The Resy Guide to Restaurants Worth a Drive From Chicago

New to the Scene

There are many reasons to make the drive to Door County in the summer, and buzzy opening  La Sirena in Ephraim is one of the newest. Chef-owners Carlos Salgado and Emilie Coulson Salgado moved back to Emilie’s home state of Wisconsin in 2023 after running Michelin-starred Taco María for 10 years in Orange County, Calif. At their homey restaurant, a nightly menu of two courses for $52 includes house-nixtamilized blue corn tortillas, oyster aguachile, and beer-battered walleye with roasted kale aioli, cabbage, and chile güero. The dining room is family friendly — but tiny — so we recommend making reservations early (they open a month out).

Former chef-owner of Viroqua, Wisconsin’s Driftless Café and Oleana alum Mary Kastman tested her Mediterranean small plates concept via pop-ups before settling into the former Ardent space on Milwaukee’s East Side in June 2025. At her new restaurant, Purslane, locals have come to love deviled eggs with smoked trout roe, braised short rib kebabs, a Midwestern-inspired walleye falafel, and Arabic espresso martinis with cardamon and rose. Hit the retail and wine shop on the way out for mezze to enjoy on the drive back.

NOLA-lovers can get a taste of the Big Easy in Indy at Magdalena in Fountain Square. Nick Detrich, who co-founded New Orleans bars Jewel of the South and Cane & Table, opened this cocktail, oyster, and small plates restaurant in 2024 with Sazerac-cured salmon, langoustines smothered in garlic aioli, crawfish Monica, chow chow pickled pears, and lemon posset on the menu. Cocktails range from the classics (think French 75s and grasshoppers) to the seasonal (pho-spiced margaritas with Tequila, lime, Thai basil, pho spice, and Tajín), to interesting spirit-free options (the Orange Vine with cream, egg, orange juice, and orange flower water).

Tried-and-True City Picks

Detroit has endless dining options, but Grey Ghost was a pioneer on the scene in Midtown when it opened in 2016. Chef-owners John Vermiglio and Joe Giacamino just celebrated 10 years with the return of a few favorite dishes (welcome back, fried bologna!) and acknowledgement of team members who have been with them since the beginning. Head up for their signature cheeseburger (do add the French fries dusted in pickle powder and served with zesty Ranch), lamb ribs, or butter-poached half lobster with shrimp cake. The cocktail list is full of specials like a summery Old Fashioned with rye, chamoy, mango, and Tajín tincture, and non-alcoholic options like Earl Grey tea with grapefruit, honeyed pineapple, lemon, and lavender cream.

Milwaukee’s Odd Duck has been synonymous with seasonal, global small plates since it opened in Bay View in 2012. Owners Ross Bachhuber and Melissa Buchholz moved the restaurant to Walker’s Point in 2022 for more space, and today, locals flock to happy hour in the bar, where you’ll find $5 draft beers and snacks like a Taiwanese hujiao bing. Regular menu items include fried halibut cheeks, crispy jerk-spiced oyster mushrooms, or their OG entrée: A wood-fired bavette steak served with a kimchi pancake, ssamjang, and green tomatoes.

The fun and festive Delicia has been bringing New Latin flavors to the SoBro neighborhood of Indy since it opened in 2013. Beef barbacoa shows up inside everything from empanadas to a corn tamal, but don’t sleep on hibiscus-glazed salmon or Venezuelan corn cakes with whipped chive ricotta and hot honey. Cocktails are a nice mix of Tequila, mezcal, and rum concoctions, but our favorite is the Fire and Ice, a hibiscus, basil, and habanero margarita with a chile-infused ice ball that lends even more heat as it melts, and is also available in a zero-proof version, too.

Near the Water

After hours in the car, gazing at a body of water is always appreciated. We suggest the less-than-an-hour drive to St. Charles, Ill., where The Graceful Ordinary is right on the Fox River. Grab a terrace seat for a front row view and enjoy chef Chris Curran’s menu of truffle fries, spicy carrot rigatoni pasta, or harissa half chicken, and playful cocktails like the Dip in the Backyard Kiddie Pool with Bayab rose gin, kiwi, lime, and butterfly pea flower tea.

If you’d rather be lake-bound, head to Michigan, where the dining and drinking options are endless up and down the shoreline. The Terrace Room at the Harbor Grand Hotel in New Buffalo offers some of the best harborside views and patio seating to enjoy weekend aperitivo hour snacks and spritzes (3:30 to 4:30 p.m.) or handmade pastas, salads, and entrées like cioppino and local rainbow trout in brown butter.

While not directly on the water, there are plenty of spots a few blocks inland as you head north towards Benton Harbor, where you’ll find BBQ carrots and Crying Tiger slow steak at Houndstooth.

Further north in Saugatuck is the beloved Pennyroyale Cafe and Provisions, with one of the prettiest and lushest outdoor garden seats in town. Pastries, skillets, and breakfast sandwiches are turned out of the open kitchen by day, and whitefish dip and crackers, campfire trout, and well-curated wines from South America and Michigan are served under twinkling patio lights at night.

Tasting Menus Worth the Trek

Tasting menus abound in Chicago, but don’t sleep on the great ones just a short drive away. At the seven-year-old Mink in Detroit’s Corktown neighborhood, you’ll enjoy New England raw bar vibes in the 25-seat space. For $90 you get five courses that change every month, from scallop ceviche to swordfish al pastor. There is a $60 beverage pairing, a $46 add-on for a dozen oysters, and Instagrammable oyster wallpaper inside this seafood favorite that fills up fast.

Feeling sushi instead? Make the shorter drive to 1033 Omakase and Sake Bar in Milwaukee’s Walker’s Point. With 10 seats wrapped around an intimate bar, guests enjoy 14 courses for $129 (a steal in our opinion), that runs the gamut from chawanmushi to a parade of fresh nigiri. The word is out and reservations go fast, but last minute spots do open up.

In Madison, one of the most storied tasting menus can be found at L’Etoile, which opened in 1976, but has been operated in a new location by Tory Miller since 2005 (he started as a chef de cuisine). The French-inspired tasting menu offers six courses for $175 with an array of wine pairings. Produce and products from local farmers, purveyors, and restaurant’s garden accompany dishes on the seasonal menu, from ancho chile-spiced wild Alaskan halibut to beef ribeye, and anise hyssop pavlova.

And to really bring it back, we recommend a quick drive to Mader’s which is Milwaukee’s oldest continuously operating restaurant (since 1902!). Located downtown and close to the Fiserv Forum, this German immigrant-founded mainstay is famous for their massive pork shank, fish fry, Reuben rolls, generous beer steins and a dining room that looks pulled straight out of Munich. Head to neighboring Knight’s Bar, where full armor and swords set the scene, for a drink before or after dinner.