Your Last Minute Guide to Celebrating Valentine’s Day in Chicago

Valentine’s Day is right around the corner, which means the pressure is on! So, if you’ve procrastinated your Valentine’s Day planning, don’t give up just yet! You’re in luck because Chicago is the perfect backdrop for fun or a romantic date.  You can cozy up at a restaurant, go to the theater, take a stroll down the Riverwalk and so much more.  Here’s our guide to Valentine’s Day in Chicago with your sweetheart.

How to Spend Valentine’s Day in Chicago

See a Second City Show

Where:  Lincoln Park

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Second City is a comedy institution and a point of Chicago pride.  So, get your laugh on!  This is one date you’ll knock straight out of the park!  You and your beloved will laugh, enjoy a few drinks, step outside of your comfort zone, then laugh some more.  Even if you know nothing about improv, this is a great date spot for any stage of a relationship.

Go for Drinks and a Movie at the Music Box

Where:  Wrigleyville  

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The Music Box offers a constant stream of fantastic indie flicks, documentaries and old classics that qualify as one of the most diverse selections of films in Chicago.  You and your date are sure to find something new to like and enjoy together that will give you something exciting to talk about at your next cocktail party.  Stop by the Music Box’s lounge for a drink to relax before you go in or after to extend the evening.

Have a Tropical Adventure at Garfield Park Conservatory

Where:   East Garfield Park

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Walk hand-in-hand with your date through a tiny slice of tropical paradise while you both ooh and ahh at the towering palms, colorful flowers and gorgeous ferns.  The conservatory’s system of greenhouses is home to more than 600 species of plants and nearly 120,000 specimens that you can’t find anywhere else.  

Dress in Your Finest for a Night at The Civic Opera House

Where:   Loop

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The Civic Opera House is the perfect place to get all dressed up for a formal date night.  The inside is absolutely dazzling – the ideal setting for a romantic evening to put a spark in any relationship. The stage is home to one of the country’s most respected opera companies, the Lyric Opera, and also plays host to the occasional concert.

Cozy Up at a Fireplace Bar

More Info:  Ideas and Locations Around Town

Who doesn’t enjoy a good cocktail, some ambiance and conversation?  There are many bars with romantic, fireplace settings all across Chicago.  Just find the one that best suits you and your beau, and cozy up with a drink next to the blazing fire.  We bet you won’t be leaving anytime soon.

Head Out to Promontory Point for Romantic City Views

Where:  Hyde Park

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If you and your date are ready to brave the cold, head out to Promontory Point for a truly fantastic view of the Chicago skyline from this southern beach.  It’s really the perfect date location any time of year – you can soak in the sunrays in summer, have picnics in fall, and enjoy icy sojourns in the winter.  

Take a Romantic Stroll Down the Riverwalk

Where:  Loop

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The still fairly new Riverwalk is the quintessential date spot that you won’t want to miss.  With more and more great spots to stop for a glass of wine or a bite to eat along the way, you and your date can venture down the path and take in the Loop in all its undeniable beauty.  

Whether you plan to go out or stay in for a Valentine’s Day date in the city, we hope you spend it with someone you love.  Happy Valentine’s Day! 

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