A Romantic Weekend in Chicago

It’s hard not to fall in love when you’re in Chicago — both with your sweetheart, and with the city itself.

Whether you’re planning a date night or a romantic weekend, Chicago is filled with things to do for couples. This three-day itinerary filled with dimly lit restaurants, beautifully landscaped parks and indoor gardens, stunning museums, and unforgettable shows. It’s perfect for an anniversary trip, Valentine’s Day, or just a special weekend away.

Overview: romantic three-day weekend in Chicago

Day one	Take a scenic stroll at the Garfield Park Conservatory. Relax at AIRE Ancient Baths. Grab tickets to a show at The Second City. Enjoy dinner in the trendy West Loop neighborhood.
Day two	Visit Lincoln Park Zoo and the Alfred Caldwell Lily Pool. Admire contemporary art at Wrightwood 659. Dine at a romantic Lincoln Park restaurant like Geja’s Cafe. See live music at Kingston Mines or a show at Chicago Magic Lounge.
Day three	Wander the Art Institute of Chicago. Take a classic architecture cruise and walk the Chicago Riverwalk. Visit a downtown rooftop bar for breathtaking skyline views. Have an unforgettable meal at Virtue in Hyde Park.

Day one: Spa day and a comedy show

AIRE Ancient Baths illuminated at night with lights both in the pool and all around the pool. — AIRE Ancient Baths

Start your weekend surrounded by natural beauty at the Garfield Park Conservatory.

One of the world’s largest gardens under glass, this lush greenhouse is filled with plants and flowers from around the world. Wander through the indoor gardens, including the stunning Palm House and Fern Room, before exploring the sprawling outdoor grounds.

Next, get some relaxation in at AIRE Ancient Baths.

Inspired by Greek and Roman baths, AIRE is a unique oasis tucked inside a restored historic building. Float in a variety of hot and cold baths, warm up in the sauna, and enhance your experience with a couples massage.

Stroll through the scenic Garfield Park Conservatory

Grab tickets for an early evening show at The Second City, known as the birthplace of improv. The iconic comedy club offers an array of show options on any given night, from mainstage revues to showcases of up-and-coming talent.

Make reservations for dinner in the West Loop, one of the city’s hottest dining areas. A few classic date night options include swanky BLVD Steakhouse, the dimly lit Trivoli Tavern, stunning Alla Vita, and intimate Avec.

Alternatively, impress your date with a dinner cruise on the Chicago River. The glass-enclosed vessel provides stunning views of the surrounding skyline as you float through the heart of the city.

Day two: Charming Lincoln Park

Spend the day in the charming Lincoln Park neighborhood, filled with local shops, award-winning restaurants, and scenic streets lined with vintage architecture.

Begin the day at the free Lincoln Park Zoo, one of the oldest zoos in the country. Wander the lakefront grounds, step inside the historic animal houses, and meet creatures and critters from all over the globe.

Just steps from the zoo, the Alfred Caldwell Lily Pool is a true hidden gem. Follow the stone pathway as you admire burbling waterfalls, blooming lilies, and landscaped native plants. You’ll see why it’s a popular spot for proposals.

Lincoln Park in fall — Alfred Caldwell Lily Pool

Next, stop into Wrightwood 659. Hidden away on a residential street, this unique gallery showcases contemporary exhibits in a stunning, reflective space.

For dinner, book a table at one of the neighborhood’s many excellent dining options. Share plates at Michelin-starred Galit, grab a booth at DeNucci’s, or enjoy elegant seafood dishes at the tucked-away mfk. Restaurant. Or indulge in a night of fondue at Geja’s Cafe, known as one of the city’s most romantic restaurants.

End the evening at Kingston Mines, known for its two stages of nonstop blues music. Or head up to nearby Andersonville to see a show at the Chicago Magic Lounge, a unique magic venue hidden away inside a retro laundromat.

Day three: Art and architecture

A group of friends hang out at the London House Rooftop. — LH Rooftop, ©Adam Alexander Photography 2019

Spend a quiet morning exploring the Art Institute of Chicago, one of the country’s largest and oldest art museums. Don’t miss the Impressionism gallery, filled with masterpieces by Monet, Van Gogh, Renoir, Morisot, and more.

Chicago South Side & Obama Presidential Center Shuttle

Next, head to the Chicago River and hop aboard a classic architecture cruise. These boat tours are the perfect way to see the city and learn more about the fascinating history of the Chicago skyline. Afterward, take a stroll along the scenic Chicago Riverwalk.

Chicago Architecture Center River Cruise Aboard Chicago's First Lady — Chicago Architecture River Cruise

While you’re downtown, stop for a cocktail at one of the nearby rooftop bars. LH Rooftop offers sweeping views of the Chicago River, Château Carbide is known for its luxe vibes, and Cindy’s has the perfect vantage point of Millennium Park from above.

To wrap up the weekend, head to Hyde Park for an unforgettable dinner at Virtue. Helmed by a James Beard-Award winning chef, the restaurant is known for its elegant takes on Southern cuisine in a welcoming atmosphere.

For a nightcap, hop over to Cantina Rosa. This colorful cocktail bar offers a fun menu of Mexican-inspired craft cocktails. It’ll be the perfect end to a romantic weekend in Chicago.