Where to Have a Romantic Weekend in Chicago

Over the past 20 years, the West Loop has become synonymous with innovative dining. Randolph Street, aka Restaurant Row, and Fulton Market a few blocks away are home to some of the city’s most celebrated establishments, including Girl & the Goat, Aba, Rose Mary, Piccolo Sogno, Ever, Leña Brava, Oriole, and Swift & Sons. You’d be hard-pressed to find a spot that isn’t ideal for the occasion.

By Dave Lifton (@daveeatschicago)

What to Eat and Drink

But the most romantic dinner in Chicago can arguably be found at Geja’s Café in Lincoln Park. The fondue restaurant regularly places high on such lists, not only locally but nationally, thanks to its intimate vibe with candlelit booths and live flamenco and classical guitarists. Elsewhere in Lincoln Park are North Pond, Boka, the Lakefront Restaurant and Mon Ami Gabi.

For brunch, consider venturing away from downtown and its surrounding neighborhoods in favor of some of the more out-of-the-way places. Those looking for a traditional American brunch can find them at Batter & Berries or Wake N’ Bacon (Lakeview), Lula Café or Daisies (Logan Square), Duck Inn or the Ramova Grill & Taproom (Bridgeport).

But if you want something with a more international flair than variations on benedicts or pancakes, try the Filipino dishes at Bayan Ko Diner (Ravenswood), Cebu (Lakeview), or Kasama (Ukrainian Village); or Taiwanese crepes at Minyoli (Andersonville). Kie-Go-Lanee (Uptown and Logan Square) and Istmo (Lakeview) focus on the Oaxacan state of Mexico. Vegetarians and vegans should head to Chicago Diner (Northalsted and Logan Square).

For drinks, rooftop bars in downtown hotels are some of the most romantic spots Chicago has to offer, with interesting craft cocktail lists and the skyline serving as the backdrop. The most popular are LH Rooftop at LondonHouse, Chateau Carbide atop the Pendry, Upstairs at the Gwen, and Cindy’s in the Chicago Athletic Association. All have food service ranging from small plates to full-service menus.

Wine lovers can sample creations made in-house at Chicago Winery (River North) and City Winery (West Loop), while Bronzeville Winery (Bronzeville), Volo (Roscoe Village), Rootstock (Humboldt Park), and J9 Wine Bar (Lincoln Park) have stellar reputations for their extensive selections of wines from around the world. And Pops for Champagne combines vintage and non-vintage Champagnes and sparkling and still wines in a lively and unpretentious space in the heart of River North.

Spas

If you’re looking to pamper your loved one, we recommend the spas found in the luxury hotels, including the St. Regis, Peninsula, Waldorf Astoria, NoMi in the Park Hyatt, Chuan at the Langham, and standalone spa Kohler Waters.  Aire, milk + honey, Allyu and the Ritz-Carlton have couples packages available.

See the Whole City

Chicago is so much more than downtown. Our neighborhoods are filled with charming stores, quaint restaurants and cafes, and ethnic enclaves that feel like you’ve stumbled upon them by accident. Check out our guide to some of our favorites—including Pilsen, Uptown, Andersonville, and Hyde Park—as well as our guide to Chinatown.

But the neighborhoods aren’t the only way to get a sense of how big the city is. You can see it all from the two observation decks: Skydeck at the Willis Tower and 360 Chicago at the former John Hancock Center. Fly Heli offers nine helicopter tours that pass through major landmarks, with date night and marriage proposal packages available. Or you can head to Navy Pier for the 200-foot Centennial Wheel or the new Flyover, where you’ll merely feel like you’re flying through the city.

Also at Navy Pier, City Cruises has numerous dinner, lunch, and brunch cruise options down the Chicago River or along Lake Michigan. You can also take a floating hot tub on the river.

Cultural Events

Chicago is very much a theatre-loving town. Broadway in Chicago brings in the tours of hit musicals. But major companies like Steppenwolf and Goodman have been nationally recognized, and there are storefront theaters in most neighborhoods that produce great work. Visit Theatre in Chicago for the latest listings. 

Our other cultural institutions—including the Chicago Symphony Orchestra, Lyric Opera, and Joffrey Ballet—are among the country’s most celebrated. And the Auditorium Theatre has a diverse array of events going on all year.

Lastly, comedy lovers can visit the world-famous Second City for improv and sketch shows, or catch local and national standups at Zanie’s or Laugh Factory.

When it comes to Valentine’s Day, the author believes in going full Chicago and heeding the advice of department store magnate Marshall Field: “Give the lady what she wants.”