Adrian Kane
Adrian oversees the Infatuation's West Coast and Midwest markets. She joined the company in 2017, and has written hundreds of reviews and guides in Chicago.
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.
Unrated: Restaurants we want to re-visit before assigning a rating. We only rate spots where you can eat a full meal. We won’t rate a coffee shop, bar that only serves peanuts, or dessert shop.
Verdict: Beaumont's is a very welcome addition to Lincoln Park, pairing the production of a downtown supper club with the casual charm of a "neighborhood spot.” And while it shares an address and name with the old sticky-floored dive before it, this upgraded version is prime for a classy-not-stuffy dinner.
Beaumont's drops reservations 14 days in advance. Tables are available within the next day or two, but only at times like 4:30pm or 9pm. They also take walk-ins at their large bar, which is at the center of the action.
Verdict: Attention boat owners: You can indeed dock at this sceney riverside spot. But for all the non-boat owners out there, Naia’s city views and pseudo-clubstaurant feel, steps away from the water, will soothe (most) nautical envy. And the breezes—even if you’re in the massive dining room—will brainwash you into thinking our current sundress temperature is the norm. However you get to this Mediterranean restaurant, plan ahead
Reservations are available two weeks in advance, but they disappear quickly. You can try three things to get into Naia: One is to set OpenTable notifications for future dates and grab them when they appear, which is even more likely if the weather forecast is looking bad. Two, their bar is always open for walk-ins. Three, you can go to Naia in person and ask someone at the host stand to book a future date within the next 14 days. And yes, you can specify that you want a table by the river.
Verdict: Kitty's, underneath the River North spot Crying Tiger, is a mix of service, scene, and cocktail quality that's hard to find anywhere else in the city. The specialty here is pricey drinks—like an old fashioned made on a trolley tableside—and fancy bar snacks like a Dungeness crab cocktail with aioli. But a night at this lush, lively place is worth ransacking the fun-night-out funds and planning a couple of weeks in advance.
Reservations drop 30 days out and vanish quickly. But sometimes late-night tables are available just a few days in advance, if you're OK with a 10pm booking. And if you're extra flexible with time to kill in River North, they have limited space for walk-ins.
Verdict: Crying Tiger comes from the people behind other solid, styled-not-gimmicky River North neighbors like Gus' Sip & Dip and Three Dots and a Dash. Here, the fun theme is nighttime alfresco in the tropics, with a soundtrack of Mariah and Janet. And like most places from the same restaurant group, the food is overall pretty good. The curries are rich and complex, like with a crispy duck confit that we have trouble sharing. And this spot has one of our new favorite desserts—a green shell of ice cream that's a crying tiger on the outside but a delicious chocolate banana situation on the inside.
Reservations are available 30 days in advance and drop at midnight. Sometimes there are spots available about a week in advance, but expect them to be around 4pm or 10pm.
Verdict: Pizz’amici’s pizza is what every young tavern-style pie aspires to be—and it’s what you should aspire to eat. This small West Town spot from the Pizza Fried Chicken Ice Cream team makes incredible razor-thin pies topped with the likes of peppery sausage and spicy giardiniera. But we’d gladly eat a pizza here even if the only things on it were the tangy sauce and cheese that drapes over the crispy edges. This is tavern-style that’s worth planning your month around.
Reservations are released a month out but get snatched up pretty quickly. If you’re not one of the lucky few to actually grab one (we’ve been there), try stopping by right when they open at 4pm—they have a few spots specifically available for walk-ins.
Verdict: Mirra’s crispy scallop taco with green curry lasts only two bites, but you’ll be daydreaming about the combination of Mexican and Indian flavors days later when you should be finishing that work presentation. The dishes at this Bucktown spot are bright, spicy, and mostly group-friendly, like the mezze with rich guacamole and achar, or a lamb barbacoa biryani with juicy beef inside a roti seal. Bring some friends who love heat, but plan ahead.
Mirra drops their reservations two months in advance, so book early for a prime weekend spot. Some reservations are available within only a day or two, but only at times like 4:30pm or 9pm. And though they do take walk-ins for some of their high-tops until 10pm, we still haven’t had any luck with that.
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.
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 30 minutes of opening.
Verdict: Kyoten was our highest-rated sushi restaurant until it was dethroned by its younger sibling, Kyoten Next Door. This small 10-seat omakase spot takes everything that’s great about the original and does it better in a more relaxed setting and for less money. It's still really expensive ($169 for 18 courses)—but compared to Kyoten’s $450 price tag, you'll still spend less even if you get a bottle of sake and take an Uber home.
Reservations are the only way to snag a seat (walk-ins aren’t allowed) and they’re available 20 days in advance. You might have some luck dining solo on a Tuesday, but otherwise, set up some Resy Notifies and be ready the instant your phone lights up.
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.
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: 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.
Reservations are released 21 days in advance at 9am. The bar area and patio are reserved for walk-ins, however. If you come close to opening time (4pm Monday and Tuesday, 11am Wednesday through Friday, 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.
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: 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.
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: 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.
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: 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.
Reservations are available 90 days out, but prime dinner times are usually snagged quickly. But if you're ok with dinner ending around 11pm, there are occasionally some 9pm slots available.
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John grew up in Albany Park and likes to play the xylophone when he isn’t busy eating and filling his camera roll with videos of pasta twirls.
Nick has been a critic since 2010. He's always on the hunt for a great slice of tiramisu, and is equally passionate about bad movies.
Veda joined The Infatuation in 2023. When she’s not eating, she’s poring over her meticulously maintained restaurant spreadsheet for fun.