5 Nearly-Impossible Chicago Restaurant Reservations (And How To Land One)

The city of Chicago boasts over 7,300 restaurants in its boundaries, ranging from James Beard winners to Michelin-starred eateries. While many diners opt for a quick and delicious slice of deep-dish pizza or gravy-soaked Italian beef from Chicago's best sandwich shops, others pine for more exclusive venues, eager to taste some of the city's most revered bites.

There's just one small catch — the near-impossible waitlists that often come with these accolades. Chicago is home to both longstanding and innovative restaurants that have only grown in popularity over time, making it increasingly difficult to book a reservation. 

But with a bit of know-how, even the most exclusive Chicago restaurants are at your fingertips. Snagging a table will likely feel less like winning the lottery and more like a badge of honor as you navigate the Windy City's fine dining scene. But the best part? Your reward for sleuthing is mouthwatering cocktails, appetizers, and entrées — in fact, it may be some of the most creative cuisine you've ever eaten.

Alinea is one of the most exclusive spots in the Windy City and holds the honor of being one of only 12 restaurants in the U.S. to hold three prestigious Michelin stars, alongside James Beard awards and a slew of other honors and recognitions. The restaurant opened in Chicago's Lincoln Park neighborhood in 2004, steered by co-owners chef Grant Achatz and Nick Kokonas.

The dining experience is a spectacle where creativity meets cooking and rises to a level few other restaurants have attained. Guests can choose from 10, 14, 16, or 18-course tasting, or opt for a slightly more casual option at the communal Kitchen Table. But with limited seating and only two rounds of dinner per night, competition is high, and seats are known to fill up within seconds of being released. 

Reservations are typically released on the 15th of each month at 11:00 am CST, 60 days in advance. They're available via the Tock app, which requires diners to pay in full at the time of reservation. To grab a table, make sure to hop on Tock right before monthly tickets release and get ready to spring on any availability. With three dining rooms, aim for your top choice, but be ready to shift to another dining area within the restaurant if your preferred option sells out quickly.

Oriole offers contemporary fine-American food, tucked in an unassuming alley in Chicago's West Loop, a lively neighborhood close to downtown. The restaurant opened under Executive Chef and Owner Noah Sandoval in 2016 and has two Michelin stars under its belt. The ever-changing menu offers delectable bites like golden Kaluga caviar, king trumpet custard, and venison with porcini mushrooms, alongside a beverage pairing.

However, with all the publicity and praise the fine dining establishment gets, don't expect to walk in and find an open table, especially at prime hours. Oriole releases seating via Tock on a 90-day rolling basis, and through sample bookings, we only found one late-night weekday table available for the current week, with no weekend seating for at least a month out. The best way to snag a reservation is to stay posted on the rolling reservations, be willing to eat at slightly off hours (you'll have better chances after 8:00 p.m., according to our research), and be flexible on whether you're seated in the main dining room or kitchen table section, the two main areas of the restaurant.

Even with limited seating and a high price tag, many diners claim it's worth the cost, with one mentioning "it's my #1 ranked restaurant and it's the best way to spend 3 hours and $500 that I know of," the diner even stated that they were going to "[fly] back to Chicago just to eat here again in September with a different menu."

Kasama crafts a fine-dining Filipino-inspired menu that combines traditional flavors with modern flair, drawing attention since its opening in 2020 in Chicago's Ukrainian Village. The restaurant was curated by power-couple Tim Flores and Genie Kwon, and holds the distinction of being the first Filipino restaurant to earn a Michelin star. Guests can enjoy 13 delectable courses  in a thoughtfully crafted tasting menu, with dishes like Wagyu bistek, truffle croissants, and a caramelized banana mochi donut.

Kasama's modern Filipino dinner tasting menu is only available Thursdays through Sundays, already tightening the restaurant's window of availability. And I can attest, after casually arriving for brunch on a Sunday morning, that lines are literally out the door and stretching along the block even early in the morning. For dinner reservations, Kasama does not accept walk-ins. Reservations must be booked on Resy, and availability drops on a rolling basis at 12:00 a.m. CST 45 days in advance.

While test booking on Resy, we learned that the best bet for grabbing a seat is by reserving a table for two, as there were a sparse few late-night tables available on weekdays in the upcoming month. Seats for single diners as well as groups of three and four were virtually non-existent, so make sure to book those seats as early as possible. Because daytime dining is first-come-first serve, consider arriving as soon as Kasama opens to ensure you can get a seat without standing in line for hours beforehand.

Top Chef finalist and James Beard award-winning chef Sarah Grueneberg opened the Italian-influenced Monteverde in 2015 in Chicago's West Loop, and the restaurant has flourished ever since. They define their cuisine as "soulful, surprising, and filled with storytelling," promising an experience far beyond the typical Italian eatery.

A "pastificio" is traditionally known in Italy as a pasta shop and factory, and Monteverde delivers fresh, traditional dough that forms the backbone of creative dishes like lasagna al forno and egg yolk ravioli. Signature house cocktails like Bay of Naples and The Leaning Tower feature Italian-centric ingredients, blending bay leaves, Cynar liqueur, and traditional bitters into concoctions reminiscent of an old-world aperitivo.

For those who wish to dine at this stand-out establishment, keep in mind that getting a table, especially during dinner, is extremely challenging. While a direct mention is hard to find, according to Food & Wine, guests can book lunch or dinner reservations at Monteverde via the Resy app, which at the time of writing has no Saturdays available for the upcoming month, and many weekday options only offer dinner seating at 9:00 p.m. Weekday lunch hours are relatively more available, and you can try your luck with walk-in bar seats and select tables. Otherwise, reservations go live at midnight on a rolling basis, 30 days in advance. Monteverde expert managing partner Jaime Canete recommends keeping an eye on your desired dates three to six weeks in advance to ensure a seat.

Armitage Alehouse is an upscale, 1920s-era British-style restaurant that reflects the characteristic look of a traditional English pub, laden with intricate carved wood details, warm lighting, plush upholstered seating, and a wood-fired hearth that keeps the dining section warm on even the most bitterly cold nights in the Windy City.

It's not just the atmosphere that attracts foodies to its doors, but the hearty and diverse menu. Guests can sample East Coast oysters, miso-glazed black cod, and a dry-aged New York strip steak, alongside a formidable beverage menu that features balanced house cocktails, wine, and British-style beer.

While Armitage Alehouse sounds like a local gem that's easy to pop into after a long day, it takes a bit more planning to get a seat here. Reservations release as soon as 21 days beforehand at 9:00 a.m. While weekday reservations aren't too difficult to come by before 5:00 p.m., dinner and weekend reservations can seem almost impossible to snag. In the fairer months, patio tables are available first-come-first serve, while bar seats are walk-in only year-round. If you don't mind passing on a table, guests can opt for these flexible options.

All details in this article were meticulously fact-checked and researched with reputable sources, including a deep dive into several lists of the most challenging reservations found in Chicago. Our research revealed these most challenging establishments are highly revered both globally and locally, have received many awards and accolades, and often have limited seating or table turnover each night, which added to their exclusivity and the challenge of their competitive reservation systems. 

Our primary reputable sources came from the restaurants themselves, noting any sections on official websites that mentioned difficulty or strictness when it came to booking a table. Local Chicago news outlets also provided topical updates that demonstrated a restaurant's availability over time. Furthermore, reviews on platforms like Reddit, Yelp, and Tripadvisor provided firsthand insight into the challenges of each booking process, detailing diners' unique experiences. 

For the best tips on obtaining reservations at these five restaurants, we scoured the booking platforms themselves, including options like Tock, as well as restaurants that offer booking directly on their websites, to test the process ourselves. Many had robust FAQ sections that further clarified when and how to book, as well as how far in advance reservations needed to be made.