11's: A No-Reservation Weekend In Chicago
All the hits from three glorious days in Summertime Chi
11's: A No-Reservation Weekend In Chicago
As I turned onto the Kennedy Expressway on my way out of Chicago last weekend, a small wave of guilt rolled over me.
This city means a lot to me. I’ve got years of great memories here: driving in for hockey camps as a kid, seeing Coldplay at the United Center in 2012, my first Lollapalooza — my seventh Lollapalooza. Moving into an Uptown sublet as a summer intern. Losing my phone at Slugger’s World Class Sports Bar. Signing the lease on my first post-grad apartment in Lakeview. The epic farewell tour before heading off to New York.
I know I haven’t slighted Chicago in any way, but I realized I haven’t shown it quite enough love. I haven’t expressed how good it feels to be back. To hit the ground running. To catch up with friends over light beers and lacy smashburgers. To bask in vibrant Summertime Chi — where everyone’s clamoring for a patio seat, the High Life bottles are sweating, and the energy is convivial from sun up to well past sun down.
Maybe I’m being hard on myself. I’ve highlighted a few of my favorite spots that feel uniquely Chicago, I’ve written about a new South Indian opening, and I’ve praised their very tasty breakfast sandwiches. I even named one of their bars the best of 2024.
But Chicago needed something proper on the Flood’s front page. A standalone piece that’s meaningful and thorough. I wanted to capture the way I’ve been experiencing the city these past few years; no longer as a local, but as a visitor. A visitor with a deep roster of hits to revisit. A visitor who’s keeping close tabs on new openings, even from afar. A visitor who’s nostalgic for days past, and eager to make new memories.
Lately, my trips have been anchored in Wicker Park, where my friends Connor and Hailey graciously play host. I couldn’t pick a better home base: a quiet tree-lined street just south of Milwaukee Ave. West of the river is where you want to be — from West Loop up to Avondale, with West Town, Wicker Park, Bucktown, and Logan Square filling the space between. It’s where most of the best shit is happening. No shade to Lakeview, Lincoln Park, or Gold Coast — they still have their hits — but these days, I’m feeling more and more aligned with the energy on this side of town.
This edition of 11’s is a proper Chicago weekend round-up. A weekend that, fittingly, included no dinner reservations. There were ideas bounced in the group chat beforehand, but really, it was a blank slate ready to be ripped. That’s one of the many lovely things about Chicago: It’s a major city with the pace and pressure turned down a notch. If you’re flexible — and willing to wait things out over a Spaghett (I am) — almost everything and everywhere is fair game.
I considered other formats for this list — I’ve been loving writing Away Game, and I’m grateful it’s been so well-received (there’s more of those to come). But as I recapped the weekend, it turned out there were exactly 11 spots I wanted to write about. Some new, others tried-and-true. Presented in chronological order.
I’ve built up many, many more Chicago hits from my four years living here, and 10+ return visits since. The complete Chicago list is included in Flood’s Worldwide, available to paid subscribers.
11's: A No-Reservation Weekend In Chicago
THURSDAY
01] Middle Brow Logan Square, Chicago, 8:00 pm
Way back when, Middle Brow was a lucky stumble-in while I waited it out for a somewhat mediocre meal at Gretel across the street. Now, it’s a must-hit every time I’m in town. Perfect sourdough pies, crunchy salads, crisp beers, and funky natural wines serve as the perfect bookend to a weekend in Chicago — either the first or final stop. This time, I hit it before even dropping off my bag.
The peak-summer “big salad” was packed with little gem, watermelon radish, and cucumbers, all coated in a creamy basil & fermented pepper dressing. The pies — sungolds and fontina; the Roberta’s-inspired soppressata + hot honey; and the mushroom pie with cream sauce, caramelized onions, oyster shrooms, and chives — were all serious hits. Crisp, airy, and finished with grated Parmesan blanketing the already flavorful crust. Middle Brow is always buzzing, but with a spacey brewery room and plenty of outdoor picnic seating, the wait rarely outlasts your first Czech pils at the bar.
FRIDAY
02] Lula Cafe Logan Square, Chicago, 12:00 pm
A tried-and-true winner, Lula Cafe is the neighborhood restaurant that everyone — locals, transplants, tourists — loves to love. With a distinctly 90s, crunchy, slightly quirky vibe and a menu of deceptively simple, carefully prepared dishes, Lula is comforting, approachable, and endlessly repeatable. Difficult ordering decisions were made, but we landed in the right place. Chilled spicy peanut noodles were undoubtedly the move on a scorching day. And the “Royale” breakfast sandwich — seared haloumi, za'atar fried egg, creamy labneh, spicy harissa, bright and acidic sumac pickles, on a toasted sesame seed bun — was the ideal companion.
03] Four Letter Word Coffee Logan Square, Chicago, 1:30 pm
It took some self-restraint not to order a coffee at Lula, but my patience was rewarded with an afternoon hang at Four Letter Word. 4LW is my favorite coffee roaster in Chicago by a fairly wide margin. They also have a sneaky hit of a cafe —unassuming and unpretentious — hidden in plain sight on Diversey Ave in Logan. Buy a bag of beans, polish off a very good cortado (free with purchase!), then slide next door and flip through their eclectic collection of used books and vinyl.
04] Queen Mary Tavern Wicker Park, Chicago, 5:30 pm
If you granted me the magical ability to bring one Chicago bar back to New York with me, Queen Mary would be my choice. Any neighborhood benefits from a dim, maritime-themed cocktail bar where the drinks are sturdy and the service is welcoming. Toward the far end of the bar, a pocket of seating opens — two stools on each side — creating the perfect intimate hang for four. Queen Mary has range, working well in so many situations — in this case, serving as the perfect bridge from late afternoon to early evening.
05] Friends of Friends West Town, Chicago, 7:00 pm
We emerged from the darkness of QMT into a still-bright evening, juiced up on navy-strength gin. A swift Divvy ride down Damen delivered us to the next stop on tour, Friends of Friends. The brand new West Town bar occupies a beautifully restored corner tavern space, revamped by industry vets who seem to be self-aware and in touch with what people want. That is, easy-drinking cocktails, $5 beers, and absolutely no pretense. Plus, the massive back patio makes this an ideal warm-weather spot.
06] Mister Tiger West Town, Chicago, 9:00 pm
Back in New York, I’ve been on a banchan bender — Kisa, Cho Dang Gol, Hahm Ji Bach, any Korean food I can find. Turns out, this bender knows no geographical bounds. We hit up the newish Mister Tiger, which is a sleek, buzzing, albeit somewhat generic-feeling Korean restaurant tucked into one of West Town’s new-build strips. The menu had some big winners, like Galbi Jjim — tender braised short ribs in a sweet, umami-packed sauce. But their takes on the classic, comforting Korean dishes — Bulgogi, Kimchi Fried Rice — were forgettable. If you need a table of 6 on a Friday night, it’s a safe and solid play, but not one I’d rush back to.
SATURDAY
07] Uncle Mike’s Place West Town, Chicago, 10:30 am
I usually keep things on the lighter side for breakfast, but after a loaded Friday, Connor’s Filipino diner pitch was easy to greenlight. We started with a quick coffee hang at Prequel, then made our way down the street to Uncle Mike’s Place — a loveable spot with just the right amount of grit. After a quick wait, we were seated with a steamy bowl of homestyle Filipino rice porridge in front of us. As tempting as the “Big Bangus,” or marinated Pacific milkfish, was, it’s best not to overthink it — get the skirt steak with garlic rice and eggs cooked however you like ‘em (for me, that’s over-medium).
08] Leavitt Street Inn & Tavern Bucktown, Chicago, 1:30 pm
Leavitt is the gathering spot. The neighborhood anchor, the lauded locale. It’s the place to bring a crew together for a celebration, or for absolutely no reason at all. An afternoon spent huddled round a picnic table, eating a burger smashed so thin it has a legitimate crunch to it — that’s an afternoon I can get behind. And that’s exactly how it went down — 10 burgers, a few piles of fries, and many Modelos. It’s a come-as-you-are atmosphere, and a spot you’ll linger for hours without meaning to. Walking south through the quiet, leafy streets of Bucktown afterward is about as lovely as it gets.
09] Brasero Logan Square, Chicago, 9:00 pm
Call it what you want: blind confidence, pure stupidity. But around 6:00 pm, we dropped a name for a 6-top at the ultra-popular Armitage Alehouse, Hogsalt’s “British pub,” positioned on a perfect corner in Lincoln Park. With no promise of a table, we pivoted to Brasero, the upscale Latin-inspired spot that took over the old Funkenhausen space. (Armitage did eventually text us about a table at like 10 pm)
Brasero ended up being a really solid play — polished, dim, dialed, maybe skewing into corporate card territory, but still, a winner. The standout dish was simply called “NOODLES”: a Brazilian-style seafood stew with shrimp, clams, and tender Akahoshi ramen, suspended in a silky, rich broth almost reminiscent of a creamy Southeast Asian laksa. The other large plates — pork shank, roast chicken — were solid dishes, and generously portioned, but nothing to write home about. Brasero is a good restaurant — probably not a spot that’ll be in my tight Chicago rotation — but a meal you’ll be more than happy with.
SUNDAY
10] Loba Pastry + Coffee Roscoe Village, Chicago, 9:30 am
With the Wimbledon final on deck, we decided to procure a spread of baked goods and coffees, and settle in to watch the match. I had a good feeling about Loba, but had no idea it was gonna hit this hard.
Tucked beneath the Brown Line in Roscoe Village, the Mexican-inspired cafe with a Japanese-minimalist design is shockingly excellent. Kyoto-style cold brew is smooth, rich, and bold. Every pastry was outrageously good. The green mole croissant (!!), the oat-custardy canelé, and the queen of them all, a cheesy gouda and fontina Kouign Amann with a caramelized curry-sugar dusted exterior, and a buttery, laminated core. Absolutely wild. Loba was, without question, my biggest hit of the weekend.
11] Tempesta Market West Town, Chicago, 12:00 pm
Staring down a 3-hour road trip back to West Michigan, I knew it would be wise to stash some provisions before I left town. There was really only one thing from one place on my mind: a damn good sandwich from Tempesta. It’s a long-standing favorite of mine, a place that’s been in my regular rotation since they opened in 2017. “The B. Franklin” has roasted turkey, aged cheddar, pickled fresnos (important), avo spread, sofrito aioli, and lots of crunchy sprouts tucked between golden slices of fresh sourdough. I’ll go out on a limb and say it’s the best turkey sandwich in existence, certainly the best one I’ve come across. Tempesta can do no wrong, and to close out a beautiful weekend, it was the perfect play.
Thanks for being here, thanks for reading. If you have a Chicago spot you think I should hit, please drop it in the comments — I’d love to hear from you. And if you haven’t yet, subscribe below and get Flood’s delivered every Sunday. Paid subscribers, keep going for a recap of all the recent Chicago adds & updates.
Flood’s Worldwide — Chicago Adds & Updates
I updated the Chicago section of Flood’s Worldwide — featuring new hits and a few changes to the star ratings.
Flood’s Worldwide is the opposite of my longer-form writing. It’s a tight, concise list of hits for those who just want to know where to go (and, just as importantly, where to skip). Organized in a 2-star system, the major hits are the destination-worthy places to prioritize on your journey. But even the places with one or no stars, I still consider big winners.
If you have questions about Flood’s Worldwide, or any of the spots within it, send me a message here or on Instagram.