Whenever I tell someone from Southern California–which is where my family and I currently reside–that I grew up in Chicago, I get one of two responses. Either, “Well, then! This (insert inclement weather event here) must not bother you at all!” or “Cool! That’s a fun place to visit!” And while I always smile and nod to the first one (despite the fact that my blood thinned out long ago, and I am now very much prone to complaining about California-style “weather”), it’s the second one that makes me laugh. Mostly because it describes my feelings exactly.
Because while I cannot even remotely imagine returning to a life involving icy windshields, fourteen different types of winter coats, or surprise snowstorms on my birthday (which, mind you, is in MAY), I do love getting to be a tourist in the enormous, exciting, and absolutely beautiful city I once called home. (As long as it’s during the summer months, of course.)
Below you’ll find a nearly-complete list of the activities my kids and I have enjoyed (when we’re not hanging at Mimi and Grandpa’s, of course) during our twice-yearly visits, and I hope that it helps you fill the days on your own upcoming trip, or, perhaps even inspires you to plan one!
Know Before You Go
Chicago, as much as I love it, is one of those places where the weather is almost never quite what you’d like it to be. While most visitors are aware that the winters can be brutally cold and slushy, the heat and humidity of the summer months can sometimes take people by surprise. If you’re planning to visit in July or August, prepare for the potential of some very hot days. Pack light clothing, plenty of sunscreen and water, bug spray or patches, and be prepared for the occasional sudden thunderstorm. All that being said, I don’t think I’ve ever had a summer trip to Chicago during which I didn’t remark at how beautiful it is (The lake! The trees! The summer nights!). Even if I’m choking on my own sweat as I say it.
Where to Stay & Transportation
While I spent many weekends in my 20s bopping around the city by foot, or via public transportation, with my children in tow, I have only ever navigated Chicago by car. And while I’m sure it’s possible to get little ones, strollers, and all the required accutrements around the city by relying exclusively on the L (Chicago’s elevated train system), or the Metra (the train that runs from downtown to the suburbs), I always recommend that my friends rent a car when they visit. (The air conditioning alone will be worth it).
Parking in the city does get expensive, but when the kids and I visit the downtown area, we tend to park only once, and stick to a certain neighborhood for the entirety of that day.
And while we rarely stay at hotels in the city with my own children (since we’ve always stayed with the grandparents), several of my friends have recommended The Fairmont Chicago Hotel (kids 5 and under eat free at the on-site restaurant, and kids 6-11 are half price. You can also upgrade to the gold level for complimentary breakfast and afternoon snacks), The Hampton Inn Chicago Downtown (it’s fancier than your average Hampton Inn, with free breakfast and on-site laundry), and the Embassy Suites by Hilton Chicago Downtown (family-friendly rooms with microwaves and fridges, free breakfast and afternoon snacks, and a grocery store right next-door).
The one time we did do a downtown hotel stay, it was at the Intercontinental Chicago Magnificent Mile, and I can’t recommend it enough. The interior is beautiful, there are several restaurants on-site, and the indoor pool is a kid’s (and adult’s!) dream. (Like most of the aforementioned hotels, it’s also centrally located, close to parks and beaches.)
Downtown Chicago’s Great Outdoors
Maggie Daley Park
Maggie Daley Park is located downtown, just east of Millenium Park, and adjacent to the lakefront. If you have active kids between the ages of 0 and 12, this is a truly incredible place to spend a summer day. The Park is enormous, and includes a variety of zones and activities for people of all ages (including a climbing wall, tennis courts, and mini-golf), but the park’s greatest asset (in my, correct, opinion) is the Play Garden, which consists of six distinct playgrounds, each with a different theme, and catering to different ages of children. There’s a boat-themed playground, a harbor playground, a wave lawn, a splash pad (which, I believe, is currently under construction), a truly incredible slide playground (with it’s own suspension bridge!) and my personal favorite, The Enchanted Forest: a space in which kids can have a variety of nature-themed sensory experiences, all while exploring over 3,000 feet of beautifully curated urban forest. There’s even a café located on the park grounds, so after hours of active play, you won’t have to walk far to find a sandwich.
Tips and Tricks: To avoid crowds (although, to be honest, Maggie Daley is almost always crowded), try visiting during the week. Dress your kids in bright colors and pick a meeting place in case someone gets lost: The park is enormous, and with so many options to choose from, it’s easy for big families to get separated. Wear close-toed shoes, as some of the terrain is bumpy and rough, and pack and picnic lunch if you don’t want to have to wait in line at the café. It’s a bit of a walk to any of the restaurants outside the park, and they are also likely to be busy. Parking is super cheap for the city ($12 for the entire day) IF you book early online for the Millennium Lakeside Garage.
The Lincoln Park Zoo
The Lincoln Park Zoo is located a few minutes north of downtown Chicago, and not only is it a truly incredible zoo, it’s also completely free to visit (that is, if you skip the balloons, t-shirts, carousel rides, popcorn, etc.). The Lincoln Park zoo is home to all your typical zoo animals (lions, and tigers and bears, oh my!), as well as a farm, at which kids can get up close and personal (by grooming and feeding) the goats, cows and chickens. There’s also a nature boardwalk, with interactive exhibits that teach kids and adults alike about all the wildlife native to the Chicagoland area.
And if the animals only manage to keep your kids’ attention for half the day, the zoo is within walking distance to the Peggy Notebaert Nature Museum, as well as the North Avenue beach—which is crawling with hot dog and ice cream vendors during the summer months.
Tips and Tricks: Arrive early in the day, as parking can get a little tight–especially on weekends. Check the zoo calendar in advance for exhibit closures or special events. If you’re planning on visiting over lunch, consider eating at the on-site restaurant, Cafe Brauer, which has a beautiful view of the pond, and great food for both kids and adults. Nearby kid-friendly restaurants include Nookies Too (brunch with an excellent kids menu), The Pasta Bowl (self-explanatory, I think), and Homeslice (family-friendly pizza and brunch joint). Parking is between $30 and $40 per day
Beaches and Water Play
North Avenue Beach
To be honest this is the only Chicago beach I ever go to. Partially because I’m a creature of habit, but also because I firmly believe there’s nothing better than an afternoon in the sun, followed by a cheeseburger and a tropical drink – all of which you can achieve here. North Avenue beach is located in Lincoln Park, walking distance from the zoo, and is big enough that there’s always space to throw a football, even during the admittedly-crowded high-summer months.
But what I really love about this beach is Castaways, which is a kid-friendly restaurant and bar shaped (to the delight of both children and, in my experience at least, plenty of adults as well) like an enormous boat, and located right on the sand. Castaways serves everything from burgers and fries to craft cocktails and acai bowls.
And if you’re feeling super adventurous, you can rent jet skis from Windy City Watersports, or kayaks from Kayak Chicago—both located at North Avenue Beach.
Parking can be found at the North Avenue Beach lot, and runs from about $15-$25
Adams Water Playground
For those uninterested in heading back to a hotel covered in sand, Adams Park Water Playground is another great place to cool off and burn some energy before nap time. This spash pad boasts several different sizes of sprinklers, as well as an enormous elevated bucket, that tips periodically, and usually at the exact same moment that a fully-clothed adult is attempting to rescue a toddler from beneath it. The water playground is located within the larger Adams Park, which is also home to a playground where siblings averse to getting soaked can play and swing.
Tours and Activities
Relax Aboard a Wendella Boats Architectural Tour
(Yes, even with the kids)
This past April, my family and I were visiting Chicago in the middle of a bizarre, early-spring heat wave, and decided to take advantage of the beautiful weather by taking all three of our kids (aged 2, 4 and 6), on a 90 minute architectural tour down all three branches of the Chicago River, put on by Wendella Boats. And while I was worried about my kids’ attention span, and the very real potential that one or more of them might try to fling themselves into the “not fit for swimming” water, the tour ended up being so engaging, that only the two year old struggled to make it all the way through (and he only required a walk around the top deck almost 80 minutes in).
The tour guide (who I imagine I will see on T.V. sometime soon–he was that funny), blew my mind with his knowledge of Chicago history and architecture. The weather was nice enough that almost everyone sat on the open-air top deck (so as to have a better view of the landmarks and buildings the tour referenced along the way), and only travelled downstairs for a snack, or a drink at the fully stocked bar.
I walked away knowing more about the city than I did after living there for the majority of my life (sorry mom and dad) and am constantly recommending it, even to friends who live locally.
Go to a Cubs Game at Wrigley Field
I may be biased, but there is no better baseball experience than watching a cubs game at Wrigley Field. The peeling scaffolding! The cramped seats! The raucous and oftentimes half-naked fans! What could be better. But seriously, Cubs fans are some of the best out there, and everyone in my family (kids and adults included) always look forward to our yearly visit to the bleachers.
If you’re hoping to attend a summer game (July and August in particular), be aware that they almost always sell out in advance, so be sure to book your tickets early. Kids two and under are free, as long as they stay on your lap the entire time (read: if you can, buy them a ticket anyway), and you can bring your own snacks into the stadium, as long as they’re packed in a ziplock or sippy cup. I recommend parking your stroller at the bike valet across from the stadium, or not bringing it at all, as there definitely won’t be room for it in the stands. If you have littles in tow, ask an attendant for the location of the “First Timers” booth when you arrive at the stadium (they’ll provide a little certificate), and consider joining “Clark’s Crew”—an adorable club for littles, centered named after the new cub’s mascot “Clark the Cub.” Parking at games is tough, so I actually do recommend taking public transit to this one.
“Tilt” Over the City at the Hancock Building
If you have a fear of heights, this one isn’t for you, but if you’re visiting the city with adventurous older kids, and want to experience a bit of a thrill, along with an incredible view, head over to the Hancock Building’s Observation Deck, and purchase an add-on ticket for “Tilt“–a ride that is essentially a block of windows which leans outwards from the building, so that you can feel like you’re floating a whopping 1,000 feet above Michigan Avenue.
Gilson Beach in Wilmette
If the city beaches aren’t your vibe, Gilson beach is a great, suburban option. Gilson is located about 40 minutes north of the heart of downtown, and tends to be a little quieter (and potentially more family-friendly) than some of the beaches downtown. Like most suburban beaches, swim passes are required, and can be purchased at the beach house located near the parking lot.
Gilson is also adjascent to the Wilmette Sailing Beach, where you can either launch your own boat, or rent everything from standup paddleboards, to kayaks, to the adorable (albeit relatively tippy) sunfish sailboats that, in my youth, I was exceedingly proficient at capsizing.
Gilson is located across the street from the Baha’i House of Worship—which is absolutely gorgeous, open to the public, and definitely worth a visit. Not to mention, it’s close to downtown Wilmette, which boasts plenty of delicious dining options (from casual, to relatively upscale), including my personal favorite, the fish-forward Pescadero.
The Chicago Botanic Gardens
The Chicago Botanic Gardens are located in Glencoe, about a 30 minute drive from downtown. The garden is enormous, and includes nearly 400 acres of beautifully manicured lawns and gardens. If you’re visiting with kids between May and October, be sure to stop at both the butterfly garden, and the model railroad garden–both of which were an absolute delight for my bug and train-loving four year old. I also recommend bringing a stroller in order to cover as much ground as possible, and stopping at the Rose Terrace Cafe for an ice cream cone before heading home.
Ravinia Music Festival
Ravinia Music Festival is an all-summer-long music festival located in Highland Park–a suburb about forty minutes north of the city. The venue is outdoors, so it’s only open in the early spring and summer months. The lineup includes everything from the Chicago Symphony Orchestra, to Counting Crows, to NeYo and John Legend. Shows run at either 2pm, 5pm, or 7pm on select weekdays and on the weekends. If you’re going with kids, I recommend buying tickets for lawn seating. You won’t have a great view, but you’ll have space to picnic and let the kids bop around. It’s a bit of a trek if you’re staying in the city, but the venue is incredible, and the lineup can’t be beat. There’s even a kids garden on the ticketed lawn, in case your kids, like mine, struggle to go two hours without climbing on something. You can find the regular schedule here, and the kids schedule here. (Kids and families are welcome at all events).
If you’re looking to experience the Chicago culinary scene in a family-friendly way, the following restaurants are some of my absolute favorites to visit with kids.
When I was visiting a friend of mine in Chicago a few years ago, and suggested we meet for pizza, she told me a much more authentic Chicago experience would actually involve a cheeseburger. Specifically, the cheeseburger at Small Cheval. And, long story short, she wasn’t wrong. It was very likely the best burger I’ve ever eaten. (I might even dream about it sometimes.) Even better, most locations (there are seven) are built around large outdoor patios, with picnic tables where kids and adults alike are free to be as loud as they’d like.
Lou Malnati’s was a staple of my childhood, and despite having been recently sold outside the family, there is still no other pizza like it. Period. There are several locations throughout the city and suburbs (including one right across the street from the Wendella Boats), all of which are exceedingly family friendly. Fair warning, however, if you are planning on ordering the deep-dish, it can take a while. So be sure to pack some crayons, or playdough, or whatever else your kids will need to keep busy while they wait.
Superdawg Drive-In or Lola’s Coney Island
When in Chicago, one must get a hot dog. And these two hot-dog forward restaurants are always my go-to’s. Superdawg was a hit with my littles last summer, as they had (gasp) never been to an actual drive through before. But Lola’s is also fantastic, and their malts and shakes may even rival the dogs themselves.
Greek Islands is located in the heart of Chicago’s Greek Town and is an experience unto itself. I can distinctly remember the first time I visited Greek Islands with a friend’s family, and was introduced to the wonder that is flaming saganaki. You might need a reservation for this one, and probably shouldn’t show up in your swim suit and flip flops, but its sure to be an experience the whole family will remember.
Heather Napoli says
The timing on this!!! I literally looked in your archives just the other day as we’re Chicago bound this summer (from Nova Scotia) and our kids are 2, 4 and 6! Can’t wait to check this beautiful city out!!