The best thing about Chicago? It’s not deep dish.
Not my photo
I landed in Chicago for a quick weekend trip with my husband - no big agenda, just a loose list of restaurants and cafés, a neighborhood to wander, and a hopeful wish for good weather (Optimistic, considering it was the first week of March).
The plan was simple: fly out of Boston early Friday, land at 9:30am, spend two full days eating our way through the city, and fly back Sunday morning.
Reality had other plans.
About 20 minutes before landing, I noticed the remaining flight time creeping up. And up. And up. Next thing we knew, we were sitting on a runway in Indianapolis while a thunderstorm rolled through Chicago. My hopes for a sunny weekend slowly dissolved into a grey, slightly dramatic cloud somewhere over the Midwest.
Five hours later, we finally made it.
Slightly delayed, very hungry, but still determined to make the most of our 40-ish hours in Chicago.
Day 1: A delayed start, but worth the wait
Getting into the city
We landed at O’Hare, about 16 miles from downtown, and made our way in via the Blue Line, switching to the Red Line before a short walk to our hotel near the Magnificent Mile.
By the time we arrived, we were completely drenched. But at that point, hunger > everything else. No time to reset, we dropped our bags and headed straight back out.
Apple with bebinca, parsnip and ginger Ice Cream
and Kaju Katli with honeycomp, Nougat, Milk Ice Cream
Dinner that made the trip
Let’s be honest: food was the main reason for this trip. And since it was our two-year anniversary, we went all in and booked a Michelin-star Indian restaurant, Indienne.
A quick sunset walk along the river later, we arrived and from the first bite, we knew this was going to be special.
The seven-course tasting menu somehow managed to feel both deeply familiar and completely unexpected. Every dish had that “wait… what is that?” moment in the best way possible.
We left full, happy, and slightly convinced the meal alone justified the entire trip.
Day 2: Coffee, long walks, and a lot of food
This was our one full day in the city, so we planned a loose loop: coffee → walk → zoo → beach → architecture tour → friends → pizza.
Ambitious? Yes. Worth it? Also yes.
A slow morning in Lincoln Park
We started by heading north through Old Town, walking past rows of beautiful townhouses and quiet, tree-lined streets. Chicago really knows how to do neighborhoods.
Our first stop: coffee at Abrah Cafe in Lincoln Park.
Two weeks later, I’m still thinking about that coffee.
We shared a double baked pistachio croissant (which I’m still not over), sat for a bit, and eased into the day in the best possible way.
Zoo + beach = unexpectedly perfect combo
View of the city from North Avenue beach
From there, it was a short walk to Lincoln Park Zoo, which, surprisingly, is free. I saw a red panda for the first time in my life, which instantly made it a top-tier travel moment.
Post-zoo, we walked over to North Avenue Beach and started heading south along the lake.
The water from Lake Michigan was this unreal turquoise, the sand was golden, and the whole stretch was filled with runners, cyclists, and people just… living their best lives.
At one point we looked at each other and went, “Should we move here?”
Architecture + a mid-day reset
By early afternoon, we had already done a lot, so the architecture boat tour felt like the perfect way to slow down.
Cruising along the river while learning about the city’s skyline was equal parts relaxing and fascinating, and a nice break for our legs before continuing the day.
The Bean (yes, it’s actually worth it)
On the way back, we stopped at Millennium Park to see Cloud Gate, aka “The Bean.”
I’ll admit, I didn’t totally get the hype before. But standing there, seeing the entire skyline reflected back at you, it just… clicks.
If we hadn’t lost half a day to flight delays, this is one place I would’ve happily spent more time wandering around.
Finally… deep dish
Over 24 hours in Chicago and we still hadn’t had deep dish. Honestly, a bit disrespectful of us. After a quick internal debate (and a very intense Reddit scroll), we ended up at Lou Malnati’s Pizzeria.
And here’s my controversial take… I was a little underwhelmed.
Maybe I ordered wrong. Maybe expectations were too high. But it didn’t quite live up to the hype for me.
The real hero of the night? Ice cream from Jeni’s Splendid Ice Creams back at the hotel.
Gone, but not for long
The next morning, we flew back to Boston, replaying our whirlwind 40 hours in Chicago.
It’s funny, we almost didn’t take this trip because we were waiting to plan something “bigger.”
But this turned out to be exactly what we needed. Small trip. Big memories.
And honestly? Chicago might just be one of those cities you keep coming back to.
