
We snuck the babe’s first road trip in just before COVID-19 quarantining took hold of the nation. Looking back, I’m so happy that we made it through the weekend in full health AND that we got to celebrate Trevor’s birthday before we huddled down in Detroit for this extended period. That’s not to say that signs weren’t becoming apparent … because of the mounting concern over the virus, we made a few decisions regarding our first-week-of-March travel plans:
- We’d skip planes and choose a drive-able destination
- If we went to a large city, we’d try to seek out a quieter neighborhood within it
- We’d avoid large crowds whenever possible
After mulling over these parameters and our options (Toronto, Grand Rapids?), we landed on Chicago’s family-friendly Lincoln Park, which neither of us had ever fully explored. It would be just more than a four-hour drive and with the little guy, that seemed doable.

Lincoln Park
Just north of Chicago’s downtown, the Lincoln Park neighborhood is a best known for its sprawling namesake waterfront park. The park might not be as well known as downtown’s Millennial Park, but it’s absolutely worth a visit, boasting a surprisingly impressive free zoo and conservatory and loads of paved walking (stroller friendly!) trails.
Even aside from the park, most of Lincoln Park is easily walkable and there are plenty of restaurants and shops to peruse during the day. That said, you’re also close to Chicago’s downtown area if you want to make a stop on your way in or out of town, and equally accessible to the northern neighborhoods (one of which we recommend exploring!).

Where to Stay
While an AirBnB would have made a lot of sense as a traveling family, I was desperate for a hotel atmosphere. I wanted to be able to take an elevator to grab lunch or order up a glass of wine in our room.
I landed on Hotel Lincoln, which is one of the few located within the borough. Its exact address – bordering the south edge of Lincoln Park – is ideal, just across the street from the park and also off of North Wells Street, where you can find a slew of cafes and eateries just a few blocks down.
The hotel’s common areas are trendy and buzzed with activity during our stay. A small lobby opens up to a cool little coffee shop – Elaine’s Coffee Call – and also offers a doorway into The Kennison, a chic restaurant that serves up breakfast, weekend brunch and dinner. Up on the top floor is one of the only rooftop bars in the area, J. Parker. Sadly, toting an infant really limits one’s availability to be warmly welcomed into a rooftop bar. So … Trevor went up and grabbed drinks each night to bring back to the hotel room.
On that note, the guest rooms themselves were admittedly underwhelming. The decor and furnishings were generally outdated and the bathrooms small and in need of more modern amenities. Our room, which was a two-room suite (booked because it seemed nice to have a sitting area away from the snoozing baby) was somewhat spacious, but also turned out to be unnecessary for our particular needs. Despite all of that, I’d still recommend the hotel, given the great location, laid-back general property vibe and strong dining options.

What to Do
We rolled into town late on Friday evening after a full day of work and the four-hour drive west. Needless to say, we were exhausted. The only item on the agenda was hitting the hay. That left us with all day Saturday (day one) and most of Sunday (day two) to soak up the sights.
Here’s how we tackled our trip:
Day One
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- 11 AM: Brunch at The Kennison, conveniently located right in the lobby of Hotel Lincoln. He ordered the breakfast sandwich and I indulged in an American breakfast plate. (Also, mimosas for both of us. Because, vacay.) Everything was delicious and we loved sitting at the bar – perfect height to roll the stroller up alongside – so that we could chat with our server about kid-friendly spots in and around the city.
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- 12:30 PM: Stroll Lincoln Park. We walked across the street to meander through the city’s largest park, which also happens to hug Lake Michigan’s waterfront. We rolled the stroller along paved trails that offered great views of the downtown Chicago landscape (photo opp!) before finding ourselves in the free Lincoln Park Zoo. Past the zoo, the beautiful conservatory was open to the public and perfect for a plant-gazing stop, and naturally, more photos.
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- 3 PM: We took a long walk toward Armitage Ave., where we popped into La Colombe Coffee to caffeinate while peeking into shops along the way. For the pen-and-paper types, All She Wrote is a sweet curation of paper goods. Down the way, you’ll find Interior Define‘s midwest showroom, Aesop‘s mod beauty depot, and Jeni’s Ice Cream.
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- 7 PM: After some down time at the hotel, we headed out to find dinner. Make note: Saturday at 7 p.m. is NOT the time to try to find an open table with space for a stroller. Thankfully, we grabbed the last seat at Gallucci Pizzaria Napoletana where we ordered wood-fired pizzas, the arugula house salad and plenty of wine. The staff was friendly and fast, and super accommodating given our clunky stroller. (If we’d been sans baby, I likely would’ve made a reservation at The VIG.) Whatever your flavor, you’re sure to find a restaurant along N Wells Street that fits, and the best part is that it’s just down the road from the hotel.
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- 10 PM: On the roof of Hotel Lincoln is J. Parker, a vibe-y bar that offers stellar views. We skipped the views and grabbed a couple of drinks to bring back to the guestroom after the kiddo was asleep.
Day Two
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- 10 AM: Since our trip was in celebration of Trevor’s birthday, I sent him over to AIRE Ancient Baths in Chicago for a massage and some water therapy. I sulked that I wasn’t going along too, especially when he returned and told me that it was the type of place I’d absolutely love. Dimly lit and relaxation inducing, it’s a splurge, and definitely one that I’ll be indulging in on our next visit.
- 12 PM: At the suggestion of hotel staff, we headed out of Lincoln Park and toward an area called Logan Square, about 20 minutes away via car. We’d never been to that part of Chicago, and it offered a bustling city square (as you’d guess) that was perfect for perching and people watching, as well as plenty of bars and restaurants. We grabbed lunch at Reno Chicago, whose menu is full of pastries, bagels and hearty sandwiches.
- 2 PM: Millennium Park is one of those spots that you’ve just got to hit up if the weather is good. And it’s also the perfect excuse to stop into Stan’s Donuts & Coffee, which is just across the street. We’d packed up our car and were ready to hit the road, so a walk through the park with donut in hand was exactly what we needed to stretch our legs before the ride home. Was this just-maybe my favorite part of the trip? A coconut donut can really brighten my spirits ;)


Planning your own road trip? We’ve tried to make it uber easy by highlighting most of the spots mentioned above in the below Google map…
As always, would love to hear your favorite Chicago (or, specifically, Lincoln Park) spots! Feel free to drop a comment.



