J. Alexander’s, the premier restaurant concept known for its exceptional steaks, fresh seafood and signature dishes, is partnering with Orin Swift Cellars for an exclusive wine dinner on Oct. 21 at 6:30 p.m. The evening will feature a four-course menu paired with award-winning wines, beginning with a welcome cocktail crafted with Horse Soldier Straight Bourbon Whiskey.

From the first pour to the final bite, each course is designed to highlight the depth, nuance and craftsmanship of both the food and wine. Guests can RSVP and view the full menu here.

Sip, savor, and create at The Gwen's A Spirited Affair, a captivating series of interactive experiences featuring premier spirit and wine brands, paired with thoughtfully curated bites. Come enjoy an evening filled with creativity and fine wine. Bring your friends or loved ones and paint your own canvas masterpiece while savoring selections from the Fess Parker Winery portfolio. This interactive experience is held in The Gwen Hotel’s Private Affairs space on the 5th floor, directly across from Upstairs at The Gwen.

Tickets are $65.99 and can be purchased on eventbrite here.

With Taylor Swift’s highly anticipated The Life of a Showgirl album dropping this October, Chicago Swifties will have the perfect place to celebrate together: a themed listening party at Bandit on Friday, October 3rd. This fan-fueled celebration will offer Chicagoans a chance to connect, sing, and celebrate one of the biggest music moments of the year.

Highlights include a listen to The Life of a Showgirl, followed by fan-favorite tracks from every era, themed cocktails and bites (with Swift-inspired names) and an Eras costume contest, friendship bracelet making, photo ops & other surprises!

Tickets are available now: here.

Dearly Beloved in Chicago's Near North neighborhood is hosting a special evening of premium Old Fashioned tastings crafted by Chicago's most talented mixologists from renowned establishments. Taking place on Sunday, September 28, 7-10 pm, the Old Fashioned Fest will feature eight old fashioned drinks prepared by local cocktail bars including Alla Vita, Ina Mae Tavern, Frontier and more! Additional cocktails will be available for purchase, along with the full menu.

The Old Fashioned Fest is part of an ongoing seasonal cocktail competition series hosted by Machine Hospitality Group’s Dearly Beloved, with past events including Martini Fest and Daiquiri Fest, and an Espresso Martini Fest coming up on Nov. 23!

Tickets are $35 per person (21+ event) and can be purchased here.

Raise a stein and celebrate Oktoberfest, goat-style. Guests will enjoy a chef-curated prix fixe brunch menu featuring seasonal favorites, a welcome pour of Märzen, festive cocktails, and plenty of good vibes. Lederhosen optional, fun guaranteed. An à la carte beverage menu and a separate kid’s menu will also be available.

Tickets are available on OpenTable here.

Cruz Blanca Brewpub is back with Das Bueno Oktoberfest on Saturday, September 20, 2025, from 12–4 PM — a one-day-only Mexican–German mashup on the West Loop patio. Guests can enjoy house-made sausages from guest chefs, including Duck Inn’s Kevin Hickey and Leña Brava’s Brian Enyart, paired with seasonal beers and specialty cocktails. Festivities also feature live music and stein-holding contests for a full street-party vibe.

Tickets are $10, which includes a souvenir stein and your first beer, and can be purchased on eventbrite here.

The Dearborn is bringing a taste of Ireland to Chicago a little early with its annual Halfway to St. Patrick’s Day celebration on Thursday, September 18, from 5–7 p.m. Guests can expect an evening filled with Irish cheer, festive music, and exciting giveaways, perfect for raising a glass six months ahead of the big day.

Highlights include:

• Guinness activations & sampling – with a special Guinness glassware engraving opportunity

• Teeling Irish Whiskey tastings – complimentary samples from their award-winning portfolio, plus $10 Lucky Old Fashioneds and Teeling Small Batch shots.

• Festive atmosphere – Irish music, beads and trinkets, and raffle prizes courtesy of Guinness, Teeling, and The Dearborn.

Master the art of Spanish cooking at Cafe Ba-Ba-Reeba!’s Paella Cooking Demo. On Friday, September 12 from 12:00 PM – 2:00 PM, learn how to make the Valencian dish from Executive Chef Eric Jorgensen. As you learn, enjoy a five-course meal featuring classic pintxos and tapas like Scallops with saffron butter, Tortilla Española, and paired beverages, ultimately leading to a serving from the paella presentation.

Tickets are $80 per person, plus tax (gratuity not included) and can be purchased on Tock here.

Sunda New Asian (110 W. Illinois St, Chicago, IL)'s popular Sushi Rolling Class is back the first Saturday of Every Month from 4:00 – 5:00pm. Learn the ancient art of making sushi with their exclusive Sushi Rolling Class, led by award-winning chefs! Experience the thrill of crafting your own sushi rolls from scratch, including vibrant salmon, crispy shrimp tempura, and spicy tuna, all wrapped in delicate seaweed and sushi rice. In this hands-on, interactive session, guests will dive into the art of sushi making with personalized guidance. This unique culinary experience is hosted in the communal-style seating for an immersive, fun atmosphere.

Tickets are $65 per person and are available on OpenTable HERE 

Lobster lovers, rejoice: Lobster Festival is making its delicious return to Shaw’s Crab House beginning Friday, August 15 through Monday, September 1!

At Shaw’s Crab House – Schaumburg, dive into a limited-time menu of lobster favorites like the Lobster BLT, Spicy Lobster Crispy Rice, Lobster & Filet, and more. To wrap up the festivities, enjoy live music on Labor Day: head to the Oyster Bar on Monday, September 1 from 4:00 PM - 7:00 PM for a special performance by The Breezy Rodio Band.

Over in the city, Shaw’s Crab House – Chicago is also celebrating with a special menu of lobster dishes like Popcorn Lobster, Twin Maine Lobster Tails, New England Lobster Roll and more, available for a limited time only. 

Leña Brava is back for another year with Pig & Vino – a one-day-only Baja-style lunch and wine BBQ event happening Sunday, August 24 from 2–6 PM on the shared Cruz Blanca/Leña Brava West Loop patio.

Guests can expect whole-hog pork carved tableside by Gunthorp Farms' Greg Gunthorp, vibrant summer sides and desserts from Chef Brian Enyart, and wines from Mexico’s Baja California – spanning Valle de Guadalupe, Santo Tomás, San Vicente and beyond – one of the world’s most exciting new wine frontiers. 

Those interested in attending can purchase tickets through OpenTable.

Currently ranked No. 29 on the World’s 50 Best Bars list, East London’s cult-favorite Satan’s Whiskers is bringing its irreverent energy and hip-hop-fueled swagger to Hawksmoor Chicago for one night only on Thursday, August 21, in partnership with Fords Gin. The award-winning cocktail bar, celebrated for its classic cocktail mastery and low-lit, high-vibe atmosphere, joins forces with Hawksmoor’s own powerhouse bar team for a night to remember.

Expect expertly crafted drinks and an unforgettable soundtrack as Satan’s Whiskers founders Kevin Armstrong and Dan Waddy take over the second-floor bar from 6:00 PM to 10:00 PM, serving up a signature lineup of cocktails, which will be available to purchase a la carte while supplies last.

The event is open to the public, with Evite RSVPs encouraged walk-ins accepted as capacity allows. RSVPs via Evite are highly encouraged, though they do not guarantee a seated reservation. The last entry is at 9:30 PM.

Be among the first to experience the spirit of Burl, Evanston’s most anticipated new restaurant, at a one-night-only summer supper hosted at the beautiful Elawa Farm. On Tuesday, August 19 from 4–7 PM, Chef Thomas Carlin and Rachel Canfora-Carlin join forces with Elawa Farm  for an intimate, open-air evening rooted in community, craft, and the bounty of the season.

Set against the backdrop of Elawa’s historic Lake Forest estate, this collaborative dinner showcases the vibrant flavors of mid-August with a five-course tasting menu that celebrates chef-farmer connection and peak local harvests. From grilled flatbreads with eggplant and peaches to Catalpa Grove lamb with mole verde and a fruit crostada finale, each dish offers a preview of Burl’s produce-driven philosophy ahead of its 2025 opening.

Tickets are $184 per person and are available now via Tock.

Dearly Beloved in Chicago's Near North neighborhood is hosting a special evening of premium daiquiri tastings crafted by Chicago's most talented mixologists from renowned establishments. On Sunday, August 10, 7-10 pm, guests will enjoy eight daiquiris prepared by local cocktail bars including Easy Does It, Untitled, Golden Years, 14 Parish, Cara Cara Club, Chicago Yacht Club, Alla Vita. Additional cocktails will be available for purchase, along with the full menu.

Tickets are $35 per person and can be purchased HERE. (Must be 21+ to attend)

Experience Napa Valley from the comfort of Chicago at The Oakville Grill & Cellar’s Summer Wine Fest on Saturday, August 2. From 11:30 AM to 2:30 PM, toast to summer sips as you taste through four esteemed California wineries and their select pourings. The team’s friends from Lieu Dit, Matthiasson, Failla, and Mallea will be there pouring California’s best! And the fun doesn’t stop there… Get in on fun summer activities and games, stop by the Charcuterie Action Station, enjoy passed appetizers & mingle throughout the afternoon!

Tickets are available on Tock and can be purchased here.

Join the team at Miru on Saturday, July 19th, as they transform the St. Regis Terrace into a Japanese “Yatai.” Experience the vibrant flavors and rich traditions of Japanese street food, featuring grilled A5 wagyu yakitori, a kampachi handroll station, made-to-order okonomiyaki, and more. Guests will also enjoy a curated selection of Japanese beer, wine, Takanome sake, and a signature cocktail infused with Kagoshima green tea.

Tickets are $98 per person (plus tax & service fee) and can be purchased on OpenTable here.

Join the team at Wildfire Chicago for an exclusive summer wine dinner, featuring the delicious California wines from Sanford Winery & Ruthferford Hill Winery, both pioneers of specializing in hand-crafted, estate-bottled wines. Each varietal will be paired with five custom courses. A winery representative will also be onsite at the restaurant as a guest speaker to discuss the evening’s pairings!

Tickets are $130.00 per person, plus tax (gratuity not included) and can be purchased on OpenTable here.

Start your Friday morning with a 45-minute Mat Pilates session along the river at Pizzeria Portofino. After class, stay for a live DJ & coffee mixer filled with fresh brews, good vibes, and even better company. Stretch, sip, and connect as you ease into the weekend. Let’s flow into the day together!

7AM & 8:15AM- Mat Pilates - Ticket includes Pilates class & access to Coffee & DJ. Yoga mat not included, please BYOM ( bring your own mat!)

8AM-9:30AM - DJ & Coffee - Ticket includes complimentary coffee bar & pastries.

Tickets can be purchased on OpenTable here.

Michelin Guide’s Sifr is setting the table for a one-night-only collaboration dinner for their 2nd anniversary! To celebrate this milestone, Chef Sujan Sarkar and Chef Sahil Sethi are joining forces in the kitchen with an incredible lineup of culinary talent - Chef Ryan Fakih of Beity, Chef Bill Kim of Urbanbelly, and Chef Diana Dáviola of Mi Tocaya Antojería. Enjoy a special menu that reflects our journey and passion for exceptional food and hospitality.

Reserve your seat on OpenTable here to be part of this unforgettable evening at Sifr!

Head to Las Fuentes’ expansive patio to celebrate the official start of summer! Guests can enjoy custom Las Fuentes x Pretty Cool Ice Cream pops, margarita flights, festive piñatas, and some of the best Mexican food in Chicago—all on a vibrant patio recently voted as one of the city’s top spots for outdoor dining by Eater. It’s the perfect way to kick off the season in the city!

Head to the Beatrix patio in River North on Tuesday, June 17th for light bites, favorite pours and a hands-on wine glass painting session! Spend the evening on Clark Street decorating a set of fruit-themed wine glasses - just in time for summer wine nights! Follow along as a Paint The Town Instructor guides guests step-by-step while snacking and sipping on two select cocktails, wine or beer. Plus, stick around for dinner after class and enjoy 20% off the entire meal.

Tickets are $74.95 per person, plus tax (gratuity not included) and include two stemless wine glasses, paint supplies, light bites and your choice of two select cocktails, wine or beer. Additional food and drink will be available for purchase. Tickets are available here.