Chicago is a culture rich city with many historical and modern day venues worth visiting.  When you think of the Windy City you may picture Chicago style hot dogs and deep dish pizza, or you may think of 1920s gangsters such as Al Capone. You may even consider architecture like the Sears Tower or Wills Tower Skydeck, or you may relate to the many die-hard sports fans with their varied emotional state that depends heavily on the City’s wins and losses. Whatever comes to mind when you picture Chicago, there is no denying it is filled with tourist attractions to experience and many more noteworthy places to get a memorable meal. In honor of the upcoming AAO-HNSF Annual Meeting, as well as the NAR Realtors Conference being held in Chicago; here are our Playback Now production staffers’ Top 5 Restaurants in CHICAGO, IL.


sports bar with center table in large room

Timothy O’Toole’s

  1. Timothy O’Toole’s– 622 N Fairbanks Ct

Located just steps from the Magnificent Mile and Navy Pier, Timothy O’Toole’s is the perfect spot for the hungry sports fan. With 48 beers on tap and an extensive menu, including healthy options, you won’t be disappointed in your experience here. This pub comes complete with two pool tables and 72 HD flatscreen TVs. They also host weekly events, such as trivia, karaoke and stand up comedians that you won’t want to miss. Established in 1992 Timothy O’Toole’s has become the go to for gathering to watch major sporting events, including PPV boxing. They are open late so swing by for that midnight meal when you are in town for your next event.

“Basement pub with lots of TVs to watch a game. The menu has a good selection of pub food and a good beer list.” – Doug M.


deep booths and vintage decorative restaurant and pub

Miller’s Pub

  1. Miller’s Pub –  134 S Wabash Ave

Miller’s Pub has been serving patrons in Chicago since 1935. An interesting legacy the pub was actually purchased by the Gallios brothers in 1950 who kept the name Miller’s because the couldn’t afford to replace the sign. The multi-level restaurant and bar is still run by the Gallios family and offers an atmosphere that is unparalleled. Hundreds of photos adorn the walls featuring Hollywood movie stars, professional athletes, Broadway actors, musicians and local politicians who have frequented the pub over the years. The American style cuisine is delicious, reasonably priced and served with a smile. The dark wood, stained glass and huge collection of vintage oil paintings, are simply the backdrop to the corner pub atmosphere that is reminiscent of the TV sitcom “Cheers!” At Miller’s 50 foot bar it does feel like you’ve arrived “where everybody knows your name.”

“Great ribs…dark, classic 1960s feel to it…under the L Train, in the heart of the city…great place to watch a hockey game on a cold winter night!” – Todd G.


  1. Bub City – 435 N Clark St

    modern bar/dinning area with bustling crowd

    Bub City

The Country Western theme of this River North bar is just the right combination of style and quirk. The Live Music and lively atmosphere make it a fun spot for a night on the town. The menu focuses on authentic Southern barbecue and includes specialties like 18-hour beef brisket and burnt ends. If you have a chance, stop by for brunch, which is served only on the weekend, you should definitely try the Fried Chicken and Waffles with bacon-jalapeno honey and country gravy. The 5,500 square foot space is all country swagger and their serious barbecue in accompanied by a serious drink menu with every variation of Whiskey known to man. (Well, maybe not quite that many but it has to be pretty close.)

“My favorite place to go on Tuesday nights in Chicago as they host live band karaoke, but the only people getting on stage are really good. While mostly country and modern hits, the MC is always a brilliant entertainer and keeps the energy up while enjoying a great meal.” – Matt G.


  1. Giordano’s– 61 North Ave

    man laughing while cheesy pizza is being served


Unlike most Chicago style, deep dish pizzas, Giordano’s is known for its famous stuffed pizza. They use choice ingredients such as Wisconsin mozzarella and hand cut tomatoes to make their cheesy masterpieces. Founded by the Bogio brothers in 1974 the recipe for their creations came with them from a small town near Turin, Italy. Critics and patrons alike give rave reviews forGiordano’ss pizzas. In fact, Daniel Zemans, a blogger for the Chicago Pizza Club says, “While pizza for breakfast is always a good thing, a cold piece of stuffed pizza from Giordano’s is a gift from the gods. At least for those among us who do not know the meaning of too much cheese.”

“Giordano’s was my first taste of Chicago style pizza, ever, and boy do they do it right! With a thick crust, melty cheese, deep layers of sauce and toppings this will satisfy any pizza lover.” – Scott H.


  1. Cindy’s Rooftop – 12 S. Michigan Ave

    rooftop terrace with view of chicago

    Cindy’s Rooftop

Cindy’s boasts a view that you must see for yourself. The expansive view showcases Millennium Park, The Art Institute and, of course, Lake Michigan. The menu is filled with delicious options that make the most of the current season, whatever that may be, and the cocktails and wine list are the perfect accompaniment to the sophisticated atmosphere. Cindy’s sits atop the Chicago Athletic Association Hotel rooftop and opens onto an open-air terrace that will take your breath away.

“Amazing view of Lake Michigan and Millennium Park from the rooftop of the historic Chicago Athletic Association.” – Matt G.


Whether you’re planning on visiting Chicago for the upcoming AAO-HNSF Annual Meeting or any other upcoming conference, you really can’t go wrong with any of these places!!