Chicago is a city where you can go out dressed to the nines, indulge in a lavish meal, see a world class show, sip fancy cocktails with a view and generally live the high life. Or…you can live it up without spending more than a few bucks. In addition to free and cheap things to do, there are lots of places where you can score cheap (and sometimes even free) food and drinks in the city. Here’s how.
It may mean a few weeks of clutter in your inbox, but if you’re planning a trip to Chicago on a small budget, it pays to sign up for as many email lists as you can. Scout out the bars and restaurants you’re planning on visiting and sign up for their email newsletters. Many places send discount coupons just for signing up.
Don’t forget to think outside of just restaurants. Sign up for the email lists of wine shops and liquor stores like Binny’s and the Poison Cup for notice of free wine and beer tasting, and check out the website of the Chopping Block to look for free events like cooking demos (with free nibbles of course). Signing up for the email list from Lettuce Entertain You, a company that owns several restaurants in Chicago, will “kill several birds with one stone” so to speak. With one sigh up, you’ll get alerted to deals at multiple spots in the city.
Sign up to be emailed a daily coupon offer from Groupon and YouSwoop as well. Every day, these two sites offer a new group coupon – you simply enter your credit card information and once enough people have signed up, you’ll be charged and receive the coupon instantly be email (very rarely does the threshold of buyers not get reached, which means you don’t get the coupon and your card isn’t charged). Coupons generally offer a significant discount over what you’d pay normally – like $75 worth of food for $30 – just check the fine print to make sure there are no restrictions on use.
You may know Yelp as the site to check business reviews (or write your own), but it’s also a great place to look for events. The Chicago site lists event by date. Some events are get togethers posted by members of the site, but others are posted by local businesses and often include free drinks. Free wine tastings, free comedy shows, and hosted happy hours are just some of the free events I’ve seen offered.
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If you’re a Yelp Elite member (earned by writing lots of reviews on the site) in another city, be sure to check the Elite calendar for Chicago and see if there are any events happening during your stay. Elite events are great way to mingle with the locals, and nine times out of ten, they include copious amounts of free food and drinks.
BrokeHipster.com and MyOpenBar.com
Even if you don’t fancy yourself a hipster (even if you aren’t quite sure what the term means), you can still take advantage of the information available on the Broke Hispter site, which puts together a calendar of free and super cheap offers from bars and restaurants all over Chicago. I’ve seen listings for everything from .25 cent wings to two-hour open bar events. For some events you have to RSVP and they tend to fill up quickly, so check the site daily the week or so before you’ll be in town.
My Open Bar (which operates in a few other cities, like NYC) offers similar listings, including events that happen every week, so it’s easier to plan ahead.
Chicago Magazines and newspapers
The RedEye is Chicago’s equivalent of the Village Voice or the Stranger. It comes out Monday – Saturday, can be found near any el station, and lists food and drink specials and events each day. Metromix does the same, though all of its content is online. Time Out comes out monthly in print, and the website is updated with great events, free things to do daily, and a lot of daily food and drink specials.
The Explore Chicago website also has a calendar of events, though finding events with free food and drink is a bit more difficult. You best bet is to look for neighborhood festivals and art walks, like the one held in Pilsen on the 2nd Friday of every month. It seems where there are art gallery openings, there is always free finger food and free wine.
Photo by PetroleumJelliffe