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

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.

THE SPOTS

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. There’s a reason why it was featured in The Bear: 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.

Verdict: This River North spot recently made our list of Best New Restaurants Of 2022, so, yes, we think it’s worth the effort. On the surface, Obelix looks like a typical, white-tablecloth French restaurant. It’s not. Obelix expertly walks the tightrope of feeling formal without being stuffy. And that same balance is present in its menu, which is filled with a mixture of classics like escargot and playful, fusion-y ones like the foie gras-filled taco. 

How To Get In: Reservations are released 90 days in advance. But while dinner seats are hard to nab (unless you want to eat at 10pm on a Thursday), Obelix recently started serving weekend and Monday brunch from 10:30am-2pm. Those reservations are much easier to come by. Well, at least they were before we wrote this.

Verdict: This River North Italian restaurant is very small, so one reason it’s hard to get a table is basic supply and demand. But Ciccio Mio is also dim, cozy, and filled with all sorts of old-timey artwork and ornate chandeliers that will make you feel like you’re hanging out in the parlor of some old mansion. Everything about the windowless space seems designed to keep you there forever—like a haunted house (but, you know, charming). And the Italian food is great. We’ve never had anything here that we didn’t really like, including wonderful antipasti, handmade pasta, and an incredible chicken parm.

How to get in: Reservations are released online 21 days in advance at 9am, and they go fast. There are a couple of tables available for walk-ins, but if you don’t want to risk it, the waitlist is your friend.

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.

Verdict: Any Chicago restaurant associated with the words “West Loop,” “Italian,” and “Boka Restaurant Group” is guaranteed to be popular. Alla Vita is designed to be a crowd-pleaser, buzzing with everyone from couples to large groups in town for the Morningstar Investment Conference. And while the menu isn’t going to blow your mind with creativity, what’s on it is good. But how long is too long to wait for a reservation just to eat some chicken parm and pizza? Your answer will determine whether it’s worth waiting two months to book a table, or walking in to snag a seat at the first-come, first-served bar or patio.

How To Get In: Reservations are released on Opentable 60 days in advance at 12:01am. Options for prime dinner times are few and far between, so plan on booking a month or so ahead of time. Or grab a seat at the bar or on the patio right when they open.

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. Until recently, Armitage Alehouse was the only spot from this group that served brunch (now Trivoli does too, with a slightly different menu). So if you want waffles in the parlor with Colonel Mustard, set your alarm to make reservations for Armitage 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 21 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 4pm Monday-Thursday and 3pm on Friday-Sunday) 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 Tuesday through Saturday, 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 waitlist 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. You can also find exclusive reservations available for Chase Sapphire Reserve® cardholders here.

Verdict: Oriole is another tasting menu spot that will give you one of the best meals of your life for a high price tag ($295). 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.

Verdict: Unlike most of Chicago’s tasting menu spots, you can get a fancy six-course meal here for around $110-$120. The food is delicious, and often has an interesting French twist, which means dishes like eclair canapes with masala cornflakes and chutney or malai tikka formed into a terrine and sauced tableside. Plus, they have a legitimately interesting cocktail menu that’s almost worth a visit on its own.

How To Get In: Reservations are released 60 days in advance, but the bar area is reserved for walk-ins. There, you’ll most likely find an empty seat or two and can order food off an a la carte menu. Or, if you’re not a gambler and need a guaranteed reservation, be willing to eat before 6pm or after 8pm.