By Lizzy Buczak

Thanks to Justin Timberlake, former ‘NYSNC crooner, we always start of May on a high note.

We decided to roll with the pop culture “It’s Gunna Be May” pun and put together a calendar for you so you can make May the best month ever!

Take a look – we think you’ll like what you see.

itsgunabemay Its Gunna Be May Calendar   Things to Do in Chicago This May



5/1 – Jam out to N SYNC’s “It’s Gunna Be May” on repeat


5/2 – Get a $1 Jimmy John’s Sandwich for Lunch during their customer appreciation day special! Details here. 


5/3 – Even though National Concert Day was May 1, Livenation has ticket specials running all week. Buy cheap tickets today to see a concert you otherwise wouldn’t have this summer.


5/4 – One of the most respected EDM producers Deadmau5 is performing at the Aragon Ballroom! You don’t want to miss this.


5/5 – Get your Ferris Bueller on at the Cubs game. The Cubs face the New York Yankees at 1:20pm!


5/6 – Start your day off at the Polish Constitution Day Parade at 11:30am along Columbus Drive then mosey on down to the Chicago Beer Classic at Soldier Field.


5/7Celebrate Cinco De Mayo at the Parade! It steps off at NOON on Cermak Rd. & Damen Ave. to Marshall Blvd. Then get your celebration on with authentic Mexican food and margaritas!


5/8 – Instead of grabbing your cup of java at Starbucks, spend some time exploring a local coffee shop. Here’s a list of our favorites!


5/9 – National Moscato Day obviously calls for a glass, or three, of Moscato!


5/10 – Treat yourself to some delicious shrimp, either made at home or bought at the store, for National Shrimp Day.


5/11 – Enjoy a taste of Spring at the Chicago Botanic Garden for their spring “Wine in the Garden” event. Sample wines from around the world while enjoying the sights and smells.


5/12 – End your hectic week by taking in a beautiful sunset at Montrose Beach!


5/13 – Cover Your Bases wants you to celebrate Chicago baseball at their baseball bar crawl! More info HERE


5/14 – Treat the most important woman in your life to Mother’s Day Brunch! There will be plenty of Mother’s Day activities happening in the city so go explore!


5/15 – Try out rollerblading or rock climbing at Maggie Daley Park.


5/16 – Carve out some time for yourself and get lost in a good book. May we recommend “13 Reasons Why” or “Big Little Lies.”


5/17 – Get over the midweek slump by throwing a pizza party for your friends or co-workers. After all it is “Pizza Party Day.”


5/18 – Party at the planetarium for Adler After Dark: Planetary Prom. It’s a dance party “with hands-on programs, theater shows, and special talks on current planetary missions” at for those 21 an older.


5/19 – Play hooky and spend a day feeling like a kid again at Six Flags. Don’t forget to ride their new Joker!


5/20 – What’s better than running? Running to EDM Music! Night Nation Run is a 5K run/walk to multiple stages that have EDM dance music, lights, lasers, and glow sticks at Soldier Field.  Get Discount tickets!


5/21 – Taste 80 wines at Lincoln Park Wine Festival but don’t forget to nibble on some apps so it doesn’t go straight to your head!


5/22 –  It’s easy to forget how beautiful Chicago is but remind yourself with a bike ride on the Lake Front.


5/23 – Spend the night jamming out with the OG Starboy, The Weeknd at Allstate Arena! Keep an eye out for B96!


5/24 – Do some touristy things in your own city – visit the Art Institute, take a sightseeing tour on the river, check out the ledge from the Sears, er, Willis Tower.


5/25 – Get ready for the FIRST EVER Smokin’ Pork in the Park on Michigan Avenue in acclaimed Millennium Park. Indulge in some baby back ribs from competitors, plus macaroni & cheese, cornbread, and coleslaw outside the Park Grill.


5/26 – Head to Oak Park for their Chicago Gaelic Park Irish Fest with music, family entertainment and food!


5/27  – Head downtown to honor veterans at the annual Memorial Day Parade which begins @ 12 Noon at State St. from Lake St. to Van Buren.


5/28 – For the 33rd year in a row, Belmont-Sheffield Music Festival is kicking off street fest season! More HERE!


5/29 – Use your day of to remember the veterans, relax and put the grill to good use.


5/30 – Since the weekend was so busy, take in an evening screening of the Baywatch screening ft. The Rock, Zac Efron and Priyanka Chopra, which opens May 25th!


5/31 – End “It’s Gunna Be May” on a high note by attending the Parody of Hamilton,  a “smart, silly, and often convulsively funny” parody with “surreal Broadway musical mash-ups” [New York Times] at Royal George Theatre. Discount tickets $49 to $65. Runs through June 29th!


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