Now that you’ve popped the question, it’s time to pop the champagne and celebrate with a delicious dinner at one of Chicago’s most romantic restaurants.
There are many romantic restaurants in Chicago that are perfect for celebrating such a special occasion, ranging from complex seven-course tasting menus to pristine plant-based vegetarian and of course, classic Italian cuisine.
Whether you’re looking for an intimate dinner by candlelight or a lively evening of drinks, these restaurants have something to suit any taste.
These romantic Chicago restaurants offer excellent ambiance, quality cuisine, and attentive service that will make your evening even more memorable.
Check out the Top 5 Chicago Most Romantic Post-Proposal Restaurants in Chicago:
233 N Canal Street, Chicago, IL 60606
Chicago’s famed Gibsons Restaurant Group is most notable for steaks, but the company expanded its portfolio in 2017 to include Italian cuisine with the opening of this elegant tri-level venue offering not only spectacular cuisine, but also unparalleled panoramic skyline views of the Chicago skyline looking east down the Chicago River.
Gibsons Italia offers a beautiful dining space and a lovely outdoor patio. The menu highlights Gibsons’ signature Prime Angus and grass-fed Australian beef plus Italian options like arancini, risotto, and fresh pasta made from a gold extruder.
My personal recommendations is the 7-Year Aged Acquerllo Risotto with Viking Village sea scallops, Parmigiano Reggiano & Baby Leeks.
Pro Tip: Order the off-menu appetizers of Filet Mignon Sliders with Truffle Butter and fries
2610 N Cannon Drive, Chicago, IL 60614
Located along Cannon Drive between Diversey Parkway and Fullerton Avenue, and perched within the trees, a meal at the Michelin-Star North Pond requires a romantic stroll among the Lincoln Park lagoon before entering. Once inside, this inviting setting sparkles thanks to elements such as rustic exposed brick, a roaring fireplace, and towering windows overlooking both the park and namesake pond. The menus, both dinner and brunch, change with the seasons, but tables are always reserved and attire is always elegant, which certifies this as a special occasion restaurant.
In the winter, warm up to Sunchoke & Black Garlic Soup with Confit Sunchokes, Truffle Purée, Yuzu Gel, Toasted Hazelnuts or in summer dive into Sweet Corn Gazpacho poured over Poached Octopus with Heirloom Cherry Tomatoes.
Pro Tip: Save room for the flourless chocolate-hazelnut cake with ganache and goat milk sorbet
1729 N Halsted St, Chicago, IL 60614
The flagship of one of the city’s most acclaimed restaurant groups serves a rotating seasonal menu, devised by James Beard-nominated chef Lee Wolen, in a luxurious dining room, lined with greenery and whimsical portraits, or on a lovely tree-shaded patio. Order a la carte from the menu of seasonal fare from local farms or splurge on a seven-course tasting menu ($165/pp, 7 courses) that changes daily. Boka has maintained a Michelin star from 2011 to 2023.
The à la carte menu starts with Grilled Hokkaido Scallops (kohlrabi, salted onion, vin jaune) and includes highlights such as the Brown Butter Roasted Atlantic Cod (celtuce, hedgehog mushroom, kombu).
Pro Tip: Enjoy al fresco dining on a cold seafood platter in warmer months on their intimate back patio
Bloom Plant Based Kitchen
1559 N. Milwaukee Avenue Chicago, IL 60622
James Beard-nominated chef/owner, Rodolfo Cuadros (Amaru; Don Bucio’s Taqueria), dazzles diners with a menu full of flavor and textural complexity.
The space feels fresh with funky light fixtures, living greenery, colorful plates and bright veggies.
Don’t expect to find any Impossible Burgers on the menu. Every dish is 100% plant-based and gluten-free from the cultured cheese plates (whipped cashew requeson with ancho chili agave, pimento goat cheese, vegetable ash truffle cheese, everything papadum crackers, house pickles) to delicious banana blossom tacos.
Pro Tip: My must-have dessert is the Camote Cheesecake (sweet potato cheesecake, almond tahini crust, coconut cream)
1350 W Randolph St, Chicago, IL 60607
Chicago’s Michelin-starred Scandinavian fine dining restaurant by Anna and David Posey, “Elske”, translates to ‘love’ in Danish. Dishes meld Nordic austerity with Midwestern warmth. The Publican oat porridge sourdough and salty cultured koji butter will literally melt in your mouth and demand more. Anna, who was previously the pastry chef at The Publican, keeps her dessert menu short but sweet.
Pro Tip: Elske traditionally boasts 4 key desserts. Sample the Lemon Myrtle Pot de Crème (melon, honeydew sorbet, and pine), Meringue (parsnip-coconut cream, pear and cardamom), dark chocolate ice cream (øllebrød and hazelnut) or the signature Sunflower Seed Parfait with sour honey, licorice, and bee pollen