At least once a year, Chicago was our playground.
For my wife and me, it was a fast, fun vacay that always delivered. Typical Chi-city night: experimental cocktails at a Wicker Park speakeasy. Multicourse dinners by a “Top Chef” champion in the West Loop. Nightcap on a rooftop in downtown. And do it all again the next day.
Then we had a baby.
Aurora is a year old now. The farthest we’d taken her was Grandma’s house in the middle of Wisconsin. She’s wild. Likes to eat with her hands. Says “no” a lot.
But we still wanted to return to the city of our former after-dark adventures. It’d be fun to go on vacation. We needed a vacation.
But could we survive the Windy City we love with a baby on board? Are we ready for diaper changes and meltdowns on Michigan Avenue? More important: Is Chicago ready?
We gave it a shot. We marveled at beluga whales, strolled through the zoo, discovered casual spots opened by big-name chefs and enjoyed our revised approach to the Windy City so much that we almost forgot about sipping cocktails in a trendy bar (but we did that, too). In the process, we learned a lot. Because that’s what you do as new parents. Learn things — often the hard way. Fellow child-rearers, heed these lessons from three days spent in Chicagoland.
1. Establish a home base, aka your Fortress of Solitude
First things first: How do you hit the restaurant scene at night if your 1-year-old needs to be in bed by 8 p.m.? Answer: You don’t.
When I started planning this trip, I pictured my wife and I trapped in a hotel room post-baby bedtime in absolute silence, just staring at each other and hoping not to wake the kid. The scenario sounded like some strange nightly prison sentence. Thus, my first goal: Find a hotel suite with a separate room. And the hotel could not be the Embassy Suites. You can’t Instagram the Embassy Suites.
Fortunately, other parents have had similar thoughts, because Chicago’s boutique hotel scene is filled with kid-friendly room packages. Hotel Lincoln had everything we were looking for. It overlooks one of Chicago’s great amenities, Lincoln Park, plus it’s a short stroller walk to the zoo and the wide sandy swath of North Avenue Beach, one of the city’s busiest. There’s also a weekly farmers market in the park and stylish kids shops nearby like Greenheart ($65 alpaca fur teddy bear?).
It’s precisely the type of hotel we would have picked pre-parenthood: boutique swank (renovated in 2012), buzzy upscale restaurant (Perennial Virant, and yes, it has highchairs), hipster coffee shop in the lobby (Elaine’s Coffee Call, serving La Colombe) and a clubby rooftop lounge that’s so bustling it has bouncers.
We took a quick peek at the 13th floor bar, called the J. Parker, and discovered that we weren’t alone as envelope-pushing parents. Lo and behold, someone else brought their newborn up there — and in a Baby Bjorn.
2. Eat like you don’t have a kid
Sometimes foodies stop being foodies when they become parents. Do a Google search for “best Chicago restaurants for kids” and you’ll get the typical answers — Ed Debevic’s, Harry Caray’s, etc. Don’t do that.
Many of the city’s top upscale restaurateurs are now dabbling in the casual market, too. “Top Chef” champ Stephanie Izard is beloved for her highbrow small-plate resto, the Girl & the Goat. It might be a little much for a 1-year-old, but Izard’s newer Little Goat Diner is just right. Both are located along a stretch of Randolph Street that’s home to some of the city’s best restaurants.
We got a reservation for 5 p.m. — because when you become parents, you eat like grandparents. At the neo diner, Izard pumps out her take on comfort food, including breakfast all day (or as the menu calls it, “cereal killers”). Get the goat chili cheese fries. I ate the succulent goat, Aurora munched on the crispy fries. She also loved the perfect pancakes, which she’d nibble on and then toss to the floor. We left a big tip.
Rick Bayless revolutionized chef-driven Mexican food in Chicago. His Frontera Grill might be overwhelming for kiddos, but his quick-service Xoco eatery works well when parents want award-winning Mexican tacos and a beer — and a child just wants to eat, now. Chef Bill Kim’s Asian-inspired barbecue joint BellyQ is more of an evening experience, but his Belly Shack in Wicker Park serves up wild sandwiches (stuffed with noodles!) that kids devour. There’s Mario Batali’s Eataly, his citadel of Italian restaurants housed under one roof. The Chicago outpost opened in 2013 (La Pizza & La Pasta is best for kids).
And don’t forget about Doughnut Vault, the no-nonsense hole-in-the-wall (literally, just a counter inside a doorway) by the owners of Gilt Bar. Often listed as among the best in the country, the old-fashioned doughnuts are worth the trek through morning rush hour.
3. Limit your landmarks
Chicago’s tourist traps — especially those aimed at kids — are actually worth the hassle. But as we found, you have to pace your kid and yourself. Trust me, an adult tantrum in the middle of Navy Pier is not a good look. For your own sanity, do not cram places like Navy Pier and the Shedd Aquarium into a single day. Pick one landmark and leave it at that. We reluctantly skipped Navy Pier, the Field Museum and the Bean. On Day 1, we went with the Lincoln Park Zoo, just a five-minute walk from our hotel. For its size and variety of beasts, the price (free) can’t be beat. My daughter took particular enjoyment in the big cat house — yelling out “kitty” to a bemused Amur tiger. The zoo is targeting millennial parents with a summer outdoor yoga program for parents and toddlers (also free; every Thursday).
On Day 2, we chose the massive Shedd Aquarium. Belugas, sharks, 4-D movies (yes, you can see SpongeBob with vibrating seats and smells. Weird). We were most excited about “Stingray Touch,” a 20,000-gallon shallow outdoor pool where you can skim your hand along the squishy backs of these gliding sea creatures. But after two hours of traversing one of the country’s largest aquariums — and just as we were rolling up to the stingray pool — our little one zonked out in her stroller.
4. Burn off energy
OK, so your kids probably don’t squeal with excitement when you say “Let’s go to a molecular gastronomy restaurant!” They’d rather drink packets of ketchup. The best way to keep them fresh (and open-minded) is to get them to nap when you’re on the go so they’re fresh for the next adventure. This calls for pit stops to burn off energy.
Here are two gems, one indoor, one out. When you see the bronze statues of Dorothy, the Scarecrow and the rest of the Yellow Brick Road revelers, you’ve arrived at Oz Park near the heart of Lincoln Park’s shopping district. “Dorothy’s Playlot,” with its rubberized surface, is reserved for toddler-aged kids. But what if it’s raining? Chicago offers a few play cafes — basically indoor playgrounds that double as coffee shops for parents. One of those is Little Beans in Bucktown, which is filled with miniature homes, storefronts and play equipment. Plus they serve Intelligentsia coffee so you can fuel up while your toddler is running around like a maniac.
5. Be spontaneous (translation: Rip up the itinerary)
Chicago is best experienced through its distinct neighborhoods — each has enough shopping and eating to satisfy an entire day. We had planned to take our daughter to a couple of kid-friendly bookstores (the Book Cellar, 57th Street Books), but when her nap interfered we drove around to let her sleep. That’s how we stumbled upon a Lakeview neighborhood gem — Unabridged Bookstore, which has a great kids section. Another fun spontaneous moment was turning the car around on the way back to our hotel and stopping at picturesque Buckingham Fountain. With the sun setting, we snapped some of our favorite family photos of the trip. On our last night in Chicago we planned to take our daughter to Eataly in downtown. She’d love the action, I thought — people slurping fresh spaghetti, shopping for incredibly priced cheese. But it was 5 p.m. rush hour. Taxis were everywhere, hordes of pedestrians clogged the crosswalks. We drove by Eataly looking for a parking spot only to discover a sign out front: “Closed for private party.” Plan thwarted.
Then a miracle: Across the street was Shake Shack, a New York chef-driven burger joint that recently opened in Chicago. But still no parking to be found, and now the kid was crying. Beads of sweat started forming on my forehead. I pulled into a ramp. Boom: $32. The price of relief, I guess. We ate our glorious burgers. Our daughter liked her fries — but loved the gobs of ketchup even more.
Lesson learned: Do your research, make a plan, break the plan. Your kid won’t know the difference.