Chicago has always been a city with amazing restaurants, and it’s also been a favorite of mine since I was young and first got the travel bug. A recent trip to the Windy City reminded me of some of the classics that people might overlook for the glitz and glamour of the new, flashy places that are opening all the time. From Gene & Georgetti to Twin Acres and Martha’s Still, these restaurant options range from the fancy and classy to the casual neighborhood spots you can’t miss, even if you will only be in the city for a short time. So, sit back, relax, and let me tell you about the best classic restaurants in Chicago:
Gene & Georgetti – Chicago Institution for Steaks and Italian Food
First on my list is Gene & Georgetti located at 500 N. Franklin. I stopped in here for a trip down Memory Lane, as I have been here before and the food menu really stood out, especially since I can’t deny a good steak and Italian food is always on my mind. This is not a hip and trendy spot. It still has a vibe that has held on since the restaurant opened in the early 1940s. It’s almost like you are pushed back in time here as you dine on Tuscan fare including Spaghetti all’aglione and Tordelli Lucchesi. Of course, they also serve steak, chops, seafood, and G&G classics like the Chicken Joe, which is a personal favorite of mine. It’s definitely worth the wait.
Gene & Georgetti
500 N Franklin St.
Chicago, IL 60654
(312) 527-3718
The Berghoff Restaurant – The Best of German Food with an American Twist (Check Out Adams Street Brewery, Too!)
For more than 125 years, the Berghoff Restaurant has been serving people in Chicago some of the best German food I’ve ever had. I have known about this place for decades, and I always try to stop in every time I’m in the city. I first went when I was a teenager on a family trip, and I keep going back as this food keeps popping into my head. From the Sausage Trio and Chicken Schnitzel to the Currywurst, the German food here is amazing. They also have every day favorites, too, like chicken sandwiches, pork chops, burgers, and a delicious pulled pork sandwich. Recently, they opened the Adams Street Brewery, too, so make sure to grab a beer while you eat.
The Berghoff Restaurant
17 W Adams St
Chicago, IL 60603
(312) 427-3170
Club Lucky – Timeless Style and Modern Hospitality
If you are looking for an authentic 1940’s cocktail lounge vibe, stop into Club Lucky. This is a retro-style bar, lounge, and restaurant tucked away in the Bucktown neighborhood. I love the 1940-s inspired decor and vintage charm, and the cocktails are amazing. Menu-wise, this classic Chicago eatery serves traditional Italian food like Linguine with Fresh Manila Clams, Fettucine Alfredo, Veal Marsala, and Chicken Parmigiana…and don’t forget to order their famous calamari for an appetizer…then you can take half of your meal home for tomorrow.
Club Lucky
1824 W Wabansia Ave
Chicago, IL 60622
(773) 227-2300
https://www.clubluckychicago.com/
Fireside Restaurant & Lounge – Casual Vibes Since 1904
If you are in the Edgewater area of Chicago, you must check out this casual spot that just celebrated it’s 120 year anniversary in 2024. It’s one of the oldest restaurants in the city, but a modern menu featuring tacos, burgers, ribs, and pasta. Always made with fresh ingredients, the good just tastes better here as you take in the history around you. I love that they have an outdoor patio for the summer that’s heated, and I highly recommend the weekend brunch. Try the avocado toast or the breakfast sandwich, which is a favorite of mine made with bacon, sausage, cheddar cheese, and a runny fried egg on a toasted English muffin.
Fireside Restaurant & Lounge
5739 N Ravenswood
Chicago, IL 60660
(773) 561 – 7433
https://www.firesidechicago.com
Twin Anchors – Frank Sinatra’s Favorite Restaurant in Chicago
Twin Anchors is a Chicago institution that is not only one of my favorite spots in the city, but also Frank Sinatra’s. In fact, his music is still played here, and there is even a phone jack in the wall that the restaurant installed for Sinatra so he could come in and make calls while he was there. Known for amazing barbecue dishes like ribs served with the Twin Anchors signature BBQ sauce, don’t miss the dining experience at Twin Anchors…and don’t forget to take a bottle of their famous BBQ sauce home. My favorite is the Zesty Sauce, which has the perfect zing.
Twin Anchors
1655 N Sedgwick St
Chicago, IL 60614
(312) 266-1616
https://www.twinanchorsribs.com/
Marge’s Still – One of the Oldest Restaurants in Chicago
Not far from Twin Anchors is Marge’s Still, one of the oldest pubs in Chicago. You have to go get some drinks and food here. They have everything from the latest craft beers at the bar to classics like Manhattan’s and Old Fashioned’s. The menu features everything from beef and turkey burgers, fish sandwiches, mussels, and even Korean BBQ Short Ribs. My favorite at Marge’s Still? The famous Chicken Pot Pie. It’s outstanding, and huge, so come hungry.
Marge’s Still
1758 N Sedgwick Street
Chicago, IL 60614
(312)-664-9775
King Crab House – Fun, Casual Seafood Restaurant
If seafood is your thing, you have to check out King Crab House. For more than 40 years, people have been coming to King Crab House for crab dished, like crab legs and crab cakes, fresh fish, seafood, steaks, and more. Many people come here for dinner before a show at the Steppenwolf Theatre, but I say go anytime. If you sit at the bar, there are great deals like a burger for less than $4, that you just can’t find anywhere else in Lincoln Park or throughout Chicago. This is definitely the best restaurant in Chicago for crab and casual seafood.
King Crab House
1816 N Halsted St
Chicago, IL 60614
(312) 280-8990
Glunz Tavern – One of the Most Iconic Chicago Restaurants
Glunz Tavern is found in the Old Town part of Chicago, and it has an interesting history. It was originally opened in 1888 by Louis Glunz, and then closed just before Prohibition. The tavern reopened in 2012, and since, it has become a neighborhood institution. The menu here at Glunz Tavern has a lot of old-world options including the Weiner Schnitzel Dinner, which includes breaded veal, spatzle cooked with browned butter, and lingonberry jam. This is a great place to meet friends for a drink or snack, too. It has a huge whiskey menu, wine, beer, and craft cocktails.
The Drake Hotel – Perfect For Those Looking for Fancy Restaurants in Chicago
When I feel like something fancy in Chicago, I always have the Drake Hotel in my mind. It is a well-known establishment, and people come to experience two things – Coq d’Or, the famed cocktail lounge, and Palm Court, known for it’s high tea experience. At Coq d’Or, definitely get a martini. They are out of this world. The bar also features live music, which just adds to the experience. At Palm Court, high tea is exceptional and it features the best tea, tea sandwiches, and cakes, which have been enjoyed by regular people and celebrities, alike, including Princess Diana and Queen Elizabeth II.
RL – Shop and Eat on Michigan Avenue At One of the Best Chicago Restaurants Downtown
RL is an American restaurant that is part of the flagship Ralph Lauren store right on Michigan Ave, though the restaurant entrance is on E. Chicago Ave. I have been here two times and both times were exceptional. The restaurant has a warm, inviting atmosphere that I would expect from Ralph Lauren, and the dishes are absolutely amazing, especially if you are looking for a semi fine dining experience. I highly recommend the Chicken Milanese or the burger, but if you are looking for something fancier, look at the filet mignon or lamb chops. You should also try the Lake Perch if you are looking for something a bit more local to Chicago.
RL Restaurant
115 E Chicago Ave
Chicago, IL 60611
(312) 475 -1100
https://www.ralphlauren.com/global-rl-chicago
Billy Goat Tavern – One of the Most Famous Restaurants in Chicago
Billy Goat Tavern is a legendary restaurant in Chicago, especially after it was made famous on Saturday Night Live. Billy Goat Tavern actually has eight different locations. The original location, on N. Michigan Ave, is a famous gathering spot for locals, but there are also locations in Wrigleyville, at Navy Pier, and at both Midway and O’Hare. The menu here features classic diner fare like grilled cheese and hot dogs, but when you are at Billy Goat Tavern, you definitely should get the Original “Cheezborger.” There might be a line, but make sure you wait to get a seat. This is a place you don’t want to miss.
Billy Goat Tavern
430 N. Michigan Ave at Lower Level
Chicago, IL 60611
(312) 222-1525
https://www.billygoattavern.com/
Shaw’s Crab House – Best Restaurant for Seafood and Steak?
Shaw’s Crab House is another Chicago favorite, especially for those who love seafood. There is one location in the city on E. Hubbard, and it doesn’t matter if you want to fill your table with sushi, seafood, salads, or steaks…Shaw’s Crab House has it. This restaurant is open for lunch and dinner dining, and they also have a Happy Hour that offers pretty good prices on appetizers, beer, wine, Bloody Mary’s, and Martinis. Though this restaurant is known for crab, I always get oysters when I go, and I love the Club Room Combination, which is a meal made from filet, shrimp, scallops, and rice. Also, save room for something sweet after your meal, because the dessert menus is amazing.
Shaw’s Crab House
21 E. Hubbard St.
Chicago, IL 60611
(312) 527-2722
https://www.shawscrabhouse.com/
Andy’s Jazz Club – Live Music, Great Good, Reservations Required
Andy’s Jazz Club is another favorite of mine. I mean, you can’t go to Chicago and not hear some jazz, right? Andy’s opened as a bar in the 1950s, and in 1975, the bar starting bringing in jazz bands. The rest is history. While you eat, you can here some of the best jazz bands around. There is a bar area that is a bit further from the stage, but you can hear the music, throughout. One thing to know about Andy’s Jazz Club — you do have to pay a cover charge and reservations are required, so plan ahead if you want to experience a real Chicago jazz club.
Andy’s Jazz Club
11 E. Hubbard Street
Chicago, IL 60611
(312) 642-6805
Green Mill Cocktail Lounge – Oldest Jazz Club in the Country
Sticking to places a jazz fan will love in Chicago, the Green Mill Cocktail Lounge is believed to be the oldest jazz club in the United States. People like Al Jolson and Billie Holiday have performed here, and it was first used as a speakeasy during Prohibition. It’s also believed that one of Al Capone’s associates, Jack “Machine Gun” McGurn was an owner of this establishment at one time, and Al Capone had a reserved table available to him at all times. You can also see the Green Mill in a handful of films, including “Ocean’s 12” and “High Fidelity.” This is a cash only establishment, so keep that in mind, and they don’t have food, but I still wanted to mention it here because it’s fair to say that this is a great place to see in Chicago.
Green Mill Cocktail Lounge
4802 N Broadway
Chicago, IL 60640
(773) 878-5552
Club Lago – Enjoy Italian Specialties From One of the Classic Chicago Restaurants
Club Lago is an old-world Italian restaurant that has been in business since 1952. Serving the city with some of the best Italian style food out there, many people say that Club Lago is one of the most “real Chicago” restaurants around. Lunch and dinner are both available from Club Lago, and I have to say, every time I have gone, I’ve had the best experience. Even the most simple dishes, like spaghetti and tomato sauce, are absolutely delicious, and you shouldn’t miss a meal from Club Lago.
Club Lago
331 W Superior St
Chicago, IL 60654
(312) 951-2849
Green Door Tavern – Built in 1921 and Still Going Strong
Green Door Tavern, established in 1921, is one of Chicago’s oldest surviving wooden-frame buildings and a beloved neighborhood bar with plenty of character. Known for its quirky décor, vintage vibe, and welcoming atmosphere, it offers hearty pub fare alongside craft cocktails and local beers. The tavern is also home to The Drifter, a hidden speakeasy in the basement, which is a fun addition for those who are interested in the history of the city. With classic dishes like burgers, fries, tuna melts, and grilled cheese, the Green Door Tavern has something for everyone.
Green Door Tavern
678 North Orleans Street,
Chicago, IL 60654
(312) 664-5496
https://www.greendoorchicago.com/
Bruna’s Ristorante – Traditional Atmosphere and Amazing Food
Another classic Chicago Italian restaurant, Bruna’s Ristorante is in the Little Italy neighborhood of Chicago, and it’s a definitely “must” if you are looking for Italian food. I have been to Bruna’s a couple of times, and I recently went back because I love the traditional atmosphere and the tiramisu, which is some of the best, if not THE best, in Chicago. I also love a certain wine they have here at Bruna’s, Vino Nobile, which pairs beautifully with my favorite pasta there, the Tortellini alla Bolognese.
Bruna’s Ristorante
2424 S. Oakley Ave.
Chicago, IL 60608
(773) 254-5550
https://www.brunasristorante.com/
Old Town Ale House – Classic Chicago Neighborhood Bar
Many people call Old Town Ale House the “best dive bar in Chicago,” and famed Chicago film critic, Roger Ebert, called this bar…“The Best Bar in the World That I Know About.” This place is definitely unique, and you can spend as much time looking at the eclectic wall art posted everywhere as you can browsing through the songs on the juke box. You can also see some of the art on the website. This is a famous place, and the perfect spot for a drink when you are exploring what Chicago has to offer.
Old Town Ale House
219 West North Avenue (at Wieland)
Chicago, IL 60610
(312) 944-7020
https://www.theoldtownalehouse.com/
Butch McGuire’s – Gold Coast Irish Bar with Daily Specials
I love a great Irish bar, and that’s why I keep going back to Butch McGuire’s. This is a great bar and restaurant on the Gold Coast of Chicago, and they have excellent food and cocktails. Since 1961, this bar has been serving Irish food, American food, and cocktails, and some of the stand out options I’ve tried include the famous Butch McGuire’s Reuben, the Deep Dish Chicago-style pizza, and even the burgers. Though I haven’t been there at Christmas time, people rave about the Christmas decorations here. I think it’s definitely worth checking out if you happen to be there in December.
Butch McGuire’s
20 W Division St
Chicago, IL 60610
(312) 787-4318
Lou Mitchell’s – Stop for Breakfast on Route 66
Many people don’t realize that Route 66 starts right here in Chicago, and Lou Mitchell’s is like the unofficial start of anyone who wants to travel “The Mother Road.” This is a very popular diner for locals and visitors to Chicago, and the food is really great. I love a good, hearty breakfast to start my day, and I know every time I go to Lou Mitchell’s that this is exactly what I will get. Fresh eggs, fluffy pancakes, baked goods, and more are all available here, and you absolutely have to try the donut holes. You don’t have to search for a good morning meal in Chicago if you remember to go to Lou Mitchell’s in the morning.
Lou Mitchell’s
565 W. Jackson Blvd
Chicago, IL 60661
(312) 939-3111
RJ Grunts – A Legendary Lincoln Park Institution
RJ Grunts, located in Lincoln Park, is a legendary Chicago eatery that first opened in 1971 as the very first Lettuce Entertain You restaurant. Known for its retro vibe and laid-back atmosphere, it combines comfort food favorites with a playful twist. RJ Grunts is credited with introducing the first-ever salad bar in Chicago, which remains a signature feature today. I love the menu there, which features juicy burgers and cute hand-spun milkshakes. I also love the funky décor, fun energy, and the history of this place in Chicago lore.
RJ Grunts
2056 N Lincoln Park W
Chicago, IL 60614
(773) 929-5363
https://www.rjgruntschicago.com/
Italian Village – One Restaurant, Four Concepts
There are a lot of Italian restaurants in Chicago, but Italian Village is one of my absolute favorites. First, it is the oldest Italian restaurant in the city, and it has been opened since 1927. Inside the building are four different concepts. The Village is a traditional restaurant with all of the Italian-American dishes we all love. Bar Sotto, a place to get amazing cocktails and nibbles. Sotto is like a “new Italian” restaurant with innovative dishes based on traditional ideals, and Vivere, a private area for up to 25 people to meet and mingle.
Italian Village
71 W Monroe St.
Chicago, IL 60603
(312) 332-7005
https://www.italianvillage-chicago.com/
Miller’s Pub – Sandwiches, Ribs, and Famous Faces
Not far from Italian Village is the highly popular Miller’s Pub. Located in the Loop area of the city, this pub has been around since 1935, and it’s known for its delicious and amazing ribs, which I can attest are the best around. The interior here is classic dark wood and stained glass, and the bar is literally 50-feet long. It often gets busiest on Friday and Saturday nights, but if you can get a seat there, do it. Celebrities coming to Chicago have stopped here for years, and it was known for being a favorite stop for people like Frank Sinatra and Marilyn Monroe.
Miller’s Pub
134 S. Wabash Ave
Chicago, IL 60603
(312) 263-4988
Exchequer Restaurant & Pub – One of the Best Restaurants in Downtown Chicago
Located a bit south of Miller’s Pub, but not quite in the South Loop, you will find Exchequer Restaurant & Pub. Known for their Chicago-style pizza and ribs, you will also find traditional dishes like burgers, salads, sandwiches, and traditional entrees. I have been here a few times, and I love the interior design. This place has a lot of history, and you can learn a lot about it simply by taking some time and looking at the historic articles and pictures that hang on the walls. The service here is just as good as the flavor of the food, and this is a space you need to take time for when you are downtown. You will be glad you did, even if it’s packed.
Exchequer Restaurant & Pub
226 S. Wabash
Chicago, IL 60604
(312) 939 – 5633
Gejas Cafe – Plan Your Chicago Date Night Right Here
Chicago is filled with pizza, pasta, and ribs…but if you are looking for something different, consider Gejas Cafe. Voted the Most Romantic Restaurant in 2015 by USA Today, dining at Gejas is like dining in a wine cellar. Fondue and flamenco are the focus here, and the premier dinners are well-worth it, especially for special occasions. Each meal includes four courses including salad, cheese fondue, assorted vegetables, meats, or other dippers, plus dessert…yes, the dessert might be the best here as it features decadent chocolate fondue with dippers, including marshmallows, which you can roast right at your table.
Gejas Cafe
340 W Armitage Ave
Chicago, IL 60614
(773) 281 – 9101
The Bagel Restaurant and Deli – Chicago’s Best Jewish Deli
For over 70 years, The Bagel Restaurant and Deli has been serving deli favorites including salads, soups, burgers, blintzes, and much more. Some of the specialties here are the Bagels and Lox, Gefilte Fish, Potato Pancakes, Borscht, and Matzo Ball Soup. Whatever you get here, you won’t be wrong with your choices. I have had the Matzo Ball Soup and several sandwiches, and everything has always been absolutely amazing. Honestly, I’d love to have these recipes! They have a huge menu, too, so there really is something for everyone.
The Bagel Restaurant and Deli
3107 N Broadway
Chicago, IL, 60657
(773)-477-0300
The Brunchery – Remodeled, But Still Better Than Ever
Originally called Frances’ Deli, The Brunchery has been serving the best brunch in Chicago since 1938. The menu features amazing comfort food in a diner like atmosphere. Some of the items on the menu are very creative, such as the Mini-Waffle Flight, Jerk Chicken Alfredo Omelet, and the huge triple-decker sandwiches. Of course, The Brunchery has plenty of the most classic brunch options, including mimosas and bloody marys. They also have amazing coffee. Best of all, this restaurant is open every day from 9am to 3pm, expect Thanksgiving and Christmas, so you can always get your brunch on in the Windy City.
The Brunchery
2552 N Clark St
Chicago, IL 60614
(773) 248-4580
The Wiener’s Circle – Classic Chicago Dog Joint
We can’t quit this list of famous restaurants in Chicago without a couple hot dog places, right? My top choice is The Wiener’s Circle, and now that they’ve expanded a bit with a new bar and outside patio, getting a traditional Chicago hot dog here is even better! Of course, they have the classic Chicago Vienna Beef hot dogs, but they also have burgers, fries, sausages, and more. There is also a lot of vegetarian options, here, too, including Beyond brand sausage and burgers.
The Wiener’s Circle
2622 N Clark St
Chicago, IL 60614
(773) 477-7444
https://www.wienerscirclechicago.com/
Mr. Beef – The Inspiration Behind “The Bear”
Have you seen “The Bear?” It’s a wildly popular television show, and it is based on this restaurant. This is a casual spot where you can get the famed Italian Beef sandwiches and other food like cheeseburgers, hamburgers, subs, hot dogs, and more. I’ve had the delicious Italian Beef sandwich here, and the last time I was there I went with the Combination Sandwich, which combines their famous Italian beef with a spicy Italian sausage. It was absolutely perfect when you prefer the best of both worlds.
Mr. Beef
666 N Orleans St.
Chicago, IL 60654
(312) 337-8500
https://www.theoriginalmrbeef.com/
Lottie’s Pub – A Piece of Chicago History
Lottie’s Pub has been around since the early 1930s, and it began as a grocery store and bar owned by Lottie Zagorski. During Prohibition, a speakeasy was located in the basement. These days, it’s a classic neighborhood bar with all of your pub grub favorites including wings, hot pretzels, burgers, tacos, and more. Lottie’s also has a great brunch on the weekends, and though the brunch menu is small, it has everything you need.
Lottie’s Pub
1925 W Cortland St
Chicago, IL 60622
(773) 489-0738
Harry Caray’s Italian Steakhouse – Where Baseball and Steak Meet
If you are a fan of Chicago baseball, you certainly know who Harry Caray is, whether you are a Sox or Cubs fan. Harry Caray’s Italian Steakhouse is located north of The Loop, and the interior is filled with photos of Harry Caray, himself along with other famous Chicagoans. The Chicago Tribune gave Harry Caray’s Italian Steakhouse the highly sought after “Best Steakhouse in Chicago” moniker, and though the restaurant has a bit of a fine dining vibe, it’s also a little bit of a sports bar, too, with major sporting events being played in the bar area. There is also a bit of Chicago and mob lore here, too, as the building that houses Harry Caray’s Italian Steakhouse was the home of Frank Nitti, one of Al Capone’s most well-known enforcers.
Harry Caray’s Italian Steakhouse
33 W. Kinzie Street
Chicago, IL 60654
(312) 828-0966
Summary
While there are no shortages of famous restaurants in Chicago, these are the ones that stand out above all. I have to give a hat tip to Gibson’s Steakhouse and Bar as we had a great time there and it’s a famous venue in Chicago as well and definitely worthy as honorable mention. If you ever find yourself visiting Chicago, make sure to drop into these iconic venues.
About Tim Schmidt
Tim Schmidt is a 20+ year Entrepreneur and Digital Marketer. A Fort Lauderdale-based "Digital Nomad," he enjoys traveling as much as possible with family and friends. AllWorld is his escape to document all of his adventures, including being a hardcore "foodie." He has property in Costa Rica and visits several times each year and is happy to offer his expert advice for planning your trip. Make sure to download the AllWorld Travel Hacks FREE ebook.
