Under-The-Radar Valentine’s Day Bar Crawl

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February 3, 2017


Ah, love is in the air and Chicago Trolley is ready to take you and your valentine out for a fun and romantic night. But this isn’t just any Valentine’s Day bar crawl – we’re taking you to the hottest bars off the beaten path. This under-the-radar list is sure to impress your date! Reserve your trolley now and let the romance begin.

The Silver Palm and Matchbox

You’ll probably want to start your night with a good meal, so we suggest The Silver Palm as your first stop. This historic restaurant is located inside an old train car and will set the mood for your adventurous night ahead. Go next door to the teeny tiny Matchbox Bar for an after-dinner drink.

The Bedford

Who could resist a drink in a bank vault? Sip champagne and enjoy delicious oysters while you marvel at the polished gold bank walls around you. You do know that oysters are an aphrodisiac, don’t you?


What’s Valentine’s Day without a little bit of fun? That’s where Bordel comes in, a secret bar on the top floor of the Black Bull tapas restaurant that is nearly impossible to know about unless someone tells you. Consider yourself told! Enjoy tapas downstairs and then head upstairs for stiff drinks and live entertainment every night ranging from DJ’s to dancers.

The Heavy Feather

When you step inside this bar-within-a-bar, you’re stepping back in time. After you enter the grungy dive bar Slippery Slope, take a left and go up the staircase and you’ll be faced with gold mirrors, ferns, and stained-glass lights that are oh-so-swanky. It’s an entirely different atmosphere from the bar downstairs and all of the drink offerings will make you feel like you’re at Studio 54 without all the trouble.

The Zebra Lounge

End your night at this historic watering hole that’s been around since 1929. To enter, you will pass through Canterbury Court where you’ll see a sign once inside the apartment complex. With a live pianist every night, you can request your favorite song while you enjoy a classic martini. This might be the perfect opportunity to request you and your loved one’s special song.