Top 10 Chicago Dating Ideas

Who said Chicago romance is dead? Surely not, after you go through our ultimate list of romance hotspots in Chicago. Whether taking a girl out on a first date, or popping the big question these are the places you want to do it in Chicago.

Some of them are well-known historical parts of the city. Others are new, and ready to be shared by your beloved and you.

The 10 Best Chicago Dating Ideas


Navy Pier CruisesHave you ever wanted a romantic cruise on Lake Michigan? Then connect with the Navy Pier Cruise companies. A number of cruise companies call Navy Pier home. From simple architecture river tours to full service dining halls to private yachts, Navy Pier has the romantic Lake Michigan cruise you want for your special night.

Signature RoomOn the 95th floor of the John Hancock’s Signature Room site one of those perfect combinations of ambiance and beauty. Sip a cocktail as enjoy stunning views of the city.

Welcome Inn Manor seriously believes they have magical alcohol, because everything is top shelf liquor. Prices on drinks range from $15 and up, not including tip. They are worth it more than the cheap $8 beers at a ballpark.

Green MillDo you want to feel like a gangster in the Jazz era. Then treat your baby doll to a fab time in the Windy City at the Green Mill. This is an old haunt for Al Capone, and has some of the best jazz in the city.

Trump Towers Donald Trump is nothing if not controversial. However, even his biggest detractors agree on one thing. The Terrace at the Trump has one of the best views of the Chicago River and lake. In true Trump style, it is elegant and awe-inspiring at the same time.

Carriage Ride-The sheer number of marriage proposals that happen in a Chicago carriage ride would probably astound most people. Every year, you hear a few new stories about how he proposed on a carriage ride in the Gold Coast. Two of the best operators are Chicago Horse & Carriage and the Noble Horse Theater. Both provide a memorable experience for everyone on the trip. During the winter, they even include blankets and hot beverages.

Bottle & BottegaA cool new concept hit the Midwest recently: wine and art. For a nominal fee, you can drink wine and paint a fancy piece of artwork; while a professional artist shows you how to turn a sample picture into the one you are painting.

Lincoln Park Zoo Top 10 Chicago Dating IdeasLincoln Park Zoo– So far we have mentioned a number of premium places. However, what happens if you are on a budget. Fortunately we have some Chicago dating ideas for you. First off would be the Lincoln Park Zoo. This zoo has a free entry policy, and is located in the heart of Lincoln Park.

Millenium Park (Downtown Sound)Listen to free music at Millenium Park. Throughout the summer, a number of different events are being played.  If nothing is playing, then bring a beach towel and picnic basket for an enjoyable afternoon within walking distance of the Art Institute, Buckingham Fountain, The Bean, and Chicago Cultural Center.

Chicago Cultural Center Which brings up the next date spot. The Chicago Cultural Center always has great programs throughout the year. During the spring and summer make sure to check out their free weekly foreign movies. Every week is a new country’s top movie.

Chicago Theater In a horrible rip off of Hamlet, “The play’s the thing where you catch your love.” Most women love a night out at the theater. The right play is enjoyable to everyone, so look swanky on your way to the theater.

What is your Chicago dating idea?

We do not have a monopoly on great Chicago dating ideas. With so many great venues and options out there, we know that we missed a few gems along the way. So, let us know either your best dating story, or some Chicago dating ideas you have.

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