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 much to offer the entire family.

night view of downtown Chicago from Skydeck Chicago

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.

downtown Chicago at night

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.

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.

Water Tower Place and John Hancock Building
360 CHICAGO and view of Chicago skyline

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.

view of Chicago skyline
looking south on Mag Mile

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 Chicago River
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.

Chicago Apple store that looks like an open MacBook
boarding was by the Apple Store which looks like an half opened MacBook

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.

Rotunda at Museum of Science and Industry, Chicago

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.

transportation gallery at Museum of Science and Industry, Chicago

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.

Saieh Hall For Economics

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.

Frank Lloyd Wright Home & Studio

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.

Frank Lloyd Wright Studio
Frank Lloyd Wright Studio

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.

Ernest Hemingway Birthplace Museum

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.

piano inside Ernest Hemingway Birthplace Museum

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!

framed pictures on the wall at Ernest Hemingway Birthplace Museum

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 Art Institute of Chicago

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!

English Drawing Room of The Georgian Period miniature
doesn’t this look like a real room?
English Drawing Room of The Georgian Period miniature
it’s a miniature!

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.

Chicago Architecture display at Skydeck Chicago

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.

American Bison

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.

Cloud Gate

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!


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