5 Restaurants Not to Miss in Chicago

5 Restaurants Not to Miss in Chicago 2004 1126 Stephanie Gravalese

Chicago, Illinois, known as the Windy City, is also home to an amazing food scene. From the Chicago hot dog to the world-renowned Alinea restaurant, Chicago is a city that is bursting with food options for any diner. I’ve had the opportunity to visit the city many times. Each visit has allowed me to explore new neighborhoods and return to some of my favorite spots.

I will not be covering or putting my two cents in on the age-old question of where to find the best pizza in the city. Chicago-style pizza could be its own article! From laid-back Jamaican food in West town to the rooftop cocktails overlooking Millennium Park, these are five of my favorite spots to visit in the city.


The team at Giant describes the food as “simple, delicious and (slightly cheffy.)” Located in the Logan Square neighborhood, their menu features pasta from several regions of Italy with a decidedly Chicago twist, like pici pasta with jalapeño and bacon, and ricotta and potato gnocchi with bolognese. Diners will also find dishes with bold flavors such as cornmeal soft shell crab with jalapeño salsa, and pecan-smoked baby back ribs. One dish not to miss is the fried uni shooter with cucumber and soy.

Giant’s intimate space and the inventive menu, along with a creative cocktail list, make it a favorite. Giant has limited seating, so it’s best to make a reservation ahead of time, and you if you have to wait a while, take a short walk over to Best Intentions, and have a cocktail in their patio while you wait. 

The Purple Pig 

Located on Chicago’s famous Magnificent Mile, chef Jimmy Bannos Jr describes his restaurant The Purple Pig as offering “reimagined Mediterranean food.” The restaurant’s tagline of “cheese, wine, and swine” says it all. The rotating menu of plates to share means that there is always a mix of favorites as well as new dishes. Vegetarians will also be happy to hear that there are many meat-free options, including whipped feta with date crackers and saffron pickled peeks and snow peas. 

The Purple Pig was the perfect place to grab a bite after a day of sightseeing. On my visit, we did not get a reservation, which meant a wait, but we were well taken care of. We grabbed some drinks, reviewed the menu, and by the time we sat down, we were ready to order. Since my visit, the restaurant has moved to a larger space across the street. 

Little Goat Diner

In the West Loop, you’ll find Little Goat Diner, one of the restaurants of chef Stephanie Izard, the first winner of Bravo’s cooking show Top Chef. I’ve dined a few of Izard’s restaurants in my travels to the city, but I keep coming back here for the playful menu and laid-back atmosphere. 

The food at Little Goat Diner is a mix of American diner food with influences from around the world. From the Japanese street food dish okonomiyaki to classic diner versions of shrimp and grits: braised pistachio and grumpy goat grits, and this little piggy went to China: sunny side eggs, Sichuan pork sausage, chili garlic chive sauce, and gooseberries on a sesame cheddar biscuit. 

This Little Piggy Went to China at Little Goat Diner

Grab a seat at the diner-style counter, and order the hot crab dip, lump crab mixed in a cream cheese base served with what feels like a whole sleeve of Ritz crackers. You won’t be disappointed.

Mr. Brown’s Lounge 

For me, one of my favorite ways to hear about a restaurant is by word of mouth, and Mr. Brown’s Lounge is one of them. Serving authentic Jamaican food in a casual atmosphere, Chef Chris Douglas along with his brother Terry are cooking from family recipes that have been passed down through generations as well as dishes that are a fusion of American and Jamaican flavors including the jerk Caesar salad and the jerk burger. 

My friend recommended we try the oxtail with brown sauce and butter beans, but they ran out by the time we got there. We went with the MBL island jerk chicken with herbs and spices, finished on a charcoal grill. Served with rice and peas, cabbage, and plantains, this dish hit the spot. The beverage menu at Mr. Brown’s Lounge beverage menu consists of specialty cocktails, beer, wine and Jamaican soft drinks and ginger beers that complement the island inspired menu. Mr. Brown’s Lounge has two locations: West Town, which is possibly a bit of a drive for a visitor and their second location, downtown in the East Loop neighborhood. 

Cindy’s Rooftop 

For those looking for a birds-eye-view of downtown Chicago, Cindy’s Rooftop is the place for you. Located at the top of the Chicago Athletic Association Hotel on Michigan Avenue, the Chicago landmark is the hotel’s restaurant. Home to creative cocktails, natural wine, and classic American cuisine, Cindy’s outdoor deck is a spot that provides spectacular views on a clear day. 

On my visit to Cindy’s, we opted for cocktails and a charcuterie board of cured and dried meats, house-made preserves, and grilled bread while we took in the rooftop views. The cocktail menu at Cindy’s strikes a balance between inclusivity and innovation. The bar list features a well curated list of cocktails and an extensive spirits section. There is also an impressive list spirit free cocktails those who don’t imbibe.

Cindy’s is right across from Millennium Park, so it’s best to book ahead, so you have plenty of time to take in the views. While the staff fit us in for a short window of time, it’s a good idea to make a reservation so you have a seat waiting for you.  

Stephanie Gravalese is a food and travel writer based in The Berkshires of western Massachusetts, where she’s improving her pasta making skills. Keep with her on Instagram at @stephanitaeats. 

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