Three Days in Chicago: A City That Completely Surprised Me
I'll be honest with you right up front — I wasn't expecting much from Chicago.
I had this picture in my head. Dirty. High crime. Gray. The kind of city you visit because you have to, not because you want to. We were flying in for a wedding, so I figured we'd tack on a few extra days, check the box, and head home.
I could not have been more wrong. Here's how the trip actually went.
Where We Stayed: Nobu Hotel Chicago
We flew in, grabbed an Uber, and checked into the Nobu in the West Loop. Now, I had no idea where to stay in Chicago - I don’t know what areas are what, which ones are safe, which ones have the vibes we like/don’t like….but this hotel was listed as the hotel for the wedding hotel block we were attending, so that’s what we picked. And boy, it was one of the nicest hotels I’ve ever stayed at. Good choice.
The welcome sets the tone immediately — hot tea and warm towels at check-in, and a bellhop who was so genuinely kind and helpful that I remembered him for the rest of the trip. The arrival is built around a traditional welcome ritual, and the lobby is anchored by a 26-foot kintsugi brass sculpture set against deep indigo walls — kintsugi being the Japanese art of repairing broken pottery with gold, so the mend becomes the beautiful part.
The room. Industrial vibes done right. Black concrete walls, bare concrete ceiling, and floor-to-ceiling windows framing the city. Our bed was almost identical to the one we have at home — low, modern, with a long headboard running the width of the room, which I loved. What really won me over were the floor-to-ceiling cabinets. Multiple of them. Enough storage that we could actually unpack and stash our luggage out of sight, which meant the room stayed tidy for three days instead of slowly disappearing under our stuff.
It's bigger than most hotel rooms, and it absolutely gives city-slicker energy. The bathroom was its own whole moment — dark, industrial, extremely vibey.
A little context on the Nobu, because I didn't know any of this going in. It's the hotel side of the empire that actor Robert De Niro and chef Nobu Matsuhisa started with a single restaurant in New York more than three decades ago. The Chicago location opened in 2020 and was the brand's first venture into the American Midwest — the group now has more than 30 hotels and around 60 restaurants worldwide. It's an 11-story, 115-room tower at 155 N Peoria St, and it sits right over the stretch of Randolph Street known as Restaurant Row.There's tfihe signature Nobu restaurant on the ground floor — black cod miso, yellowtail sashimi, rock shrimp tempura — and a rooftop lounge on the eleventh floor overlooking Restaurant Row with what are genuinely some of the best skyline views in the city.
There's also a fitness center and an indoor pool.
The neighborhood itself is worth the stay. Fulton Market is a formerly industrial area that's become home to some of the city's best restaurants and nightlife. You can walk out the door and land somewhere excellent without a plan.
Night One: Fioretta
Walking distance from the hotel, which was exactly what we needed after travel.
The restaurant Fioretta is dim and dramatic — big bold wallpaper, elevated tones throughout, and a piano player doing live music all night. We got a cozy booth near the pianist, which felt like winning.
Bread service was a gentleman circulating the room handing warm slices to each guest individually. Small thing. Made the whole night feel more considered.
What we ordered:
A Caesar salad big enough to split — one of those big-leaf situations you have to cut up yourself. Lemony dressing and enough parmesan to feed a small town, which is precisely how I want it.
Then filets and mashed potatoes. I got mine parmesan crusted. They brought out a roasted garlic clove that was, I am not exaggerating, larger than my seven-ounce filet. I still don't know what I was supposed to do with it. They also set down a house salt blend for the table that was phenomenal.
Steak rating: 9/10. Cooked perfectly. Not over-charred. Tons of flavor, smooth texture, zero gristle. It's hard to make me that happy with a steak and they did it.
Day Two: Breakfast, Deep Dish, and the River, Stetsons & an Arcade
Breakfast at Beatrix
Phenomenal. There were six of us and every single person raved about their meal, which basically never happens.
It's a coffee shop crossed with a full breakfast spot crossed with a pastry case. I had the Greek yogurt. But it wasn’t just any greek yogurt - it had brulee’d bananas, chia seed honey, strawberries, flowers….mmm. So good.
Around the table we had overnight oats, waffles, pancakes, bacon, hash browns — a full survey of the menu, and no complaints from anyone.
Actually, Beatrix was SO good, we even went back a 2nd time before our flight out on Sunday.
Lunch at Lou Malnati's
We had just eaten. We were not hungry. But you cannot go to Chicago and not eat Chicago-style pizza, so we went anyway.
Lou Malnati's is the one known for that buttery crust, and the space we ended up in had a proper downstairs basement pizza-parlor feel. My husband and I split a small personal deep dish, cheese.
Here's my confession: I don't love a lot of sauce, and the idea of Chicago-style pizza with the sauce sitting on top had me nervous. It was delicious. Maybe ordering small meant we avoided the bucket-of-sauce situation I was bracing for, but whatever the reason — it worked. I'd absolutely go back.
The Architecture Boat Tour
We walked around a bit, and then met up with some other friends and family for the Architecutre Boat Tour. We spent the morning watching the forecast and worrying about rain. It ended up being great — a little hot at points, but great.
We did the Chicago Architecture Center cruise, which is a 90-minute tour and the only architecture boat tour on the river led by trained expert docents. It's run by a certified nonprofit, so ticket purchases go back into their education and community programs.You cruise all three branches of the river with open-air 360-degree views, and the docents tell the stories behind more than 50 buildings and 13 bascule bridges along the way — Art Deco, neoclassicism, mid-century modernism, postmodernism, all of it.
Practical details: It departs from the Riverwalk at Michigan Avenue and Wacker Drive — three blocks north of Millennium Park and steps from the Magnificent Mile. Look for the black awning at street level on the southeast corner of the Michigan Avenue Bridge. Tickets run roughly $44 to $54. Cruises operate rain or shine with both open and covered seating, and departures frequently sell out — book ahead.The boats hold up to 250 passengers and have open-air upper decks, full-service bars, and climate-controlled lower cabins.
One honest note: the drink line was about a twenty-minute wait for essentially the entire ride. We still had a great time and learned a genuine amount, but plan accordingly.
Shopping We Could Not Afford
After the boat we walked and shopped in the very fancy part of town. I'll be transparent — the people we were traveling with vacation differently than we do - they shop all the Gucci, LV, fancy stores that we can’t afford. We mostly tagged along and admired things from a respectful distance. Zero regrets. Excellent people-watching.
Dinner at Stetson's
Steak and sushi inside the Hyatt by the park. I had a filet and a sour cream potato purée that I'm still thinking about.
Emporium (The Barcade)
After dinner we Ubered to Emporium, which is a barcade — full bar, and wall-to-wall arcade games. Foosball, pinball, air hockey, skee ball, all the machines we grew up on.
My favorite pinball machine of all time is the Addams Family, and they had one, which genuinely made my night. Only downside: the place was loud enough that I couldn't hear any of the machine's sounds, which is half the joy of that game.
Then we discovered Hamburger Town and lost the rest of the evening. It's like Pac-Man meets build-a-burger, and I became obsessed. I'm now seriously considering buying one for the game room at our Tennessee house. (An Addams Family pinball machine is unfortunately out of my price range, so I'm relegated to playing it whenever I happen to stumble across one in the wild.)
Day Three: Coffee, the Bus, and the Riverwalk
We woke up and just wandered the blocks around the Nobu until we found a random spot for coffee and a breakfast sandwich. Some of my favorite travel moments are these — no plan, no reservation, just walking until something looks good.
The Hop-On Hop-Off Bus
Then we Ubered down toward Millennium Park (which is, yes, where the Bean lives) and got on the double-decker hop-on hop-off bus.
We'd done one of these in Pittsburgh and loved it. Seeing a city from up high early on is such a smart move — you get the lay of the land and figure out which neighborhoods you actually want to go back and explore on foot.
In Chicago that's Big Bus, which runs a single loop called the Red Route connecting the Loop, the lakefront Museum Campus, the Magnificent Mile, and Navy Pier. A full circuit without hopping off takes about two hours, and buses come around every 30 to 45 minutes. There are 11 stops covering 37 points of interest, and pricing starts around $49 for a 24-hour adult pass. The Millennium Park stop is at 200 S. Michigan Ave, in front of Potbelly's.
Our honest take: we enjoyed it, but we didn't love it the way we loved Pittsburgh's.
Pittsburgh had a live guide with a microphone — explaining things, telling jokes, reading the crowd. The bus wasn't crowded and we could talk to our family and friends easily. It was a social experience.
Chicago's was packed, and the commentary is pre-recorded with headphones, so everyone's sort of sealed into their own little audio bubble. Informative, sure. But not the shared, laughing-with-your-people experience we'd had before.
Would I still do it? Probably yes, especially on a first visit. Just know what you're getting.
Riverwalk Lunch and a Nap
We ate lunch along the Riverwalk, then went back to the hotel for naps like the responsible adults we are.
Saturday Night: The Wedding
The reason we came.
It was one of the most beautiful weddings I've ever attended. Seventeenth floor of a Chicago high-rise, floor-to-ceiling glass on every side, so the entire cityscape was the backdrop. The florals against that skyline — I don't have words that do it justice. Just one of those nights that gets filed permanently in your memory.
Final Thoughts: I Was Wrong About Chicago
I said it at the top and I'll say it again because it's the honest headline of this whole trip: I went in with low expectations and Chicago dismantled every one of them.
I never once felt unsafe. Everywhere we went was clean and grand — rich history in the architecture, vibrant flowers everywhere, patio cafés spilling onto sidewalks, and shopping that runs the whole spectrum from small boutiques to the kind of stores where you look at price tags recreationally.
What struck me most is that it feels like a real, living, cool city. Not a place you pass through. A place with an identity.
I want to go back, and next time I'm bringing the kids. They'd love the city parks, the aquarium, the rooftop pools, the shopping, all of it. Three days barely scratched it.
If Chicago is sitting on your maybe-someday list because you have the same assumptions I had — move it up. It's so much more than I gave it credit for.