Some great sandwiches and strong coffees draw folks into Cafecito daily. The popular cafe specializes in pressed Cuban sandwiches, including an outstanding Cubano made with citrus-garlic-marinated and cumin-rubbed lechon asado, ham, Swiss cheese, pickles, and mustard on toasted bread. Wash it down with a cup of sweet cafe con leche for a caffeinated jolt. Order online here.

Located 18 floors above ground, WoodWind is a contemporary American restaurant that celebrates the freshest local ingredients. Chef Matt O’Neill uses refined techniques to create elegant-yet-approachable dishes packed with bold flavors. Guests have intriguing choices like buffalo chicken “chicharrón,” tater tots and caviar, “elote” corn gazpacho, Nashville hot chicken and sourdough waffles, and al pastor-style pork belly tacos. The food is paired nicely with inventive seasonal cocktails and the outdoor patio provides sweeping views of downtown. Online orders can be placed here.

Long considered one of the finest French restaurants in the city, Les Nomades has been impressing diners since 1978. The white tablecloth, jackets-required experience takes place across two floors of a charming and intimate brownstone. Chef Roland Liccioni presents a four- or five-course prix fixe menu full of luxurious ingredients like truffles, foie gras, king salmon, Dover sole, and wagyu beef. Service is similarly spot-on, making this a perfect place for a romantic evening or to celebrate a special occasion.

Housed inside Hotel EMC2, this New American spot pays homage to the great Albert Einstein with a chic dining room and chef-driven dishes. The menu highlights local and seasonal ingredients and guests can expect to feast on housemade pastas and ever-changing specialties, such as 72-hour braised short ribs and tomato-braised and charred octopus. The cocktails are equally imaginative and include concoctions like “Red Matter” (tequila, mezcal, pomegranate molasses, St. George Green Chile Vodka, CH-Dogma Amargo, Thai chili bitters).

The neighborhood’s first brewery arrived in the middle of the pandemic and has been enticing locals and passersby with experimental craft beers and unique pizzas. Grab a flight or growler to go and pair it with pies coming out a $25,000 PizzaMaster electric oven. Dubbed “Double Oven Pizza,” the dough is baked twice to produce a crust that’s crispier than standard Neapolitan-style offerings. Options range from a Margherita to a taco-inspired “Un Mejor Hawaian” (al pastor sauce, pork, mozzarella, pineapple, onions, cilantro, lime). Carryout orders can be placed here.

Though it’s located right off of the Mag Mile, Labriola is a far from a tourist trap. The restaurant, which has a bakery and cafe attached to it, bakes seriously impressive deep dish pizzas. The focaccia-like dough is lined with cheese, resulting in a crispy caramelized crust layered with sharp mozzarella and chunky tomato sauce. Diners can choose pre-customized topping combinations, such as the “Danny’s Special” (sausage, mushrooms, green peppers, onions), or build their own. The menu also offers tavern-style and ciabatta-crust pies as well as classic Italian fare. Place online orders here.

Navy Pier is one of Chicago’s most visited attractions and also home to the nation’s largest rooftop venue. Encompassing 36,000 square feet, the all-seasons bar and lounge offers fun vibes and unparalleled views of the lake and skyline. The space is decked out with fire pits, a DJ stage, plenty of cozy seating, and a glass-enclosed area for the colder months. To eat and drink, guests will find chilled seafood, pizzas, shareable plates, and a variety of wines and refreshing cocktails.

A suburban favorite has arrived in Chicago to get give downtowners a serious spot for hand-pulled noodles, Yu-Shang pork, and Chinese-American favorites like orange chicken. Shang Noodle also offers mini hot pots, filling a large void in the neighborhood. As with most noodle shops, don’t sleep on the dumplings which are freshly made and have a great wrapper to filling ratio.

The legendary ice cream shop makes an appearance at Navy Pier. On a warm day, nothing beats the classic combination of chocolate, strawberry, pistachio, Palmer House (vanilla with walnut and cherries), and orange sherbet flavors in a cone. It’s an iconic creation that should be experienced by both locals and tourists alike.

A few years ago, Carson’s left its longtime River North home for a new space near Navy Pier. While Chicago’s barbecue game as a whole has gotten strong since Carson’s was founded in 1977, the baby back ribs still provide quality nostalgia. True Chicagoans can hear the restaurant’s commercial jingle in their head while order a rib dinner with cole slaw and au gratin. If folks don’t act too jaded about regional barbecue, they just may enjoy their dinner.

Tavern-style may reign supreme over other types of pizza in Chicago but locals shouldn’t overlook the remarkable thin crust at this Streeterville restaurant. Robert Garvey, a certified pizzaiolo who relocated his shop in 2019, spent two decades refining the dough recipe. Baked in a Marsal gas oven, the light and airy crust strikes a good crunch-to-chew balance and cracks when folded. Try winning topping combinations like “A Walk in the Woods” (truffle cream, mushrooms, double-cream washed rind cheese, mozzarella) and a seafood pie loaded with clams, shrimp, calamari, extra virgin olive oil, and white wine sauce. Online orders can be placed here.