As my first official travel post (the coffee ode doesn’t count), let’s set the record straight—I don’t do itineraries. Vacation schedules? No thanks. I prefer to wing it, gathering tips from locals and trusting chance encounters. That’s why I started this blog—for the adventurers who dive headfirst into experiences.

For my birthday binder weekend, I set my sights on Chicago but skipped the tourist checklist. No Bean selfies, no Sears Tower. Okay, I accidentally saw Wrigley Field, but I was there for other reasons. Instead, I lived my weekend like any local would—embracing the city as it unfolded around me.

River North & the Infamous Riverwalk

We stayed in River North, right next to the Riverwalk—”a little posh,” according to a local, but perfect for easy access to great pubs and a killer view. The Riverwalk? Absolutely worth it. Picture yourself on a bridge, the autumn breeze in your hair, the river shimmering green-blue beneath a gloomy sky. It’s the kind of moment that preps you perfectly for a long night of drinking. Because, yes, this was my birthday binder weekend.

Chicago’s Nightlife: Late Nights and Last Calls

In L.A., bars close at 2 a.m. (and push you out sooner), but Chicago’s nightlife? Glorious. Bars stay open until 4 a.m., and I made the most of every minute. Shout-outs to some standout spots:

• Mother Hubbard’s – Rowdy but friendly, with a solid neighborhood vibe. Try Revolution’s Freedom of Peach sour.

• O’Callaghan’s – Classic Irish dive with friendly bartenders and a quirky breast cancer campaign where patrons design paper bras to hang on the mirror. Revolution’s Hazy IPA hit the spot—bright, hoppy, and smooth.

• Emporium – A barcade with craft beers, vintage games, and THC drinks.

• Logan’s – Another barcade where the night got hazy after three free birthday shots.

One tip: If you’re an IPA lover, craft options can be hit-or-miss. Revolution Brewery is your best bet, with occasional offerings from Lagunitas, Voodoo Ranger, and Goose Island.

Eating Your Way Through Chicago

“You could eat your way through this city,” a late-night security guard told me—and he wasn’t wrong. Chicago’s food scene is a must-experience. Here are a few highlights:

• Chicago-Style Hot Dog – A poppy seed bun, all-beef frank, mustard, relish, onions, tomato, pickle spear, and celery salt. It’s an overload of flavor, but trust me—it works.

• Italian Beef Sandwich – Locals debate between Portillo’s and Al’s. I went with Portillo’s, and it saved me during a 24-hour drinking binge. Thin-sliced beef, gravy, and sweet peppers—pure magic. Add cheese if you like, but either way, it’s unforgettable.

• Deep-Dish Pizza – Lou Malnati’s or Pequod’s? I asked a bartender to level with me—he said Pequod’s, no contest. I stumbled in, three sheets to the wind, just before closing and lucked into a canceled order. Shout-out to Noah, the kind soul who handed me that glorious pie for free. That caramelized cheese crust? Life-changing. I tipped him and the hostess the cost of the pizza because, honestly, they deserved it.

The Birthday Comedy Crawl

As a certified comedy nerd, Chicago’s comedy scene was a major reason for my visit. It’s one of the three big comedy hubs in the U.S., along with L.A. and New York. Before my trip, I consulted two Chicago-based comedians to make sure I hit the best spots, and here’s the rundown:

• The Green Mill’s Paper Machete – Every Saturday from 3–5 p.m., the Green Mill (yes, once owned by Al Capone) transforms into a “live magazine,” featuring comedy, music, and quirky performances. We witnessed everything from a hilarious rivalry between Cubs and White Sox fans to a puppet professing love for Edgar Allan Poe—complete with musical interludes. It was easily my favorite show.

• Second City’s Baby Wants Candy – This improv troupe blew my mind, creating a fully improvised musical about fish on the spot, accompanied by a live band.

• The Lincoln Lodge’s Down and Dirty – For those who like their comedy raw, the late-night sets here were unfiltered, raunchy, and had me in stitches.

If you’re into comedy, seeing live shows in Chicago is non-negotiable. When in Rome, right?

A Nightmare on Clark Street: A Spooky Tiki Dream

As a hardcore horror fan—yes, I’m the type who falls asleep to Terrifier—October in Chicago had to include a haunt. A Nightmare on Clark Street at the Bamboo Club didn’t disappoint. This haunt merges jump scares with a pop-up tiki bar, featuring themed cocktails and souvenir cups. It was worth every penny.

The scare actors were well-placed, and the fully black tunnel and the lab with monsters strapped to tables gave me genuine chills. Leading a group of grown men through the maze? Less thrilling when they decided I should go first.

Halfway through, we hit the Beetlejuice-themed bar, where I sipped Freddy’s Tequila: a killer combo of Patron Reposado, lime, agave, pineapple, and jalapeños with a salt rim. And yes, the creepy tiki cup souvenir was 100% worth it.

The Absolute Best Part of Chicago: The People

Not to get too corny, but the thing that stood out most was the people. From hilarious Uber drivers to late-night hotel staff who sat down to share a slice of Pequod’s with me, to bartenders who went out of their way to make my birthday unforgettable—the kindness and warmth in this city were unmatched. I’ve never experienced hospitality like this anywhere else in the country.

So, thank you, Chicago, for the architecture, the rowdy nightlife, the food, the comedy, and, most importantly, the incredible locals. This trip was truly one for the books.

Whether it’s for the sights, sounds, or those unexpected moments that only happen when you embrace the unknown—Chicago is a must-see. Happy travels, and remember: Don’t just visit. Get lost.