How to book the hardest reservations in Chicago

This modern Filipino restaurant and bakery from husband-wife duo Genie Kwon and Timothy Flores became an immediate sensation upon its debut at the beginning of the pandemic. During the daytime, Kwon’s pastries and options like chicken adobo and a killer breakfast sandwich cause lines to form down the block. But at night, Kasama transforms into a 13-course fine dining experience full of bold and exciting flavors.

How to book: Reservations are released at midnight on Resy 45 days in advance and you’ll definitely need to stay up because they go right away.

Grant Achatz and Nick Kokonas’ temple of molecular gastronomy is widely regarded by many as one of the best restaurants in the world. And it’s the only place in Chicago that’s been awarded a coveted three Michelin stars. So you’re not only battling fellow Chicagoans for a table, but out-of-towners as well who plan their trips around this esteemed dining destination.

How to book: Alinea offers three experiences: a 10-14 course tasting menu on the second-floor salons, 16-18 courses in the restaurant’s gallery and an intimate kitchen table for parties of six. Reservations open up on the 15th of each month, approximately two months in advance, at 11am. The kitchen table and the gallery tend to sell out first, as there are only two seatings per night. Bookings can be made on Tock, the reservation system founded by Kokonas.

Joe Flamm, the winner of the 15th season of Top Chef, opened his first restaurant to much anticipation in 2021. Inspired by Flamm’s wife (who is Croatian-American) and his time at Spiaggia, the menu is a mix of Croatian and Italian cuisine. That means you’ll find dishes like mafaldine pasta tossed with lamb ragu, and plump cevapi flanked by ajvar—a roasted red pepper sauce.

How to book: Unless you’re willing to eat at 9pm or later, you’ll have to make reservations on OpenTable a month or more in advance. You can also try walking in and snagging a seat at the bar.

Curtis Duffy’s latest venture has lived up to the lofty expectations set by his previous work. Ever, which currently holds two Michelin stars, takes guests on a refined culinary journey through the land and sea, complemented with seasonal veggies, fruits and more. The eight- to 10-course tasting menu is loaded with surprises and inventive dishes that will leave you in awe from start to finish.

How to book: Reserve a few weeks before your desired date on Tock. Seats are generally released two months in advance at 9am on the first Tuesday of the month.

James Beard Award winner Sarah Grueneberg’s Italian palace has been one of the talks of the town since the day it opened back in 2015. You’ll see chefs making pasta behind the bar to showcase in dishes such as cacio e pepe that incorporates whey plus egg yolk raviolo filled with ricotta and goat cheese. The refreshing cocktails, strong wine list and tantalizing desserts boost the experience from great to must-try.

How to book: Monteverde books a month out on Resy so you’ll need to plan ahead. However, walk-ins are accepted for spur-of-the-moment diners.

The city’s best sushi can be found at this nondescript spot in Logan Square. Chef Otto Phan provides guests with a front-row view of the action as he slices premium raw fish and works with other delicacies like A5 wagyu and uni in order to craft Edomae-style sushi. The omakase will set you back a pretty penny, though—it’s priced at $440-$490 per person depending on the day.

How to book: There are only eight seats and one seating a night, so availability is extremely limited. Weekends will require you to book weeks ahead on Tock while weekdays have the occasional openings here and there.

Transport yourself to 1920s London at this British-inspired pub from the group behind some of Chicago’s hottest spots, Hogsalt Hospitality. The interior is a sight to behold, sporting dim lamps, framed paintings, chandeliers, a wood-burning fireplace and other vintage touches. On the food side, you’ll enjoy steaks, pot pies, curries and more.

How to book: You won’t have to wait too long to attend a reservation—they’re taken 14 days in advance, with each new day opening up at at 9am on Resy. Tables for lunch or late hours have the most availability. Walk-ins are accepted at the bar and on the patio.

Perched on the 13th floor of the Chicago Athletic Association, Cindy’s offers gorgeous views of the skyline and Millennium Park. As a result, the airy, beach house-inspired space is very popular with both locals and tourists alike. The menu, featuring large-format plates, encourages folks to come in groups and share a variety of seasonal fare.

How to book: Tables open up 30 days in advance on Resy and the restaurant can accommodate parties of up to 12 people. You’ll have to book a few weeks ahead for dinner; there’s greater availability during lunchtime.

Hogsalt Hospitality’s subterranean lair below Green Street Smoked Meats is one of the best spots in the city for ramen. And with only 16 seats, it’s one of the toughest to get into. Those that do are rewarded with bowls of springy noodles in a rich, savory broths. Even the most seasoned spicy food fanatics should be cautious of the kanabo spice, though, which promises to deliver “face-numbing, tear-jerking, unbearable” properties.

How to get in: No reservations are taken here and due to the tiny space, seats fill up pretty quickly. So if you don’t want to wait awhile, your best bet is to start lining up before the restaurant opens at 4pm.