Travel Destinations

A Magical Family Weekend in Chicago

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Just because you’re a family of Disney fans doesn’t mean you can only ever run away to Orlando to have a good time. Since we live in the Midwest, it’s much easier for us to travel to locations in the middle of the country, and the past weekend we did just that. Our family of four spent some time in Downtown Chicago. I used a lot of my Disney touring tips and tricks to help things go more smoothly, and to guide some of our activities and dining. I want to share some of the fun that we had, and some of the ways I apply my Disney touring knowledge to our non-Disney family vacations! I’ll cover what we did just this weekend, and then some more generic recommendations from other Chicago trips too.

Where To Stay

I don’t like recommending specific hotels because SO much can change so quickly with things like price, service, staffing and amenities. But I do have very firm ideas about the general area you should try to stay in, especially if you have shorter-legged folk in your family. Once I narrow things down to the appropriate area, then I just hunt for the best deal at a hotel with great ratings on sites like Google, Priceline, and Tripadvisor.

We always aim to stay in the Loop, as close to the north-east “corner” of that area as possible. By that I mean an ideal location for us is the corner of Michigan and Wacker, just south of the river and just west of Michigan Avenue. From this location, it’s easy to get up onto the Magnificent Mile, down onto the Riverwalk, or over to Millennium Park and all of its fun. There are also plenty of dining and shopping options nearby, theaters if you want to catch a show, and the Chicago Cultural Center, which I consider to be something of a hidden gem.

On a previous trip, we stayed at StayPineapple, which had a great theme and feel for families with young kids. But on this trip we got even luckier and stayed at the exact ideal location I mentioned above. At that corner I mentioned is LondonHouse Chicago, which is the #1 rated hotel in all of Chicago on Tripadvisor. I found an Express Deal a few weeks earlier that seemed to be “broken” (aka, was priced much lower than it should have been) and pounced on it when I cross-checked enough to feel comfortable that it would end up being LondonHouse. It was!

We booked a “blind” room (aka, no specific room type – just one that promises to fit 4 humans) for $180/night, which was already a crazy deal. The cheapest room type available directly on the LondonHouse website for our same travel dates was a double/double room for $485/night. When our room got assigned, it was actually a very large King 1 Bedroom Suite. We had SO much space in a room that was retailing for at least $579 a night. I joke that we can now never come back to Chicago. We will always be paying way more money for way less space in the future. We enjoyed it thoroughly while we could.

Shopping as a Family: Souvenirs, Budgeting and More

Chicago is ALL about shopping. And elementary-age kids love things. Even Disney satisfaction scores show that they love attractions that result in take-home items (droids, lightsabers and the like). We have lots of budgeting tricks that we utilize in the parks, and we use some of the same techniques on non-Disney trips.

For example, this weekend included stops in a lot of our recommended stores:

But each store came with its own unique rules. First, we never intend to walk into a store unless we intend on making/allowing purchases. During this trip, we had one exception to the rule. Our girls have been promised that if they read all of the chapter books for a single historical American Girl doll, they can have that doll. So that visit was used for motivation – not purchasing.

In the other shops, we set rules and/or spending limits. For example, in Primark, each girl got to pick one “nightgown” (aka, adult shirt that they can wear as a nightgown) and one shirt. Anything beyond those purchases came out of their own spending money, not ours. At It’Sugar, they got to pick some select-your-own candy to go into a parent-supervised baggie as an afternoon snack. And at the Lego store, they got to pick out a Lego set that was priced at or under $10. All of this allowed them to browse and have fun while also knowing the limits and not breaking the bank.

360 Chicago: A View from the Top

During our last family visit to Chicago, our girls were astonished by the towering view … from our 5th floor hotel room. So I knew that on this trip we needed to get higher. There are two obvious choices for that goal – Skydeck Chicago (in the Willis-formerly-Sears Tower) and 360 Chicago (in the formerly-Hancock Building). Willis is taller, but also more expensive and further out of the way compared to the rest of our itinerary. At 94 floors up, 360 Chicago would be plenty tall for our kids who were gleeful about their 5th-floor view.

There are many ticket packages available for 360 Chicago, from admission to admission + TILT (where you stand in a glass box and they tilt you toward the ground), to “sip + view” where you get a voucher for a drink from the bar, and even a skip-the-admission-line ticket.

Here’s the secret. You don’t need a skip-the-admission-line ticket. Your regular old timed ticket, if you purchase it any time before you’re on-site, will allow you to skip the admission line. Reservation holders have a separate entrance. And once you’re past admission, there is almost never any wait. We went mid-afternoon during a BUSY summer weekend, and had maybe a 2-minute wait for an elevator. Not worth paying more to skip any supposed line. But you do want to purchase in advance – that admission line was crazy-long and chaotic.

We didn’t do TILT because you have to be 42 inches tall … and because my fear of heights is manageable but not that manageable. TILT also has timed tickets, but the line for reservation holders was filling two different switchbacks and had to be at least 30 minutes long. Can’t really recommend that unless you just feel like you need a “thrill”. The views are plenty stunning from all around the 94th floor. Our family spent about 30 minutes wander and taking pictures and absorbing everything there was to see.

Pixar Putt

We are the core demographic for Pixar Putt. Our family loves to mini-golf, and we obviously love Disney. Still, I was skeptical. A family-pack of tickets for the weekend we were visiting was well over $100. We can play fun mini-golf for a lot less. But I had to try it out … for science.

Pixar Putt is a seasonal installation at Navy Pier during the summer (and in several other cities during various times of year). There are 18 holes and each is themed to a different Pixar movie. Now, I’ll fully admit that the theming is next-level. Only a couple of holes felt really phoned in. But on the whole (it’s a mini golf pun), there was a lot of careful attention paid to having designs and functionality that matched the movies. You had to go over a marigold bridge for Coco and down a piano for Soul. On hole 18, your ball travels into the air in the Up house before falling down Paradise Falls. It was all delightful and fun.

That being said, there are certainly some downsides – price being the major one. Am I glad we did it once? Yes. Everything on Navy Pier is pretty wildly expensive, so it was worth the time and money for us. But I wouldn’t do it again.

Most of the holes were not designed to consider space for standing. This resulted in many awkward shots, and eventually cause our 4 year old to tumble off the side and get a pretty bad scrape to her leg (which all of the attendants stood around watching us try to address and clean up without helping at all). And all of the holes are subjected to the elements throughout the summer, so many of them were pretty worn-down and worn-out by the time we played. This led to golf balls meandering back to where they started from because of uneven surfaces, major decorative elements fallen down or missing, and more.

Still – we got a lot of cute pictures, and even with the big knee boo-boo, our girls rated it as one of their favorite activities of the weekend.

Ed Debevic’s: A 50’s Prime Time Cafe Comparison

I’m pretty sure Ed Debevic’s qualifies as a Chicago classic. I distinctly remember eating there when I was younger, and I even have a mini souvenir sundae glass that is now at least 2 decades old. Vintage! And since I already have 50s Prime Time Cafe reservations for later this year, I wanted to see how my kids would react to dinner and service all being an act.

They LOVED it. Ate it up. Participated in the fun and laughed at all of the shenanigans. Servers at Ed Debevic’s are mean. Rude. Silly. And they are great at their job. I don’t know how they keep the energy up. If you’ve been to Prime Time Cafe, think about that kind of interaction, but dialed up to a level of obnoxious even above what you might experience at Whispering Canyon Cafe. It’s LOUD thanks to the in-house DJ. There is lots of yelling. Your servers will even dance on elevated platforms between the tables.

But it’s so much fun. The food is decent too – my burger was easily the best I’ve had in several months, and our girls devoured their kids meals. You’re not here for fancy dining, but what they offer is made well and served up quickly.

If your kids are shy, or you don’t like forced funny interactions with servers, this is not the place for you. But if you want something fun and different, give Ed’s a try!

Chef Art Smith’s Reunion: This Is No Homecomin’

Chef Art Smith’s Homecomin’ in Disney Springs is perennially well-rated in our dining satisfaction surveys. It’s not winning any awards from readers, but it’s popular and generally has positive reviews. I decided to try out the Chicago equivalent during our trip, and got dinner reservations on a Sunday at Reunion, which is located on the Navy Pier.

Things started out well – the weather was beautiful, and all of the doors were opened up to the outside. We were seated as soon as we walked up and checked in for our reservation. And we even got complimentary “shots” of lemonade when they brought us our waters.

After that, everything was a bit of a mixed bag. I tried ordering the Brown Butter Old-Fashioned, but they were out of some critical component, and could not make any old-fashioned. I could have gotten up and left after just that news. But instead I opted for a Southern Sour made with the same bourbon. It was decent. My husband tried to order a no-jito. 2 minutes later our server came back and said they were also out of mint. So he just defaulted to a full-sized lemonade instead.

We ordered the Goat Cheese Buttermilk Biscuits as an appetizer. The portions were large, and the flavor was phenomenal, but the texture was off. If I was Paul Hollywood, I would be complaining about the amount of goat cheese resulting in no discernable crumb. For a biscuit, that’s a major no-no. And the bottoms of each biscuits were all hard and almost sticky. Very odd, but I’ll give them a pass because they were so tasty.

Kids meals at Reunion are expensive. $12 each and no included drink. That’s more expensive than Homecomin’, for what appears to be the exact same meals in both locations. One girl got a cheeseburger (she ate less of this burger than her Ed Debevic’s burger), and the other got chicken fingers, which was the much superior choice. Both spent more stomach space on their mac than on their main.

My husband ordered the salmon and thought it was great. For the price, it was certainly a smaller portion and he totally cleaned his plate. I ordered the fried chicken sandwich, and requested no pickles. The pickles arrived intact, desecrating my bun (pickle-haters know what I mean). I took off the fried chicken and tried to eat the tomatoes too – but they were disappointingly a shade of pink that was very close to white, and one had inedible core in the middle. I may have gotten a bad piece of fried chicken, but it was very tough. And my sandwich came with a gigantic bowl of fries … which had no salt and were all soggy.

After the drink dilemma and the unimpressive entrees, we cut our losses and didn’t even order dessert. I can’t recommend a meal at Reunion to anyone – unless you want to gamble on ingredient availability and quality.

Other Chicago Recommendations for Families

We’ve been to Chicago as a family twice now, and I grew up going at least once a year with my family. If you’ve got young-ish kids, here’s a slightly more robust list of recommendations, in no particular order:

  • I lied about the order. But only for this top tip. Maggie Daley Park is the hidden gem of Downtown Chicago. It’s got mini-golf and open spaces to hang out, and climbing walls, and all kinds of other activities. But mostly it has a play garden. A well-maintained, generally shade-covered, mostly-enclosed play garden. There are several different areas like a splash pad, two different types of swings, a lighthouse slide, a large boat, several smaller boats, an “enchanted forest” and a whole complex of slides. We spend hours here on every trip, and it’s my number one recommendation for kids.
  • You’ll find plenty of food options for even the pickiest eaters. But if you need some special treats for the sake of bribery or buoying tired legs, we really really love Stan’s Donuts (multiple locations) and Molly’s Cupcakes (also multiple locations). The Ghiradelli locations on Michigan Avenue can also be a lot of fun.
  • The Chicago Cultural Center is another spot that doesn’t make a lot of “with kids” lists, but I consider to be a diamond in the rough. The architecture inside is amazing, and there are often whole ballrooms empty where you can blast “We Don’t Talk About Bruno” on your phone while you dance around wildly. Not that we’ve ever done such shenanigans.
  • The exterior of Tribune Tower (very conveniently located near Michigan Avenue and the river) has its own sort of seek and find game, with rocks from every state and many historic sites integrated into its stonework. Our girls love pointing out what they find and learning about where it’s from. Educational and entertaining. I’m here for it.
  • Shedd Aquarium is at least a half-day adventure that is enjoyable for even the littlest of littles. It does get crowded, so approach it with a touring strategy. Rope drop (line up before it opens), and go immediately to the lowest level. You’ll have the place to yourselves while everyone else explores the first things they happen upon.
  • Museum of Science and Industry and Field Museum are also both stunning and well worth the price of admission. MSI is good for the roughly elementary aged set, although it offers a LOT of tempting upcharges that can quickly get parents in trouble. Field Museum could be good for elementary and middle schoolers depending on how you approach it and your kids’ interests.
  • The Riverwalk and various boat cruises help show a different side to the city and can help kids learn about some history and architecture in a fun and not-boring way. We haven’t done a boat tour yet with our girls, but they very much enjoyed walking along the river during a weekend where almost every spot was bustling with something to look at.
  • If you’ve got kids that like to shop, stick to State Street rather than Michigan Avenue. Everything is cheaper, and you won’t have to mortgage your house if they break something in one of the State Street shops. The exceptions to this rule are mostly the Lego store and the American Girl store, both located in Water Tower Place.

Do you have any questions about spending time in Chicago, or other suggestions for visitors? Share them in the comments! And please let us know if there are other travel destinations you’d like us to post about in the future.

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Becky Gandillon

Becky Gandillon was trained in biomedical engineering, but is now a full-time data and analytics nerd. She loves problem solving and travelling. She and her husband, Jeff, live in St. Louis with their two daughters and they have Disney family movie night every Saturday. You can follow her on LinkedIn: or instagram @raisingminniemes

4 thoughts on “A Magical Family Weekend in Chicago

  • We love Chicago! It’s a very walkable city, and the food is fantastic.

    • Yes! Us too. Since it’s just a few hours from home, we try to visit once a year.

  • Thanks for this post! I have been to Chicago several times with friends, as several friends from college live or have lived there. We have been talking about taking DS9 this fall.

  • Look at Groupon for the yearly family pass for MSI. It is usually a great price and includes parking, discounts, and some free experiences.


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