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Chicago: Best Casual Bars and Restaurants

Casual Bars and Restaurants to Try in Chicago

by Bob Glaze

I enjoy going to fine dining restaurants in Chicago, but many of my favorites are the casual bars and restaurants that you can find throughout the city. Here are some of my top recommendations:

Twin Anchors is located at 1655 N. Sedgwick. Since 1932, it is known for its great burgers and ribs. A favorite spot of Frank Sinatra’s, his music is still played. It is a perfect place to go on a cold Chicago night. Drinking a single malt Scotch while listening to Frank Sinatra is the best. My new favorite is the pulled pork sandwich with the zesty barbecue sauce. I also recommend going for lunch. I went on a Saturday, and it was great getting a table with no waiting. 

Also ask your server to show you the phone jack that was installed for Frank Sinatra so he could plug in his phone to take calls.

Made famous by Saturday Night Live, “Cheeseburger! Cheeseburger! Cheeseburger! No Coke! Pepsi! No Fries! Chips!”, the Billy Goat Tavern is located below 430 N. Michigan Ave. Walk down the stairs to the lower level and stop in for a burger in this fun, casual spot. I also like the ham and cheese sandwich! I just read that they are open another location in Wrigleyville on N. Clark St. I am excited to try it.

Old Town Ale House: This Classic Chicago neighborhood bar from 1958 is the perfect spot for a Manhattan or other cocktail. It was a favorite of Anthony Bourdain. The music on the juke box is great.  The art throughout the bar is painted by the owner and features such people as Donald Trump, Sarah Palin, Newt Gingrich and Vladimir Putin in a pink tutu. 219 W. North Ave.

Butch McGuire’s: Butch McGuire’s is a long-time staple on the Chicago bar and restaurant scene since 1961. They have a good brunch with excellent sandwiches and burgers. Their reuben sandwich was excellent, so I went back again recently to have another one! The decorations at Christmas are not to be missed. 20 W. Division.

Located at 3107 N. Broadway is The Bagel Restaurant and Deli. This is a classic Jewish deli/diner, started over 70 years ago, with an extensive menu of traditional favorites from salads, sandwiches, blintzes, soups, burgers, fish dishes, omelettes, breakfast dishes, fountain treats and desserts. Their Old Orchard location recently closed. According to owner Danny Wolf, “at our Chicago location we will continue our tradition of home-style cooking and hospitality established by my parents and grandparents when they brought their recipes and kitchen skills from Europe.”

I was very pleased to have found it and really enjoyed the diner atmosphere and the avocado toast with lox. It was a perfect choice before a performance at the Timeline Theatre nearby.

Just north of Frances’, at 2622 N. Clark, is The Wiener’s Circle, a classic Chicago hot dog joint. They also serve burgers, sides and sandwiches. I went back after many years and had a great traditional Chicago hot dog! They have a new bar and outdoor patio in the rear which is a great addition to the walk-up counter in the front. Their slogan is “to get your dogs with a side of abuse. The staff is so fun!

With a similar vibe is Mr. Beef at 666 N. Orleans. I read about it after it appeared in the first season of the television series “The Bear”. According to Variety Magazine, “The Bear” creator Christopher Storer — who the owner Chris Zucchero has been friends with since kindergarten — based the show on the classic establishment and shot about 90% of the pilot there.”

It is a casual spot that originally opened in 1963 and has counter service and a long table for dining in the other room. They are known for their traditional Italian beef sandwiches served with sweet or spicy peppers. You can also have a cheeseburger, hamburgers, subs and hot dogs along with fries and onion rings. I enjoyed the experience.

Steingold’s of Chicago: Originally opened in 2017, this popular Jewish Deli opened their Lakeview location in 2021 at 3737 N. Southport Ave. They are known for their New York bagels, bagel sandwiches, breakfast sandwiches, soups, salads and coffee drinks. Be prepared to wait in line during the popular weekend times. I loved their classic lox sandwich on a sesame bagel with Nova lox, cream cheese, tomatoes, red onions, lightly pickled cucumbers, capers and a side of potato salad.

Located at 2954 N. Sheffield is DMK Burger Bar. This is a casual, popular spot that has a large menu of grass-fed burgers, shakes and fries along with beer and cocktails. I was not aware of it until I watched a segment from 2011 on the Food Network’s Diners, Drive-ins and Dives hosted by Guy Fieri. I then met friends there for lunch and tried his recommended bison burger with a blueberry barbecue sauce, goat cheese and marinated onions. It was great as were the sweet potato fries. He also loved the salmon burger with Thai curry mayonnaise and Asian coleslaw. I will try it on my next visit.

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Lou Mitchell’s: This popular breakfast and lunch spot has been a Chicago institution since 1923. It is located along the original Route 66 that started in 1926 in Chicago. You can find a large number of egg and pancake dishes along with salads, burgers and sandwiches. 565 W. Jackson Blvd.

I enjoyed my trip to Manny’s Coffee Shop & Deli at 1141 S. Jefferson for the first time. This is a classic Jewish deli and diner in Chicago’s South Loop dating from 1942. It is cafeteria-style, where you go through the line to pick your massive and delicious pastrami or meat sandwiches or an array of other hot dishes from the steam tables. It was recently redone, but still retains its old charm along with its decades-old newspaper clippings, photographs and letters from Chicago luminaries that line the walls. The space also now houses a new deli expansion for bagels, sweets, coffee, and food to go. You certainly won’t leave hungry!

Another great new find is Lottie’s Pub 1925 W Cortland St. I have driven by it many times, but had never been. On May 17, 2024, I heard on WGN TV that this historic bar was celebrating its 90th anniversary of opening in 1934, so I went a week later for lunch. It started as a grocery store and bar by Lottie Zagorski who transformed it into a full-service bar with a speakeasy below during prohibition.

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According to their website, “Zagorski’s soon became a place of anonymity for public officials and gangsters. The rathskeller was a concealed spot where horse betting, gambling, stripping and plenty of other vices thrived. Photo/Lottie’s Pub Backdoor deals between city officials and mobsters were also a daily occurrence at this neighborhood spot. Zagorski’s rathskeller became an escape from Mayor Kelly’s fight on crime.”

It has a fun atmosphere with a menu of drinks along with a food menu of soups, salads, sandwiches, tacos, burgers, Venezuelan arepas and pizza. I enjoyed the Chicago Med Turkey Burger with cheese that was named after the NBC television show, Chicago Med, which was filmed at the bar past seasons. They are also a place where you can watch the University of Kansas basketball and football games, along with other events from Team Trivia, Chicago Cubs Game Day specials, Chicago Blackhawks Game Day specials and the Kentucky Derby.

Nookies on Wells which is a fun diner, since 1973, for all-day breakfast at 1746 N. Wells. I have always enjoyed it. I just went back again in 2023 and loved my frittata on the outdoor patio. The portions are huge!! They also have a full lunch menu with sandwiches, salads and entrees. I also liked the newly remodeled interior.

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In Old Town near Division and Wells, is Glunz Tavern, next to the House of Glunz, one of Chicago’s oldest wine merchants. Originally opened in 1888 by Louis Glunz, the popular neighborhood gathering spot sat vacant for more than 90 years following its closure just prior to Prohibition. It was reopened in 2012 by his family members. It is known for its selection of beer, wine and European influenced cuisine. It has a casual, old-world atmosphere. I was recently back and enjoyed an excellent meat loaf dish on their outside terrace. The House of Glunz has a large selection of wine and spirits for sale. The Old-World Tasting Room is a treasure trove of hand-carved furniture and drinkware from the neighborhood’s German past.1202 N. Wells.

I hope you enjoy these spots as much as I do.

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