I live for a long brunch with friends. The kind where the server brings more bubbles before your glass is even low. If you’re plotting your own weekend hunt for bottomless brunch in the Windy City, take these notes along. I’ve tried a bunch of bottomless spots around Chicago. Some were perfect for a big group. Some were loud. Some were… well, they were a lot. Here’s my honest take, with real plates, real bills, and a few tiny hiccups I didn’t expect.
Quick note before we start: most places cap bottomless at 90 minutes. Last pour can come a bit early. I set a timer on my phone, and I book on Resy or OpenTable. It saves me stress.
Fremont — the “we came to party” brunch
River North, Saturday, around 12:30. I wore sneakers. Good call.
Fremont is loud, packed, and fun. There’s a DJ. People stand at their tables. I went with five friends for a birthday. We did the package that covered the brunch spread and mimosas. It wasn’t cheap, but we knew that going in.
(Pro tip: Food-focused friends can scope The Infatuation’s deep-dive on Fremont Chicago for a peek at the expansive buffet and bottomless mimosa setup.)
Food felt like a buffet that went to the gym. I grabbed chicken and waffles, an omelet made to order, and mac and cheese. My friend Jess went for the carving station and came back like she won a prize. The orange juice leaned sweet. Refills were fast. Service moved like a small swarm—lots of staff, all rushing, but kind.
- What I loved: big energy, fast pours, lots of food choices
- What bugged me: we waited 20 minutes past our res; it was hard to hear each other
Would I go again? For a birthday or bachelorette. Not for a calm brunch with my aunt.
Highline Bar + Lounge — sports bar vibes, solid buffet
Also River North. I went on a Sunday with my brother after a gym class. He wore a Bears hoodie. No one blinked.
They run a boozy brunch with a buffet and bottomless mimosas. Think tater tots, mini sliders, a salad bar, and a build-your-own Bloody setup if you want to switch lanes. I stuck with mimosas and grabbed a plate with tots, bacon, and a pile of scrambled eggs. It tasted like a comfort blanket.
- What I loved: easy seating for groups, TVs everywhere, friendly staff
- What bugged me: the bathroom line was a journey; the music flips from chill to very not chill
Tip: Ask for a table by the windows. It’s brighter and less noisy.
Whiskey Business — rooftop, 80s heart, sunny pours
Wicker Park, warm day, sunglasses on. The rooftop feels like summer even when it’s not summer yet. They offer a bottomless mimosa package with a time cap. Our server gave us a “last call” heads-up, which I appreciated.
(If you’re weighing rooftops, The Rooftop Guide’s write-up on Whiskey Business highlights the nostalgic 80s/90s theme, 100-plus whiskeys, and sunshine factor.)
For a different rooftop narrative—equal parts sparkle and side-eye—check out my candid take on Sunroof Chicago before you pick your perch.
I ordered cinnamon roll pancakes that tasted like a fair, and wings with a sticky glaze. I know, odd mix, but it worked. The wind knocked our napkins around, so I tucked mine under my water glass like a pro.
- What I loved: fast refills, fun theme, great group tables
- What bugged me: if it’s windy, your brunch becomes a tiny workout
Bring a light jacket. Chicago likes to pretend it’s colder near noon. Because… it is.
El Mariachi Tequila Bar & Grill — Lakeview’s cozy bottomless
Lakeview brunch with my cousin, who’s obsessed with chilaquiles. They do bottomless mimosas (and they’ve offered margaritas, too, when I’ve gone). We ordered chilaquiles verdes and huevos rancheros. Salsa leaned mild, which my cousin liked, and the chips were warm and a little salty.
Our server kept our glasses full without hovering. Time limit was clear from the start. I actually prefer that. No games.
- What I loved: friendly staff, steady pours, strong brunch plates
- What bugged me: tables are close, so you might learn a stranger’s life story
Good for a mellow Sunday that still feels special.
Old Grounds Social — rowdy, game-day energy
Lincoln Park with a big group of friends. We celebrated a promotion. There were jerseys. There was shouting. They run bottomless deals, and it’s very “let’s go” energy.
I had a hot honey chicken sandwich and shared a pizza with the table. Drinks arrived fast, then slowed a bit when the place hit peak volume. Our server warned us about the time cap right away and did a last-pour lap.
- What I loved: perfect for groups, easy to split checks, lively music
- What bugged me: it gets loud and sticky by the bar when it’s packed
If you want quiet, go elsewhere. If you want a party, this hits.
A quick aside: not bottomless, still fun
Machine in Wicker Park does playful mimosa flights and flower add-ons. It’s cute. It’s not bottomless, but the flights are great for folks who want variety without the rush.
Craving maki more than mimosas? My real-deal list of the best sushi in Chicago can switch up the weekend vibe.
My little brunch playbook
- Book early. I use Resy or OpenTable.
- Ask on the phone about time limits, last pour rules, and what “bottomless” covers.
- Eat before you… eat. A banana saves me from wobble-town.
- Tip your server well, especially with packages. They’re sprinting.
- Check the weather for rooftops. Wind is a thief.
One mildly off-menu discovery my table couldn’t stop laughing about: someone wondered aloud where all the confident, brunch-loving single moms head after a 2-p.m. last call. If that kind of neighborhood intel sparks your curiosity too, swing by MilfMaps for a crowd-sourced heat-map of Chicago hang-outs and upcoming events, helpful if your post-mimosa mission involves meeting like-minded, seasoned brunch pros.
Heading out east for work or play? When that brunch-in-Chicago buzz follows you to D.C. and you’re hunting for after-dark connections in a new zip code, the refreshed classifieds hub at Backpage Georgetown compiles real-time local listings, user insights, and safety pointers so you can line up Georgetown plans with confidence before you even touch down.
If you want a quick primer on pacing your pours so the fun lasts all day, the responsible-drinking checklist from ARECO is a surprisingly handy read.
Final word from my crumb-covered heart
If you want full-on party mode, pick Fremont. If you want sports and comfort food, Highline works. For a sunny rooftop with fun plates, Whiskey Business. Want a cozy sit and steady service? El Mariachi. Big group with rowdy vibes? Old Grounds Social.
When the curtain’s dropping downtown and you’re after a twinkly, carb-forward warm-up, I’ve spilled all the details on Italian Village. And if brunch somehow rolls straight into midnight, my story-driven wander through Chicago’s hidden bars at Speakeasy Chicago has you covered for the after-hours plot twist.
You know what? Chicago brunch is a mood. Pick the one that matches yours, set a timer, and let the bubbles do their thing.