Valentine’s Day in Chicago


Made-up holiday or important testament of love, Valentine’s Day means different things to different people. If you’re single in Chicago, it can either be any old day or annoying reminder of your relationship status (in that case, simply head to the nearest dive bar and you’ll be in good company). But if you’re coupled up and ready to celebrate your love on the “most romantic day of the year,” Chicago doesn’t disappoint when it comes to options sure to make you swoon. If you’re celebrating Valentine’s Day in Chicago, here are some tips for planning a date that would make Cupid proud.

1) Plan ahead

On the average Friday or Saturday night, the best restaurants in Chicago will be jam packed. If you don’t have a reservation, you’re out of luck. Don’t even attempt to walk into a classy restaurant without a reservation on Valentine’s Day. In fact, if you haven’t made a reservation at least two weeks in advance (which means now), you’ll find your options dwindling by the hour. Of course, if you’re up for a more low-key or unconventionally romantic spot (think casual bistro, lounge that serves food, sitting at the bar of a nicer restaurant) then your spontaneity won’t be a detriment.

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2) Be flexible

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Valentine’s Day only falls on a Friday or Saturday every few years. Who says you have to do your big night out on the weekend, or even on the actual day? If you can’t get reservations for Valentine’s Day itself, plan something special the night before or after, or go for a leisurely weekend brunch. Sipping mid-day mimosas can be just as romantic as a candlelight dinner, if you want to be.

3) BYOB to save money

Many of Chicago’s best restaurants will be offering multi-course tasting menus for the big day. They’re sure to be decadent, but they won’t come cheap. Add in the cost of wine or champagne and you could drop a few hundred dollars on dinner. If you’re on a budget, opt for one of Chicago’s more romantic BYOB restaurants. While many are casual joints, there are a few – HB, Mixteco, and Tango Sur among them – that are totally date-worthy but won’t break the bank.

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4) Think outside the “romantic dinner” box

There are so many romantic things to do in Chicago that don’t involve sitting in a restaurant. Go see a show, take a cooking class for two, spend a day at the museum, or linger over drinks at one of Chicago’s romantic lounges, like the speakeasy-style Violet Hour, the legendary jazz club the Green Mill, or a swanky hotel bar like NOMI at the Park Hyatt.

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