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Elite Matchmaking in Chicago, IL

Matchmaking in Chicago

Chicago is an amazing town with its own strong culture and is a fantastic place for matchmaking and for going on some incredible dates.

Known locally as the “Second City”, Chicago is known for more than just the Cubs & White Sox and their Napolitano-styled pizza.  The “Windy City” is a cultural hotspot home to more than 2.7 million people, making it our 5th largest city.   Perched on the edge of Lake Michigan, which gives its nickname of “The Third Coast”, the city has a lot of lake-based recreation, views and dining opportunities.  You can follow the Chicago River up through town and dine at the many restaurants and cafés along its banks.

Chi-town offers matches a wide range of culture from great museums (e.g. The Field Museum, the Art Institute of Chicago and the separate museums of Science & Industry, African American History and the museum of Contemporary Art) and theatres (like Steppenwolf, the Logan or the Chicago theatres). 

Destin & Rachel of make matching singles in Chicago fun and effective with great events where you can match, meet and mingle, as well as VIP Love Introductions that connect you with singles who are custom matched based on your specific qualifications.  Love And Matchmaking uses advanced data analysis blended with the high-end personal “hands-on” attention paid to their busy affluent clientele, enabling them to meet and date in a much more relaxed and time-efficient manner while meeting dates who are highly pre-qualified matches.

Great Date Ideas:

Step down to the Chicago Magic Lounge in Andersonville.  This place of prestidigitation will blow your mind, from secret entrances to great magic and lots of laughs.  You’ll see how the best trick is how any date jitters disappear.  Not only do they have some fantastic bars but a menu of small-food that is to die for.

The Barrel-Run Brewery Tour gives lovers of beer and spirits a fun and fascinating tour of the great Chicago breweries and distilleries.  Not only that, you get to travel in a beer barrel-shaped bus!  Sample great draughts and amazing food while taking a tour around town in a safe and fun atmosphere.

The Riverwalk

The Marina and the Marina Plaza offer both walkers and boaters the chance to enjoy great food and drinks along with the amazing views.  Perfect for your waterfront date or after a romantic sail.

The Cove is ideal for having a snack and taking in the sites as you walk the river.  You and your date can grab a bite after a fun kayak ride along the shore.

The River Theater offers a more green and lush setting perfect for a romantic stroll among the shady trees growing right out from the steps.

The Water Plaza lounge around or walk through the refreshing jets of water.  Then head to The Jetty for some history and fish-watching and then on to The Riverbank which is surrounded by floating gardens and a view to die for.

The Riverwalk offers sightseeing boat tours if you want to get out on the river.  Or walk along and dine at one of the many cool restaurants along the way.  You’ll be surprised by the variety of choices!

Chicago boasts a thriving LGBT scene focused on Andersonville and Boystown.  With bars, clubs, shops and street festivals, show your pride and you’ll find and fun-filled time awaits.  

If you are looking to meet the perfect match, the matching process is specifically designed and refined to provide very accurate matches based on more than just data.  As world-renowned Matchmakers, Destin & Rachel have many years of experience in matching amazing singles based on those more personal things that really matter.

If you want to meet great successful singles in the Windy City don’t hesitate to join our Chicago Matchmaking database or reach out to us for information on our personal matchmaking services.

Live in Chi-town and want to meet amazing successful singles?  Sign-up for our Love Database.



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Elite Matchmaking in Chicago:  Millionaire Matchmakers Destin & Rachel help VIPs and affluent executives find love.

LGBT Matchmaking in Chicago:  Millionaire Matchmakers Destin & Rachel help VIPs and affluent executives find love.