Chicago’s in Key West opened at 610 Greene Street just over a year ago on Valentine’s Day 2015. Co-owner’s Ben Hennington, originally from Chicago, and Scott Loose, originally from Michigan, have been in Key West for over 20 years before opening a restaurant designed with the motto of “Bringing the Midwest to Key West.” Chicago’s, a restaurant, bar, and blues club offers a wonderful alternative to Key West’s standard Floribbean fare.
Walking up to Chicago’s in the heart of Old Town you’ll a see a porch with comfortable chairs and a large sitting area designed to maximize people watching, enjoying good drink and eats, and puffing on a full-bodied cigar. Chicago’s offers over 230 different cigars for sale, all stored in their temperature controlled humidor. With one of the largest walk in humidors in Key West it is worth a visit to see the cigars on display under a classic portrait of Hemingway smoking a stogie.
Inside Chicago’s you’ll find a large wrap around bar and tables for both large groups of friends and intimate dining for two. Delicious and earthy food is the focus of the restaurant. Seafood options include local Key West yellowtail and mahi mahi, as well as hard to find options like catfish and freshwater lake perch, a true treat if you’ve ever had the chance to savor these delicate, mild fish fillets from up north. Many of the seafood entrees can be served grilled, blackened, or breaded. And if you want a Chicago-based delicacy that you can’t find anywhere else in Key West go for an order of the frog legs!
In addition to seafood, Chicago’s offers a variety of hearty fare including ribs, pork chops, cornbread, smoked tomato soup, and mac and cheese. A special mention, however, must be made for Chicago’s pizza options. Chicago’s offers both New York style and authentic deep dish Chicago style pizza. The deep dish pizza is 16 inches in diameter, holds up to three pounds of cheese, and can feed ten to twelve people. It takes a while for this pizza to cook; one good tip is to order the pizza before you arrive at the restaurant to reduce wait times. Of course, it’s not hard to wait at Chicago’s: nightly a jamming blues band will be playing in the corner stage and there’s also live music at happy hour between 3:30 and 6:30 pm, Monday through Friday. Chicago’s also offers a smaller 8 inch deep dish pizza that serves four people.
Chicago’s is open 7 days a week, 11:00 am to midnight Monday through Friday, 11:00 am to 4:00 am Friday and Saturday. On Saturday Latin dancing starts at midnight and goes to 4:00 am. Locals get a 10% discount. Chicago’s is a great place to relax, eat delicious food, and chill to the blues.