Grant and I couldn’t quite decide how to “do” Chicago. We had booked cheap flights months ago—one of those fares that pops up and feels irresponsible not to buy—and told ourselves we’d figure out the details later. As the trip got closer, we still didn’t have a real plan. That’s when I did something bold: I let Grant take the lead.
He had a vision. I didn’t fully understand it. But I trusted it.
The flight out was uneventful—in the most glorious way possible when traveling with a toddler. Ripley has quietly become a seasoned flyer. He knows the drill. He spent half the flight narrating what he saw out the window and the other half calmly watching Paw Patrol. We kept waiting for turbulence—literal or emotional—but none came.
We landed in Chicago, grabbed the rental car, and headed to Embassy Suites. Ripley was fading fast in the car—eyes heavy, voice quieter by the minute. But the second the hotel door opened, he revived like someone plugged him into a charger.
If you ever need someone to properly break in a mattress, he’s your guy. The kid immediately launched into quality-control mode—jumping from bed to bed, testing bounce levels, squealing with delight. Jet lag? What jet lag?
The next morning, I woke up with one priority: Lou Malnati’s. Deep-dish pizza in Chicago isn’t optional. It’s a ritual. The pro tip is to order ahead—otherwise you’re staring at a 45-minute bake time. So we planned ahead. Or so we thought.
We accidentally ordered from a pickup-only location. No dining room. No cozy booth. No cast-iron pan theatrics. Just a storefront and a handoff.
So we ate Chicago’s finest deep dish in the rental car.
Was it ideal? No.
Was it still delicious? Absolutely.
There’s something humbling about eating world-class pizza in the front seat while your toddler kicks the back of your chair and screams in your ear.
Then Grant casually announced we were heading to Wisconsin Dells. He shared this, but I completely forgot he mentioned it. I paused. “Okay,” I said. Because this was his plan. And I had surrendered control.
On the drive north, we stopped at Cracker Barrel. Ripley loves Cracker Barrel—not for the biscuits like Grant, but for the toy section. He walked in and immediately locked onto the wall of wooden puzzles and plush animals, as if he had found his people. We could have left him there and picked him up at closing time.
Eventually, we continued north and made a stop in Madison to see the Capitol. Madison sits on a narrow isthmus between Lake Mendota and Lake Monona, meaning the wind hits from both sides. It was beautiful. It was also brutally cold.
Ripley hopped out of the car and immediately chased squirrels across the lawn like he was training for a wildlife documentary. Within minutes, our California bones were frozen. We retreated to the sanctuary of heated seats and kept driving.
Wisconsin Dells feels like a town built entirely for spring break—but open year-round. Mt. Olympus essentially owns half of it, acquiring smaller properties and building a waterpark-and-theme-park empire.
The draw? Indoor waterpark. Indoor amusement park. In winter. While snowing. How could you not want to do that?
Our hotel room… was an experience. $75 for a family suite with two queen beds and bunk beds. The beds were lumpy. The heater didn’t work. The TV didn’t work. We called the front desk and were told we were “in the phone log.” Translation: best of luck.
But we weren’t there for luxury. We were there for chaos.
There is something surreal about racing down a waterslide while snow falls outside the window. The air inside was thick with chlorine and shrieks of joy. Ripley was wide-eyed, running from splash pad to lazy river to kiddie slide like he had found paradise.
Grant might have loved it even more. For a few hours, we forgot about the lumpy beds and the broken heater. We were warm. We were laughing. It was the kind of memory that doesn’t photograph perfectly but feels huge in the moment.
Dinner was at Hot Rocks, a restaurant where they serve you raw or partially cooked meat on a scorching stone, and you finish cooking it yourself.
The concept? Campfire meets steakhouse.
I was hungry enough to believe in it.
We ordered filet and skirt steak. The filet was solid. The skirt steak was rubbery. The waiter looked genuinely apologetic and quietly brought out more filet without us asking. It was one of those meals where the effort was appreciated more than the execution.
The final eExhausted but determined, we bundled up for Aquavia Lumina—an outdoor nighttime light show in the woods. The experience is guided by a glowing deer spirit animal who leads you through illuminated pathways and storytelling about nature and light.
It was beautiful. It was magical. It was also freezing.
We power-walked the entire trail like competitive mall walkers. Ripley alternated between fascination and demanding to be carried. Still, the glowing lights against the snow made it feel special—like we had stumbled into a winter fairy tale.
Back in the room, Grant “fixed” the heater. Which meant he turned it up until it became a dry sauna. The beds were uncomfortable. I couldn’t sleep. Ripley couldn’t sleep. Which meant Grant couldn’t sleep. We rotated in shifts—four hours down, three hours awake, grumbling, then another stretch of fragmented rest. Technically, we slept eight hours. Functionally, we aged five years.
The next morning, we leaned fully into the Dells experience.
Top Secret: An upside-down White House attraction. You walk through looking up at the Oval Office and press room. It felt like stepping into a 1997 roadside dream. Long stretches of empty space. Faded displays. Grant muttered that commercial rent here must be astonishingly affordable.
Tacos: I liked them. Grant didn’t. Ripley ate cautiously and sided with Grant.
Lost Temple: Egyptian-themed walkthrough for $5. Dramatic music. Foam hieroglyphics. We got what we paid for.
Haunted House: $6. Surprisingly decent. Ripley actually jumped at one moment—our fearless Halloween-conditioned child startled by a loud noise. It was both adorable and slightly validating. After that, we’d had enough and it was time to return to Chicago.
The drive back was peaceful. Ripley watched Paw Patrol. We listened to a podcast about Scream 7. Balanced parenting at its finest.
That night we checked into the Hilton on the Magnificent Mile. The beds were glorious. Heavenly. The kind of bed that forgives you for Wisconsin Dells.
Dinner at Siena Tavern felt like redemption. Coccoli. Butternut squash ravioli. Brick chicken. Everything tasted extraordinary—perhaps elevated by how bad the food we had in the Dells was. I savored every bite.
That evening, we executed a child swap. I went to Second City first, while Grant stayed with Ripley. Then we switched. The show was sharp, funny, hungry performers hovering at that edge between “about to break out” and “this is as big as it gets.” It might have been the best show I’ve seen there. When Grant returned to the hotel, it was time for bed, and this time, no one had any issues falling asleep.
The next morning, we visited The Bean. Ripley had seen photos and seemed intrigued. In person? Indifferent. He lasted thirty seconds before requesting the warm car.
Grant had one final mission: drive to Winnetka to see the Home Alone house. Thirty minutes later, we stood outside snapping photos like respectful movie nerds. We even walked to the nearby grocery store—fully committed to the cinematic pilgrimage. Grant knew where everything was. I think he planned this whole trip for this moment, so I am glad he was having it. Grant was happy. Which made me happy.
We returned the rental car, boarded the plane, and were home by midday Sunday. Ripley found a new game of hanging onto the seat and seeing how long he could last before he dropped. The people in front of us hated us.
When you list it out, the trip sounds chaotic:
Car pizza. Frozen capitols. Waterparks in snowstorms. Rubber steak. Spirit deer. Upside-down White Houses. Haunted houses. Comedy shows. Movie houses.
But somehow, it worked. It’s nice having two planners in the family. Now we just need to train Ripley to plan the next one.
