CHICAGO— This city has been a part of my life for the past thirty-five years. It’s a city that holds a special place in my heart, not only for the food but for the people and the memories that have shaped my career in hospitality. Since I started writing this weekly column 26 years ago, I’ve been asked countless times for restaurant and hotel recommendations, not just in Chicago but across the country and especially in Europe—Italy being the most requested.
New Orleans is at the top of the request list in the U.S., but Chicago follows close behind. Over the years, I’ve kept a running list of my favorite places—a fluid document that changes as new spots emerge and old favorites evolve. Several years ago, I started putting out an annual list of my favorite restaurants and dining experiences in New Orleans. This is my first-ever published list of my favorite U.S. destinations: Chicago
My first visit to Chicago was unique and special. I was brought here, almost 40 years ago, by my friend Bud Holmes, who was Walter Payton’s agent. We had dinner at Harry Caray’s with Walter, and just as we were piling into the limo to leave, Harry Caray himself—who had clearly been called and pulled out of bed by his staff—came rushing outside to speak to Walter. He stuck his head in the limo window, and the whole thing felt like a Saturday Night Live skit, with Will Ferrell playing Caray. It was the perfect Chicago welcome.
Subsequent trips with Bud led to introductions with some of my biggest restaurant idols, including Richard Melman. He also introduced me to Arnie Morton, the founder of Morton’s steakhouses and father of Peter Morton, who founded Hard Rock Cafe. Arnie graciously sat with me for an hour, patiently answering every question I had as a fledgling restaurateur at the time. Beginning in the late 1970s and continuing through the 1980s and 1990s, Melman was the most creative force in the restaurant industry. He owned Chicago. Whenever he spoke at the National Restaurant Association convention, it was standing room only. He had an unmatched eye for design and concept development, always staying ahead of the curve. His company, Lettuce Entertain You, is still thriving in Chicago and beyond. His son now runs the show, and I had the opportunity to meet him a few times during the pandemic through the Independent Restaurant Coalition’s daily calls.
In 1997, Blackbird burst onto the scene, courtesy of Donnie Madia and Paul Kahan of One Off Hospitality Group. Located on the edge of the West Loop, they were pioneers who sparked the cultural renaissance of what has become today’s thriving restaurant, bar, and hospitality scene in that neighborhood. They followed up with Avec next door, then several other standout concepts, including The Publican, Publican Quality Meats, and Big Star, which has become a regular favorite of mine. Killer tacos, queso fundido and guacamole. My wife loves The Violet Hour, one of the early innovators of the craft cocktail renaissance.
For a while, I was mesmerized by Brendan Sodikoff and his company, Hogsalt. His concept Bavette’s left a lasting impression, as did The Doughnut Vault, and Au Cheval. His restaurants have a distinct style—dark, moody, and steeped in a sense of place. They feel like they’ve always been there, which is a testament to his ability to create lasting concepts.
The pandemic brought many challenges, but it also introduced me to some of the most inspiring restaurateurs I’ve ever met. BOKA Restaurant Group, founded by Kevin Boehm and Rob Katz, has recently been voted one of the top 10 restaurant groups in the country. I’m a huge fan of everything they do, and even more so of how they operate. Their culture is spot-on, and they elevate service and food quality to another level.
Boehm and Katz came from different worlds—Katz was a real estate investment guy dabbling in nightclubs and bars, while Boehm had worked his way up through various restaurant jobs, starting with a tiny seven-seat restaurant in Florida before moving to Nashville and beyond. When they joined forces in Chicago, they used the first two letters of their first names to create BOKA, their Michelin-starred flagship fine-dining restaurant. They’ve grown substantially since then, and their impact on the industry is undeniable.
During the pandemic, I got to know Boehm personally, and his steady leadership, vision, and enthusiasm during a time of extreme crisis were inspiring. I’ve only met Katz once, but I had the opportunity to collaborate on a project last year with their director of development, Gabe Garza— a multi-city southerner from Houston, Baton Rouge, and New Orleans— Garza brings a brilliant restaurant mind covering all aspects of the business and an exceptional understanding of how to structure a deal.
Now, for the part that people ask me about the most—recommendations. This list isn’t definitive because food is subjective and ever-changing, but these are the most recent places that have left the biggest impression on me in Chicago:
Fine Dining:
Alinea
The pinnacle of avant-garde dining in America. Grant Achatz’s three-Michelin-starred experience is one for the books.
1723 North Halsted Street, Chicago, IL 60614.
Phone: (312) 867-0110. alinearestaurant.com
Oriole
Tucked away in an unassuming alley, this two-Michelin-starred spot offers an intimate and exceptional tasting menu.
661 West Walnut Street, Chicago, IL 60661. Phone: (312) 877-5339. Website: oriolechicago.com
BOKA
The restaurant that started it all for BOKA Restaurant Group. It’s consistent, elegant, and always an experience.
1729 North Halsted Street, Chicago, IL 60614.
Phone: (312) 337-6070 bokachicago.com
Steakhouses:
Swift & Sons
My favorite steakhouse in the Midwest. Classic elegance, top-tier service, and outstanding steaks.
1000 West Fulton Market, Chicago, IL 60607.
Phone: (312) 733-9420. swiftandsonschicago.com
Bavette’s Bar & Boeuf
Dark, moody, and reminiscent of a bygone era. The steaks are good, but don’t skip the crab-stuffed avocado.
218 West Kinzie Street, Chicago, IL 60654
Phone: (312) 624-8154 bavettessteakhouse.com/chicago
Gene & Georgetti
A mainstay for me forever. The waiters here were probably the same ones serving Sinatra when he dined there often.
500 North Franklin Street, Chicago, IL 60654
Phone: (312) 527-3718 geneandgeorgetti.com
Casual Must-Tries:
Big Star
Killer tacos, queso fundido & guacamole.
1531 North Damen Avenue, Chicago, IL 60622.
Phone: (773) 235-4039 bigstarchicago.com
The Publican
Pork, oysters, and beer in a communal setting. One of the most fun and satisfying meals in town.
837 West Fulton Market, Chicago, IL 60607.
Phone: (312) 733-9555 thepublicanrestaurant.com
Au Cheval
The best burger in the country, and it’s not even close.
800 West Randolph Street, Chicago, IL 60607
Phone: (312) 929-4580 auchevalchicago.com
The Purple Pig
For devout carnivores with a penchant for Spanish cuisine.
444 North Michigan Avenue, Chicago, IL 60611
Phone: (312) 464-1744 thepurplepigchicago.com
Pizza:
Coal Fire Pizza
Recommended by my friend Donnie Madia. A must-try for pizza lovers.
1321 West Grand Avenue, Chicago, IL 60642
Phone: (312) 226-2625 coalfirechicago.com
Spacca Napoli
*Note* I am not a fan of deep-dish pizza. If Neapolitan-style pizza is more your thing, this is the best in town.
1769 West Sunnyside Avenue, Chicago, IL 60640
Phone: (773) 878-2420 spaccanapolipizzeria.com
Breakfast & Brunch:
Cira at The Hoxton
My favorite breakfast in Chicago, located in the West Loop
200 North Green Street, Chicago, IL 60607
Phone: (312) 761-1777 cirachicago.com
Nobu Hotel
A unique and very good breakfast experience.
155 North Peoria Street, Chicago, IL 60607
Phone: (312) 779-8800 chicago.nobuhotels.com
Lou Mitchell’s
A classic, bustling big city breakfast that hasn’t changed since the Truman administration.
565 West Jackson Boulevard, Chicago, IL 60661
Phone: (312) 939-3111 loumitchells.com
Cocktails & Bars:
The Violet Hour
A pioneer of the cocktail renaissance. Order something stirred and boozy.
1520 North Damen Avenue, Chicago, IL 60622.
Phone: (773) 252-1500 theviolethour.com
Three Dots and a Dash
A modern tiki bar with some of the best rum-based cocktails in the city.
435 North Clark Street, Chicago, IL 60654.
Phone: (312) 610-4220. threedotschicago.com
Other Favorites:
Longman & Eagle
My favorite restaurant in Chicago’s Logan Square area. It’s a dive bar with a Michelin star.
2657 North Kedzie Avenue, Chicago, IL 60647.
Phone: (773)276-7110 longmanandeagle.com
Frontera Grill/Topolobampo
Best Mexican by far. Probably the best Mexican restaurant in the country. I have always said that Rick Bayless is the best Mexican cuisine chef in America, and anywhere you dropped him in Mexico, he would instantly be the best Mexican cuisine chef in Mexico.
445 North Clark Street, Chicago, IL 60654.
Phone: (312) 661-1434 | rickbayless.com/restaurants/frontera-grill
Momotaro
My favorite Japanese and sushi spot in town.
820 West Lake Street, Chicago, IL 60607
Phone: (312) 733-4818 momotarochicago.com
Publican Quality Bread
My favorite bakery, and it’s not even close. Donnie Madia and Paul Kahan graciously gave me an in-depth tour before I opened Loblolly Bakery.
1759 West Grand Avenue, Chicago, IL 60622
Phone: (312) 619-5540 publicanqualitybread.com
Hotels:
The Hoxton
An excellent hotel in a prime West Loop location. Great scene, great nightlife, three great restaurants, and three great bars.
200 North Green Street, Chicago, IL 60607
Phone: (312) 761-1700 thehoxton.com/chicago
Nobu Hotel
Perfect location, luxurious rooms, attentive staff, and world-class sushi attached. What’s not to love?
155 North Peoria Street, Chicago, IL 60607.
Phone: (312) 779-8800 chicago.nobuhotels.com
I have always believed that Chicago is a more accessible New York and, after spending substantial time in each over the past three decades, would choose Chicago over New York nine times out of ten. Chicago is an ever-evolving city for dining, and I’ll keep adding to my running list. If you find yourself heading this way, trust me—there’s no shortage of great food to be found.
Onward.
