Every month there are a ton of exciting events to fill up the calendar, from food festivals and cultural events to music concerts and so much more. You will never get bored in this city! Let me take you through a few of my favorites, for a full list of events check out Choose Chicago.

November-January

Winter Wonderfest takes over Navy Pier bringing joy and fun for the whole family. With giant slides, rides, ice skating and holiday decor, you will surely get in the holiday spirit!

November-March

The Millennium Park McCormick Tribune Ice Skating opens with free admission to take a spin on the ice (toe-pick!) under the iconic Bean (aka Cloud Gate). Its like Chicago’s version of Rockafellar Center.

January

Winter Wonderfest makes it worth a visit to Navy Pier which is packed with winter fun. Great for families looking for some holiday cheer.  If you’re good for a laugh, check out Chicago’s Sketch Comedy Festival that is held this month. Restaurant Week runs the last week of January and the first week of February and is a great time to experience all of the delicious wonders in Chicago! There are sooo many, you could spend the whole week enjoying brilliant cuisine! (My mouth is watering just thinking about it) You would def gain a few pounds, but it would be damn worth it!

February

Restaurant Week continues the first week of this month. The Chicago Auto Show is also held this month, along with several beer festivals and Theater Festivals including Chicago Theater Week.

March

With spring looming, flower shows and Saint Patrick’s fun will wash away those winter blues. Spend your St. Patty’s day doing Irish car bombs on a downtown bar crawl, ‘cause aren’t we all Irish that day??

April

Spectator sports come alive this month, but if you’re not a sports fan there’s always Baconfest, Winefest and the James Beard Eats Week. If you like food and wine as much as I do, this is a great month to visit!

May

Finally it’s warming up and it’s time to get outside! There’s tons to do in this lively city! James Beard Eats Week continues and the coveted awards are handed out. Also this month look for music festivals, arts festivals, IL craft beer week, Greek Fest, Taste of Mexico, Science Fest, markets, parades and fireworks to light up the nights from Memorial Day to Labor Day on Navy Pier.

June

The Millennium Park Music Series begins with free outdoor concerts on select Mondays & Thursdays from June-August. If music is your must, then June is your month. And let’s not forget, Chicago Pride Parade and Pride Fest bring a festivities of love to the windy city. Come out (pun intended!) and celebrate LGBTQ+ life, culture and the community.

July

The Millennium Park Music Series continues and the calendar is jam packed with events! 4th of July Fireworks will be dazzling Navy Pier. My favorite thing in July? The world’s largest food festival! Taste of Chicago visits Grant Park for a five-day event with live music, tons of amazing food, and (best of all) FREE admission. Thank God for flowy summer dresses! Food, beer, yachts, tacos & margaritas-no matter what it is there is probably a festival for it this month!

August

The Millennium Park Music Series comes to a close mid month. The infamous Lollapalooza rocks Grant Park for its annual four day festival the beginning of August. Did you know Chicago is the only city in the US that holds this festival anymore? There are also plenty of free events like Chicago SummerDance and the Chicago Jazz Festival.

September

The World Music Festival and the Throwback Music Festival will have you booty bumpin’. For my foodie friends- there are several enticing food festivals like Dessert Fest at the Zoo, Bourbon & Barbecue Fest, and Chicago Gourmet. The Chicago International Latino Theater Festival rounds out the month and continues into next.

October

The International Latino Theater festival continues. Autumn events scatter the calendar this month like Lincoln Square Apple Fest, the Chicago Marathon, parades, and an International Film Festival.

November

Gearing up for the holidays, Chicago sparkles with light festivals and tree lightings. The Thanksgiving Day parade proceeds the start of Winter Wonderfest at Navy Pier, which continues through January.

December

Holiday cheer bustles around the Randolph Street Holiday Market, while Winter WonderFest continues at Navy Pier and the new year is welcomed by fireworks.