer festivals! The weather was manageable since we were prepared and dressed for it, but it was COLD! We’ll pick a better month to go next time so we can enjoy the water and lake trails.
Oh my gosh, your kids are growing up so fast! I am starting to feel old! Haha! I’m glad you all had such a nice time in Chicago!
Hi Lion, we feel old looking at them too! LOL
I love the museum of Science and Industry. Especially the U Boat. Just thinking about how claustrophobic that space is, still gives me the willies. I can’t imagine the sheer terror those sailors felt being 300ft under water and explosions going off around them. I have anxiety thinking about it and I used to be in the navy
Hi Scott, we wanted to see the inside but the tour was all sold out. Our son was so into it and what an amazing piece of history for the museum to display.
Beautiful photos and writing – although I could almost feel how cold it was! Still makes me want to go back to visit Chicago. And when did your kids get so grown up?!
Hi Alison, it was so cold so we’ll plan our trip next time after May. Our kids became teenagers over the past 2 years, we’re still getting used to it as well.
Thank you for travel blog Mr JOC and of course, Nami. Makes me want to visit Chicago again, taking in things that you did, that we missed entirely. I look forward to your next blog…the eats in Chicago, as that is what you and Mr JOC are about.
Hi Kurtis, thank you for your kind comment! We only did so many things to maximize the Go City. It was a lot of running around even though we had 5 days. Next time, we’ll take it slow and enjoy each location a bit more in depth.
What a great trip!!! So inspiring too!! Thank you for sharing all your pictures and the detail information. Never thought about visiting Chicago, but now it’s definitely on our list!!! Oh, by the way, what camera/lens did you use for this Chicago trip??
Hi Alves, we never thought about Chicago before too but it’s was so cool and really happy with the decision. People are very friendly, it’s also clean, and there’s so much to do. We used an iPhone 13 pro for all the photos.
Enjoyed the trip, Nami, especially the Frank Lloyd Wright House… and everything, really.
Hi Jenny, thank you so much for stopping by!
Thanks Nami, for taking us along with you. What a fabulous trip! Thanks to Mr.JOC we felt like we were right there with you visiting every site. Looking forward to “going along with you” on your next trip.
Hi Mayi! Thank you for stopping by! Any particular city you would be interested in?
Beautiful pictures. Thanks for sharing. What camera did you use to take the pictures?
Hi Min, all the photos were taken with an iPhone 13 pro.
What beautiful family pictures. I lived near Chicago , it’s a beautiful town with a lot of things to do. Thanks for sharing. ❤️
Hi Yeny, you’re so lucky! There’s so much to do there and such a beautiful town. We can look at the pictures of it every day.
Nice photos. Where is Misso?
Thanks Dennis! Miso was away at sleepover camp.