Valentine’s Day is a bright spot in the otherwise bitingly cold and slushy month of February in Chicago. Couples can brave the chill air in these picturesque neighborhoods or enjoy the stark beauty of Chicago in winter from the warmth of a dimly lit restaurant. Create the perfect Valentine’s Day in one of these four spots.

Lincoln Park

Lincoln Park is an obvious choice for couples looking to celebrate the year’s most romantic holiday. The neighborhood’s stately brownstones and lakefront setting make it a beautiful location even in the starkness of winter. 

There are many casual yet cute brunch spots for the start of the day, while Lincoln Avenue and Armitage Avenue have a bountiful selection of boutiques for last-minute gift shopping. Weather permitting, a stroll along the neighborhood’s Lakefront Trail allows couples to walk arm-in-arm beside the chilly but always striking waters of Lake Michigan.

Spots to check out: 

  • Geja’s - Linger over a multi-course fondue meal in an intimate setting with flattering lighting.

  • Lincoln Park Zoo - Feel the love tonight with a brisk stroll through this free zoo’s collection of animals from across the world. 

  • North Pond - A classic Valentine’s Day option with an emphasis on local ingredients and a location overlooking a pond.

The Loop

Couples looking for a uniquely Chicago evening out on the town will find the Loop an appealing option. As the heart of the city, the Loop is rich in restaurants, hotels, and shopping options. By day, the Loop is packed with businesspeople and tourists, but at night its streets become quieter as diners hurry out of the cold to make their reservations.

Between the classic Valentine’s Day dinner and a show, the Loop strikes a romantic pose with some of the city’s most beautiful architecture (think the Chicago Cultural Center) and iconic sites (Millennium Park and the Bean among them).

from flickr

Spots to check out:

River North

River North is practically the epicenter of Chicago’s dining and bar scene. Craft cocktail bars and steakhouses crowd this neighborhood. Take your pick of cuisine this Valentine’s Day.

River North also appeals to the romantic crowd with its riverfront location, particularly stunning when lit up by area’s towering buildings at night. It’s location right across the river from the Loop makes it easy for residents who work downtown to make a seamless transition from the workday to a romantic evening.

Plus, any couples looking to indulge in a Chicago staycation have plenty of hotel options in the area as well. Between sleeping late and embarking on culinary expeditions, couples enjoying River North can sneak in a massage at one of the neighborhood’s several spas. 

Spots to check out:

  • Richard H. Driehaus Museum - This historic mansion turned museum is a study in opulence.

  • Gilt Bar - Warm light washes over red velvet booths and library-themed decor at this River North destination.

  • Portillo’s - For some couples, Chicago hot dogs, fries, and decadent chocolate cake are the true meaning of love.

Uptown

A romantic Chicago experience does not have to be limited to the center of the city. This North Side neighborhood is a strong Valentine’s Day contender with some of the city’s most revered live music venues and Asia on Argyle, a district rich in restaurants, bakeries, and shops.

Uptown residents are already sold on their neighborhood’s charm, but anyone from outside this Chicago neighborhood will find it easy to reach via the CTA Red Line or Purple Line.

Spots to check out:

  • The Green Mill - Live jazz and cocktails at this Uptown staple are ideal for a romantic evening.

  • Agami - Indulge in artfully prepared sushi in a funky, intriguing atmosphere.

  • Ceres’ Table - Opt for a more casual evening with wine and bites at the bar, or reserve a table to fully explore the menu’s regional Italian cuisine.