Diners' Choice: Good for special occasions restaurants in Chicago

OpenTable

Updated May 05, 2026

Looking for the best special occasion restaurants in Chicago? You’re in the right place. Each month, OpenTable analyzes nearly 2 million global diner reviews from the past four months. We sort the results by location and category to help you discover new favorite restaurants. It's a great partnership: you reserve, eat, and review. We listen...and deliver the results for all to benefit. Enjoy!

Charlie Trotter's

5.0

5 (905)

$50 and over

Contemporary American

Lincoln Park

About the restaurant

Behind an elegant Lincoln Park façade lies one of the most storied addresses in American gastronomy. Charlie Trotter’s defined an era—not just through visionary cuisine, but through its relentless pursuit of excellence and hospitality. Revered as the birthplace of the vegetarian tasting menu and the pioneering kitchen table, Trotter’s was never just a restaurant—it was a philosophy. Now, the spirit of 816 W Armitage quietly returns. Led by Dylan Trotter, the Guest Chef Dinner Series invites acclaimed chefs to interpret the legacy in their own voice. Each evening is singular. Each menu ephemeral. Every detail, intentional. For those who remember, it’s a return. For those who never knew, an invitation. Welcome to Charlie Trotter’s—once again.

Top review

EthanGold

Dined on Mar 1, 2026

The best meal I’ve had in this city. Perfect food, service, and ambiance. Thank you to Dylan for coming to our table and chatting with us!

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Experience

Guest Chef Series Vol 14: Honoring James Beard

The Omakase Room at Sushi-san

5.0

5 (123)

$50 and over

Japanese

River North (Chicago)

About the restaurant

The Omakase Room at Sushi-san is a culmination of Master Sushi Chefs Kaze Chan and Shigeru Kitano’s combined experience defining the Chicago sushi scene. While the menu and service are informed by tradition, guests can expect a transcendent experience that breaks down the formality and austerity usually accompanying omakase dining. Each dinner in the warm, modern, and intimate ten-seat space features luxury ingredients from around the world. Sophisticated and carefully curated beverage pairings are available to complement the meal.

Top review

Daniel

Dined 3 days ago

The service was impeccable. Each dish was described and presented flawlessly and tasted uniquely amazing. The entire experience was worth every penny

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Experience

Omakase Reservation Deposit

Experience

Master Sake Brewer Omakase Deposit

Jeong

4.9

4.9 (941)

$50 and over

Contemporary Korean

West Town

About the restaurant

Modern Korean dining in an elegant yet approachable atmosphere.

At the moment, we are very limited in regards to accommodating dietary restrictions. We can only accommodate pescatarians. We are a very small team at the moment and once we are streamlined we will be accepting more dietary restrictions! Please bear with us!

Top review

Ely

Dined on Apr 17, 2026

Amazing experience. Delicious food, staff and service. What a treat.

Valhalla

4.9

4.9 (87)

$50 and over

Contemporary American

Bucktown / Wicker Park

About the restaurant

Valhalla is a culinary gem in Chicago's Wicker Park, offering a unique gastronomic journey where modern elegance meets global flavors. The minimalist Scandinavian decor creates an intimate atmosphere, with warm woods and soft lighting that enhance your dining experience. Chef Stephen Gillanders' tasting menu showcases his creativity, featuring seasonal ingredients and diverse influences. Each course, from ocean trout lumpia to vibrant seafood ceviche, highlights his mastery of flavor and technique. Desserts by Pastry Chef Tatum Sinclair are a revelation, with each creation a stunning masterpiece that delights the senses. Valhalla is not just a restaurant; it's an unforgettable experience that invites you to savor every moment.

Top review

Alexia

Dined on May 22, 2026

Valhalla was an ✨experience✨ starting with the outside, we were like??? Whaaaaa? Then we came in and immediately began with a gin tasting with an incredible bartender who hooked us up throughout our entire meal. Food was spectacular and daring and beautifully presented, not once lacking in flavor or balance. Our night was personalized and unforgettable.

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Experience

Valhalla Tasting Menu at The Chef's Counter

AJI

4.9

4.9 (159)

$50 and over

Japanese Speciality

Lakeview / East Lakeview

About the restaurant

Discover an unforgettable dining experience at one of OpenTable's top restaurant destinations for ambiance, led by the talented Chef Kristian Cho. Recently named a 2024 Diner's Choice winner, our restaurant offers a 15-course omakase menu that pairs perfectly with our intimate, cozy setting—ideal for anniversaries, special occasions, or a memorable date night out. With over 30 years of collective expertise, our team is passionate about delivering exceptional service and a warm, inviting atmosphere, complete with a charming backyard for a unique evening. Join us and create lasting memories with those you love.

Top review

OpenTable Diner

Dined on May 17, 2026

My daughter wanted Omakase for her 18th birthday, and after some research I settled on AJI and I chose WELL!! It was an amazing evening for the 4 of us from start to finish. The restaurant has an intimate, warm vibe...like a small dinner party in someone's home. The Omakase is 15 courses and each course was outstanding! The drinks menu has delicious cocktails (and Sake), expertly mixed...we tried a few. Kristian and his staff are very warm, welcoming, attentive and knowledgeable. They explain each course in great detail and welcome questions about the ingredients etc. Kristian is very helpful and responded timely to my questions prior to our reservation. I cannot say enough good things about Kristian, the staff and our dining experience. Highly Recommend!!

Maggiano's - Chicago

4.8

4.8 (3744)

$30 and under

Italian

River North (Chicago)

About the restaurant

Welcome to Maggiano's Little Italy, located in downtown Chicago on the corner of Clark & Grand. Our restaurant is a quick trip from the Water Tower Mall, Navy Pier & the Art Museum. Our dining room is ideal for family-style dining with our Italian–American cuisine, reminiscent of a Sunday night visit to your grandmother’s house -- or as they say in Italy, nonna’s casa! These delicious dishes paired with great service, generous portions and a warm atmosphere keep our guests and their families coming back for more. The outdoor seasonal patio has an old-world feel of dining on the bustling streets of Florence.

Join us soon! We look forward to hosting your next business or family gathering.

Top review

VivianeGold

Dined 4 days ago

Excellent quality and quantities are huge. Service is outstanding and overall I highly recommend this place if you are in the neighborhood. We ordered the seafood pasta, the carboranara with lobster pasta as two main dishes, plus a side of the Italian salad. Quantities are huge even if you are hungry. These dishes can easily be split between two people. As dessert, I am a big fan of crème brûle, and theirs is to die for. Great meal in an expensive area, but you get more than what you pay for and thanks for the great service and friendly chat with Kevin ( we are the couple who drove all the way from Canada to taste the great food and enjoy the lovely old songs by Frank Sinatra. 😀👍🙏

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Center-Cut Filet Mignon

Enoteca Roma

4.8

4.8 (566)

$30 and under

Italian

Bucktown / Wicker Park

About the restaurant

Enoteca Roma invites you to experience the heart of Italy right in Chicago. This charming restaurant offers authentic Roman cuisine in a warm, inviting atmosphere. Our menu features classic Italian dishes made with fresh, high-quality ingredients. Start with antipasti like crispy fried calamari or a selection of salumi and formaggi. For your main course, indulge in hearty pasta dishes such as cacio e pepe or carbonara, or enjoy our rustic Roman pizzas, expertly cooked in a wood-fired oven. Complement your meal with selections from our impressive wine list, showcasing Italian wines from small-batch producers. Our knowledgeable staff is ready to help you find the perfect pairing. Whether you're planning a romantic dinner or a fun night out with friends, Enoteca Roma is the ideal destination for authentic Italian cuisine. Enjoy our beautiful outdoor patio during warmer months, or reserve our private dining room for special occasions. Come and savor the best of Italy!

Top review

Sherri

Dined on May 22, 2026

I love this restaurant, sitting outside in the back is a nice change of ambiance. We always end up talking with the people at tables around, the owners say hi. And most important the food is always amazing!

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4.8

4.8 (834)

$31 to $50

Sushi

West Loop

About the restaurant

Est. 2014 - family owned & operated

We are offering a NYE Menu! Guests are able to make a reservation for the menu specifically, but are still able to make a regular booking otherwise.

We are participating again for Restaurant Week 2026 (menus available in gallery photos).

Try our unique omakase where our chefs will work around your restrictions to course out a mix of traditional, and non-traditional, fare. With signature dishes like our fish & chips and bluefin truffle sashimi, dressed nigiri pieces, and our off menu "special rolls" (including vegetarian options). Otherwise, order from the menu with many small-bite options, nigiri/sashimi, maki, entrees, or order the special rolls à la carte. We pride ourselves on our fish quality.

We have a full bar, which features a full selection of Japanese whisky, sake, cocktails, and more.

(We have no affiliation with any other Tanoshii and Sushi Mike, and are completely separate)

Top review

RoyelleGold

Dined on May 23, 2026

Tanoshii is the best sushi in the west loop. Great quality and very authentic. Been to all of the sushi places in the west loop, and tanoshii is the best. They also have a great happy hour where they offer a variety of menu items at a really good price. And to top it all off, the service there is amazing. They take great care of their customers. It is my go-to place in the west loop.

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Experience

14 course, 10 Piece Nigiri Omakase

The Berkshire Room

4.8

4.8 (87)

$30 and under

Cocktail Bar

River North (Chicago)

About the restaurant

The Berkshire Room is an upscale lounge specializing in craft cocktails all created by a talented team. The atmosphere is retro classy and definitely worth a visit before or after dinner for cocktails with friends. There is ample seating either in the private side rooms, the booths in the lounge area or at the bar. The clientele that frequent the Berkshire Room rave about the dealers' choice, which allows guests to choose the spirit, flavor profile and glassware. The bartender then customizes a unique and customized cocktail.

Besides the tasty cocktails and the relaxing ambiance, the Berkshire also offers bar snacks and small dishes. The Berkshire room is located within River North's swanky ACME hotel.

Top review

Jason

Dined 7 days ago

My wife and I celebrated our 29th anniversary at The Berkshire Room, and it was an outstanding experience from start to finish. The ambiance was exceptional—great music, a wonderful vibe, and the perfect atmosphere for enjoying cocktails and conversation. It felt special without being pretentious, making it an ideal setting for a memorable evening. The mixologist was fantastic, creating custom cocktails tailored to our preferences. Each drink was expertly crafted and showcased both creativity and skill. Our server, Brandon, was attentive, personable, and added to the overall experience with excellent service. The manager was also warm and welcoming, helping make our anniversary celebration even more memorable. As for the food, the kettle chips were very good, but the real standout was the house-made onion dip. It was absolutely delicious and is something I would highly recommend ordering. Overall, this was a 10 out of 10 experience. Between the atmosphere, exceptional cocktails, outstanding service, and thoughtful hospitality, The Berkshire Room exceeded our expectations. My wife and I both agreed that we will definitely be back, and we would highly recommend it to anyone looking for one of the best cocktail experiences in Chicago.

Kitty’s Cosmopolitan Club

4.8

4.8 (50)

$50 and over

Cocktail Bar

River North (Chicago)

About the restaurant

Tucked into the lower level of Crying Tiger in River North, Kitty's Cosmopolitan Club is a cocktail lounge from Beverage Director Kevin Beary and the award-winning team behind Gus' Sip & Dip. The opulent interior, designed in collaboration with David Collins Studio, sets the stage for an elevated experience where all cocktails are ordered, crafted, and served by expert bartenders.

The bar program is organized around three experiences: From the Cold Room, cocktails held in Chicago's first -16°F walk-in freezer for concentrated flavor and luscious texture; From the Bar, made-to-order classics elevated through modern technique and spirit selection; and From the Trolley, cocktails prepared tableside and served in fine crystal. Low- and no-alcohol options are also available, alongside coffee and tea.

The food menu is a collaboration between James Beard-nominated Chef Thai Dang and Chef Bob Broskey, featuring a raw bar and curated dim sum designed to complement the cocktail program.

Top review

TaylorGold

Dined 2 days ago

Amazing cocktails the 20th Century martini is INSANE! Eli is also the absolute best!

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