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. 🙂

A great weekend in Chicago

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.

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.Weekend in Chicago - be sure to take the L

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.Ways to spend one weekend in Chicago

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!

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.

Sample the food! - best things to do in Chicago

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.Cruz Blanca - weekend in Chicago itinerary

Things to do in Chicago - tacos at Cruz Blanca

After getting our fill of homemade guacamole and tacos, we were off to our next stop, retail therapy at Michigan Ave.!

Chips and guac at Cruz Blanca - things to do in Chicago this weekend

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.

Brunch at American Girl - fun things to do in Chicago with kids

Andrew hung in there, but knowing the Lego Store was next door might have been the only thing keeping him alive (chuckle).

Things to do in Chicago with kids - American Girl StoreVisit the Lego store - things to do in downtown ChicagoThings for kids to do in Chicago - visit the Lego store.

I Spy With My Little Eye…360° Chicago

360 Chicago - top things to do in ChicagoNext 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.

Things to do in Chicago today - 360 Chicago Observation Deck.

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.


Even if you’re not doing Chicago with kids, this is awesome! The views are gorgeous, and well worth it.

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.

Art Institute of Chicago - visiting Chicago with kids.

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!

Picasso at the Art Institute of Chicago - top 10 things to do in Chicago

This was the highest on my to-do list, and it didn’t disappoint. It was fantastic!

Georges Seurat at the Art Institute of Chicago - Chicago with kids.

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!

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.

Visiting Sue the T-Rex - family activities in Chicago

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.

Visit the Field Museum during a weekend in Chicago.

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!Visiting the Field Museum - Chicago with kids.

Onward and Upward – Literally – at Skydeck Chicago

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!

Skydeck Chicago - fun things to do in Chicago this weekend.

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.Visit the Skydeck during a weekend in Chicago.

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.Ride up to the Skydeck - best things to do in Chicago.

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.Indoor things to do in Chicago - Skydeck Chicago with kids.

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.

Sit on the ledge of Skydeck in Chicago with kids.

The wait can take a few minutes, but if you’re looking for fun family activities in Chicago, give this a shot!

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.

Things to do in Chicago tonight - pizza at Giordano's.

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.

Deep dish pizza at Giordano's in Chicago things to do this weekend.

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!

Back to Reality – 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.

Things to see and do in Chicago with CityPASS

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:

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.

Spend a weekend in Chicago at the Radisson Blu Aqua downtown

Visiting Chicago with kids at the Radisson Blu Aqua downtown.

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.Spending a weekend in Chicago with kids

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.Pictures at Cloud Gate - top activities in Chicago.

Has your family been to Chicago? What are your favorite things to do?

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