Drinks and Dining
Eat and drink the best of the city
Lou Malnati's
In terms of hometown heroes, Lou Malnati’s is a legend. It’s also a Chicago-based chain with a unique, ultra-crisp, buttery and pie-like crust, which is crumbly and thin at the edges. If you order one with sausage (you should), be prepared to encounter a disc of meat on top that spans the entire pizza, covered in a chunky, brightly acidic layer of tomatoes. If you’re a visitor to Chicago and ask for recommendations, be prepared to hear about this place from almost everybody, as its ubiquity means it’s a very nostalgic place for many people. There are many locations, ranging from take-out-only counters to large, shiny full-service restaurants all around the city.
Pequod's
Pequod’s looks and feels like an old dive bar, but step inside and you’ll find a pizzeria packed with both native Chicagoans and visitors alike. The pies are technically pan pizzas, which have a thicker bottom crust with crispy, greasy fried texture to it. Pequod’s is best known for the dramatic halo of toasty, nearly blackened cheese around the rim of the pies. For a lot of deep-dish pizzas, the edges can be (and often are) neglected, but the crisp cheese exterior is as prized as the edge of a Detroit-style square pie. The house specialty sausage pie is definitely the way to go; Pequod’s sausage pieces are the size of gumballs and are plentiful and juicy.
Al's Italian Beef
The purported origins of the Italian beef sandwich can be traced back to this Taylor Street stand in Little Italy. That’s where Al Ferrari and his sister and brother-in-law, Frances and Chris Pacelli Sr., set up shop in 1938 and started popularizing what would become one of the city's iconic foods. Today, the original location is still in business and the beef remains unchanged — marinated in secret spices and dipped in gravy. So stop in, assume the proper upright eating stance, and savor a bit of Chicago history.
Jim's Original
The legend of "Jim's Original" started over 80 years ago, with a young, bright-eyed immigrant named "Jimmy" and a hot dog stand he has made literally "World Famous." Established in 1939, Jim's Original is the longest operating hot dog stand in Chicago. Jim's has been serving up the Original Maxwell Street Polish Sausage Sandwich for over 82 years, still made today as it was back when Jimmy first "invented" it in 1943 — with sweet grilled onions & a smear of mustard. Visitors to Jim's can agree, there has never been a pleasure as great and as simple as taking a bite into one of Jimmy's original sandwiches.
Kindling | Downtown Cookout & Cocktails
James Beard Award-winning chef Jonathon Sawyer has taken on the project of creating what might be Chicago’s most opulent Italian beef. The $26 sandwich takes each component to it’s most over-the-top form: its beef is sourced from a boutique farm in Georgia and its bread is from 3D Baking, a well-regarded local commercial bakery. Chicago’s famed J.P. Graziano’s makes the giardiniera, and those who like to gild the lily can add “raclette whiz” for a slight upcharge.
Monteverde
The first restaurant from former Top Chef and Spiaggia chef Sarah Grueneberg has quickly cemented itself as one of Chicago’s top Italian destinations. The pastas are the stars at this West Loop hot spot, and customers can see cooks hard at work behind the counter rolling out dough and creating delectable noodles. The restaurant’s pandemic takeout menu remains, but the dining room offers lively options like whole-bird chicken Parm. There’s also a notable gluten-free menu.
Girl & the Goat
Girl & the Goat has been serving fun foods, craft beers, and making wine in a rustic and kick-butt environment since summer 2010. The Goat's menu is divided into three categories: Vegetable, Fish, and, of course, Meat. Bread is baked daily, and there are always new creations on the menu. Girl & the Goat sits in the West Loop smack dab in the Randolph Restaurant Corridor, but the location is still gritty enough to appeal to the chef’s integrity. They feature their own blended wine, along with a selection of beers on tap — and if you're lucky, you might come across the elusive collaboration beers that Stephanie personally crafted with a couple of beer buddy cohorts. Girl & the Goat accepts reservations but always welcomes walk-ins, nomads, adventurers, and those of you who don’t like to plan.
Manny’s Cafeteria & Delicatessen
Corned beef is a big deal in Chicago, and one visit to Manny’s and you'll know what all the fuss is about. A South Loop institution since 1942, thanks to its massive and delicious corned beef and pastrami sandwiches, an array of hot homestyle dishes on steam tables, and a family-friendly atmosphere cultivated over generations. The cafeteria-style setting is plastered with decades-old newspaper clippings and letters from Chicago luminaries. The space also now houses a new wing for bagels, sweets, coffee, and food to go. In its heyday, Manny’s was where Chicago politicians were often seen brokering deals.
Harold’s Chicken
There’s fried chicken, and then there’s Harold’s fried chicken. The famed chicken shack — which has been serving locals since 1950, becoming a Chicago institution with locations throughout the city. Lucky for us, Harold's Chicken #62 is located less than a block from Hilton Chicago. Make sure to order your chicken with Harold’s famous mild sauce.
Harry Caray’s Italian Steakhouse
Deep dish pizza, Italian beef, chicken Vesuvio … the list of Italian contributions to Chicago’s cuisine is long and legendary. Order the “best Chicken Vesuvio in the city” (according to the Chicago Tribune) at Harry Caray’s Italian Steakhouse, where half a bone-in chicken is roasted with quartered potatoes, sweet peas, garlic, and white wine.
Twin Anchors Restaurant & Tavern
Among barbecue restaurants, Twin Anchors is one of the city’s oldest (1932) and best (receiving a Bib Gourmand award from the esteemed Michelin Guide). Located in an historic Old Town building that dates back to 1881, Twin Anchors Restaurant & Tavern is one of the oldest restaurants in the city of Chicago. Since its founding in 1932, Twin Anchors has always been known for great, tender, barbequed baby-back ribs that can be enjoyed in a quaint neighborhood tavern.
88 Marketplace
Chicago has many food halls, but none offer the same type of experience as 88 Marketplace, the Chinese grocer in East Pilsen. The grocery store stocks tons of ingredients not readily available at chain supermarkets. That alone makes it a destination, but the second-floor food court offers wonders, headlined by 312 Fish Market, a sit-down restaurant with one of the most creative sushi menus in town at affordable prices. Find dumplings and other delights from A Place in Northeast, barbecue duck, and more from BBQ King 88. On the first floor, there’s Holu Steakhouse, where diners can find rare, pricey, and delectable cuts of beef along with top-notch cocktails. No stuffy River North steakhouse can compare. Then find Qiao Lin Hotpot, possibly the best hotpot in Chicago. Finally, get something sweet at Pure Tea. It took a while for 88 Marketplace to get going, but it’s now chugging on all cylinders.
Carnitas Uruapan Restaurant
Chicago’s Mexican community and food enthusiasts worldwide flock to this longtime family-owned counter-service institution in Pilsen that celebrates all parts of the pig. Order carnitas by the pound at the front counter and settle into a table — if one is available — to craft your own individual tacos with a mix of salsas, tortillas, and beans, or order tacos, soup, and cactus salad ready-made. Prepare for lines and waits during peak weekend hours.
The Duck Inn
The Duck Inn is the ultimate neighborhood restaurant, a family-friendly place that Bridgeport locals could regularly visit — to nosh on Italian beef and duck fat-infused hot dogs while drinking a cold brew. But with special dishes like rotisserie duck, the restaurant also caters to special occasions thanks to chef Kevin Hickey’s fine dining edge. The cocktail and wine list is not just great in general, but it’s also one of the best to find a good drink on the South Side and that scarcity makes the restaurant even more remarkable.
Smyth
John and Karen Shields have brought their vision to life in Chicago, pushing fine dining boundaries delivering an extravagant tasting menu. The techniques, ingredients, and service are all top notch, and they are one of a handful of restaurants that have attained a full three-star rating from the Michelin Guide. Developing close relationships with purveyors all of the Midwest, Smyth dishes out creative dishes with fantastic produce in one of Chicago’s most expensive meals.
Rose Mary
Joe Flamm and his partners went big in Fulton Market, opening a meticulously designed restaurant that’s become a destination for out-of-towners who know Flamm from his Top Chef win. But Rose Mary, described as “Adriatic drinking food,” is also locally beloved for its European notes that fuse Italian, Croatian, and Midwestern sensibilities. The pastas would be at home at Spiaggia, one of the best Italian restaurants in Chicago before it closed, where Flamm cut his teeth. The ribs have a sticky sauce that breeds a familiarity to those who grew up on both the Southwest or Northwest sides. Try the cevapi, a Balkan-style sausage. The octopus, cooked over a wood grill, is perfect. There’s a great energy in the restaurant, which also offers a seasonal tasting table during the warmer months. Reservations are a must for the latter.
Ever Restaurant
Let’s do a favor for Ever’s PR team: unlike at the end of Season 3 of The Bear, the real Ever continues to serve patrons. Chef Curtis Duffy became a superstar when he opened his first award-winning restaurant, Grace, on Randolph Street, and he’s brought that energy a few blocks west to Fulton Market, where Ever opened in 2020. Duffy is offering only one tasting menu (vegetarians will be accommodated), but he remains committed to showing off precise techniques with playful execution. Case in point: artfully cut ribbons of freeze-dried hamachi. Fine dining tends to be polarizing, but for folks who want a meal with a dash of theatrics, Ever fulfills that niche better than any Chicago restaurant. It’s so synonymous with fine dining that a semi-fictionalized version of the restaurant had a starring role in seasons 2 and 3 of The Bear. Just note that this is one of the most expensive meals in Chicago.
The Berghoff
Beer and brats are Chicago staples, and The Berghoff serves some of the best. This family-owned restaurant has been in business since 1898 — an era when a beer cost a nickel and came with a complimentary sandwich on the side. Another historical nugget: The Berghoff obtained the first liquor license in Chicago after Prohibition ended.
Miller's Pub
A Chicago institution, Miller's Pub has been serving up traditional American grub and craft brews since 1935. Once one of the most famous late-night spots Chicago had to offer, where on any night of the week you might find Marilyn Monroe, Mayor Daley, or Chicago baseball legends Bill Veeck and Harry Caray (regular customers and lifelong friends of the Gallios family) in a booth next to you. Every day thousands of customers visit the multi-level restaurant and bar to enjoy its extensive menu of American cuisine and nostalgic ambiance, accentuated by dark wood, stained glass, and a huge collection of vintage oil paintings. Be sure to check out the numerous photos of Hollywood movie stars, professional athletes, Broadway actors, musicians, and local politicians who have frequented Miller’s over the years.
Moody Tongue Brewing Company
Based in the South Loop neighborhood of Chicago, Moody Tongue presents a selection of chef-driven beers and beer-centric dining experiences. Their Chicago-based production brewery offers beer selections available across a number of states and international cities. The Dining Room at Moody Tongue presents an intimate fine dining experience showcasing a 15+ course tasting menu with curated beer pairings. Or visit The Bar for a lively tasting room and restaurant, featuring a la carte menu items as well as a collection of seasonal, perennial, and specialty beers.
The Green Mill
Want to get a glimpse of where Al Capone once hid his bootlegged booze? The Green Mill was Capone's favorite hangout back in the day, when he’d swirl a cocktail and listen to live jazz. His pal, Machine Gun McGurn, part-owned the club, which was central to their bootlegging operation. If it’s not too busy, ask the bartender to show you the trapdoor behind the bar that leads down to tunnels where they hid the hooch.
The art deco décor hasn't changed much since the 1920s. Seasoned bartenders will shake up a Sidecar or Manhattan or pop open a Pabst for you. But they're best known for their Martini: a crystal-clear, up-with-two-olives, non-fancy-pants gin bracer. Order that Martini in the afternoon, and it'll be you and a handful of grizzled regulars minding their own business in the dim light. At night, the crowd sharpens, and you'll be drinking alongside serious jazz-heads who will shush you for talking during the sets. Imbibe on a Sunday, and poets will be your companions. The Green Mill is the birthplace of the poetry slam, still held each Sunday evening, which explains why much of the bathroom graffiti is written in verse.
As for sitting where Capone sat, you really can do that, too. His booth is the one at the end of the bar, on the north side—the only seat in the house that has a view of both doors.
Hello Jasmine
Voted Yelp’s #1 Fried Chicken in Illinois, Hello Jasmine is a local staple for authentic boba tea and Taiwanese food. After moving to Chicago from Taiwan, the founders were determined to create Taiwanese bento, snacks, and bubble tea that deliver the exact flavor they grew up loving. They pride themselves in producing genuine Taiwanese dishes and drinks by sourcing high-quality, "real" ingredients responsibly — including loose-leaf tea and brown sugar imported from Taiwan, fresh fruits, and the finest tapioca pearls. Their freshly brewed teas and slow-cooked bubbles are made by the staff daily, along with their celebrated Taiwanese bentos (a lunch box that typically includes protein, vegetables, and rice).
The Original Rainbow Cone
They say “life’s too short for just one flavor.” The Original Rainbow Cone is a Chicago institution whose signature namesake treat is a cone stacked with slices of orange sherbet, pistachio, Palmer House (New York vanilla with cherries and walnuts), strawberry, and chocolate ice cream. Try the ultra-photogenic treat at Rainbow Cone’s original Beverly location or their Navy Pier outpost.
Garrett Popcorn Shops
Circa 1949, you could have found Gladys Otto, Garrett Popcorn Shops founder, selling bags of flavored popcorn for 5 cents a bag on the streets of Chicago. Today, these treats are still made in copper kettles, much like they were three generations ago. In addition to Buttery and Plain, Garrett’s handcrafted recipes also include Spicy CheeseCorn and four different CaramelCrisp recipes in Pecan, Macadamia, Cashew, and Almond. Don’t pass up trying their best-selling, world-famous Garrett Mix: an addicting mix of cheddar and caramel popcorn.