8 Toughest Reservations To Score In Chicago’s Dining Scene

Chicago’s food scene is hotter than ever, with some restaurants now so popular that you’d have better luck winning the lottery than actually snagging a table on short notice. The city’s culinary landscape has become a high-stakes game, where securing a reservation can feel like a victory in itself.
Over the years, I’ve spent countless nights refreshing reservation pages, setting alarms, and even planning months in advance just to experience these coveted dining spots. The anticipation builds as you finally get the chance to taste what’s been hyped up for so long.
Ready for a real challenge? Here are the eight restaurants in Chicago where getting a seat is almost as impressive as the food itself—places where the culinary masterpieces aren’t just limited to the plate but also to the reservation process.
1. Oriole – The Hidden Gem of Fulton Market

Last month, I tried booking a table at this two-Michelin-starred haven and ended up setting three different alarms on my phone! The multi-course tasting menu at Oriole is worth every bit of the reservation hassle.
Their reservations open exactly 90 days ahead, and I’ve watched slots disappear within minutes. My secret tip? Try for Tuesday or Wednesday evenings instead of weekends. Also, their 5:30 pm seating tends to be slightly easier to book than prime time slots.
The restaurant’s intimate setting only accommodates a small number of diners each night, making each reservation that much more precious.
2. Kasama – West Town’s Filipino-American Wonder

My calendar has a recurring reminder set for Kasama’s reservation release day! This Filipino-American hotspot drops new reservations at high noon, exactly 45 days before your desired date.
The first time I tried booking, I was literally seconds too slow. Their pastry case alone draws lines around the block during daytime hours, but the dinner service is where the real reservation battle happens.
Pro tip from a seasoned veteran: have your credit card ready and your clicking finger warmed up before the clock strikes twelve. Their tasting menu experience sells out in what feels like milliseconds.
3. Mirra – Bucktown’s Mediterranean Sensation

Remember when I stayed up until midnight just to book a birthday dinner? That was for Mirra. Their Mediterranean-inspired menu changes with the seasons, making it impossible to visit just once.
The restaurant’s popularity exploded after a certain celebrity chef posted about their olive oil cake on social media. Now everyone and their cousin is trying to get a table! Their online booking system crashes regularly due to high traffic when new dates are released.
My strategy involves joining their email list for last-minute cancellation alerts. I’ve scored a table twice this way when someone else’s plans fell through!
4. Bavette’s Bar & Boeuf – River North’s Time-Travel Steakhouse

The first time I walked into Bavette’s, I felt like I’d stepped into a 1920s speakeasy! This vintage-inspired steakhouse releases reservations exactly 21 days ahead, and I’ve literally set alarms to remind myself when to book.
Their online reservation system opens at midnight, and prime weekend slots vanish by 12:03 AM. No joke! The dimly lit ambiance and red leather booths create an atmosphere that’s worth the booking battle.
For those who strike out online, they do save some tables for walk-ins at the bar area. I’ve waited up to two hours on a Friday night, but their perfectly cooked ribeye made me forget all about the wait.
5. Monteverde – The West Loop Pasta Paradise

My pasta-loving heart nearly broke when I tried booking Monteverde three weekends in a row without success! Chef Sarah Grueneberg’s Italian haven serves house-made pasta that’s worth planning your entire month around.
Their online reservation system opens at midnight, and weekend slots disappear faster than fresh bread at a family dinner. One Monday afternoon, I refreshed their website and miraculously found a Thursday lunch opening – I canceled a meeting to make it work!
The restaurant’s bar offers first-come, first-served seating, where you can order the full menu. I’ve shown up at 4:30 PM (30 minutes before opening) and still found myself fifth in line.
6. Pizz’Amici – The West Town Pizza Phenomenon

Who knew a neighborhood pizzeria would have me setting monthly calendar alerts? Pizz’Amici’s tavern-style pizza has created such a cult following that reservations get snatched up within hours of release.
Their reservation system opens exactly one month in advance. My friend once booked a table for her anniversary dinner 30 days ahead, only to discover she was one of the last to secure a spot that evening!
The tiny dining room only has 12 tables, contributing to the reservation madness. Their crispy-edged square-cut pies have been featured in so many “Best of Chicago” lists that scoring a table feels like winning a small lottery.
7. Akahoshi Ramen – Logan Square’s Noodle Nirvana

The steam rising from Akahoshi’s tonkotsu broth haunts my dreams! This tiny Logan Square ramen shop has only 24 seats, making it one of the toughest tables to snag in the city.
Their online booking system opens every Sunday at 10 AM for the following week. I’ve literally canceled brunch plans just to be at my computer when reservations go live. The chef makes a limited number of broths daily, adding to the exclusivity factor.
My friend tried walking in on a Tuesday night and still faced a 90-minute wait. Their homemade noodles and 48-hour broths have created such a following that even weekday lunch reservations now require advance planning.
8. Schwa – West Town’s Culinary Mystery Box

Calling Schwa for a reservation feels like trying to win a radio contest! This BYOB culinary wonderland doesn’t use online booking systems – you must call their notoriously hard-to-reach phone line.
My personal record? Calling 37 times before someone actually answered. The small, chef-driven restaurant offers an ever-changing tasting menu that’s worth the reservation runaround. Sometimes they’ll text you back instead of answering calls, adding another layer of reservation mystery.
When I finally scored a table last year, I felt like I’d accomplished something truly significant. The chefs serve you directly, explaining each creative dish in a casual, intimate setting unlike any other fine dining experience in Chicago.