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Dating Face-Off: The Chicago Version

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Chicago’s vibrant fall delivers nothing short of a magical experience. From trees splashed in bold oranges and reds to the abundant sunshine and fresh crisp air found on the shores of Lake Michigan, one can’t help but feel alive during Chicago’s amazing autumn months.  And if you’re one of the lucky singles currently living in The Windy City, then you can be sure your love life is bound to come alive as well! There’s a reason Chicago is also called the “Heart of America.”

As a Northwestern University alum, I spent four amazing years in Chicago and can safely say The Second City is one heck of a town for finding love. Famous for its history, sports, entertainment, culture and academics, Chi-Town has a lot to offer singles. You can impress your date with breathtaking views of the city from the Western Hemisphere’s tallest building: Sears Tower. Or, you can share an intimate evening wandering the shores of Lake Michigan with someone special. To prove your dating options are limitless in in Illinois’ largest city, here are my five favorite date ideas that can only be found in Chicago:

1. Hold a Viewing Party

From the rooftop restaurants offering a peek of the stellar skyline to quaint cafes looking out over Lake Michigan, Chicago is full of great views. Chicagoans are lucky; they can take a date to any one of these visual spectacles and the conversation will flow effortlessly based on the view alone. Run out of things to talk about? No one will ever question first-date silence when there’s a stunning view of waves crashing onto the shore in front of them!

2. Bond Over Cold Weather

Surprise, surprise: The cold weather can actually be the driving force that brings you and that someone special in your life together! When things start to get chilly, use those frosty temps to heat up your love life. Ask that cute 100hookupr® you’ve been eyeing out for hot cocoa (forget coffee), set up a roaring fire in your living room, or just find a lounge nearby with a good toasty fire where the two of you can get to know each other better while seated near a cozy fireplace. At the very least, the frosty temperatures give you a good excuse to sit very close to your date.

3. Sit on the Sidelines

If you’re looking for something a little more low-key, you can catch a game at Wrigley Field and see if your date will score a homerun for your heart! Not into the Cubs? Head over to U.S. Cellular Field to watch the White Sox take on an American League team. Not into baseball? Take in a Bears game at Soldier Field. Not into football? Then you can opt for a Chicago Bulls basketball game, a Blackhawks hockey game, or even some horse racing to get your heart pumping fast! If you’re into sports of any kind, this city is for you!

4. Laughter is the Best Medicine (for Love)

Bust a gut with someone cute and you’re bound to have one of the best dates of your life! If you want to take the object of your affection out for an evening of laughs, then there is no better place than The Windy City to laugh till you cry with someone special. From The Second City comedy club to ImprovOlympic, you literally have hundreds of hilarious options upon you!

5. Be All Smart and Cultural Together

Are you into music, theater, film, dance, or anything else performance-related? If you live in Chicago, then you’re in luck! The Chicago Cultural Center is not only one of the most comprehensive arts showcases in the United States, but it’s also free! That means you can take a date, show off your advanced knowledge of all things art-related and do it without spending a dime (you’ll even have money left over for a nightcap if you hit if off)!

Chi-Town singles will never run out of places to take their date in The Windy City, and their options go way beyond meeting for coffee or grabbing dinner and drinks. Yes, the “Heart of America” sure makes it easy to put a little love in your heart and that’s why it’s my pick for one of the best cities for dating in America.

Dear Mrs D is an online dating strategist and writer. She hosts a radio call-in show, Dates & Mates with Dear Mrs D and has appeared on many other news and radio programs. You can catch her online on Twitter, YouTube, and Facebook. If you want a teacher for your own personal online dating school, reach out to her at
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