Who else is still recovering from the event scene come-back in April?? Now that the weather is starting to show hope towards #patioseason, events for Spring and Summer are in full swing. Read below for a roundup of things to do in Chicago this May! Listed in order by date 🙂
Fyre Festival Pop-Up
May 3 – 19, 2019
Replay Lincoln Park‘s newest pop-up experience is themed around the infamous Fyre Festival (celebrity models not included). Some “luxury” items that will be featured include “gourmet cheese sandwiches” and yummy frozen cocktails. Admission is free!
National Fitness Day @ Athleta Oak Street
May 4, 2019
Celebrate National Fitness Day with aSweatlife Ambassadors and Athleta’s Oak Street location! Two fun classes will occur: HIIT Bootcamp and Yoga Sculpt. There will also be an Instagram scavenger hunt challenge to participate in for the chance to win prizes! Grab your ticket here.
Celebrate Derby Day
May 4, 2019
Before celebrating Cinco de Mayo, it’s time to bring out your best Kentucky Derby Day hat! Derby Days is upon us, and many Chicago bars are celebrating. Not sure which one to go to? Check out the lineup before!
- Derby Day at J. Parker
- Derby Day – Infinite Juleps! at Z Bar
- Kentucky Derby at Chicago q
- Derby on the Runway at Bounce Sporting Club
- Kentucky Derby Watch Party at Apogee
- Kentucky Derby Party @ Joy District & Hubbard Inn
- Chicago Derby Day at Haymarket Pub & Brewery
- Kentucky Derby Watch Party at Clutch
- Kentucky Derby Watch Party at Bounce
- State’s Kentucky Derby Party
- All-Inclusive Kentucky Derby Party at 80 Proof
- I|O Godfrey Kentucky Derby Viewing Event 2019
Celebrate Cinco De Mayo Weekend
May 4-5, 2019
It’s time to Cinco de Drinko! There are many festivities occurring around the city for Cinco de Mayo, including bar crawls and bar parties. You can find a list of them below!
- Cuatro de Caballo at Cerise Rooftop
- The Tequila-N-Tacos “TNT” Bar Crawl
- Cinco de Mayo tribute to Frida Kahlo
- Cinco de Mezcal Party at J. Parker
- Chicago Memorial Weekend Pier Pressure White Party Cruise
- Cinco de Mayo Celebration at IO Godfrey Rooftop Lounge
- Cinco De Mayo River North Bar Crawl
- Cinco de Mayo Comedy Jam
- Cinco De Mayo Fiesta: Charity Event
It’s Britney Brunch
Every Saturday in May (4, 11, 18, 25)
It’s Britney…Brunch! Sounds like the best brunch ever to me. Join AceBounce every Saturday in May from 12pm-3pm for Britney karaoke led by house DJ, bottomless mimosas, and unlimited ping pong. For just $39 you can rock out to one of the most iconic artists of our time for a three hour package. Make sure to book your reservation to attend!
Yoga & Brunch at Pinstripes Chicago
May 5, 2019
Start your morning off right with bottomless brunch and an hour Corepower Yoga class at Pinstripes! Your $5 ticket includes the class, one complimentary mimosa, and $5 off Pinestripe’s bottomless brunch. Reservations for brunch are strongly recommended and it is BYOM (bring your own mat)!
Food Truck Social
May 11, 2019
This food truck soir̩e features over 15 popular restaurants Рincluding some I love like La Cocinita and DaPizzaDude Рperched at the Lincoln Park Zoo. What could be better than roaming around the zoo and trying different food from a variety of trucks?? General Admission for the 6pm time slot is sold out, but you can still grab a 7:30pm spot for only $10!
Celebrate Mother’s Day
May 11 – 12, 2019
Chicago is known for having great brunch spots, especially when it comes to celebrating a holiday. This includes Mother’s Day! Find a quick list below of where to have Mother’s Day brunch in the city.
- Mother’s Day Brunch at Café Brauer (Lincoln Park Zoo)
- Mother’s Day Floral Workshop
- Mother’s Day Blooms at Tapster Chicago
- Mother’s Day MakeOver Mixer at BellaNiecele
- Mother’s Day Brunch at The Metropolitan
- Mother’s Day Facial at Olivo Med Spa
- Mother’s Day Afternoon Tea & Sweets
- Mother’s Day Brunch and Cooking Class
- Mother’s Day Shopping Party
- The Millennium Knickerbocker Presents Mothers Day Brunch
- Mother’s Day Market at The Gwen
- Mother’s Day Upside Down Tea Party
Lincoln Park Wine Fest 2019
May 17 – 19, 2019
Do you like wine? Of course everyone does! Lincoln Park Wine Fest is back with their 5th annual wine fest for Chicagoans to cheers to summer. Located at Jonquil Park, this festival features over 90 different wines to taste with your 12 drink tickets. Make a note – Friday’s night will focus on rosé and sparkling wines only!
Gourmet Puerto Rico
May 18, 2019
First off, YES. As a fellow Puerto Rican, I was so excited to see Latinicity’s Gourmet Puerto Rico event. This nighttime event will feature five food stations cooking up the best fare to celebrate Puerto Rico’s finest chefs, cuisine, music, culture, and more. Proceeds benefit the Segundo Ruiz Belvis Cultural Organization and the Dia de la Mujer Latina Organization. Purchase your tickets here!
Sweat Cause: Namaslay for ABTA
May 18, 2019
Who’s ready to namaslay for a cause?! Join Sweat Cause for their official launch at Yoga Six. The event’s proceeds will benefit the American Brain Tumor Association, the charity that motivated Sweat Cause to form. Choose to do either a $40 yoga or yoga sculpt ticket!
Zoo-ologie 2019
May 18, 2019
Zoo-ologie is an annual cocktail party supporting the Lincoln Park Zoo – one of my favorite Chicago landmarks. Proceeds will benefit the Auxiliary Board of the Lincoln Park Zoo’s efforts towards their capitol campaign, The Pride of Chicago. Attendees will enjoy open bar, bites from Chicago’s favorites, a silent auction, and dancing at this festive event. Come party with the animals! VIP tickets are sold out. General Admission is available for $125.
Namas-tea (Yoga & Tea)
May 19, 2019
Tiesta Tea says it best: There’s nothing better than Sunday than savasana and sipping tea mimosas! Love it. Hoping to go this event myself! Hosted by HolisticRX & Tiesta Tea, $10 will get you a goodie bag, tea mimosa samples, a 45-minute all-levels Vinyasa Flow, snacks, and services from local Chicago companies.
Summer Cocktails Fest on the Beach
May 24, 2019
Yum, summer cocktails! My favorite thing aside from champagne. Summer Cockails Fest on the Beach will be held at the Shore Club off Lake Shore Drive. Your $50 ticket will include 3 hours of cocktail tastings, giveaways, and more. Sounds like a great event to kick off summer to me! Make sure to use my code below for a discount 🙂
Use code ALYSSA at check out for a ticket discount!
Crawl of Thrones
May 25, 2019
Join other GOT fans at this one-day bar crawl in River North! The crawl is based off HBO’s popular Games of Thrones TV show and is in honor of it being in it’s last season. For less than $20 you get general admission, an LED bracelet, 16oz color changing cup, and access to photo ops and giveaways.
Celebrate Memorial Day Weekend
May 27 – 28, 2019
Ahoy! It’s time to plan your beachy, sunny Memorial Day Weekend plans in Chicago. From yacht parties to bar crawls, there’s something for everyone to relax and have fun. Read a list of things to do below!
- Memorial Day Booze Cruise by Chicago Party Boat
- Chicago Memorial Weekend Pier Pressure White Party Cruise
Wine Fest on the Beach
May 31, 2019
Shore Club is a great beachy spot located at Fullerton Beach. What better place to hold a wine fest by the water! The event includes three hours of wine tastings and giveaways, all while welcoming Chicago’s summertime weather. Pre-sale tickets are currently $50!
The Next Collective Women’s Conference
May 31, 2019
Join other #bossbabes at this one-day, women-only conference in Chicago. If you are interested in entrepreneurship or a career pivot, this is the event for you. The topic will be finding a personal purpose through listening to a panel of inspirational speakers. Early bird tickets go for $165. Hurry and buy yours before they go up to $180!
Which of these great events will you be going to? Comment below and let me know!
