I’d been to the Windy City six years ago. But fast forward to this spring as I was adding to our family travel bucket list and started drawing up our ideal Chicago with kids itinerary, and HOLY HECK — the list was long. Between best-in-class museums and fun kids’ restaurants to plays in Chicago that rival Broadway (that’s accessible and affordable to boot), there are so many kid-friendly things to do in Chicago.
That two-day, solo trip to Chicago back in 2013 for a conference really didn’t count. Yeah, I zipped out to power-shop the Magnificent Mile and I scarfed down some deep-dish pizza (because stereotypes), but I could barely say I’d been there.
By the time my four-day visit with Miss Q was finished, we couldn’t wait to tell Big B and The K Man all the reasons why we need to go back together (and soon). In fact, we started GPSing the drive time from Toronto to Chicago and plotting our return on the drive home from the airport.
We didn’t even talk about leaving the kids at home for round two, because, yeah, Chicago with kids is that awesome.
Planning your family vacation in Chicago
There’s a lot to cover when you’re planning the perfect Chicago family vacation — so get ready! Let me start with an overview of what you’ll find in this post:
- Things for kids to do in Chicago
- Plays in Chicago (the Chicago performing arts scene, kids’ theatre in Chicago and why you might want to pick up Chicago show tickets vs. NYC/Broadway)
- Best hotels in Chicago for families
- Kid-friendly restaurants in Chicago
- The Chicago CityPASS
- Exploring Chicago with kids — how to get around
And while Chicago may be known for its sports franchises and dogs (hot dogs, that is), there is so much more to this great place with something for every member of the family.
Here are just a few awesome things to do in Chicago with kids…
Look, in four days, I feel like we barely scratched the surface. To me, Chicago is one of those great cities — like London, San Diego, Manhattan and Toronto — to which you could return year after year and still find new things to explore.
If you’re looking for fun things to do with kids in Toronto, consider Medieval Times, Harbourfront Centre or the annual Santa Claus Parade.
There are enough family activities in Chicago to fill any number of days — whether you’re planning a quick peek during a stop-over or a week-long, deep-dive into Illinois’ biggest city — or any kind of themed trip, like an arts and theatre-centred visit.
Let me start with the free things to do in Chicago with kids, since that’s part of what makes it an affordable vacation option…
Just look around
There are so many art installations around the city and murals on different building walls, that you could spend days on end just wandering and looking up.
Don’t discount the importance of having nowhere to go on vacation. Some of our favourite memories from this trip to Chicago are those that weren’t planned and didn’t cost a dime.
Millennium Park & The Bean
No Chicago family vacation would be complete without a visit to award-winning Millennium Park. We originally didn’t even have plans to see the park in our itinerary, but after reading about “The Bean” in our airplane’s in-flight magazine, we knew we had to find it.
Getting to Millennium Park is easy, but with four million visitors each year, I’d personally avoid trying to find parking for a rental car. We walked over after going to the Willis Tower (more on that below), and simply asked people on the street for directions — Chicagoans are about the nicest, friendliest folks around and were only too happy to give us directions everywhere we went.
As you approach the park, the city landscape goes quickly from urban sprawl to welcoming green space.
What was once an industrial wasteland — owned from the 1800s into the late-’90s by the Illinois Central Railroad — is now a massive 24.5-acre town square, with digitally interactive water features, spectacular gardens and more art than you’ll be able to take in even if you spend several hours wandering around.
The top three things you need to see in Millennium Park are:
1. The Crown Fountain.
Catalan artist Jaume Plensa designed a stunning pair of 50-foot glass block towers, which are set in black granite from Zimbabwe, and create a plaza-style public square that doubles as the most beautiful, interesting splash pad you’ve ever seen. There are many kids running from one tower to the next, barefoot — splashing and playing in the art. Each tower shows LED-enabled videos that change every few minutes, as water beautifully cascades down all four sides. While we were there, the videos were of local residents. Stay long enough, and you’ll see how interactive it is, too, with certain faces “spitting” water out at people below — a welcome reprieve if you’re in Chicago with kids who may not be able to face the searing summer heat for long.
Pro Tip: If you’re arriving from Michigan Avenue, The Crown Fountain — which operates from May through October — is an ideal place to start your Millennum Park self-guided tour. Here’s a map.
2. The Bean.
Created and named “Cloud Gate” by artist Anish Kapoor, locals have dubbed this incredible installation art piece The Bean with good reason. If you’ve ever seen Elsa Peretti’s silver bean jewelry at Tiffany & Co., it’s very much a blown-up version of it. What makes The Bean super impressive, however, is that despite its very large size (at 33′ x 66′ x 42′ around), there isn’t a single visible seam. Made up of 168 stainless steel plates, creating that seamless exterior alone was a feat. We walked around The Bean in its entirety — including underneath its arch — running our fingers along the polished steel…and it’s perfect, everywhere. It’s a busy spot, so expect to have strangers in your photos — but the upside is that there are plenty of people available to take your family’s picture! Note that if you want a shot of yourselves with Cloud Gate and no tourists, you’ll probably have to arrive at dawn.
3. The Millennium Park Great Lawn.
It’s a stadium. A concert venue. A grassy playground. An outdoor yoga studio. A public art space. And more. Keep walking past The Bean after you get to the park from Michigan Avenue to find the Great Lawn, which features an architectural wonder all on its own: The Pritzker Pavilion. Designed by world-renowned (cough, cough, Canadian-born) architect Frank Gehry, this 120-foot-high structure is part art, part function.
The Magnificent Mile & Water Tower Place
Chicago’s famed Magnificent Mile is home to the city’s largest shopping district. While it’s technically free to walk The Mag Mile, don’t be surprised if you’re tempted to do more than just a little window shopping along the way. It’s as upscale as NYC’s Fifth Avenue with brands like Burberry, Harry Winston and Armani dotting each side of the road, but there are also “high street” stores for we commoners.
Look for the multi-floor NikeLab store, which has some of the coolest athleisure-wear and footwear I’ve seen outside of the UK, the new Roots concept store — currently the biggest Roots in the world (which seems largely unfair since it should belong in Canada!), and the Cubs Team Store at 668 N Michigan Ave (look up — it’s on the second floor), where you can nab some official Cubs gear for souvenirs.
Water Tower Place is, predictably, near the Chicago Water Tower. It’s a 74-storey mixed-use skyscraper — eight floors of which are shopping, restaurants and entertainment.
The two-floor American Girl flagship store lives here. And even for a girl like Miss Q who’s been a bit less enamoured with her American Girl dolls in the past year, it was a WOWer. Because when you walk into this store, it’s more like walking into a high-end carnival with something to look at in every direction — one attraction after the next. If your little one brings along his or her doll, there’s a doll hair salon, spa (I kid you not) and ear-piercing studio (for your kid AND her doll!); a cafe (I think they even have special doll seating) serving brunch, lunch afternoon tea and dinner; and a number of events every week.
The LEGO Store in Water Tower Place is a smaller, but no less awesome, version of the one in Disney Springs, with life-size LEGO characters throughout — including the entire LEGO Friends entourage surrounding a bench just outside the store, perfect for photo moments.
The Art of Dr Seuss Collection is geared more toward nostalgic parents looking for collectable, Seussical art.
Unicorn World by Lola & The Boys is a sequin-filled, unicorn-y heaven that’s a must-see if you’re in Chicago with kids who are part of the ongoing unicorn craze. But heaven comes with a price and you can expect to pay big bucks for any of the flippable-sequin-emblazoned jackets that your wee princess will no doubt bee-line for upon entry. If you have “the talk” (we.are.just.looking) before heading in, it’s worth it just for the colourful, dream-worthy whimsy you’ll find inside.
One of the final FREE family activities in Chicago we enjoyed was Navy Pier.
Originally completed in 1916, and re-opened in 1995, this huge waterfront attraction is a joy to discover. Give yourself several hours and wear comfortable, sturdy running shoes. It’s one of the most stroller-friendly and wheelchair-accessible attractions in Chicago, and home to some of the city’s key arts and cultural wonders. Not to mention its 3,300-foot-long pier!
You must, must, MUST visit the Crystal Gardens — a one-acre, indoor botanical garden that’s free to visit and so tropical you’ll feel instantly transported to a lush tropical land like Hawaii.
Pro Tip: Visit Navy Pier on a Tuesday from June 11 to September 3 for a GINORMOUS list of great deals.
Now onto the pay-to-play things to do at Navy Pier…
The Centennial Wheel
An iconic part of the Chicago skyline that reaches heights of almost 200 feet, The Centennial Wheel has enclosed gondolas — like the London Eye or Montreal’s La Grand Roue — so it operates year-round, keeping guests warm in cooler weather and cool in warmer weather.
The city views are outstanding, and it’s also one of the best ways to see Lake Michigan while staying on land. Your group will be given its own private gondola, so you can ogle the landscape in peace.
It took a lot of convincing for me to get Miss Q to agree to go on this speedboat adventure with me. She was worried it would be too fast. Mistakenly, she really enjoyed the speed but didn’t particularly like getting pummeled with lake water over and over — at sundown when the air was already cool, no less.
Although you’ll probably get at least a little wet no matter where you sit, the back rows and the seats on the outside will be the wettest. I mean, we were DRENCHED. That said, I’d do it again in a heartbeat — just mid-afternoon in the hottest months, please.
Our one-hour “cruise” was an awesome way to see Navy Pier from the water, and get a glimpse of the incredible Chicago architecture along the waterfront. It’s fully guided, and the host did a fantastic job of providing us with some city history and a bit of the inside scoop on the many buildings we floated past.
Seadog Cruises also offers longer, 75-minute architecture tours by boat, which I have heard from several people is one of their favourite things to do in Chicago. I don’t know if I’d do it on a follow-up trip to Chicago with kids, but I’m definitely going to do it when I have more time.
There’s also a Children’s Museum in the Navy Pier Pavilion, which is reportedly one of the best places for kids in Chicago. We simply ran out of time at Navy Pier and only managed to pop our heads into the vibrantly coloured gift shop. I asked staff to describe the museum, and they said it’s three floors of exhibits and hands-on activities that focusing on reading, science, math, and the visual and performing arts. Sounded so fun!
The Field Museum
This has got to be one of the most kid-friendly things to do in Chicago. I liken The Field Museum — for those of you who’ve museum-hopped in Toronto and Ottawa — to the Canadian Museum of Nature, ROM and Science Centre, combined.
We spent about four or five hours here and definitely didn’t hit every corner of the place.
Originally built to house the biological and anthropological collections assembled for the World’s Columbian Expo of 1893, The Field Museum’s collection now has a mind-boggling 24 million objects, some dating back as much as 4.6 billion years.
We went in search of everything from ancient mummies to the most complete T-Rex fossil in the world (they named her Sue). We walked through an exhibit devoted to an African country that showed us how people live and work there. We shrunk down to 1/100 of our size and explored what’s going on in the soil beneath our feet. We learned about Maximo the Dinosaur in The Field Museum’s huge 3D movie theatre. And Miss Q had a 2.5-inch cockroach crawl all over her hand, with the help of a bug expert. (Ew.)
One of the coolest things about this museum is that there are several labs where real scientists are working!
Our visit coincided with the Wildlife Photographer of the Year temporary exhibit, which we absolutely loved. Kids as young as eight — Miss Q’s age — had their award-winning nature photos on display. So much talent.
The next time we go to Chicago, we’re going to carve out six to eight hours just for The Field Museum and take a much bigger bite out of it.
Pro Tip: Every Wednesdsay from August 14 to November 13, 2019, admission is free.
Art Institute of Chicago
This was another huge hit! And another kid-friendly Chicago attraction that deserved more than the few hours we could devote to it.
The Art Institute of Chicago — which is just a block or two away from Millennium Park — offers free admission for kids under 14 and Chicago teens under 18, making it a cost-friendly part of any Chicago family vacation. In fact, if you decide to take your littles only to the Ryan Learning Center, admission is always free for everyone (adults included).
I recommend starting your Art Institute experience at the Ryan Learning Center if your kids are in the four to 12 age range. Because here, you’ll be able to access JourneyMaker. This digitally interactive map helps your children choose their own adventures, essentially customizing your family’s museum tour.
With themes like superheroes, time travel and strange beasts, there are eight different storylines that JourneyMaker uses to personalize your gallery experience — putting your kid in the driver’s seat. Simply sit down at one of the touchscreens, and follow the directions. Once your child goes through the JourneyMaker process, a print-out booklet is prepared in minutes (just ask a staffer to help you fold it properly — it’s tricky).
Borrow a pencil and start exploring. Your JourneyMaker has mapped out an efficient route to find the artwork, sculpture or historical artifacts that caught your child’s eye. The booklet also has different questions and activities to look at and respond to art together as a family.
There are thousands of possible journey combinations, so you could come back a dozen more times and the Art Institute would be a completely different experience.
Miss Q’s JourneyMaker took us from impressionist art to Hindu headdresses and Warhol to Byzantine goddesses.
Pro Tip: Only the ground floor connects to each series of buildings that makes up the gargantuan series of galleries that is the Art Institute, so don’t be afraid to stop and ask for directions if you find yourself unable to follow the map. It’s very likely that you’ll need to descend to the main level and change buildings before going back up to the area you were trying to find.
The Ledge at the Willis Tower
The Ledge is part of the Skydeck on the 103rd floor of Willis Tower. It’s a series of four glass balconies that extend four feet outside the building itself, making you feel like you’re suspended in mid-air. It’s a neat experience and one that differs from, say, the glass floor at the CN Tower in Toronto, because of the way it’s built.
I strongly recommend getting to the Willis Tower by 9 a.m. There was already a line outside when we got there about 9:10 a.m. Once inside, head to The Ledge first because you can do the rest of the Skydeck afterwards without worrying about another line that will only continue to build as more throngs of tourists pour in.
Offering stunning panoramic views — that span up to four states! — there’s also a lot of interesting Chicago trivia in murals all around the Skydeck.
Art on theMART
If you’re in search of art and culture in Chicago like we were, Art on theMART is super cool! The longest-running and largest digital art projection in the world, it’s a series of digital art projected across 2.5 acres of theMART’s exterior river-façade. Local and international works are on display and freely accessible as public art with no branding.
Stand on the bridge, or head down to the Riverwalk area where those in-the-know have chairs and blankets set up to take it all in.
If you have data available on your smartphone, you can also listen along to exlusive audio (there’s a “play” button on the home page).
Projections begin about 15-30 minutes after sunset — running seven days a week from May 13 to September 22 (in 2019) for the next 30 years minimum! Since this is a later-evening activity, you’ll want to be sure that if you’re visiting Chicago with kids who need to be in bed long before sundown that you plan this for a kid-free vacay.
I know I’ve probably left out a pile of kid-friendly activities in Chicago that locals would tell you are “can’t-miss,” but we jam-packed our days and squeezed in as much as we could to report back and provide you with our best kid-approved fun for those of you heading to Chicago with kids.
Plays in Chicago & how it stacks up to Broadway
I’m just going to kick off this section with a quick story about Hamilton — the Broadway sensation that has since made it to London and Chicago, coming to Toronto in 2020.
It took me three years to get through the lottery process to score tickets to Hamilton on Broadway. My friends and I built an entire NYC itinerary around those tickets, spending thousands between airfare, hotel, meals and other fun NYC activities to round out our visit.
Heading to NYC with kids? This Greenwich Village cupcake tour will hit the spot!
Well, we get all the way to New York — those prized Hamilton tickets in-hand, prime orchestra seats that rang in at US$250 a pop — and arrive at the theatre to pure chaos. It was the night of the 2019 NYC blackout. OF ALL NIGHTS.
And, just like that — POOF — the show was cancelled. Our show. Our three-years-in-the-making show. Done.
I mention this story because if you’ve been trying as hard as I was to get Hamilton tickets for Broadway, might I suggest you simply redirect your attention and focus it on Chicago? Because:
(a) Chicago show tickets are far, far easier to procure (you can probably pick up a great pair less than a couple of weeks ahead of time)
(b) tickets are less expensive (our centre orchestra seats were US$185 and better than the ones I had for Broadway)
(c) the production is still going to blow you away (which I can write with full confidence, because I saw the West End production last summer), and
(d) the Chicago theater district is just as vibrant as Broadway.
Plays in Chicago are world-class like London and NY. Broadway in Chicago IS A THING, people.
And Hamilton certainly isn’t the only show on stage. Right now, you can also see Cats, Come From Away, Phantom of the Opera, Mean Girls and more.
Hamilton: The Exhibition
I need to give a massive shout-out to Hamilton: The Exhibition. Although it’s not a play itself, it was instrumental in framing the context of Alexander Hamilton’s story for Miss Q before I took her to the musical.
Tucked away in a converted warehouse that feels pretty off-the-grid — you can drive or UBER there easily, but there are also free shuttles to and from the Exhibition from both the Shedd Aquarium and Adler Planetarium — Hamilton’s life is told through his eyes in this remarkable 360-degree immersive experience.
You’ll get an audio tour that’s enabled both by Bluetooth zones around the Exhibition and through a “point-and-shoot” option for individual visitors to proceed at their own pace. Narrated by the musical’s author, Lin-Manuel Miranda, Hamilton: The Exhibition will take you back to Hamilton’s birthplace and orphaned childhood in St. Croix, and chronicle how he came to the United States in his early teens with nothing, ultimately becoming an integral part of the American Revolution and the creation of the United States and its entire banking system.
Miss Q was enthralled. She wanted to stop for every part of the tour, and I often found her listening intently while gazing longingly at the different artifacts and multimedia areas throughout the Exhibition. Before we saw the show that night, she already had a good understanding of the characters she’d soon meet.
Hamilton: The Exhibition will be in Chicago until January 2020 before it moves on to its next still-undisclosed location.
Kids’ theatre in Chicago
Part of what makes the performing arts scene here so exceptional for introducing kids to plays and musicals is that there is specially produced kids’ theatre in Chicago.
Miss Q and I enjoyed a fantastic production of The Wizard of Oz at the Jentes Family Courtyard Theater at Navy Pier’s Chicago Shakespeare Theatre. Aside from wonderful storytelling and singing, the set was clearly constructed taking a child’s imagination into account. Plus, the performance was only 75 minutes and flowed uninterrupted since there wasn’t an intermission.
While this particular show is only running until August 25, 2019, the Chicago Shakespeare Theatre has new productions all year long for young and old, making it one of the premiere places to see plays in Chicago.
This was our only experience with kids’ theater in Chicago, but we noticed there were several other dedicated theatres around the city devoted to child-friendly programming, so you could easily create your itinerary around kids’ plays in Chicago if you prefer not to expose them to some of the more adult themes and language you’ll usually find in mainstream theatre.
The best hotels for kids in Chicago
Like most major cities around the world, Chicago is rife with choice when it comes to accommodations.
With all of the great family activities in Chicago you’ll have planned, you’ll want a great hotel to go with it. One that thinks of your kids as their best guests and treats them like the VIPs they are.
In the heart of the Magnificent Mile, the Omni Chicago Hotel offers the only all-suite luxury accommodations on Michigan Avenue.
But what makes it one of the best hotels for kids in Chicago? With only 300 guest suites — each with its own living area and pull-out sofa (hello, parents, you get your own room!) — service is more personalized than you might find at a 1,000+ room hotel.
Take check-in, for example, when the front desk staffer passed a goody bag to Miss Q while we sorted through our reservation. It had treats, crayons and activities like playing cards and DIY binoculars in it. And each night, milk and cookies arrived for her.
In addition to separate rooms for parents and children, kid-friendly hotels in Chicago better also have an onsite restaurant to take care of those urgent hunger pangs — and the Omni delivers. I’ll write more about it in the restaurant section below.
Fun food & kid-friendly restaurants in Chicago
There are more restaurants for kids in Chicago than we could possibly hit in four days — but, boy, did we do our best!
And as we uncovered different places to eat, it was easy to find lots of options to satisfy every kind of eater and every kind of budget.
What I would suggest, however, is finding a few gems you know you want to visit and building them around your family activities in Chicago so you’re not going here, there and everywhere just to eat. Make this vacay as easy as possible!
Some of the most-fun kid restaurants in Chicago — like Ozzie’s Popsicles, for example — are located at Navy Pier, so have those planned into your Navy Pier day. Others — like The Dearborn — are closer to the plays in Chicago, so make a reservation for the afternoon or evening of your show.
JoJo’s Milk Bar
I’m playing favourites here and mentioning JoJo’s Milk Bar first because, without a doubt, it is one of the very best kid-friendly restaurants in Chicago — as awarded by Miss Q herself. This is where the ’90s are having their ultimate revival and what must be the freak-shake capital of the world.
Located in Chicago’s River North area, the restaurant takes its “Milk Bar” name from an older term that basically means there’s something for the young (milk) and old (a bar). Everything is OTT to the max here, so come hungry and ready to selfie.
Important foodie notes: the shakes are extremely sweet, even when you add the alcohol option. Food portions are enormous and very shareable. The JoJo’s fries and honey fried chicken sandwich were awesome and Miss Q said her chicken noodle soup was the “best ever.”
Lou Malnati’s Pizzeria
The oldest family name in Chicago pizza is Lou Malnati’s, and his legacy is a sweeping chain of pizzerias featuring the quintessential deep-dish pizza. Whether you’re visiting Chicago with kids or not, everyone needs to eat at least one deep-dish pizza in the Windy City. It’s also the epitome of family restaurants in Chicago because it’s still a family-run business.
Important foodie notes: Try the Malnati Chicago Classic, an authentic buttercrust deep-dish ‘za that’s an inches-thick pie filled to the brim with gooey cheese, vine-ripened tomatoes and huge chunks of sausage. Veggie lovers will go crazy for The Lou, with its garlicky spinach mix, basil notes, massive mushroom slices, topped with three cheeses and Roma tomato slices on a garlic buttercrust. The Malnati salad blew me away; the dressing is on the sweet side, but the burst of flavour thanks to an onslaught of ingredients, is sooooo good. If you are somehow still remotely hungry by the end of your meal here, a family of four could easily share the deep dish cookie dessert (which comes covered in mounds of vanilla ice cream and whipped cream). Warning: you will not fit into the outfit you brought to wear to Hamilton after eating here.
Ozzie’s Pops and Pretzels specializes in seasonal popsicles and hand-twisted pretzels. I can’t speak to the pretzels (though they looked delicious), but the strawberries & cream popsicle I shared with Miss Q was OMG-like-the-most-amazing-popsicle-ever. And I have had some tasty artisan popsicles in my travels!
It’s a good thing we only went to Navy Pier one day because it would have been dangerous being in such close proximity to this place more than once.
Garrett Popcorn Shops
You cannot come to Chicago and not treat yo’self to some Chicago Mix popcorn. You just can’t. And the only place to do it is at one of the many Garrett Popcorn Shops around town. You probably don’t even need to look up directions — just follow your nose.
Although some kid-friendly restaurants in Chicago will definitely be considered a splurge, they don’t all have to cost a small fortune. Portillo’s is the perfect example. The one we went to, just a short walk from the Omni Chicago at 100 W. Ontario Street was like walking into the Big Top — if the Big Top sold food. There were lights, there was action, there were announcements being called out like they were the next attraction, and there were people vying for seats in every direction.
Perhaps that’s because you can get a loaded Chicago hot dog — affectionately called a dog dragged through the garden — for around $3.
Other important foodie notes: A kids’ spaghetti and meatballs combo meal is a steal at $5.99 (which came with a HUGE plate of spaghetti and a meatball bigger than my child’s fist, a carton of milk and a bun). A super-sized milkshake is only around $4 and could easily be shared between two kids. And be sure to get a strawberry shortcake; at only $3.89, I had very low expectations and was shocked at how big and how good it was.
You know you make good stuff when you can close once the place is sold out of food. Because that’s what they do at Doughnut Vault — they open at a set time each morning, but close up shop once all the doughnuts are gone.
It’s standing-room-only in this galley-style shop — home to some of the best donuts in Chicago — and you can expect a lineup out the door. Doughnuts are $2-3 apiece and there’s always a buttermilk old fashioned, gingerbread stack and classic glazed roundup, but there may also be daily specials (like red velvet) available. But once they’re gone, they’re gone.
Other important foodie notes: the $1 coffee ain’t too shabby either.
Revival Food Hall
Revival Food Hall — an easy walk from the Willis Tower on one side and both Millennium Park and the Art Institute on the other — is a concept that spotlights the best of the city’s culinary scene under one roof. The 24,000-square-foot space is a foodie-lovers marketplace with 15 stalls that offer grab-and-go menus.
And that’s what makes it one of the best places to eat in Chicago for families — choice. One kid wants a soup? Check. Another wants BBQ? Check. Dad wants seafood? Check. And Mom just wants a glass of wine? Check.
Important foodie notes: the Mother Clucker ramen bowl from the Furious Spoon was delish, and by adding the dumplings, it was enough for Miss Q and I to share for lunch. We really enjoyed the ginger lemonade from The Fat Shallot, which was the perfect blend of zesty and refreshing. And we grabbed some treats from HotChocolate Bakery to nosh on throughout the day — all of which were crazy fresh and oh-so-good. You can also refill your water bottle near the Revival Cafe-Bar for free!
Dylan’s Candy Bar
OK, OK — this isn’t a restaurant. At all. It’s just pure candy, and it’s kid dreams brought to life. It’s much smaller than the flagship NYC shop, but no less fun. Plus you can make your own GIF!
This is another food hall-inspired eatery, but instead of each stall being independently owned, you just get a swipe card when you arrive and order what you want with it, then pay all at once at the end. Unless of course you come on Sunday like we did, and it was an all-you-can-eat brunch!
It’s all Latin street food or an interpretation of it. The eight innovative kitchens serve up handmade, cooked-to-order dishes featuring everything from noodles and sushi to tacos and burgers.
Important foodie notes: the brunch is amazing value at $19.99 per adult and $8.50 per kid. The Mexico DF Dog from the Burguesa stall was killer. Grab yourself a chicken poblano empanada from the Saladero stall. The Sushi & Ceviche Bar’s salmon tostada looked amazing but we were in a hurry and I didn’t have the 10+ minutes to spare on having one made, so we went with the volcano roll that Miss Q liked so much she went back for round two. The pork al pastor taco from the Taqueria was a fan fave of ours.
Half Sour in the artsy Printer’s Row neighbourhood is perfect for those lazy nights when you just want a great patio with easy food for the kiddos and craft beer or an inventive cocktail for the parents in a no-fuss, come-as-you-are environment.
Important foodie notes: “Half sours” are pickles, and they’re not like any pickles we’d ever had — worth trying if you’re a pickle aficionado. We both LOVED the fried artichokes, and if you need a carb fix, the latkes were fab. Miss Q LOVED the ice cream sandwich. I can’t see the cocktail menu online, but I had the best cocktail here — called Early Weddings (with Bahnez mezcal, Cocchi vermouth, Amaretto and Sichuan bitters). Just wow. You can find it featured prominently in my Chicago Insta-Stories I loved it so much!
Just steps from many of the plays in Chicago you’ll find The Dearborn, owned by an Irish-born lassie who has created the perfect balance for a restaurant that will appeal to tourists and locals, couples and families, and theatre-goers and business folks alike. Why? Great food, great vibe, great drinks and great location. You don’t need to be dressed up, but if you are, you won’t feel out of place.
This will be your splurge meal in Chicago. And it will be worth every freaking penny.
Important foodie notes: the burrata salad (served with marinated beets and a sweet miso vinaigrette) is the stuff of dreams. So is the Rohan duck breast entree, served two ways with a warm Brussel’s sprouts salad. We should have been embarassed to order the chocolate-cherry bomb between the two of us — but we weren’t and it was divine. I wanted to try the house-brand db gin, which I did in a delightfully refreshing cocktail called First Class Flight, but E’s Azteca Old Fashioned blew me away with its cinnamon-chocolate-orange flavour fest.
676 Restaurant & Bar
Omni’s signature restaurant — on the hotel’s fourth floor — has to have an honourable mention here, not because it’s the most kid-friendly restaurant in Chicago necessarily, but because for price and ease-of-use as a hotel guest, it deserves to be here. Get a table overlooking the Mag Mile to start your day, and enjoy either the daily breakfast buffet, a yummy smoothie or even just a bagel with cream cheese.
Important foodie notes: if you want to crank out your morning in style, I suggest ordering the banana bread pancakes (which are more or less someone’s brilliant idea of pan-frying fresh banana bread batter with spiced pecans). The bottomless coffee is perfectly roasted and you can ask for one to go before you leave!
Why you need a Chicago CityPASS
Doing a whole bunch of family activities in Chicago with kids in tow can get pricey. So if you have a good idea of what you want to cover ahead of time, and most of the attractions are part of the Chicago CityPASS, it’s a worthwhile investment that will save you time and money.
Not only is your pay-one-price passport going to help you skip a lot of the ticket lines, but in some spots you’ll even get VIP admission with shorter lines still. Better still, some places give you the extras that most guests have to pay extra for, like the audio tour at the Art Institute (normally an extra $7, its included with your CityPASS) and ALL of the special exhibits at The Field Museum, which were our favourite parts.
The Chicago city pass provides access to:
- Skydeck Chicago (and The Ledge)
- The Field Museum
- Art Institute of Chicago OR the Adler Planetarium
- This one was the only real bummer for us; we would have preferred to visit the Planetarium since we don’t do Aquariums that have mammals in them
- Shedd Aquarium
- Museum of Science and Industry OR 360 Chicago (we didn’t even have time to get to these!)
There are also some pages at the back of the CityPASS booklet with additional deals, like the extra 15 per cent off I scored on clearance merchandise at Macy’s.
You can buy your pass ahead of time, online or (sometimes) in stores like Costco. The Canadian price online is $150 per adult and $123 per child. They may be cheaper at Costco so shop around. And once you hit your first attraction, your CityPASS is valid for nine consecutive days, so you have plenty of time to go at your and your kids’ own pace.
Pro Tip: take into careful consideration how much the attractions each cost so you can be sure a CityPASS will benefit you financially, and also take note of attractions that may offer free entry for kids (like the Art Institute) where it may make more sense to use the Planetarium portion of your CityPASS for the entire family and just pay for the adults at the Art Institute.
Exploring Chicago with kids — how to get around
Getting around Chicago was pretty painless. I admit that we didn’t even try public transportation, because it was so easy to get by on foot or a combination of UBER/Lyft and taxi rides.
Overall, I thought the taxi drivers were far better here than the UBERs, navigating the city streets with much more confidence — and that’s not always the case but it was here. And there was no real noticeable difference in price here between the two either.
Most of the big attractions had ample parking if you’ve driven to Chicago or have a rental car, and parking prices were very in-line with what we’d pay in Toronto (so much, much cheaper than parking in NYC but much more expensive if you’re not used to big-city prices). Personally, I’d leave the car at your hotel.
So with all of these activities, attractions and restaurants in mind, you should be able to piece together a really solid Chicago family vacation! And if you can’t get to all of the family activities in Chicago we’ve listed here in one visit, the good news is that there’s always next time.
DISCLAIMER: Several, but not all, of the elements of this trip were provided by Choose Chicago to facilitate coverage. All suggestions and opinions, however, are completely my own.
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