Update: This post was originally published in 2018, but we've since visited this great city a few more times. We're adding some more kid-friendly activities, so if you've got more time, try adding these other activities to your weekend in Chicago itinerary.
As you may know by now, when we land in a destination, we hit the ground running. With school schedules often dictating our travel schedule, we aim to see as much as we can in the time that we have. We travel with a certain….intensity. 🙂
When we were looking for places to visit over Labor Day weekend, we tried to focus on a destination where we could pack in a lot of activities in a short amount of time. A weekend in Chicago won out, so armed with our CityPASS booklets, we set out to dominate the Windy City in just 48 hours.
Spending a great weekend in Chicago with kids
1.) Enjoy some local cuisine (mmmmm tacos)
2.) Michigan Ave. and Water Tower Place - home of Lego and American Girl
3.) 360° Chicago in the John Hancock Building
4.) Art Institute of Chicago
5.) The Field Museum of Natural History
6.) Skydeck Chicago in Willis Tower
7.) Deep dish pizza at Giordano's
Other activities for a weekend in Chicago with kids
8.) The Shedd Aquarium
9.) Pullman National Monument
10.) Take a Chicago Architecture Cruise
11.) Visit Navy Pier
Using a Chicago CityPASS
Rockin' a weekend in Chicago with CityPASS
Where to stay in Chicago with kids
Radisson Blu Aqua Downtown - perfect for a weekend in Chicago
Getting to Chicago
Disclosure: Please note that this post contains affiliate links, meaning we earn a commission if you click through and make a purchase. There is no additional cost to you, and it helps to support this site. Also know that CityPASS provided us with 2 coupon booklets. We purchased the other 2 for the kids. All opinions are our own. Thanks for you support!
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A Weekend in Chicago with Kids
First Things First
We arrived in Chicago in the afternoon and took the train from the O’Hare International to downtown. This is a great feature about Chicago – cheap and easy public transit from the airport.
After arriving downtown, we checked in to the Radisson Blu Aqua Chicago which is a fun, chic hotel right in the heart of the action. We dropped our bags, and it was off to dinner. We decided to try Rick Bayless’ new place, Cruz Blanca.
Want to get a sense of Chicago ASAP? Book a Hop on-Hop off bus tour!
Consider booking a tour with Big Bus to hit the major sites when you arrive and get a feel for the city. It’s a great way to get oriented, get some air, and rest tired feet. Book ahead to save!
1.) Sample the local fare
Rick Bayless: A National Treasure (and hometown culinary hero for Okies!)
Ok, we’re a little biased here, but for those who aren’t familiar, Rick Bayless is a Chicago chef and restaurateur known for his Mexican cuisine. You may recognize his packaged food brand Frontera (named after his Frontera Grill restaurant in Chicago) which is showing up in grocery stores everywhere, or you might know him as one of Bravo’s Top Chef winners.
Carrie and I dined at his upscale restaurant Topolobampo during an earlier Chicago visit, and it was amazing.
We were introduced to his cooking from his show, Mexico One Plate at a Time, which airs on public television. We then discovered his cookbooks. We own several now and love everything in them. Chef Bayless is originally from Oklahoma City, and we desperately wish he’d open a place closer to home…
Cruz Blanca is one of his newer establishments (only four months old at the time of our visit), and it was fantastic! Street tacos, craft beer, authentic margaritas, and comfortable surroundings are what it’s about, and like always, it’s delicious. With details like local, fresh ingredients and craft beers being brewed right on the premises, Cruz Blanca is a winner.
After getting our fill of homemade guacamole and tacos, we were off to our next stop, retail therapy at Michigan Ave.!
2.) Checking off the Kids’ Bucket List at American Girl and Lego
Two ‘must-see’ places for Andrew and Cadence in Chicago were the American Girl flagship store and the Lego Store. Fortunately, they are right next door to each other inside Water Tower Place.
Related: We booked an excellent brunch at the American Girl Cafe for Sunday morning and you can read all about it here.
Andrew hung in there, but knowing the Lego Store was next door might have been the only thing keeping him alive (chuckle).
3.) 360° Chicago
Next up were the incredible views from 360 Chicago in the John Hancock Building, and is one of the best things to do in Chicago. The pictures don’t really do it justice.
I actually preferred the views here over the ones at Skydeck Chicago because you’re near the shore of Lake Michigan.
We visited in the morning after our brunch (they are across the street from each other) and breezed right through the VIP entry line. CityPASS rocks in this regard, because when we popped in the night before, the regular line was 2 hours long.
Ouch!
Even if you’re not doing Chicago with kids, this is awesome! The views are gorgeous, and well worth it.
4.) Art Institute of Chicago – Bueller? Bueller?
Next on the the list was a visit to Art Institute Chicago. You may recognize some of the pieces from the movie Ferris Bueller’s Day Off.
The museum is home to a dizzying array of Modern and Impressionist art (among others). In fact, they have the finest collection of Impressionist works outside of Paris. It’s easily one of the top 10 things to do in Chicago and highly recommended.
Related: If you want to explore Paris with kids, check out our post!
This was the highest on my to-do list, and it didn’t disappoint. It was fantastic!
After all this, a saner family than us might have turned in for the day.
Not us! We were just getting warmed up! Keep reading for more fun things to do in Chicago!
5.) The Field Museum – a Bone-i-fied Chicago Experience!
The first thing you may notice when you walk into the Field Museum is their rock star Sue. Sue is a T-Rex, and she’s pretty special. You see, Sue is the most complete, largest, and best preserved T-Rex skeleton ever found.
As far as family activities in Chicago go, the Field Museum is one of the best! Other awesome things to discover here are tons of animals, birds, mummies, and even a special exhibit of Chinese terracotta warriors.
The extensive collection of dinosaur skeletons is really impressive, and we all had fun reading about them.
We were able to spend ~3 hours at the museum which was just enough to (briefly) see almost everything. We would like to have stayed longer, but alas, there’s always more of Chicago to see!
6.) Skydeck Chicago – Onward and Upward – Literally.
We took an Uber over to Skydeck Chicago next. We were a little deflated when we drove up and saw a line of people literally wrapping around the bottom of the Willis Tower, but with CityPASSes in hand, we weren’t deterred!
We ended up waiting around 30-45 minutes to get to the top. That was just a drop in the bucket compared to the 2.5 hour wait non-CityPASS holders had to endure.
The ride to the top is interesting because they have TV monitors in the elevators that tell you how high you are and what buildings and monuments around the globe are that height. It’s fun to see in real-time how high you are actually going.
Of course, you’re rewarded with amazing views at the top and the whole family ‘ooohed and ahhhed’ as we walked around the observation deck.
Skydeck Chicago has a unique attraction that lets you walk out into a clear Plexiglas box and look straight down to the street. It took my breath away a little bit when I stepped out.
The wait can take a few minutes, but if you’re looking for fun family activities in Chicago, give this a shot!
7.) Deep Dish Pizza at Giordano’s – “MMM Good We Crust”
This play on words hangs from the ceiling of Giordano’s Pizza across the street from the Willis Tower and Skydeck Chicago. Of course, no trip to the Windy City is complete without sampling some good deep-dish, and Giordano’s hit the spot. The deep dish pizza in Chicago is legendary, so this was absolutely one of our top things to do in Chicago during our visit.
The wait was long, so they had us put in our order while we waited for a table. We didn’t mind much, because we were all pretty exhausted. It gave us a chance to reflect on our epic day in Chicago and look at some of the great pictures we had taken.
The pizza was delicious! Obviously there are many places you can get a deep dish pie in Chicago, but we wouldn’t hesitate recommending Giordano’s. Our decision was based mostly on proximity to Skydeck Chicago and other reviews I had read, but it was a great choice!
Other activities for a weekend in Chicago with kids
8.) The Shedd Aquarium
The Shedd Aquarium is part of the CityPASS Chicago booklet and is really worth visiting if you have the time. We couldn’t make it during our first trip, but have since visited and we loved it.
The star attractions are the beluga whales and you’ll want to attend the short show in the theater to learn more about these amazing animals.
Although the part of the aquarium was undergoing refurbishment during our visit, we still were able to spend a few hours exploring the exhibits. The amount of sea life is remarkable and kids will love it – especially the younger ones.
The Shedd Aquarium is located right next door to the Field Museum of Natural History and is very easy to get to, especially if you are staying in downtown. If you are staying along Michigan Ave, you may even be able to walk.
9.) Pullman National Monument
For fans of National Park Service Sites, be sure to check out the Pullman National Monument. This Monument and State Historic Park tells the story of George Pullman and his industrial town that was built to facilitate the manufacturing of his luxury sleeper cars.
This unique National Park is both a museum but also a partially restored community. Visitors can visit the Pullman Palace Car Works factory and administration building, the Hotel Florence, Arcade Park, and the Greenstone Church among others.
The monument is just a short ride from downtown Chicago to the south and is open year round. Admission is free.
Be sure to check out the Illinois National Park here. Indiana Dunes National Park is also nearby.
10.) Chicago Architecture Cruise
Our most recent to Chicago was over St. Patrick’s Day, and while I wouldn’t recommended bringing the younger kids to town this weekend, it is a GREAT time to take a cruise on the Chicago River. 
Chicago has some of the best architecture in the world. From modern to neo-classical to Art Deco, there’s plenty to see here. Even if it’s cold, bundle up and enjoy the views. Highly recommended!
11.) Visit Navy Pier
Chicago’s Navy Pier offers great views of the lake and is a fun way to spend a sunny afternoon in Chicago. 
Enjoy a ride on the wheel or a good Chicago dog for lunch and a cruise on the lake.
You might also enjoy a visit to the Chicago Children’s Museum. Whatever you decide, Navy Pier is a great way to get some sunshine and some fresh air, albeit a little windy.
Wrapping Up Our Weekend in Chicago
Because of a mid-morning flight back home, we weren’t able to visit the last destination on our CityPASS booklet (which annoys the frugal part of me), but we felt like we got some really great value. We crammed a lot of Chicago into just a small window, and CityPASS definitely helped us with that. VIP access was a lifesaver.
Putting It All Together
CityPASS Chicago – like a coupon book for your bucket list!
CityPASS was great for our family because it offered us just the right amount of activities at a great discount. In fact, purchasing our tickets through CityPASS knocked down the cost by over half. They’ve put together the best things to do in Chicago with kids, all in a handy booklet.
Disclosure: We were given 2 booklets, and we bought the other two ourselves. The views and opinions are, as always, our own.
Another great perk of purchasing a CityPASS booklet was the fact the you get expedited entry into the attractions. We didn’t realize how big of a deal this was until we arrived at some of the more popular attractions like Skydeck Chicago, and the normal standby line was over 2 hours long.
CityPASS got us to the top in about a half hour. Bam!
So What Do You Get?
The best family activities in Chicago! Here’s the rundown:
- VIP Entry to the Shedd Aquarium
- Fast Pass Entry to Skydeck Chicago at the Willis Tower
- VIP Entry to the Field Museum of Natural History
- VIP Entry to the Museum of Science and Industry – OR – Express entry to 360 Chicago
- VIP Entry to Adler Planetarium – OR – Fast Pass Entry to Art Institute Chicago
In addition to Chicago, CityPASS destinations include Dallas, Atlanta, Boston, Philadelphia, San Francisco, Houston, New York, Seattle, Southern California, Tampa Bay, and Toronto. We were worried that we wouldn’t be able to see everything we wanted to, but we were really pleased with how our trip turned out. CityPASS really made our short weekend in Chicago with kids achievable, and we wouldn’t hesitate to purchase another for a different city we were visiting.
Note: The Chicago Big Bus tour makes stops at all of these places (and many more!), so consider using them to get around if you don’t have a vehicle or don’t want to taxi or Uber. It makes a great combo with the Chicago CityPASS!
Other Trip Details
Our two nights at the Radisson Blu Aqua were great. It was comfortable, clean, and the kids enjoyed the pools and hot tub. Like I said earlier, it’s a chic hotel with modern, funky decor that fits perfectly with their branding.
You can even see a bit of the fireworks at the Navy Pier at night out on the patio, or if you have a room on a higher floor.
It’s very close to the ‘Bean’ and just a short walk to Michigan Ave and shopping at the Magnificent Mile. It’s also just a short walk to catch the “L”. We also used Uber to quickly get around to various destinations.
Getting to Chicago
O’Hare (ORD) and Midway (MDW) airports serve a large number of cities making Chicago really easy to get to. I booked our flights on points (BA flying on AA), but many times cheap United, American, or Southwest fares make it worthwhile to just pay with cash.
We fell in love with this city and wish we could’ve had another week there (at least) to explore. However, if you’ve only got a weekend in Chicago, you can see and do a lot! We hope this post gave you some ideas.
Has your family been to Chicago? What are your favorite things to do?
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