We’re finally back into the swing of things this week after a whirlwind experience in Chicago – and a rare Monday off! While we had what may have been one of our favorite trips together to-date, the quick turnaround (we were there just over 24 hours) left us wishing we’d extended our trip by a few more days.
All the more reason to go back, right?
Before I share a recap of our adventures, I want to send out a big THANK YOU! to everyone who shared their favorite Chicago spots with us. We checked several off the list and will certainly attempt to continue doing so on our next visit. Not a single one of your recommendations let us down!
We were hoping to leave a little earlier in the morning than we did, but hey, life happens. After a quick stop to drop Rosie off at my parents, we hopped back on the road for the three hour drive. We took a new route this time, mostly through the country, and it was by far the quickest we’ve ever made it to Illinois.
Just outside of Chicago, though, it started pouring rain and we hit a small cluster of traffic. At this very moment, with Jeremy white-knuckling the wheel and asking me if he was clear to get in various lanes while cars weaved around us at dangerously close distances and speeds, I felt my nose begin to run. Blast! A cold before we even begin? Ah, no! Rather, the beginnings of the most massive nosebleed of my entire life.
Ten minutes, four sopping napkins, and a pair of bloodstained hands later, it stopped. All of it. The rain, the traffic, and the bloody nose. We were finally driving off of the highway in search of our first stop: Lagunitas Brewing Company. Fitting, because we both really needed a drink.
When we finally arrived, we were greeted by a sign that read, “It doesn’t matter how you got here, YOU MADE IT!”
Once we left the car, we entered a surreal land, of sorts.
$ | 1843 South Washtenaw Avenue | Website
Lagunitas greets visitors with a long, dark hallway, lit only by the black-light art along its walls and a few windows that peer into the production rooms, filled with massive amounts of equipment and kegs. All the while, “Pure Imagination” from Willy Wonka echoes throughout the building.
In our awestruck state, we momentarily forgot that we were in a brewery at all, and that we should keep moving along to the tap room.
I’ll leave more of the brewery description to Jeremy, who will be sharing a review of it soon enough, but in short, it was truly out of this world – and one place that we have not stopped raving about with anyone willing to listen (even each other) ever since.
From Lagunitas, we drove towards the Lincoln Park neighborhood, where we were staying and where the music venue for the concert we were there to attend is located.
$$ | 1816 North Clark Street | Website
We stayed at the Hotel Lincoln and I cannot recommend it enough! While it’s a tad pricey – at least for us – you absolutely get what you pay for here. Especially location. Had we been staying several days, we may have sought out a cheaper option or a more affordable area to stay in – I had several Airbnb options saved – but for one night, it was totally worth the “splurge!”
After booking our room several days prior, I began receiving e-mails leading up to our stay, letting us know about the hotel and the area, and even an early check-in e-mail – much like an online flight check-in – where I could take care of that and make note of any special requests we had.
Actual check-in was a breeze and the receptionist was incredibly helpful when we asked about the area. He even gave us a ring a few minutes after we got to our room to make sure everything was okay.
We snagged a room with a view of both the park and the lake, and I could have spent hours just looking out of our window watching that small, bustling corner of the city.
The J. Parker
$$$ | 1816 North Clark Street, 13th Floor | Website
We took a few minutes to settle in, then took the elevator up to the top level of our hotel to check out the J. Parker – a restaurant and lounge situated in a retractable rooftop with 360° views of Chicago. We each enjoyed a drink and the stunning views of the city as the sun went down, then decided to brave the cold to find dinner before the show.
$$ | 1655 North Sedgwick Street | Website
We ended up at Twin Anchors, which I absolutely loved because it’s situated on a little corner, somewhat hidden, in a rather residential part of Lincoln Park. I’ve been to this area of Chicago twice now and one of my favorite things about it is, as we walk through the streets, we get a fleeting sense of what it would be like to actually live there – not just visit. And Twin Anchors seemed like that local spot we’d frequent on Friday nights if we lived in the neighborhood.
Bonus points: They are known for being one of Frank Sinatra’s favorite Chicago establishments, they are super affordable, and they have a vegetarian sloppy joe. Sold.
We were provided such quick service, we had a couple of hours to kill before the show. So, we walked down Wells Street and peeped into a couple of shops. We only (very randomly) stopped into one: an aquarium shop full of fish and other sea creatures.
The Pour House
$$$ | 1419 North Wells Street | Website
During our trek, we spotted The Pour House and decided to stop in for a drink each. This spot was awesome, but overwhelmingly crowded (as you might expect on a Friday night in Chicago!) We had a rather lengthy chat over our drinks and before we knew it, it was time to head toward the venue.
Lincoln Hall + Schubas
$$ | 2424 North Lincoln Avenue | Website
Immediately upon walking into Lincoln Hall, we were greeted by Julien Baker’s merchandise table, and seconds later, Julien Baker herself. I had to nudge J out of his star-struck state so we could catch her before she left. We exchanged a few words with her (randomly discussing our shared thoughts about cloud services) while buying her vinyl, and she was just as sweet, awkward, and humble as you might imagine.
Her performance was unbelievable. It’s the first show of that size (about 500 people) I’ve ever been to that you could hear a pin drop during every single song. In fact, people rarely even chatted between songs. While pausing to tune her guitar, she even commented on it – referring to us as church mice. If you’re not familiar with Julien Baker, she writes beautifully deep, poetic, sad songs that literally (I saw several instances at the show) make grown men cry. After the depression that swept over us last week – the death of David Bowie and Alan Rickman, the sudden jolt of cold, wintry weather, and the general blues that come with January – the emotional release is exactly what we, and likely everyone in the venue, needed.
$$ | 2429 North Lincoln Avenue | Website
Following the show, we set off to eat our feelings because we were somehow hungry all over again. We walked across the street to Pizano’s Pizza to share a small, deep-dish, Chicago style pizza and a dessert. If you ever find yourself there, order the chocolate chip cookie. It’s baked in a pizza pan, with a layer of vanilla ice cream, whipped cream, and chocolate drizzle on top. So. Good.
From there, we called an Uber to take us back to our hotel, where neither of us even remember going to sleep because we were zonked!
Side note: We chose to keep our car parked and rely solely on Uber, Lyft, and walking on foot to explore the city. It saved us a ton of stress, and with all of the promotions and deals these services offer, we were able to snag several rides for free!
The next day, we took our time getting around and checked out of Hotel Lincoln late in the morning. Before leaving the area, we grabbed some coffee from Elaine’s Coffee Call (aka the interior design space of my dreams), located just off of the hotel lobby, and hopped into the car for a quick drive down Lakeshore Drive to take in the sights along Lake Michigan.
We were shocked to see so many people out running along the beach and through the park, many with their dogs or strollers, in such cold weather. It was a magical scene to take in – a mix of colors and sculptures and buildings and green grass and lake and beach and sparkling snow all buzzing by.
We parked near a small harbor and walked along the water for a bit, until we came upon some lighthouses. The city skyline peeked through a bit of fog, and it was a lovely few minutes, until we could no longer feel our faces or our toes.
The Chicago Diner
$$ | 2333 North Milwaukee Avenue | Website
Nothing warms a person up better than brunch, am I right? So, we looked at our options and chose to make the journey to The Chicago Diner – a restaurant that caters to vegetarians and vegans. We decided on the Milwaukee Avenue location, since it was an area that was recommended to us by a few of our friends. We found a place to park our car for the day (using this app) and started on our way.
Guys. For the first time in my life, I had a country fried “steak” and eggs. And I haven’t stopped thinking about it since! Of course, it was a totally vegan-ified version, but J stole several samples off my plate only to repeatedly say how convincing it was.
Next time we’re in Chicago, we will no doubt be doing lunch or dinner here – there were so many options (a Rueben sandwich, a Cuban sandwich, poutine, gyros, a BLT…) of foods that I can’t normally enjoy while dining out as a vegetarian. Five stars.
$$ | 2323 North Milwaukee Avenue | Website
Luckily for us, right next door was a brewery J had been hoping to try: Revolution. I loved the cozy vibes this spot had going – walls made from strips of old beer barrels, a roaring fire, shelves full of classic books. The beer was good, too! (Again, more on that to come from J.)
After Revolution, we walked along Milwaukee Avenue for some time, stopping to check out street art or pop into a little shop every now and then.
$ | 1560 North Damen Avenue | Website
It took us quite awhile to make it to the bustling part of Milwaukee Avenue. We weren’t quite sure where to walk into first. But, our dilemma was soon resolved. Because neither of us can walk past a donut shop without caving, we immediately bolted for, and squeezed our way into, Stan’s Donuts, which was a full house, seconds after spotting it. We soon found out why it was the place to be on a Saturday afternoon when we learned that they had nitro coffee and the most delightful sounding donuts you’ve ever heard of.
I opted for the Dreamsicle Bar and J got a Biscoff Banana Pocket, and they were both, by far, the best donuts we’ve ever had. Part of me really wanted to go back in and get an entire box full, but alas, we had many more stops to make and very, very long walk back to the car.
We did a little more window shopping – stopping into several unique vintage/thrift shops and bookstores, and walked until night fell.
At that point, we realized it would probably be wise to head toward the car and start for home, but not before getting in one last bite to eat.
$$ | 1800 North Clybourn Avenue | Website
J recommended Goose Island, as he’d been there before, and we both ordered a bowl of veggie chili to warm our bones before the drive home. And just like that… we were saying goodbye to Chicago.
Ugh. This was SUCH a beautiful trip, through and through. I’m so thankful we were able to take a little time out and experience it together.
Can’t wait to see you again, Chicago.