Despite the cold weather, romance still permeates the air as Valentine’s Day in Chicago approaches. And, Chicago’s incredible food scene represents a variety of cuisines and ambiances to give you the most unique, romantic night you and your date can find anywhere on this side of Lake Michigan. We reached out to our Chicago team for their insider recommendations. Here are their picks brought to you straight from the locals.

Live in the heart of Chicago’s food scene with help from our local apartment experts. AptAmigo has real estate agents standing by, ready to support you during your next apartment hunt.

Best Things to Do on Valentine’s Day in Chicago

Siena Tavern

Neighborhood: River North

Address: 51 W Kinzie Street

Cost: $$

Siena Tavern is well known for their classic, upscale Italian cuisine that comes from the mind of Chef Fabio Viviani, a previous Top Chef contestant. From wagyu meatballs to squid ink pasta and to-die-for burnt pepperoni pizza, they take Italian food to a whole new level, especially since all of their pasta and pizza dough is made from scratch. Don’t skip out on dessert either; the Bombolini and the Cookie Jar are some of our favorites. With classy decor and cool low lighting, this restaurant will make for a perfect romantic Valentine’s night.

What to Order: Wagyu Beef Meatball, Burnt Pepperoni Pizza, Carbonara in a Jar, Brick Chicken Diavolo, Bombolini, Cookie Jar

Swift & Sons

Neighborhood: Fulton Market

Address: 1000 W Fulton Market

Cost: $$$

If you are looking for a truly indulgent evening, Swift & Sons serves up some of the best steaks in town, no question about it. Choose from oysters and foie gras torchon, and opt for the wagyu steaks. You can’t go wrong with any plate you choose. They spare no expense when it comes to high-quality ingredients, and the attentive wait staff will make you and your date feel like royalty. Insider tip: don’t skip out on dessert. 

What to Order: Bone-In Pork Chop, Swift & Sons Surf & Turf, Crispy Brussels Sprouts, Brown Sugar Upside-Down Cake

Teatro ZinZanni

Neighborhood: Theater District 

Address: 32 W Randolph Street

Cost: $$$

Surprise your significant other with a circus, a show, and a 4-course meal all in one when you make your way over to Teatro ZinZanni. This incredible production lies in the heart of the Theater District inside the Cambria Hotel, where you take an elevator to a rare Spiegeltent (a mirrored circus tent). World-renowned performers, such as acrobats, musicians, aerialists, and illusionists time their performances with the food service, mixing the entire experience into one thrilling show. This place comes highly recommended from our local experts for a whimsically romantic evening.

Fun fact: the menu was created by the Goddess herself Debbie Sharpe, founder of the Goddess and the Baker.

What to Order: Baked Goat Cheese, Crispy Brussel Sprouts, Chicken Vesuvio, ZinZanni Cake Slice


Neighborhood: Fulton Market

Address: 565 W Randolph Street

Cost: $$

Sister restaurant to Sepia, Proxi is an Asian-fusion restaurant perfect for worldly travellers. This restaurant is effortlessly sleek and modern with high-vaulted ceilings and a cozy ambiance. They offer a Chef’s Menu option (made by the highly-esteemed Chef Andrew Zimmerman), for which you can enjoy a 4-course meal, including Szechuan braised lamb, tempura elotes, and an incredible honey almond cake, or you can order from their á la carte menu. Here, you can travel the world with your loved one all in one restaurant on a single Valentine’s Day night in Chicago.

What to Order: Tempura Elotes, Szechuan Braised Lamb, Coal Roasted Mussels, Honey Almond Cake

Willow Room

Neighborhood: Ranch Triangle

Address: 1800 N Halsted Street

Cost: $

For a more casual spot that won’t break the bank, head to the Willow Room with your laid-back partner for Valentine’s Day. You can’t go wrong here for dinner or Sunday brunch. Their American cuisine is served in a chic, rustic space with super cozy velvet couches. Some highlights include jamón croquettes, scallops, and lobster ravioli. So sit back, relax, and enjoy a cozy meal with your partner.

What to Order: Jamón Croquettes, Burrata, Gnocchi, Scallops, Orange Ricotta Donuts

Chez Joel Bistro Français

Neighborhood: Near West Side

Address: 1119 W Taylor Street 

Cost: $$

Celebrate love at Chicago’s pièce de résistance of romance, french restaurant Chez Joel Bistro Français. This quaint, family-owned bistro imbues the flavors of southern France into simple dishes made with high-quality ingredients. With plenty of traditional French dishes, such as escargot, magret et confit de canard, and bouillabaisse Marseillaise, you’ll find romance in its simplest and most elegant form. Make a reservation at the Chez Joel Bistro and order an extra bottle of champagne.

What to Order: Escargots á la Bourguignon, Magret et Confit de Canard, Filet de Saumon Grillé, Moelleux au Chocolat

Moving to Chicago Soon?

Whether you are moving to Chicago from another state or simply moving neighborhoods, Chicago never disappoints in its cuisine. You can explore these Valentine’s Day ideas while living in the heart of it all, and we can’t wait to help. If you’re looking to move into your perfect Chicago home, we offer plenty of local recommendations (find out how to spend summer here) and one-on-one support during your apartment search. What’s more? Our service is completely free. AptAmigo has got you covered! 

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About the Author
Mo Sanderson

Maureen is a Content Marketing Specialist here at AptAmigo. They are in charge of all the company’s video and photography needs, so Adobe Photoshop and Premiere Pro are their best friends. If you ever need any recommendations for the coolest, most unique, and slightly out-there Chicago activities, Maureen’s your person.