15 Of The Hardest Restaurant Reservations To Get In Chicago

Chicago is one of the best culinary destinations in America, enticing locals and out-of-towners alike with irresistible staples like the deep-dish Chicago-style pizza and the Italian beef sandwich. The Windy City houses nearly 12,000 restaurants, many of which book out weeks — if not months — in advance. While celebrities probably have no trouble getting into the most exclusive and trendiest venues, aspiring patrons often have to battle through several attempts before finally securing their seats. What's more, not all of these massively sought-after eateries are upscale places; some of them are unassuming joints whose public relations and social media-savvy managers excel at creating a buzz around simple hearty dishes.

Behold some of the most difficult reservations to secure in Chicago, spanning various cuisines and types of establishments. Have you ever been able to try their food and cocktails? Is it worth the hype, trouble, and, sometimes, hefty price? Reviewers have certainly not held back on their mixed feelings online, so let's see what those elusive bookings and dining experiences typically entail.

Founded in 2020, Kasama is a fine-dining Filipino-American restaurant and bakery located in the Ukrainian Village. It gets very busy during dinner service and in the daytime, likely because it's the world's first Filipino restaurant to earn a Michelin star. Customers sing the praises of specialties such as the longanisa sandwich, truffle croissant, ube huckleberry Basque cake, apple hand pie, and blueberry tart. While no reservations are needed at the bakery, open Wednesday to Sunday, you're likely to find long lines even before opening. Preordering your items for pick-up is therefore highly recommended.

As for dinner, it's from Thursday to Sunday and by reservation through Resy. That modern 13-course tasting menu with optional beverage pairings is extremely coveted, though. Spots are released at 12 a.m. on a 45-day calendar, but fret not if you're unable to secure yours; you can always add your name to the notify list. However, keep in mind that the restaurant can only accommodate groups of up to six guests, and cancellations or a drop in guest count within 48 hours will incur a menu charge per guest.

For the most part, those who have scored that two to three-hour dinner experience state that their countless attempts are worth the effort. They're most impressed with the nilaga (cabbage, bone marrow, and short grain rice), sinigang (salmon, tamarind, and smoked trout roe), mussels adobo, and halo-halo (leche flan, rambutan, melon), not to mention the elegant plating and attentive service. Meanwhile, those unable to score a dining slot will be found standing in line for those scrumptious baked goods.

kasamachicago.com
(773) 697-3790
1001 N Winchester Ave Chicago, IL 60622

Established in the Bucktown neighborhood in August 2024, Mirra is a cozy and elegant restaurant and wine bar that has quickly become one of the most coveted weekend spots in Chicago. It specializes in the seamless and elegant fusion of Mexican and Indian dishes, resulting in popular menu items like the roti quesadillas, maitake mushrooms with coconut mole and South Indian braised cabbage, and tres leches cake infused with cardamom and saffron. An innovative and interactive five-course tasting menu is also available.

That seems enticing enough in theory, but the reality is that this venue only opens from 4:30 p.m. to 10:30 p.m. (the last reservation is at 9:30 p.m.), which makes it all the more difficult to access. Although it occasionally takes walk-ins for high-top seating, table reservations are at least a month in advance and available through OpenTable. Many of those who manage to score seats have to settle for the very first or the very last slot. 

mirrachicago.com
(773) 687-9610
1954 W Armitage Ave, Chicago, Illinois 60622

Located on the second floor of The St. Regis, Tre Dita, open daily, has built itself quite a reputation for being one of the most romantic venues in Chicago, offering breathtaking views of the Chicago River. Its Tuscan-inspired dishes are meticulously prepared by Chef Evan Funke, who caters the Vanity Fair Oscars party and has published the award-winning cookbook, "American Sfoglino: A Master Class in Handmade Pasta."

With its flavorful homemade pasta dishes and 700 wine labels, this elegant venue has quickly become one of the hardest Chicago spots to access. Reservations are only accepted seven days in advance and the spots are released at midnight; you'll therefore have to stay up late for your attempts.

Per one frustrated Yelp reviewer who has likely given up, "Was the food great? I'll never know, because you don't open up reservations. Were the cocktails epic? I'll never know, because you don't open up reservations."

treditarestaurant.com
(312) 725-1724
401 E Wacker Dr. Chicago, IL 60601

Laidback venues specializing in ramen dishes are some of the most popular types of Japanese restaurants around the world. Established in Logan Square and open from Tuesday to Saturday for dining, Akahoshi Ramen is one such casual place that serves house-made soup, noodles, and rice "influenced by Japanese and American ideals." There is also a good selection of sake and both Japanese and American brews.

Nonetheless, don't let the communal table and simple décor fool you, as this is one of the hardest bookings to score in Chicago. Reservations are available five weeks in advance, only possible through OpenTable, and released every Monday at noon. What's more, there's no official phone number for follow-up. Though walk-ins may be accommodated on weekdays between 5 p.m. and 7 p.m., it's best to arrive at least 30 minutes before opening time to make the waiting list.

One customer reported waiting for months before she finally received her notification, and she admitted to finding the experience underwhelming and rather expensive for such a small selection of items. Another guest had to wait 10 minutes to be seated despite having secured a slot, and then an additional 20 minutes for the order to arrive. Apparently, not everyone thinks their time is well spent trying to obtain a seat at a modest ramen place.

akahoshiramen.com
2340 N California Ave Suite B, Chicago, IL 60647

Alinea is a New American, Michelin-starred, award-winning venue nestled in the Lincoln Park neighborhood and open daily for dinner. Thanks to its creative multi-course tasting menus, it has turned into a bucket-list choice for special occasions, even for out-of-towners.

Unfortunately, reservations are mandatory and released on Tock (with no phone number attached for follow-up) on the 15th of the month at 11 a.m., two months in advance. What's more, those coveted spots can be gone within the first minute, as reported by a frustrated reviewer on the waitlist who received her notification two months after her birthday.

Other customers were only able to secure their desired slots after several attempts and using different people and accounts simultaneously. That certainly sounds overwhelming. Also, keep in mind that canceled bookings are non-refundable, but reservations may be rescheduled with at least 72 hours notice.

alinearestaurant.com
1723 N Halsted St, Chicago, IL 60614

With its intimate, dimly-lit jazz-era vibe and comfy red leather booths, Bavette's is one of Chicago's most renowned steakhouses. Its extensive menu includes a wide variety of wines and cocktails, seafood towers, dry-aged bone-in ribeye, spiced fried chicken, and lemon meringue pie.

Reservations open at 9 a.m. on Resy and are available up to 21 days in advance, and prime-time tables (6:30 p.m. to 8:30 p.m. slots) typically get booked out within the first few minutes. Consequently, securing seats at the desired time, especially on weekends, may require several attempts, so much so that the notify list can grow up to 1,400 names.

Except for private events, the restaurant can only accommodate parties of up to six guests, as it can only offer them two tables upstairs and one table downstairs. As for walk-ins, they're only welcome at the bar, should there be any availability.

bavettessteakhouse.com
(312) 624-8154
218 W Kinzie St, Chicago, IL 60654

Located in Lincoln Park, this upscale 1920s British-style pub restaurant features hand-carved woodwork, roomy booths, and an inviting fireplace. It offers hearty dishes, eclectic cocktails, and weekend brunch, with menu items ranging from pot pies to East Coast oysters, miso-glazed black cod, wagyu double cheeseburger, and flourless molten chocolate cake.

Armitage Alehouse reservations open at 9 a.m. and are available 14 days in advance, though walk-ins are always welcome at the bar. Aspiring patrons typically find it extremely hard to grab a dinner spot, even when using different credit cards simultaneously. One Yelp reviewer even goes as far as calling the challenging booking process "an extreme sport."

Still, those who do succeed agree that the experience is well worth the effort because of the impeccable service and wide variety of dishes. As for those who are still unable to secure the elusive dinner slots, they usually opt for brunch or lunch.

armitagealehouse.com
(773) 270-6402
1000 W Armitage Ave, Chicago, IL 60614

Set in Mode Logan Square, Kyōten is one of the most renowned and priciest sushi places in Chicago. It offers a two-hour, 18-bite omakase dining experience from Wednesday to Sunday, using prime and fresh ingredients that are mostly imported from Japan.

The menu itself is 75% nigiri sushi and 25% small plates, with a rotating selection of high-quality beer, sake, wine, and whiskey. Omakase venues typically have limited seating, and Kyōten isn't any different in that aspect. Those coveted reservations open up on Saturdays at 10:00 p.m. and go out four weeks in advance, but they can also stay offline for an extended period of time. Persistent patrons can attempt to book their desired slot via Tock and, if successful, they'll have to leave a deposit.

kyotenchicago.com
(312) 880-9402
2507 W Armitage Ave Chicago, IL 60647

Monteverde Restaurant & Pastificio is a modern, award-winning Italian restaurant located in the West Loop neighborhood, inside Loft Lucia, a chic boutique and event venue. Open Tuesday to Saturday, it's been one of the most booked tables in Chicago over the past decade, owing its success to its various regional Italian dishes and selection of fine international wines. Some of its star menu items include gluten-free pesto rigatoni, prime bone-in ribeye, braised pork osso buco, tiramisu, and dark chocolate sorbet.

Walk-ins are always welcome at the bar, which can seat 16 guests. Tables are a different story, as reservations are 30 days in advance via Resy, and they go live at midnight, which isn't very practical. Dinner slots, in particular, are booked out for months and have a notify list of up to 1,400 names. Therefore, you might want to aim for a lunch slot, as its notify list rarely exceeds 160 names. Large groups may need to book their seats six weeks in advance.

Many of those who have been trying to get into Monteverde for a while have only managed to grab early slots, but they claim their experience is well worth the effort. After all, a romantic lunch date at one of Chicago's most renowned Italian venues isn't too bad.

monteverdechicago.com
(312) 888-3041
1020 W Madison St, Chicago, IL 60607

Founded in 2016, Oriole is a New American restaurant nestled in the West Loop area of Chicago. There are two reasons why reservations – released on a 90-day calendar via Tock – are so elusive.

First, this upscale establishment has nabbed two Michelin stars so far. Second, despite producing elaborate, versatile, seasonal, award-winning tasting menus, Oriole doesn't impose a specific dress code. Enjoying egg noodles with caviar and kabocha (sweet squash) or seared scallops with trout roe and chives in comfortable attire? Yes, please!

There are three types of bookings to choose from: the dining room, for parties of one to six; the kitchen table, for parties of one to four; and the loft and kitchen table package, which provides couples with a world-class getaway that includes a luxury overnight stay and a special menu. Though that premium experience is seemingly worth the wait, some customers have voiced their disappointment at having their dining date postponed without prior warning.

oriolechicago.com
(312) 877-5899
661 W Walnut St, Chicago, IL 60661

If Ever's sleek, minimalist interior seems familiar, it's because it was featured on "The Bear" series. Located on Fulton West Street, this fine establishment is open for dinner from Tuesday to Saturday. Its kitchen proposes a premium two-and-a-half-hour experience of up to 10 creative seasonal courses, under the supervision of award-winning Chef Curtis Duffy.

As tempting as it seems, you can only secure your table by paying a $100 deposit per person on Tock, since it's one of the most sought-after venues in Chicago. The seats are released two to three months in advance on the first Tuesday of the month, at 9 a.m.

Here's a consolation tip for those who still can't get lucky at Ever: you could always try booking a table at the sister venue next door, called After Lounge, where walk-ins are also welcome.

ever-restaurant.com
1340 W Fulton St, Chicago, IL 60607

Known for its elaborate and creative cocktails, fresh oysters, charred meats, handmade pasta, and coal-fired seafood, Trivoli Tavern welcomes walk-ins at the bar – if they're lucky enough to find empty seats. Table reservations may be harder to secure, though; they're released up to 21 days in advance on Resy and can accommodate parties of up to eight guests.

As a result, satisfied customers generally recommend signing up for alerts, in case there is a last-minute opening, especially during the in-demand happy hour slot. Thanks to its cozy wooden décor, dim lighting, relaxed elegance, attentive and friendly service, extensive menu, generous portions, and strong drinks, Trivoli seems to be both a romantic and convivial venue that may well be worth your time and effort.

trivolitavern.com
(312) 366-2646
114 N Green St, Chicago, IL 60607

Pizz'amici is a welcoming, intimate venue with neon red lighting that opened on Grand Avenue in late 2024. Its motto simply boils down to "Where friends eat." That's because the menu mainly proposes hearty Italian-American dishes, such as Italian sausage with roasted green peppers, onions, and potatoes, and Chicago thin-crust pizzas with a choice of toppings that include halal pepperoni, Italian beef, artichoke, and anchovies. 

Open for dinner from Wednesday to Sunday, this very popular, cozy restaurant offers reservations via OpenTable, with seats released a month in advance. Since it can only accommodate 30 guests at tables and seven at the bar, a spot may not be that easy to secure. You could always try your luck right before opening time, but the wait list for walk-ins may very well exceed two hours.

pizz-amici.com
(312) 285-2382
1215 W Grand Ave, Chicago, IL 60642

"Yume" means "dream" in Japanese, and that's exactly what this Michelin-starred omakase experience promises to deliver with its premium 16-course tasting menu and a la carte selection of fine wine, craft beer, and sake. The dishes are seasonal but typically consist of an appetizer, several elegantly plated sushi and seafood creations like botan ebi (spot prawn), shima-aji (a warm-water fish), king salmon (the largest salmon in the Pacific), and a dessert.

As is typical with this kind of intimate restaurant, spots are very limited: six per seating, to be exact, at 5 p.m., 7 p.m., and 9 p.m. They're released on Resy every first of the month, and that small, 300-square-foot space often books out two months in advance. Therefore, the notify button is your best bet in case there's a last-minute cancellation.

omakaseyume.com
(312) 265-1610
651 W Washington Blvd Suite #101, Chicago, IL 60661

Alla Vita, meaning "to life," promotes itself as "Your neighborhood Italian eatery." Unfortunately, those casual, friendly crowds are precisely what makes it so difficult to snag a table reservation — or even seats at the bar for walk-ins.

From the wood-fired meatballs to the house-made pasta dishes, carbonara pizza, eggplant lasagna, chicken parmesan, and citrus panna cotta, the menu is all about elegantly plated comfort food. Guests have even raved about the wood-fired bread drizzled with orange blossom honey, dubbed one of the best table breads in Chicago.

Slots are released on OpenTable 60 days in advance, and some people have had to wait for eight weeks to secure a dinner reservation. Even successful customers have had to stand by the door for 20 or even 30 minutes before finally being escorted to their seats. 

allavitachicago.com
(312) 667-0104
564 W Randolph St, Chicago, IL 60661