If you ever find yourself with a long weekend and an appetite for architecture, art, and deep dish, Chicago is your girl. This city balances its skyscraper glamour with Midwestern charm—and in just 72 hours, you can soak in the best of both. From the glittering river to skyline cocktails, here’s how I spent a chic, unforgettable three days in the Second City.
Day 1: Arrivals & A River View
After checking into my downtown hotel and perusing the landscape (pro tip: stay near the Magnificent Mile for easy access to everything), I kicked things off with the ultimate Chicago welcome: an architecture boat tour along the Chicago River. As the boat glided through a canyon of high-rise pillars, I got a crash course in the city’s architectural legacy—from Gothic Revival to sleek modern towers. The guides? Funny and full of facts mixed with a little snark about the weather (winter must be particularly harsh). It’s the kind of history lesson I’ll happily sit through in sunglasses with a breeze in my hair. I took the tour that started just before sunset so I got to see the city in both daylight and nighttime, the best of both worlds. Magnificent.
Dinner that night? Deep dish pizza, naturally. I went classic at Lou Malnati’s—golden crust, tangy sauce, and cheese for days. It’s a fork-and-knife affair, so come hungry and unashamed. Pro tip – I found that Chicago natives feel strongly about which pizza restaurant is best so be cautions if you ask for a recommendation. A full on raised voice argument could ensue, as did in my hotel lobby.
Day 2: Cloudy With a Chance of Cocktails
No trip to Chicago is complete without a stop at Millennium Park, and yes, The infamous Bean (officially Cloud Gate) is as reflective and ridiculous as you expect—in the best way. I spent the morning strolling the gardens, watching the Crown Fountain, and sipping a coffee from a local café. It’s a dreamy, art-meets-urban-oasis kind of place.
After a quick outfit refresh, I headed out for a night at the theatre. Chicago’s performing arts scene is top-tier. I scored tickets to a Broadway-in-Chicago show, and the historic architecture inside the theatre was almost as captivating as the performance itself. There’s something transportive about velvet seats and spotlights, isn’t there?
Nightcap? The CloudBar at the top of the St. Regis Chicago. It’s high above the city, with floor-to-ceiling windows and panoramic views that make your drink taste even better. I ordered a gin-based cocktail that was as smooth as the skyline. Ladies – for the best view, check out the restroom. You won’t regret it.
Day 3: Pier Pressure & Playful Vibes
For my final evening in the city, I made a beeline to Navy Pier—a playful, lakeside icon that blends classic boardwalk charm with urban flair. The moment you arrive, it feels like summer—even if it’s not. Street performers, local art installations, and that crisp breeze off Lake Michigan set the tone.
I started with a ride on the Centennial Wheel (yes, I’m a sucker for a good view). From the top, the lake sparkled endlessly, and the skyline looked like it had been arranged just for me. Afterward, I strolled the pier, picking up a couple of cute souvenirs and grabbing a coffee from a local stand to sip as I wandered.
If you have time, Navy Pier also offers museums, gardens, and even mini cruises—perfect for families, solo travelers, or anyone who loves a little amusement with their architecture. I kept things low-key, but you could easily spend half a day here.
Then, just like that, it was time to walk back to the hotel to pack for tomorrow morning’s trip to the airport. One last look at the lake, one last snapshot of the skyline—and off I went, already plotting my return.
The next morning before heading to the airport, I made one last pit stop: a loop back through Millennium Park to say goodbye to The Bean. Call me sentimental.
Chicago Tips, From Me to You:
- Footwear matters. You’ll walk a lot. Cute but comfy is the vibe.
- Reserve theatre tickets in advance, especially for hot shows.
- Try the boat tour early in the trip. It helps you get your bearings and fall in love fast. Go at sunset.
- Layers are your friend. Chicago weather has mood swings.
Here are my Chicago essentials to get you packing!
Chicago is big but never cold (well—except in February), bold but always welcoming. In just 72 hours, it offered me art, architecture, theatre, carbs, and a skyline I’m still dreaming about. If you need a city that feeds the soul and your camera roll, this is it.
Until next time, Windy City. You were a breeze.
