‍‍May is an ideal time to visit Chicago, as the city comes alive with spring's beauty and the summer's anticipation.

From vibrant tulip displays to outdoor festivals and cultural events, there is something for everyone to enjoy in the Windy City this month. 

In this comprehensive guide, we will take you through the must-see attractions, weather conditions, what to wear, and the best activities to make the most of your visit to Chicago in May.

How Is The Weather In Chicago In May?

During May, Chicago shifts from spring to the early stages of summer. The climate gradually warms up, with average high temperatures reaching approximately 68°F (20°C) and lows averaging around 50°F (10°C).

As the city bids farewell to winter, occasional cooler days may still occur, but the overall trend leans towards milder and more enjoyable weather.

It is common to experience rainfall during May, leading to intermittent showers. However, this month marks the commencement of the outdoor season in Chicago, as residents and visitors delight in the emergence of greenery and the more pleasant temperatures.

Things To Do in Chicago in May

This city unfurls its true colors, offering a multitude of things to do in Chicago in May. Whether you are an art aficionado, a food enthusiast, or a sports fan, Chicago in May caters to all tastes and interests, providing a unique experience for every visitor.

With the weather warming up, the city's cultural scene also comes alive, promising a month filled with memorable adventures and explorations.

Ready for a springtime escapade? Continue reading to plan your Chicago itinerary for May!

1. Exploring the Tulips of Michigan Avenue

Tulips of Michigan Avenue

One of the most iconic sights in Chicago in May is the blooming tulips along Michigan Avenue. Each fall, the City of Chicago plants tens of thousands of tulip bulbs, and in April, these bulbs burst into a kaleidoscope of color, creating a stunning display.

As you stroll along Michigan Avenue from Oak Street to Roosevelt Road, you'll be greeted by a vibrant sea of tulips, filling the air with the joy of spring.

The tulips on Michigan Avenue make for a marvelous sight and have become synonymous with spring in Chicago. The colorful blooms add a touch of beauty to the city's already impressive skyline.

Don't miss the opportunity to capture Instagram-worthy photos and immerse yourself in the vibrant atmosphere of the city's most famous street.

2. Admiring the Cherry Blossoms in Chicago

Cherry Blossoms in Chicago

Another breathtaking floral spectacle in Chicago in May is the blooming of cherry blossom trees.

While options for viewing cherry blossoms in the city are somewhat limited, the beauty of these delicate flowers is not to be missed.

Typically, the Sakura blooms start showing in early April and peak at the end of April and early May.

To experience the cherry blossoms in their full glory, head to Jackson Park. This beautiful park is home to a cherry blossom tree collection, creating a stunning canopy of pink and white flowers.

Take a leisurely stroll under the blossoms, soak in the peaceful atmosphere, and capture the beauty of nature in bloom.

3. Indulging in Spring Flower Shows at the Conservatories

Spring Flower Shows Chicago in May

Chicago's conservatories come alive with vibrant spring flower shows in May. Two must-visit locations are the Garfield Park Conservatory and the Lincoln Park Conservatory.

These botanical havens offer visitors an escape into a world of blossoms, colors, and fragrances.

At the Garfield Park Conservatory, you can explore the 2023 Spring Flower Show titled "Bee's Knees." This show highlights the fascinating relationship between bees and blooms.

Beautiful spring bulbs like tulips and daffodils, hydrangeas, delphiniums, and azaleas will surround you.

The conservatory's beekeeping program is also showcased, allowing you to learn more about the world of these essential pollinators.

The Lincoln Park Conservatory presents its Spring Flower Show, "Cooler by the Lake." This show features a variety of flowers in cool marine color tones, evoking the essence of Chicago's Lakefront.

As you wander through the conservatory, you'll encounter flowers, exhibits, and installations inspired by the beauty of the lakefront, including the iconic Chicago Harbor Lighthouse.

4. Immersing in Art on theMART Projections

Art on theMART, the world's largest permanent digital art projection, is a must-see attraction in Chicago.

Located on the 2.5-acre river façade of the Merchandise Mart, Art on theMART showcases captivating artistic projections that light up the Chicago Riverwalk.

Returning in mid-April, Art on theMART celebrates its 5th anniversary with new commissions by renowned artist Derrick Adams and projections of work by local Chicago Public Schools seniors.

These mesmerizing projections can be enjoyed nightly from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

As dusk falls, make your way to the riverwalk and witness the transformation of the Merchandise Mart into a canvas for artistic expression.

The vibrant colors and dynamic imagery create a truly immersive experience, inviting you to explore the intersection of technology and art.

5. Kayaking and Enjoying the Riverwalk

Riverwalk Chicago in May

As the weather warms in May, it's the perfect time to explore the Chicago River by kayak. Urban Kayaks on the Riverwalk offers kayaking and paddleboarding experiences for all skill levels.

Whether you're a beginner or an experienced paddler, gliding along the river provides a unique perspective of the city's architecture and skyline.

Kayaking on the Chicago River allows you to appreciate the city's beauty differently.

As you paddle, you'll pass under iconic bridges, admire the towering skyscrapers, and soak in the vibrant atmosphere of the riverfront.

It's a peaceful and invigorating way to connect with nature while still being in the city's heart.

After your kayaking adventure, take a leisurely stroll along the Riverwalk. Lined with restaurants, cafes, and shops, the Riverwalk offers a bustling and lively atmosphere.

Grab a bite to eat, relax on one of the many benches, and watch as the city comes alive around you.

6. Delving into the World of Harry Potter™: Magic at Play

For all the Harry Potter™ fans, Chicago is hosting a magical experience that shouldn't be missed. The Harry Potter™: Magic at Play exhibition takes place at Water Tower Place on Michigan Avenue and offers an immersive journey into the world of Hogwarts™.

Spread across three floors, this interactive exhibition allows fans of all ages to interact, explore, and play through iconic moments from the Harry Potter™ series.

From casting spells in the Defense Against the Dark Arts classroom to exploring Diagon Alley and Hagrid's Hut, countless opportunities exist to feel the magic come to life.

Step into the shoes of a wizard or witch, discover hidden secrets and create unforgettable memories as you venture through this enchanting experience. Don't forget to grab a butterbeer and immerse yourself in the wonder of the wizarding world.

7. Dining in the Dark for a Unique Culinary Experience

Prepare to have your senses heightened as you embark on a unique dining experience at Hubbard Inn.

Dining in the Dark offers an unforgettable journey through taste and texture, where your sense of sight takes a backseat and your other senses take center stage.

During the dining experience, you'll be guided through a three-course meal in complete darkness.

Without the ability to see, your sense of taste, smell, touch, and hearing become more acute, allowing you to fully savor each dish and engage with the flavors in a new way.

Choose from vegan, seafood, or red meat options and let your taste buds be the guide as you indulge in a culinary adventure like no other. This surreal dining experience is perfect for a date night or a memorable outing with friends.

8. Indulging in Mother's Day Brunches

Mother's Day Brunches

Celebrate Mother's Day in style by treating your mom to a decadent brunch at one of Chicago's top spots. M. Henry in Andersonville, Batter and Berries in Lincoln Park, and Offshore Rooftop at Navy Pier are just a few of the incredible locations to enjoy a delightful meal with your loved ones.

These brunch spots offer a range of delicious options, from fluffy pancakes and eggs benedict to bottomless mimosas and flavorful cocktails.

Show your mom how much you appreciate her by giving her a memorable dining experience in the heart of Chicago.

9. Sipping Tea at Thorn Restaurant and Lounge

Thorn Restaurant and Lounge is dedicating a special tea service to celebrate mothers this May.

From May 13th to 14th, you can indulge in a curated selection of Teavana Teas and Blooming Flower Green Teas as you enjoy a delightful afternoon with your loved ones.

Sip on fragrant teas, sample delicious tea sandwiches, and savor sweet bites in an elegant setting.

This Mother's Day tea service is the perfect way to spend quality time with your mom while treating her to a refined and relaxing experience.

10. Floral Workshop with Leelee's Garden

Floral Workshop

Get your creative juices flowing at Leelee's Garden's spring floral workshop. On May 17th, at InterContinental Chicago, you can learn the basics of floral design and curate your centerpiece with Leelee, a floral expert.

For $90 per ticket, you'll have access to a wide selection of flowers and botanicals, botanical-inspired cocktails, and a night of crafting and mingling with fellow flower enthusiasts.

Take home your masterpiece and showcase your newfound floral arranging skills.

11. Candlelight Concerts for a Magical Evening

Experience the enchantment of Candlelight Concerts in Chicago's most extraordinary venues. These concerts combine the flickering glow of candles with the melodic sounds of talented musicians, creating an ambience that is both captivating and intimate.

Throughout May, there are several candlelight concerts taking place in Chicago. From classical masterpieces to contemporary favorites, each concert offers a unique and immersive musical experience.

Whether you're a classical music aficionado or simply looking for a memorable evening, these candlelight concerts will leave a lasting impression.

Locations and addresses vary. Visit the Candlelight Concerts website for more information.

12. Mayfest: Live Music and Fun in Lincoln Park

Lincoln Park

Mayfest brings the party to Lincoln Park with live music, food vendors, cover bands, and carnival games. Held from May 12th to 14th at the intersection of Armitage and Sheffield, this annual street festival is a beloved tradition in Chicago.

In addition to the live entertainment, Mayfest features the Armitage Art Show, showcasing the work of Chicago's top artists.

Interactive art demonstrations and exhibits add extra creativity to the festival, creating a vibrant and engaging atmosphere.

By attending Mayfest, you'll have a great time and support the area's local neighbourhood, small businesses, and public schools. So grab your friends, get ready to dance, and immerse yourself in the lively spirit of Mayfest.

13. Mole de Mayo Street Festival in Pilsen

Celebrate Mexican cuisine and culture at the Mole de Mayo street festival in Pilsen. Held from May 26th to 28th, this annual event pays homage to the traditional Mexican mole sauce.

Get ready to sample a variety of delicious bites, enjoy live music and performances, and immerse yourself in the vibrant atmosphere of Pilsen.

The highlight of the festival is the mole cook-off, where local chefs compete to create the most flavorful and authentic mole dishes.

From classic red mole to unique variations, you'll have the opportunity to taste the rich and complex flavors of this beloved Mexican sauce.

Don't miss the traditional dances, wrestling competitions, and artisanal crafts that showcase the rich cultural heritage of Mexico. Mole de Mayo is a feast for the senses and a true celebration of Mexican traditions.

14. Cellared Beer Festival at Northman Beer & Cider Garden

Beer Festival

Beer enthusiasts, rejoice! The first-ever Cellared Beer Festival is coming to Northman Beer & Cider Garden. On May 20th, this European-style outdoor tasting festival will offer over 40 cellared beers to savor and enjoy.

Immerse yourself in the world of craft beer as you sample a wide variety of unique brews. Each beer has been carefully aged and selected from barrel-aged stouts to vintage ales for this special event.

Live music, buffet options, and a vibrant atmosphere add to the festivities, making it a day to remember for beer lovers.

15. The Dark Side of the Moon: A Pink Floyd Show at Adler Planetarium

Experience the iconic music of Pink Floyd like never before at Adler Planetarium's show, "The Dark Side of the Moon."

 Celebrating the 50th anniversary of the album, this immersive experience combines the band's timeless music with a mesmerizing laser light show.

Step into the auditorium with its 180-degree, 36-foot domed ceiling and prepare to be transported to another world.

As the music fills the space, lasers dance across the dome, creating a visual spectacle that complements the music in perfect harmony.

"The Dark Side of the Moon" show runs for a full year, allowing you ample time to plan your visit and immerse yourself in the magic of Pink Floyd's music.

Whether you're a long-time fan or new to their music, this show is a must-see for music and visual art enthusiasts alike.

16. Color Factory's Spring Confetti Room

Step into a world of vibrant colors and joyful celebrations at Color Factory's spring confetti room.

Located in Chicago, this immersive art installation features a room filled with tulip-inspired confetti and a stunning spring flower installation.

Color Factory invites visitors to explore interactive rooms, each offering a thoughtfully curated experience.

In the "Night Woods" exhibit, you'll encounter 10 miles of colorful ribbon, while the "Chicago" confetti room boasts over 500 pounds of tulip-inspired confetti.

Let your imagination run wild as you immerse yourself in a world of color and creativity. Whether snapping photos, dancing in the confetti, or simply taking in the sights and sounds, Color Factory promises an unforgettable experience for visitors of all ages.

17. Activate Games: A Futuristic Gaming Experience

Activate Games

Prepare for a thrilling adventure at Activate Games, an indoor interactive gaming experience.

This Winnipeg-based company has opened a new location in Chicago, offering a futuristic form of entertainment that combines technology and physical activity.

At Activate Games, you'll find many high-tech, real-life games designed to test your physical and mental agility.

From live-action challenges to team competitions, hundreds of combinations keep you engaged and entertained.

Challenge yourself and your friends as you navigate through exhilarating game scenarios, from solving puzzles to engaging in friendly competition.

Experience the excitement of being fully immersed in a virtual world while actively participating in the action.

18. Restless Leg Tour with Tina Fey and Amy Poehler

Get ready for a night of laughter and entertainment with the Restless Leg Tour featuring Tina Fey and Amy Poehler. This limited-date tour is stopping in only four cities, and Chicago is fortunate to be one of them.

As Second City alums who started their careers in Chicago, Fey and Poehler bring their comedic genius back to their roots.

Tina Fey and Amy Poehler have made their mark on the comedy world, and their chemistry on stage is undeniable.

Prepare to be entertained by their hilarious anecdotes, brilliant improvisation, and witty banter. This is a comedy show you won't want to miss.

19. Sauced Night Market: A Foodie's Paradise

Sauced Night Market Chicago

Calling all foodies! Sauced Night Market is the place to be for a culinary adventure. This vibrant night market brings together food vendors, artisans, and local businesses, creating a lively and immersive experience for visitors.

Sample various delectable bites, from international street food to gourmet desserts. Explore the vendor booths, discover unique flavors, and indulge your taste buds in a feast of culinary delights.

Live music, art installations, and a festive atmosphere add to the excitement, making Sauced Night Market a must-visit destination for food lovers.


Is May a good time to visit Chicago?

May is a favorable time to visit Chicago. The weather begins to warm, providing an ideal climate for exploring the city's attractions.

Additionally, May sees various festivals and events occurring, and the tourist crowds are not overwhelming, allowing for a more enjoyable and manageable visit.

Can it snow in Chicago in May?

Snow in May in Chicago is extremely rare. While the month typically sees very little snowfall, it's not impossible, as weather can be unpredictable.

Generally, you can expect warmer and more pleasant conditions as Chicago transitions into summer.

Can you wear white jeans in May?

White jeans are perfectly acceptable to wear in May in Chicago, provided the weather conditions are suitable.

If there's no snow or excessive rain creating muddy conditions, feel free to sport your white jeans with confidence and style during your visit.


No matter your interests, Chicago is full of exciting and unique experiences for everyone to enjoy. From virtual reality gaming to comedy tours and foodie havens, there is something for everyone in the Windy City.

With various activities, you can make the most of your time in Chicago. Check out the websites for each activity and dress appropriately for the weather to ensure a fun and enjoyable experience.