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TripSavvy's editorial guidelines Updated on 06/26/19 Share Pin Email Jon Hicks/Getty Images It doesn’t matter how cold or hot it is outside, Chicago never slows down. That means that there’s always something to keep you occupied no matter what time of the year you visit. But when you think of all there is to do in the Windy City, you should be keeping a bucket list, and we've outlined the absolute top picks in the following slides. 01 of 12 January: Chicago Restaurant Week Photo courtesy of Eden Chicago's annual celebration of its rich culinary scene takes place at restaurants downtown, in local neighborhoods and in the suburbs. The official Chicago Restaurant Week showcases more than 350 local eateries with prix-fixe menus. It allows diners to check out as many restaurants as possible, so if you’re in Chicago during those two weeks, it should definitely be on your social calendar. 02 of 12 February: Chicago Auto Show Chicago Auto Show The Chicago Auto Show bills itself as North America's oldest and largest auto show. First held in 1901, this year marks the 109th Chicago Auto Show event. Chicago is known as a frequent launching ground for new trucks. 03 of 12 March: St. Patrick's Day Parades When the Chicago River is dyed green every March, it puts everyone in the mood for St. Patrick's Day festivities. Chicago is also one of the few cities featuring two major parades, with the Downtown St. Patrick’s Day Parade and South Side St. Patrick’s Day Parade occurring within a week. And since we’re all about honoring the authentic, of course, we’ve gathered some of Chicago’s top Irish bars where you’re guaranteed a great Guinness pour and more. 04 of 12 April: BaconFest Chicago Baconfest Chicago Love pork? You've come to the right place if you dig all things swine because BaconFest boasts the country's premier event featuring top local chefs and bartenders determined to outdo each other with the most creative offerings ever. It's pretty sweet (yes, there's even bacon in the desserts), but get ready to smell like bacon for at least a couple of days. Oh well. Live a little! Continue to 5 of 12 below. 05 of 12 May: Chicago Craft Beer Week Hotel Lincoln The Windy City’s thriving craft beer community continues to grow--and we have our favorites--so it should come as no surprise that the Chicago Craft Beer Week is one of the most anticipated events of the year. It's a 10-day celebration held in more than 300 venues, and it coincides with American Craft Beer Week. Expect tastings of rare beers, new releases and other special events. 06 of 12 June: Chicago Gay Pride Parade Northalsted Business Alliance Chicago Pride's most famous event, its colorful and celebratory annual Chicago Gay Pride Parade, kicks off at noon the last Sunday in June. It's considered one of the largest events of its kind and occurs in the heart of Boystown. 07 of 12 July: Taste of Chicago Photo courtesy of KrupaliRai Everything at the Taste of Chicago in Grant Park, with the exception of food, drinks and ticketed concerts, is free. Prices vary for concerts. It is one of the country's largest food festivals featuring delights from local restaurants and food trucks. This year the festival runs July 5-9. 08 of 12 August: Lollapalooza Photo via City of Chicago The traveling music festival organized by Jane's Addiction singer Perry Farrell started in 1991 and has grown into one of the world's largest--and most annually anticipated--live music events. Lollapalooza takes place in Grant Park during the first weekend of August. It consists of several stages, including one for children and a main stage, plus Chowtown (where restaurant vendors reside), a retail component and more. It has been expanded to four days. Continue to 9 of 12 below. 09 of 12 September: Chicago Gourmet Gail Reich The annual Chicago food festival--sponsored by Bon Appetit, the Illinois Restaurant Association and Southern Wine & Spirits of America--occurs in Millennium Park. Chicago Gourmet showcases local, national and international culinary talent during a three-day festival. 10 of 12 October: Chicago International Film Festival Chicago International Film Festival The esteemed Chicago International Film Festival launched in 1964 and celebrated its 50th anniversary in 2014. It presents more than 150 narrative feature, documentary and short films from more than 50 countries over a two-week period. 11 of 12 November: Magnificent Mile Lights Festival Photo courtesy of Chuck Cherney Mickey and Minnie Mouse, plus others, kick off the holiday season during the annual Magnificent Mile Lights Festival on the famed Magnificent Mile shopping district. More than one million lights on 200 trees will be lit during the event that will also include a number of family-friendly performances. 12 of 12 December: Christkindlmarket City of Chicago The Christkindlmarket Chicago holiday market takes place in Daley Plaza from Thanksgiving to Christmas Eve and offers unique crafts and gifts for sale, live entertainment, as well as German-focused food and drinks. It is the largest event of its kind in the United States. Was this page helpful? Thanks for letting us know! Share Pin Email Tell us why! 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