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Fun Things to Do in Chicago this May 2024

Last Updated: May 2, 2024

Last Updated: May 2, 2024

things to do in chicago in may

Spring is blooming in every corner of Chicago, and people are ready to serve you the best time ever in the Windy City! May 2024 brings back so many annual events and festivals, which are the pride of May in Chicago. We have made you an amazing list of fun things to do in Chicago this May full of musical events🎶 and so many fun festivals that will fill your schedule with events in Chicago! May full-fledged dives into the beautiful smell and colors of Spring in the city of Chicago!🌸I know you are the most excited about something special (shush!!) this month. Let’s count what’s there for you!

The May month begins with the festival of the year, Cinco de Mayo, making the first weekend a chill zone! The musical lineup of this month is a beautiful blend of classical music and symphonic festivals. But wait, there’s more! Mother’s Day is celebrated dedicatedly this month with beautiful events in Chicago, bringing a smile to every mother of your life! End your month with a Memorial Day food festival and parade to pay your respects! Plus, the annual and quirky festivals, exhibitions, and parties 🌟are always in the limelight! 

Explore events and things to do in May in Chicago as it unfolds its spring wonders, inviting you to savor the unique offerings that make this weekend in Chicago special.

Experience Mexican Culture at Cinco De Mayo Festivals

Events on May 4th and 5th 


The fabulous days are coming to you as this weekend is going to be filled with Cinco de Mayo festivities the whole time! Cinco de Mayo in Chicago makes the weekend extra ✨sparkly✨. Don’t miss the liveliest time of the month. 

1) Cinco de Mayo DAY Party -$25 All-Inclusive Brunch & Booze Party

If you are in the Windy City, you just need the smallest reason for day drinking!🍺 Well, Cinco De Mayo weekend in Chicago isn’t any minute reason to have fun, right? Visit the biggest Mexican bar to have a whole-hearted experience of the festival, including a Mexican Brunch Buffet🌯, Live DJ, giveaways, and so much more (that you will find out if you go!!)😏. My last advice: This isn’t just a fun thing to do in Chicago; it is the best time spent in May! 

📍Chicago, United States

🗓️ May 5th, 2024

2) Cinco de Mayo Bar Crawl – Tacos, Tequila & Cerveza

One, two, three… and losing track because that’s how drunk and bubbly you will be at the Cinco de Mayo Bar Crawl in Chicago!😵‍💫 Step one by one into the best bars of River North to celebrate the weekend with your friends and get hammered like no other day!🍺 Tacos and Tequila are never a bad combination, and a weekend of drinking—ohh, that is something no one says no to!🤷 

📍Chicago, United States

🗓️ May 4th, 2024

Strengthen Your Bonds on Mother’s Day

Events from May 1st to 15th 

Our mothers are the source of the love that each of us carries!💕 They never hesitate to express their love for us, nor should we. Mother’s Day events in Chicago are an incredible way to learn a skill💐, as well as gift them your hand-made things! Today, give all of your mother figures a sense of specialness and love! It’s their day; make it extraordinary! 

1) Kids Card Making Workshop for Mother’s Day

Isn’t it wonderful to see kids’ enthusiasm for doing something special?🤗 Here’s an event for kids to craft beautiful cards and express their creativity through colors! At last, who loves mothers more than their kids? Just for $10, your kids can enroll for the workshop and have a delicious meal,🍲 too! The cute and quirky art will definitely make you emotional! It is one of the best things to do on Mother’s Day in Chicago. 

📍The Old Plank, Chicago, United States

🗓️ May 11, 2024

2) Mother’s Day Brunch and Blossoms

At one point or another, someone always takes the role of being a guiding light and a mother figure in your life apart from your mother!👨‍👩‍👧 You can also appreciate them by taking them to brunch and making beautiful bouquets💐 with them this weekend in Chicago. A selection of breathtaking flowers and a vase is provided; all you need is the company of your mother (or someone who has taken care of you just like your mother) and a bond with them as you have never before!💗 

📍The Walk In, Chicago, United States

🗓️ May 12, 2024

3) Pre-Mother’s Day Chicago Day Trip

This Mother’s Day, start the celebration early with a fantastic day trip to downtown Chicago!🤩 I am sure your mother would love to spend quality time with her family! Start by savoring the famous deep-dish pizza, taking beautiful pictures at Millennium Park, and riding on a Lake Michigan cruise. Browse the Magnificent Mile until you drop and take in the breathtaking vistas from the 360 Chicago Observation Deck.👀 It isn’t difficult to make mothers happy; all they need is love! 

📍Chicago, United States

🗓️ May 4th and 5th, 2024

Spring Brings the Best Music Festivals in Chicago

Events from May 1st to 31st

The one living in Chicago knows what it means as Spring steps into the city! Yes, it’s time for the best music festivals in Chicago!🎶 Music is in every vein of the Windy City and Spring brings out the best of music for people. Come enjoy the ones which you fancy the most 

1) Suenos Music Festival

An unfiltered and outspoken festival🎤, yes, I am talking about the Suenos Music Festival happening this summer (AGAIN!). Reggaeton and Latin artists from all over the world come together in Chicago, unapologetically and with pride, to experience the joy of unfiltered music in its purest form!🎼 To make their fans feel heard and part of the community, they accept feedback and new ideas from fans! A music festival in Chicago is always an exhilarating experience but such festivals are rare to find. They want El Festival Latino to be the greatest yet as they approach its third year!🥳 

📍Grant Park, Chicago, United States

🗓️ May 24th and 25th, 2024

2) Belmont Sheffield Music Festival

Chicago is just fabulous in summer, jampacked with festivals! It truly is one of the most fun things to do in Chicago this May! One such festival returns for the 39th time, not just for two days (like its usual dose) but for THREE days🥹, completely sorting out your weekend plans! The incredible lineup of bands, insane street dancing💃, delicious food, and the iconic and most loved ice-cold brews😦 are back!! Bring your dogs over to socialize too, no one can stop you! 

📍Lakeview East, Chicago, United States

🗓️ May 24th and 25th, 2024

3) Bach Week Festival 

If you are like me, classical tunes also hit just the right amount of euphoria for you! To experience that happiness for the last time, you must immediately book yourself for Bach Week this May in Chicago! Why is 2024 the last time you asked?🤔 Well, it opens its doors one last spring for its 50th Anniversary this spring! Since its opening in 1974, it has been a pioneer for classical music!🪕 The lineup is gigantic and pleasing to the human soul in every emotion! 

📍St. Luke’s Episcopal Church Evanston, Chicago, United States

🗓️ May 05, 2024

4) Lunar Solar Tide

Enter the cosmic dance of Lunar Solar Tide 2024 Chicago’s most thrilling music event, where the moon’s mysticism and the sun’s zest collide! Prepare yourself for a weekend filled with varied genres and eclectic beats that will light up many stages with anything from hip-hop grooves to indie songs. The festival atmosphere changes when the day sets and the moon begins to shine, luring you into a night of deeper, more entrancing rhythms.

Here’s the lineup of artists for you!

  • Commodo
  • Distinct Motive
  • Halogenix
  • Joker
  • Monty
  • Nic Baker
  • Sicaria
  • Taili Nulight
  • The Widdler
  • Torcha

📍Patio Theater, Chicago, United States

🗓️ May 10th to 12th, 2024

Polish Constitution Day Parade 

Event on May 4th

People paint the town red and white, celebrating one of the most festive events in Chicago every May! The vibrant Polish Constitution Day Parade is a joyous commemoration of Polish heritage!🤩 

Poland’s groundbreaking 1791 Constitution is honored at this celebration with vibrant floats, traditional folk costumes, upbeat polka bands, and cultural displays. The lively community, joyful dancing, and traditional music make it exciting, and be a part of it! 

Mole de Mayo Festival

Events on May 24th and 26th 

Started with a few food stands and local musicians filling the air, the Mole de Mayo Festival has now become the only outdoor mole cook-off event.🧑‍🍳 Their growth from 2009 to 2024 in Chicago has been a journey worth remembering for them! The traditional celebration is for Latino culture and Mexican cuisines,🍛 where local chefs and restaurants fight for the “Best Mole” and “People’s Choice” Awards!🏅 

All that is amazing, but what will you love? The three days will be full of music, dancing, savory mole dishes, and the ultimate exciting part: Lucha libre wrestling!🤼 18th Street will be as alive as ever (only if you join, too!). 

The Delight of Annual Festivals in May

Events from May 1st to 31st

Did you miss out on some amazing festivals last May? Don’t worry; there’s a spectacular lineup of annual festivals in Chicago that you can cover up! These thrilling traditions happen like clockwork each May, so if you missed out last time, get ready to check off some bucket-list moments!

1) Mayfest and Armitage Art Show

As summer starts, the festival that’s first in line swooping in and starting the summer festivals in style is the Mayfest! The Historic District of Lincoln Park 🏞 is where the festival comes with a breeze and makes everyone happy and cheerful! The two stages will always be filled with Chicago’s most acclaimed musicians🎸 and DJs, making you groove limitlessly! The best part of the festival is good food😋, even better drinks🤭, and the best community🤗. You will go crazy at this summer festival in Chicago this May!

📍1000 W Armitage Ave, Chicago, United States

🗓️ May 17th to 19th, 2024

2) 27th Annual Art in Wilder Park

Manifesting the art crazies at Wilder Park this spring for the Art show! This two-day event in Chicago May where you can not just find one-of-a-kind art; let’s just say it’s all too inclusive! More than 10,000 people attend🧑‍🤝‍🧑, with 120+ vendors right to serve you all kinds of accessories, paintings, sculptures, prints, fiber arts, and saliva-dripping food! You can also roam public art installations🖼️, have an adventure with a scavenger hunt, and participate in hands-on activities hosted by the museum! The best part? Everything is for FREE! It is the best event in Chicago for May 2024, people!

📍Elmhurst Art Museum, Chicago, United States

🗓️ May 4th, 2024

3) American Writers Festival

Is there a heaven for Writers in Chicago? Yes, there is at Harold Washington Library! The Literature freaks and geeks🤓 gather up for a free event by the American Writers Museum and Chicago Public Library! With leading authors, poets, artists, and playwrights, it is truly a space to have in-depth conversations about the literary world.📖 Discuss the past, promote the present stories, and inspire writers (like me) for the future of writing! Kids are welcome too for children’s storytimes, literary crafts, and mini writing workshops✍️ to make them writers just like you! Shushh, you might find your favorite authors signing new copies of books for sale, too!📚 

📍Harold Washington Library, Chicago, United States

🗓️ May 4th, 2024

4) Manifest Arts Festival

Taking the reigns of Southloop, Columbia students produce and run an all-day festival😌 of the arts! The students’ ingrained and polished creativity is quite evident as you experience the festival throughout the day. Roam the gallery exhibitions, where live music will be playing to set the vibe. There will also be film screenings🎞️, original video games, fashion shows👠 (and an amazing one!), literary readings, and more! I bet one of these fun things to do in Chicago this May is manifesting you at the Manifest! 

📍South Loop, Chicago, United States

🗓️ May 10th, 2024

Memorial Day: Pay Respect with Pride  

Events from May 26th to 27th 

Set to sizzle with an array of unforgettable events this Memorial Day in Chicago! From the mouthwatering delights at the WingOut Chicago to the scenic Memorial Day Cruise on Lake Michigan🛳️, and the patriotic fervor of the Southside Memorial Day Parade, there’s something to captivate everyone🥰. Dive into a weekend of food, fun, and honor in the heart of the Windy City!

1) 9th Annual WingOut Chicago

Do you feel the smell of delicious food pulling you? It is not the food you cooked (TRUST ME!)😂 but the wave of Wingout Chicago coming closer and closer! Chicago’s top vendors are here to make your mouth water from miles away! Want me to make you miss good food more?🤤 You can have Honey Chili, Jerk, Wood Smoked, Sweet and Spicy, Spicy Garlic, Asian Ginger, Southern BBQ, and so much more that I keep to myself for now! Plus the musical lineup is the best part! Still want to miss this?🫥

📍Gallagher Way Chicago, Chicago, United States

🗓️ May 25th and 26th, 2024

2) Memorial Day Cruise on Lake Michigan

Cruising down Lake Michigan with music and drinks is a good weekend! The skyline of Chicago looks almost unreal from the cruise🛳️ because it looks perfect! With two professionally staffed bars serving you whatever your poison is🍸, along with one of Chicago’s top DJs🎛️ playing all the sick beats that will not keep you from dancing! The special Memorial Day cruise only allows 21+ people because it’s time to party! 

📍Sightseer Boat located at Monroe Harbor, Chicago, United States

🗓️ May 27th, 2024

3) 9th Annual Southside Memorial Day Parade

To honor the brave service members and pay tribute to heroes, the community gathers in Chicago 2024 for the 9th Annual Southside Memorial Day Parade in Chicago! With local marching bands🪇, veteran groups, and colorful community floats, it is a huge patriotic parade in Chicago! It is open for all events, all you need to do is register!🎫 Pay respects and unite for the ones who sacrificed for freedom! 

📍7750 S Emerald Ave, Chicago, United States

🗓️ May 27th, 2024

See you at the Events! 

So there you have it, the amazing list of events that will fill you with thrill, excitement, adventure, and serenity and groove you into a festive vibe at once! It was my job to share the best events from the list with you! Now, it’s your turn to go to the best ones you found. 

If you wish to explore any events in Chicago further, click on the link below to have the events that will make your May a blast! 

Author Bio

Rashmi Ramchandani

With a passion for exploring new cities, Rashmi Ramchandani loves creating a bucket list of things to do and places to visit. Her hand-picked events and the undertone of reliability, sarcasm, and wittiness will hit you to the core. Let her create this weekend’s to-do list for you. You are indeed in good hands.

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