The Toughest Reservations In Chicago Right Now (And How To Get Them)

Our thoughts on the most exclusive restaurants in Chicago and advice on how to get a table.

The Toughest Reservations In Chicago Right Now (And How To Get Them) guide image

photo credit: Sandy Noto

At any given time, there are a handful of Chicago restaurants where trying to get a table is like trying to exit the Dan Ryan at 6pm. Right now, these are those restaurants. The spots on this list aren’t necessarily the best restaurants in the city, but they are the hardest places to book a reservation. We think you should know if they’re actually worth the effort, and if so, the best way to go about getting in. Below, you’ll find our verdicts, along with info that’ll help you snag that table (or bar seat). Check back for regular updates.


Kasama review image


Verdict: This cafe-by-day fine-dining-by-night West Town spot is one of the best restaurants in Chicago with the only Filipino tasting menu in the city. Everything is incredible and consider it your solemn duty to come here. We don’t care how dramatic that sounds.

How To Get In: Reservations become available every day at midnight, for 45 days out. If you can’t snag one, get on their Resy notify list. We’ve had success with reservations opening up even as far as a week in advance. Another option is to come here for breakfast or lunch, which is walk-in only. The daytime menu is more casual (but still incredible). Just come early (they open at 9am) because the line for their pastries gets very long within 15 minutes of opening.

Rose Mary    review image

Rose Mary



open table

Verdict: Rose Mary is hyped, and has been since before it was even opened summer of 2021. It’s so hyped, in fact, that you’ll hear people claim that the food here isn’t even any good. That is untrue. The Croatian food here is consistently delicious, and the service is always top-notch. This is a very good restaurant that’s worth your time.

How To Get In: Reservations are released 60 days in advance, but the bar area is reserved for walk-ins. If you get there close to or before opening time (5pm), you’ll most likely find an empty seat or two.

The Verdict: Any Chicago restaurant associated with the words “West Loop,” “Italian,” and “bottle sparklers” is guaranteed to be busy. Such is the case with Gino & Marty’s, a buzzy Italian spot on Randolph. It’s also expensive, chaotic, and not very good. The dining room is cramped and crowded, overflowing with people waiting 40 minutes past their reservation time. Once seated, you’ll have an uninspired meal that’ll take way longer than it should, filled with overdressed salads, mealy pasta, and entrees like an overcooked $75 steak. Skip this place. 

How To Get In: Make friends with one of the 25 hapless people sanding outside, steal their identity, and take their place. Don’t feel bad, you’ll actually be doing them a favor. 

Verdict: The best stuff on the menu at Armitage Alehouse (like pot pies, a burger, and tenderloin tartare) can be found at their other restaurants, Trivoli Tavern and Gilt Bar. Those places also look like they belong in the Clue mansion, but are easier to get into, and you can have very similar experiences there. But Armitage Alehouse is the only spot from this group that serves brunch, so if you want waffles in the parlor with Colonel Mustard, set your alarm to make reservations when they become available.

How To Get In: Reservations are released 14 days in advance at 9am CST. The bar area and patio are reserved for walk-ins, however. If you come close to opening time (4:30pm on Sunday through Thursday, 12pm on Fridays, 10am on Saturday and Sunday), you’ll most likely find an empty seat or two.

Verdict: We’d like to be eating at Bavette’s right now. In a city full of steakhouses this is the best. That said, some of our favorite dishes here (like the fried chicken, chocolate cream pie, and complimentary bread—yes it’s that good) aren’t even steak at all. Unfortunately, this steakhouse in River North hasn’t become any easier to get into since it opened in 2012. 

How To Get In: Reservations are released online 30 days in advance at 9am. They have bar seating and a couple of tables in the bar area available for walk-ins, and if you get here early (they now open at 3:30pm) you’re likely to get one.

Verdict: This is the best Italian restaurant in Chicago, and the first place we try (and often fail) to make reservations when someone from the East Coast tells us they're visiting. The menu is full of hits, from cacio e pepe to the ragu alla Napoletana—a tomato-braised pork shank with three soppressata meatballs, two cacciatore sausages, and a pile of fusilli we want buried with us when we die.

How To Get In: The regular dinner service is booked out for months, but they serve lunch on Friday, and your chances of getting a table go up exponentially if you look for a reservation then. The bar is first come, first served, so come here alone and plan to take up an absurd amount of space for you, your pastas, and your pork shank.

Verdict: If you have a fancy restaurant bucket list, Alinea is probably on it. Of course being famous doesn’t necessarily mean a place is worth your time (or in this case, hundreds of dollars)—but dinner at Alinea is a delicious experience (think fog machines) and there’s nothing quite like it. Accept no substitutions.

How To Get In: Bookings become available on the 15th of every month at 11am CST, for two months in advance. And by 11:01 they’re gone. So, the wait list is your friend. You can only put yourself on the list for a limited number of dates, so tag team with your dining companion to double your odds.

photo credit: Garrett Sweet

Oriole review image


$$$$(312) 877-5339

Verdict: Oriole is another tasting menu spot that will give you one of the best meals of your life for a high price tag ($285). Reservations are available 90 days out on a rolling basis, and get scooped up almost as soon as they are released.

How To Get In: Just keep checking. Another option is to forgo the 12-course menu and look for their “Night Cap” reservation. You’ll get to drink cocktails in their bar and lounge, and it’s the only time their ham sandwich is available, which is (unsurprisingly) incredible.

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