Last updated: October 25, 2019


Is it just us or does it feel like the city truly comes alive every year around this time? With outdoor events ramping up and a little more sun each day, we can’t help wanting to hit the town.

If you’re feeling the same way, you’ll dig our curated list of must-do Chicago events happening over the next week.


Go’s Eisley Cantina Pop-Up

May 3-5 at Go’s Tavern & Liquors

For Star Wars fans everywhere, May 4th has come to be a fan holiday since “May the fourth” sounds a whole lot like “May the force.” To celebrate in style, head to this three-day only themed pop up bar at Go’s Tavern & Liquors in Logan Square. Visitors will be able to enjoy themed cocktails and décor in a place where costumes are highly encouraged.


CHIRP Record Fair

May 4 at Plumber’s Hall

While some folks are always anticipating the newest technology, many ludites and classic music lovers alike still prefer to keep it old school with vinyl. At this fest, you’ll find over 100 tables of records in addition to CDs, DVDs and posters. There will also be live music and DJ sets, food, alcoholic beverages and kids’ activities if you want to make it a family day.


Kids & Kites Festival

May 4 at Lincoln Park Cricket Hill

Head to Montrose & Wilson for this springtime celebration of sunshine and good ol’ fashioned kite flying. This family-friendly fest runs from 10am to 4pm and is hosted by the City of Chicago, who will provide free kite kits for anyone who would like to build and decorate a new kite. The young and young at heart will also enjoy demonstrations by professional kite flyers, face painting, balloon artists, circus arts and craft activities.


Cinco de Miler

May 4 at Montrose Harbor

If you love running just as much as you love tacos, this event is tailor made for you. After speeding through a 5-mile course, you’ll arrive at a Mexican fiesta at the finish line. After all, what better way to celebrate a run than with breakfast tacos and a Mariachi band?


Cinco de Mayo Dance Party

May 3 at Duet Dance Studio

Have you always wanted to learn how to do classic Latin partner dances like Salsa, Cha Cha and Merengue? Beginners are welcome at this Cinco de Mayo themed dance lesson and party. The evening starts with a beginner Salsa class and ends with a BYOB fiesta.


Cinco de Mayo Bar Crawl

May 4 in River North

For those who would prefer more of a classic party celebration of the Mexican holiday, check out this bar crawl that will travel to 8-10 bars in the River North neighborhood. Your ticket price includes a t-shirt, brunch buffet three $4 drink tickets to use on the crawl.


Chicago Beer Classic

May 4 at Soldier Field

Soak up the best of Chicago in the spring by drinking beer, eating delicious local food and sampling beer right where the Bears play. This popular beer fest will feature beers from over 80 breweries (local and national), fun activities and educational events.


Kentucky Derby Party

May 4 at Chicago Q

Can’t make it to Churchill Downs this year for the most exciting two minutes in sports? Well, then this may be the next best thing. Don your best seersucker suit or sundress and big hat to watch the event on TV while enjoying Southern cuisine, bourbon drinks, live music and prizes for the best dressed.


Lincoln Park Uncorked 2019: An Armitage-Halsted Wine Stroll

May 9 in Lincoln Park

Sip and stroll through one of the city’s most beautiful neighborhoods at this upcoming celebration of spring, wine and local businesses. You’ll sample over 25 curated red and white wines along with small bites and special offers from the shops along the route.