Romantic Things to Do in Chicago

The Crown Fountain in Millennium Park in Chicago.The Crown Fountain in Millennium Park in Chicago.

The city of Chicago may be windy and cold half of the year, but that should not prevent a spark from igniting in the hearts of a young couple. As a matter of fact, the chilly lake breeze provides an excuse for a young man to cozy up close to a special girl and enjoy the windy city. From winter events and summer festivals, Chicago is flourishing with romantic locales.

Best Summer Ideas

Navy Pier at dusk.

In Chicago, summertime is a time for love. The cool air from Lake Michigan is like a shot in the behind from Cupid's arrow. It's hard to not fall in love under the awning of the Jay Pritzker Pavilion during a concert in front of a fountain synchronized to the music, or over the Chicago River looking upon Trump Tower. Chicago offers a host of romantic (and often free) events throughout the summer months.

Millennium Park offers walking tours through the gardens, free evening concerts to which guests can bring wine and cheese, the famous Cloud Gate sculpture and the Crown Fountain. Grant Park hosts weekly dance lessons on Michigan Avenue and is home to many festivals including the Taste of Chicago and the Blues Festival. Buckingham Fountain is also in Grant Park and is the perfect place to view Saturday night fireworks. Navy Pier is a must for couples looking for a romantic evening. Ride the ferris wheel, take a cruise or enjoy dinner in any one of the pier's great restaurants. Try Riva Restaurant at the tip of the pier for breathtaking views of the skyline while enjoying some of Chicago's most delicious seafood. Don't forget to check the schedule for movies in the park throughout the city to catch a showing of Casablanca with your sweetheart.

Grant Park

337 E Randolph St

Chicago, IL 60601

(312) 747-2474

Millennium Park

201 E. Randolph Street

Chicago, IL 60602

(312) 742-5222

Movies in the Park

Various parks throughout Chicago

Navy Pier

600 E. Grand Ave.

Chicago, IL 60611

(312) 595-PIER

Riva Restaurant on Navy Pier

700 E. Grand Ave.

Chicago, IL 60611


Best Winter Ideas

Find authentic ornaments and nutcrackers at Christkindlmarket.

Just the same as Jackfrost nipping your nose, Cupid's arrow strikes again. The blistering cold may seem unromantic until you try some of the best winter activities Chicago offers. Take your date ice skating on Michigan Avenue at Millennium Park or singing carols at Cloud Gate. Shop on the Michigan Avenue and watch as Mickey Mouse lights the street lights during the Magnificent Mile Lights Festival. Head over to Daley Plaza for the annual tree lighting or to enjoy shopping and indulging in German fare at Christkindlmarket. Visit Lincoln Park Zoo in the evenings for Zoo Lights or walk down State Street to see the Macy's window displays in the old Marshall Field's Building. No matter where you are, cozy up to the one you love and keep them warm in the cold Chicago winters.

Daley Plaza

Christkindlmarket and Tree Lighting Ceremony

118 North Clark St.

Chicago, Illinois 60611

(312) 644-2662

Lincoln Park Zoo

Zoo Lights

2001 North Clark Street

Chicago, IL 60614

(312) 742-2000

Macy's State Street

Holiday Window Displays

111 North State Street

Chicago, IL 60602


Magnificent Mile

Shopping and Magnificent Mile Lights Festival

Michigan Avenue between Chicago River and Oak Street

Chicago, IL 60611


Millennium Park

Ice Skating

201 E. Randolph Street

Chicago, IL 60602

(312) 742-5222

Best Restaurant Ideas

Chicago restaurants offer unique dining experiences.

Whatever the season, Chicago offers great stops for couples to enjoy during a romantic evening out. As most Chicagoans can confirm, one of the greatest pastimes in Chicago is eating. Whether you're indulging in fondue, unlimited food at a Brazilian steakhouse or feeding each other sushi, Chicago has it all. Geja's Cafe offers a romantic dining experience with a complete three-course meal and extensive wine menu. Sai Cafe in Lincoln Park offers an intimate and cozy dining room, specializing in high-quality Japanese fare prepared fresh and to your specifications. Brazzaz is a unique and unforgettable dining experience featuring a Brazilian-style menu and gauchos serving patrons 16 different unlimited meats table-side. For dinner with a view, try the Vertigo Sky Lounge on the rooftop at the Dana Hotel and Spa or catch movie and a dinner on the Terrace at the Conrad Hotel five stories over Michigan Avenue.


539 North Dearborn Street

Chicago, IL 60654


Geja's Cafe

340 West Armitage Avenue

Chicago, IL 60614


Sai Cafe

2010 North Sheffield Avenue

Chicago, IL 60614


The Terrace at Conrad

521 North Rush Street

Chicago, IL 60611


Vertigo Sky Lounge

2 West Erie Street

Chicago, IL 60654


Year-Round Ideas

The sweet sounds of jazz make for a great date.

Chicago also offers great indoor entertainment options for romantic dates. For an interactive gaming experience, visit Dave and Buster's, the Imax Theatre at Navy Pier, or play WhirlyBall in Lincoln Park. Travel up to the 103rd floor of the Willis Tower and step out on the Ledge with that special someone or relax with a loved one for a couple's massage. Most importantly, sit back and enjoy the sound of Chicago in a jazz or blues club.

Buddy Guy's Legends

700 South Wabash Avenue

Chicago, IL 60605


Dave & Buster's

1030 North Clark Street

Chicago, IL 60610


Green Mill (Jazz)

4802 North Broadway

Chicago, IL 60640


House of Blues

329 North Dearborn Street

Chicago, IL 60654


IMAX Theatre

Navy Pier

600 East Grand Avenue

Chicago, IL‎ 60611


Jazz Showcase

806 South Plymouth Court

Chicago, IL 60605


The Ledge

The Willis Tower

233 South Wacker Drive

Chicago, IL 60606


Lincoln Park Massage

630 W. Webster Avenue

Chicago, IL 60614



1880 West Fullerton Avenue

Chicago, IL‎ 60614


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About the Author

Amber Laxton has been working in higher education since 2003. Her work focuses on continuing and professional education and workforce development. She works with various professional associations in fields including human resources, project management, operations management, financial planning and marketing. She has a Master of Science in public service management from DePaul University.

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