Chicago Style Brings Fun and Flavor to Southwest Michigan

Chicago and Southwest Michigan have been in a relationship for quite some time. Big city tastemakers paired with the laid back vibes of beach towns make for a perfect coupling. As Chicago extends its influencer status to the area, you can explore the Windy City’s reach throughout New Buffalo, Bridgman, Sawyer, and St. Joseph. Let the local experts at Bluefish Vacation Rentals help you find Chicago-adjacent old and new favorites with your next stay.

A Taste of Chicago

Feeling hungrier than the starting lineup of the ‘85 Bears? Venture to newly opened hotspot PostBoy in New Buffalo. You won’t find hot dogs and Italian beef sandwiches here. Instead, you’ll enjoy Chicago-trained Chef James Galbreath’s fanciful spin on American food and dishes like their loaded potato gnocchi. Creative cocktails and a relaxed, yet swoon-worthy interior and expansive playful outdoor space invite you to linger and enjoy. The casual dining restaurant’s name pays homage to the boat of Wessel D. Whittaker, the founder of New Buffalo. Chef Galbreath, along with business partner Ben Holland, are continuing their big city connections by partnering with popular Chicago-based restaurants for guest chef dinners hosted at PostBoy.

Beyond the “Friendly Confines” you can celebrate the Chicago Cubs with a visit to the Getaway Cubbie Grille in Bridgman. This former biker bar takes northside baseball fandom seriously with a menu filled with Chicago favorites and Cubs decor both inside and out. Don’t miss the ivy-covered walls or the replica of the curse-inducing Billy Goat.

Shop Local Wherever You Are

City slickers and suburbanites alike delight in selecting farm-fresh produce at their local Farmers Market. St. Joseph-based Mick Klug Farms is a favorite supplier of quality fresh fruit and vegetables at area Chicago Farmers Markets including Lincoln Square Farmers Market, 61st Street Farmers Market and Green City Market. But in downtown New Buffalo, you can find a uniquely charming outpost of Mick Klug farms. Tucked in an alleyway, the seasonal farmstand offers fresh produce and local finds while sharing a picturesque patio ideal for sipping coffee and enjoying in-season specialties. 

Look to Sojourn in Sawyer to bring city sophistication to a retail store in Harbor Country. Shop the collection of home goods along with vintage and modern objects curated by owner Stacia Garriot Cass. Cass also owns the stylish home store Tribute, in Chicago.

Stay and Explore Michigan in our Premier Vacation Rental Homes

Let Bluefish Vacation Rentals guide you in finding more ways to experience a taste of Chicago at some of the hottest restaurants in Southwest Michigan. Bluefish offers the largest and most inviting portfolio of more than 100 homes available for the summer season and beyond. With new homes recently added, you are invited to discover all our listings now and book a place designed for rest, relaxation and the exploration of all that Harbor Country has to offer.