My Most Favorite Chicago Restaurants

I had the privilege of living and working in the heart of Chicago for five years.  This city offers the incredible energy of a major city, combined with a melting pot of cultures and flavors through its diverse network of neighborhoods.  I have since moved to Pittsburgh, but I still get asked from time-to-time my list of favorite local restaurant suggestions for people planning to visit the city I adore.

My recent weekend trip to Chicago for Blues Fest inspired me to pull together a list of my favorite Chicago restaurants I happened to frequent the most while living there.  This list is just a small sampling of the eclectic and diverse cuisine Chicago has to offer.  I know I could go on for hours with stories of the many places I had explored over my short five year period.

If you haven’t been to Chicago, it certainly needs to be added to your list.  If you live there or have visited, what are some of your favorite places to eat in Chicago?

Decadent Brunch Spot: The Bongo Room

If you are looking for decadent brunch involving stacks of pumpkin carrot pancakes or a wide variety of eggs benedicts with rich hollandaise sauces, then the Bongo Room is the place to go.  Located in Chicago’s trendy Wicker Park neighborhood, my friends and I would put our names on the list and explore a few nearby shops.  The best way to order is to each get your own entrée and then order one of the absolutely incredible dessert-like items to share.  Get there early or expect an hour wait.  It’s totally worth it.

Quick Downtown Lunch: Go Roma

I used to work in downtown Chicago and this was one of my most favorite quick casual restaurants.  The restaurant’s fare is primarily Italian with stone-fired pizzas, pastas and Panini sandwiches.  Their salads are the best with great ingredient combinations including pears, candied pecans, blue cheeses and house dressings.  A modern décor and open kitchen is a perfect place for entertaining clients or having a casual dinner while watching the world go by.  Located off the beaten path from the busy Michigan Avenue shops, this tree-lined location is flavorfully satisfying.

Fabulous Beer and Mussels: HopLeaf Bar

There are few things more relaxing than a heaping bucket of white wine steamed mussels and an ice cold imported beer.  HopLeaf is located in the heart of Chicago’s Andersonville neighborhood just north of the downtown loop.  This restaurant offers a wide selection of draft beers and is known for their steamed mussels.  Once your bellies are sufficiently full with the crusty bread you dipped into the creamy white wine liquid, make sure to explore the collection of nearby shops.  My favorite furniture store, called Urbanest, is only a few doors down from this bar.  In fact many of the pieces I now own is from having mussels and stopping by “just to look”.

Nicest Bartenders and Burger Special: T’s Bar and Grill

As a food marketer for the early part of my career in Chicago, I was regularly required to review and write multiple complex reports on a weekly basis.  I was a classic example of a young professional who took their work home just to stay ahead of the game.  Reading the long and boring reports in my small one bedroom apartment quickly got old, so I started to take them with me to read at the bar at T’s.  Sounds like a crazy idea I know, but sipping in a cold beer and eating a burger always made things more bearable.  The best part about it all was when the bartenders would actually help me with my “homework” and gave me ideas for new marketing programs to develop.  It was a match made in heaven.

I strongly recommend stopping by T’s on Monday’s for their burger special and eat at the bar to get to know the friendly bartenders.  Also, order a side of house-made garlic mayo for your fries.  It’s got so many calories, but oh so delicious.

Alfresco Dining of Dreams: Chief O’Neill’s Pub & Restaurant

Like most major cities, outdoor seating is at a premium in Chicago.  However, this Irish pub offers one of the best outdoor patios around.  The fully fenced space is located just off of the main dining room with grassy paths and a fountain for added ambiance.  My first impression was that while it’s considered an Irish pub, it was very kid-friendly inside and out.  The food is classic Irish with Shepherd’s Pie, Irish Nachos and Guinness Steak Crostini.  Be sure to try a “Snackbite” as your adult beverage of choice, and try their Sunday brunch buffet if you get real hungry.

A Bad Date Discovery: Cozy Noodle & Rice

Brent and I always joked that most of our favorite restaurant picks were actually discovered from previous bad dates.  Cozy Noodle, located just one block from Wrigley Field, was a bad date discovery for Brent.  Shortly into our early dating stage, he suggested it as a place to have lunch.  He later explained that his previous date experience was so bad, but the restaurant was so good, he needed to have a positive date experience to cancel out the past.  Well, we have been together over 2 ½ years, so I guess I must have done something right that day.

My Most Favorite Chicago Restaurant of All Time: Café 28

Words cannot describe how much I absolutely love everything about this restaurant.  Located between two elevated commuter tracks and on a busy street, it could easily be missed by the average tourist.  However, the locals are well aware of its bounty of Cuban flavors and freshly shaken martini’s since it’s packed almost every night of the week.  The price point is a little higher than most, and I typically saved this place for special occasions.  They offer an outdoor patio with an urban flare of exposed brick walls and comfortable seating.  I recommend planning on relaxing and ordering your food in multiple stages.  This is the type of restaurant that should be savored and enjoyed slowly with amazing company.

Photo Notes:  These are a few of my favorite photos that really seem to capture the energy of what makes Chicago so wonderful to live and visit.

 Print This Recipe  Subscribe to Culinary Cory