When you and your special someone are looking for something fun to do, there is no better place to be than Chicago. Dating in Chicago gives you so many singular and diverse experiences that simply can’t be found anywhere else on Earth.

You name it, and you can do, see, hear, taste, or experience it in Chicago. Dating can run the entire gamut – simple or extravagant, budget-friendly or expensive, worldly or uniquely American – whatever you can imagine you can find right here in the Windy City.

Don’t settle for the same old boring “dinner and a movie”. You are in one of the planet’s truly great cities, so whether you have recently moved here or are a life-long resident, start discovering (or re-discovering) what your city has to offer.


A Chicago Cubs baseball player stretching

Going to see the Cubbies play is a great date idea!


Kayaking or Canoeing

Not for the faint of heart or timid of spirit, this is nonetheless a great couple’s activity that takes advantage of Chicago’s unique geography. You and your date can choose your destination – the Chicago River, Skokie Lagoons, or Lake Michigan.

It doesn’t matter if you are new to water sports, because there are several Chicago companies that offer affordable rentals and lessons. This is your chance to get a different kind of workout while spending a memorable day exploring the waterways around the city.


Watch the Cubs Play the Sox

Whether you consider yourself a “North Sider” or “South Sider”, there is no denying the appeal of rooting for or against the Cubbies or the Sox in a game known as the Crosstown Classic. The rivalry between these two teams goes back more than 100 years, coinciding with the founding of the American League. If you and your date are cheering opposite teams, try to keep one thing in mind – it’s only a game.

Interesting Fact: the original name of the Cubs – from 1876 to 1889 – was the “White Stockings


Attend the Chicago Symphony Orchestra

This is Chicago dating at its finest, and every couple should have this pleasure at least once on their life. The Chicago Symphony Orchestra is one of America’s “Big Five” orchestras, meaning it leads the field in musical excellence. In 2008, it was voted the best orchestra in the United States and the fifth best in the world.

This is an opportunity to dress up to the nines in your finest and gain a new appreciation as you listen to world-class music in an acoustically perfect environment.

Sober Dating Website

Sink Your Teeth Into an Italian Beef

You can choose this iconic Chicago creation like you choose your date – “hot” or “sweet“. There is nothing else like juicy, thinly-sliced roast beef, seasoned just right with oregano, garlic, and other spices – piled high on an Italian roll. Make sure you dip – or double-dip – your sandwich in the famous au jus.

According to locals, the sandwich was first served to the public in 1938 by Al’s Beef, and from there, it has grown into a local legend in Chicago. A date doesn’t have to be fancy – all it needs is good food, good times, and good company.


Take a Tour of Chicago’s Ethnic Museums

Chicago is one of America’s most ethnically-diverse cities, with a rich cultural history second to none. People of all races, nationalities, and ethnicities have all made contributions throughout history to make the city what it is today.

For a one-of-a-kind Chicago dating experience, why not go on a tour of the city’s 25 ethnic museums and cultural exhibits? This is the Chicago dating idea that keeps on giving, because it will give you “somewhere to go” for months.

While this list is by no means comprehensive, some of the highlights include:

  • The Polish Museum of America – Considered the “crown jewel” of Chicago’s Polish-American community.
  • The Chinese-American Museum of Chicago – Located in Chinatown, this small but important Museum celebrates the ancient heritage of the city’s Chinese-American residents.
  • The Ukrainian National Museum – For more than 60 years, this museum, located in Chicago’s Ukrainian Village, has ensured cultural continuity with an amazing display of fine and folk art, textiles, metal work, embroidery, and ceramics. Do not miss the impressive collection of psyanky – Ukrainian Easter eggs.
  • The Swedish American Museum – One of the permanent highlights of this museum explores the struggles and triumphs of Swedish immigrants as they left their homeland to make a better life in the New World.
  • The National Museum of Mexican Art – Founded in 1982 and located in the Pilsner neighborhood, this museum, showcasing the art and culture of the Chicano, Latino, and Mexican communities, is the only Latino-focused museum in America with an accreditation by the American alliance of museums.
  • The Balzekas Museum of Lithuanian Culture – Opened in 1966 in the West Lawn neighborhood, this is the largest museum in America specifically devoted to the history, culture, politics, language, and immigration experiences of the Lithuanian people.
  • The Indo-American Heritage Museum – This museum began operating independently in 2008 with a mission to promote a better understanding of the diverse history and heritage of the Indian people and the roles they have played in building America.
  • The Mitchell Museum of the American Indian – Although not technically in Chicago, it is worth it to take the short drive to Evanston. Focusing exclusively on the art, culture, and history of North American native people, the museum showcases tribes of the South Eastern Woodlands planes, Southwest, Northwest Coast and American Arctic.
  • The DuSable Museum of African American History – founded in 1961 on the South Side, this museum was developed to interpret and preserve the achievements and experiences of Americans of African descent. The museum is named for John Baptiste Point DuSable, a Haitian of French and African descent, who in 1779 established the permanent settlement that would one day be known as… Chicago.

There is no need to stand on ceremony or settle for the “same old – same old” when you’re going out in Chicago. Dating doesn’t have to be formulaic – bars, clubs, and the whole empty, banal experience. Get out there, experience all the wonder that is Chicago, and have fun while you’re still young or young at heart.


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