The Jaime Elaine Creative

Windy City Made Spring Gala
2023-03-05 12:00 - 19:00 (America/Chicago) | Stan Mansion, 2408 N Kedzie Blvd, Chicago, Illinois, 60647, United States
The Jaime Elaine Creative will have a booth at the Windy City Made Spring Gala, hosted by The Twentieth.
Tickets can be found here.
Read the flier for more details!

Southport Art Fest 2023
2023-07-08 10:00 - 2023-07-09 19:00 | Southport Art Fest, W. Waveland Ave. & N. Southport Ave., Chicago, 60657, United States
The Jaime Elaine Creative will have a booth again this year at the Southport Art Fest!

This festival was Jaime’s very first art festival ever last year, and she is absolutely thrilled to be back again this year! The festival takes place July 8-9 on Southport between Byron and Waveband. If you visited last year, Jaime’s booth will be in the same location, just north of the Dairy Queen!

The festival is free to attend. It runs from 10am-9pm on Saturday and from 10am-7pm on Sunday!

Stop by and say hi!

Saugatuck Village Square Art Fair
2023-07-29 10:00 - 17:00 | Saugatuck Village Square, 428 Butler Street, Saugatuck, MI, 49453, United States
The Jaime Elaine Creative is participating in their first ever out-of-state art festival this month in Saugatuck, MI!
The Village Square Arts and Crafts Art Fair takes place On July 29th in Saugatuck, Michigan. This festival is one day only, so if you are in the area, mark your calendars and be sure to stop by!
The fair runs from 10am – 5pm rain or shine!

Fall Paint Party at Southport Fundamentals!
2023-11-02 18:00 - 20:00 | Southport Fundamentals, 3827 N Southport Ave, Chicago, IL, 60613, United States
Paint and Sip classes with Jaime are BACK!
Come join the Jaime Elaine Creative on Thursday, November 2nd from 6-8pm to learn a fall-themed painting with your pals! All supplies are provided for this BYOB paint-and-sip night where Jaime will walk you through a guided painting. All levels of artistic experience are welcome, and every participant with have their very own masterpiece to bring home at the end of the evening!
This Fall’s painting event will take place at an exciting new community center in Lakeview: Southport Fundamentals! This space has amazing offerings for adults and children alike, and it is located in the lovely Southport Corridor right across from Blaine Elementary School.
Spaces will be limited, so be sure to reserve your spot in advance!
Sign up for this event here: https://www.hisawyer.com/southport-fundamentals/schedules/activity-set/553807
*The class fee is $45 per guest
*All painting supplies provided
*Wear clothing you don’t mind getting paint on as acrylic paint does stain
*This event is BYOB. Feel free to bring beverages of your choice to enjoy throughout the evening!

One of a Kind Holiday Show 2023
2023-12-07 10:00 - 2023-12-10 17:00 | The Mart, 222 W Merchandise Mart Plaza, Chicago, IL, 60654, United States
The Jaime Elaine Creative returns once again to the One of a Kind Holiday show at the Merchandise Mart!
We are so excited to be back at the OOAK Holiday Show this December in Downtown Chicago. The One of a Kind Show features over 500 artists from all over the country, and Jaime is thrilled to be among this incredible lineup. This event is the perfect place to shop for holiday gifts for friends and family, or to seek out unique and hand-crafted art to decorate your home! Jaime will have original acrylic paintings, prints, hand-painted earrings, watercolor cards, and more.
Stop by and find us at booth #2070. And read on for some special promos from TJEC for those of you visiting the Show!
Show dates:
Thursday, December 7th from 10am-7pm
Friday, December 8th from 10am-7pm
Saturday, December 9th from 10am-7pm
Sunday, December 10th from 10am-5pm
Tickets:
Tickets are typically $15, but for a free admission code, email hello@jaimeelainecreative.com and I will send you the link! Each ticket will get you into all 4 days of the show! No need to buy multiple tickets if you want to come more than once.
SPECIAL PROMO: If you are interested in booking Jaime for a live wedding painting, be sure to stop by this festival! I will be offering $150 off live event painting packages to attendees of the OOAK show. To receive this offer, come by my booth in person and mention this promo. I will have a limited number of unique promo coupons to hand out during the festival!

See my info on the OOAK website here: https://oneofakindshowchicago.com/holiday/artists/the-jaime-elaine-creative-llc

Spring Musings Gallery
2024-03-13 08:00 - 2024-05-12 17:00 | Southport Fundamentals, 3827 N Southport Ave, Chicago, IL, 60613, United States
This Spring, Jaime is presenting her work at a surprise pop-up gallery in Lakeview, Chicago!
Visit a smattering of original paintings at Southport Fundamentals, a new community center in the Southport Corridor of Lakeview. Located at 3827 N Southport Ave, this community center also offers many classes for adults and children alike!
View their offerings and more on their website!
These paintings will be displayed until Jaime’s summer market schedule begins in mid-May! Come check these works out while you can!

Armitage Art Show 2024
2024-05-17 17:00 - 2024-05-19 21:00 | Mayfest, 1000 W Armitage Ave, Chicago, United States
The Jaime Elaine Creative is excited to kick off the 2024 Art Fest Season with The Armitage Art Show at Mayfest!
Join us from May 17th-19th in Lincoln Park to enjoy lots of Music, food, and art!
Event Details:
Located at Armitage and Sheffield in the Lincoln Park neighborhood of Chicago
Friday, May 17th 5pm-10pm
Saturday May 18th 12pm-10pm
Sunday, May 19th 12pm-9pm
Specific booth location information TBA
From the event website:
Chicago Mayfest kicks off the summer festival season on May 17th through the 19th! Located in the Historic District of Lincoln Park at Armitage & Sheffield, this incredible event benefits the Ranch Triangle Community Conservation Association. Join us this year as we celebrate our 27th Season.
Two stages will showcase Chicago’s most acclaimed musicians while festival goers enjoy a variety of delicious food and all the libations needed to light up your weekend. You won’t want to miss this celebration of the sights, sounds and tastes of Chicago’s glorious Summer Season. Now with the Armitage Art Show in the heart of the festival, you’ll get to experience Chicago’s top artists as they showcase and sell their work. Now with interactive art demonstrations!

North Shore Artisan Market 2024
2024-06-22 10:00 - 2024-06-23 16:00 | North Shore Artisan Market, 1810 Walters Ave, Northbrook, IL, United States
Join Jaime at the North Shore Artisan Market this June!
Jaime is excited to announce that we will have a booth at the first Northshore Artisan Market this summer! The Artisan Markets have been so fun for Jaime to attend as a patron, with the Chicago Artisan Market in Ravenswood being one of her favorites to walk around. This will be her first market as a vendor with Artisan markets, though, and this org is affiliated with even more Artisan markets throughout the greater Chicago land and surrounding suburbs! They are always well-curated and diverse markets, and we can’t wait to be included in the awesome vendor list this June!
Details:
Saturday and Sunday, June 22 – 23, 2024
10:00 am – 4:00 pm both days
Booth number and location TBA
From the website:
“Our first North Shore Artisan Market will kick-off Summer 2024 outdoors in picturesque Village Green Park in the heart of downtown Northbrook, IL. We love the park’s community feel and central location.
“This market is conveniently located one block from METRA’s Northbrook Station (Milwaukee District North line), and is surrounded by downtown Northbrook’s neighboring small businesses.
“We look forward to contributing to the vibrancy of Northbrook and its local businesses.”

North Shore Artisan Market map

Southport Art Fest 2024
2024-07-13 10:00 - 2024-07-14 20:00 | Southport Art Fest, W. Waveland Ave. & N. Southport Ave., Chicago, 60657, United States
Stop by Southport Art Fest this July!
As our inaugural show back in 2022, we are beyond thrilled to be back for our third year in a row at the Southport Art Fest! This show is in Jaime’s own neighborhood, and it is such a joy to be able to share her art with local families and friends!
This year, the show takes place from July 13th-14th. Check out the music, all the incredible artists, and even support local schools when you grab a drink at one of the drink tents!
Details:
July 13-14, 2024
Saturday: 10:00 am – 9:00 pm
Sunday: 10:00 am – 7:00 pm
Booth location TBA.
UPDATE: Jaime is beyond thrilled to announce that one of her paintings was selected for the festival’s poster this year! This is the second time Jaime’s art has been chosen for the Southport Art Fest Poster, and we are very excited! And with an abstract piece this year which is quite exciting as well!
A throwback to the poster from Southport Art Fest 2022!

Saugatuck Village Square Art Fair 2024
2024-07-27 10:00 - 17:00 | Saugatuck Village Square, 428 Butler Street, Saugatuck, MI, 49453, United States
We are excited to be returning to the Saugatuck Village Square Art Fair for the second year in a row! This was one of Jaime’s favorite shows of 2023, and it was her first out-of-state art fest!
If you already live or play in Michigan, be sure to stop on by! If you’re a collector from Chicago, this one is worth the short trek from the city!! Come visit the beautiful lakeside town of Saugatuck, Michigan for the weekend and enjoy the art fair on Saturday, July 27th from 10-5! This festival takes place the same weekend as the Venetian Festival which is also a huge draw to the city, so enjoy these events as well as the lovely restaurants, fun shops, lakefront activities and more that Saugatuck has to offer!!
As a note, Saugatuck is a popular spot for Chicagoans to vacation for the summer, and lodging fills up pretty early in advance, so if you’d like to visit for this show weekend, be sure to book your stay sooner rather than later!

Bucktown Arts Fest 2024
2024-08-24 10:00 - 2024-08-25 19:00 | Bucktown Arts Fest
The Jaime Elaine Creative will be making our debut at the Bucktown Arts Fest this summer! We are so excited to be invited to this festival and cannot wait to bring our art to a new neighborhood (for us) in Chicago!
The Bucktown Arts Fest is taking place August 24th and 25th. More details about the art show will be coming soon, so check back!

Ravenswood ArtWalk 2024
2024-09-14 11:00 - 2024-09-15 18:00 | Ravenswood Art Walk, N Ravenswood Ave and W Berteau Ave, Chicago, IL, 60613, United States
Jaime is excited to wrap up the Summer Art Show Season with the Ravenswood Art Walk this September!
Join us September 13th-14th to check out one of Chicago’s quaint north side neighborhoods and a festival that extends not only to the tents lining the street, but also to the local arts storefronts which are dense in this neighborhood!
Event Details:
Saturday, September 13th ・ 11am-6pm
Sunday, September 14th ・ 11am-6pm
Ravenswood Industrial Corridor, Lawrence to Irving Park Rd
From their website:
“The Ravenswood ArtWalk (RAW) Tour of Arts and Industry is a weekend-long celebration of our local creative community. Stretching from Lawrence south to Irving Park along Ravenswood Ave, RAW features: open studios and galleries, pop-up performances and activations, and an outdoor arts market featuring 60+ local makers, two stages of live music, a pop-up beer garden, kids activities, food trucks, and more.”

PAINT PARTY at Free Mvmt Shop
2025-01-17 18:00 - 20:30 | Free Mvmt Shop, 3868 N Lincoln Ave, Chicago, 60613, United States
I am thrilled to announce that I am collaborating with Free Mvmt Shop this month for a PAINT PARTY!
WHEN: Friday, January 17th at 6:00pm
WHERE: Free Mvmt Shop – 3868 N Lincoln Ave. 1st floor, Chicago, IL 60613
WHO: All levels of painter are welcome, from “never picked up a paintbrush” to “my art hangs in famous galleries, thank you very much.” Each participant will leave with a lovely masterpiece at the end of the workshop!
WHY: We love community! Free Mvmt Shop’s Care and Share series is a series of workshops, classes, and events led by community members of the studio sharing their passions. Sign up for this paint workshop to connect with other creatives, enjoy the meditative practice of creating a painting, or maybe even try something brand new!

DETAILS: Tickets will be on a sliding scale between $30-45 based on your comfort level.
Sign up HERE!
Join me as I guide participants in a step by step recreation of my “Cascading Roses” Painting. Throughout the workshop, I will demonstrate the step-by-step process of this piece as you paint along – while we (of course) listen to jams, enjoy some light refreshments, take stretch breaks, and socialize. I like to give lots of opportunities for artistic expression with things like color choices so each guest can make the piece their own!
***Be sure to wear a paint shirt or apron, as acrylic paint stains fabric!***

Have an idea you want to paint that is totally different than the painting I’m guiding?? No problem! Feel free to do your own thing, chicken wing! Our goal is to share in a creative experience together, and walking away with a piece of art is merely a side effect! 😘
P.S. Have a song request for my playlist? Send it my way!

Art in the Village with Craft Marketplace - Cleveland, OH
2025-05-31 11:00 - 2025-06-01 17:00 | Legacy Village, 25001 Cedar Rd, Lyndhurst, OH, 44124, United States
To all my Ohio friends, family, and collectors… I’m officially participating in an art show in my home state! I’m thrilled to be a vendor at Legacy Village’s 34th Annual Howard Alan Art in the Village art show! Located in the Beachwood-Lyndhurst suburb of Cleveland, this art show closes out May and ushers in June with a flare!
WHEN:
Saturday, May 31st · 11am-6pm
Sunday, June 1st · 11am-5pm
WHERE:
Legacy Village, Cleveland, OH
No admission fee to attend
From the show listing:
We return to the fabulous downtown streets of Legacy Village in Ohio to put on one of our greatest and longest running shows of the season. Shutting down the streets to create an exclusive art experience, we bring 100 of the country’s leading artists and fine crafters to the affluent Cleveland suburb Lyndhurst-Beachwood. Legacy Village provides the perfect ambience for our art festival by providing a venue already established with fine dining, designer boutiques, and upscale retail stores along its streets.

Kalamazoo Institute of the Arts Fair 2025
2025-06-06 15:00 - 2025-06-07 17:00 | Kalamazoo, Bronson Park, 200 S Rose St., Kalamazoo, MI, 49007, United States
I am thrilled to announce that I have been invited into the exclusive Kalamazoo Institute of the Arts Fair this June in Kalamazoo, Michigan! That makes TWO Michigan shows this year, and I cannot wait to bring my work to a brand new audience!
DETAILS:
Friday, June 6th 3pm-8pm
Saturday, June 7th 9am-5pm
The 74th Annual Kalamazoo Institute of Arts Fair is a two-day juried art show featuring up to 135 fine artists. Staged in shady, historic Bronson Park in downtown Kalamazoo, this outdoor Arts Fair is acclaimed for its friendly atmosphere and large crowds of arts patrons from across Michigan, Indiana, and beyond. The KIA Arts Fair also features live music, food trucks, family activities and artist demonstrations to draw visitors in.
Kalamazoo’s historic Bronson Park is located downtown, adjacent to the Kalamazoo Institute of Arts and bordered by beautiful architecture. The park is used regularly as a place for community events, rallies, and concerts.

Wells Street Art Festival 2025
2025-06-14 10:00 - 2025-06-15 21:00 | Wells Street Art Festival, Wells Street, Chicago, IL, United States
The Wells Street Art Festival has long been one of my absolute favorite festivals to attend as a patron in Chicago, so I am thrilled to announce that this summer I will be a vendor at this iconic art and music show! This will be the show’s 50th year, and I am thrilled to be included in this milestone show in the Old Town Neighborhood of Chicago!
DETAILS:
Saturday, June 14th 10am-10pm
Sunday, June 15th 10am-9pm
Located on Wells Street in Old Town, between North Avenue and Division.

The Wells Street Arts Festival is celebrating its 50th year in 2025!
The Wells Street Arts Festival in Chicago’s Old Town neighborhood has a rich and vibrant history. It is one of the most prestigious Arts Fairs in the US and continuously ranked in Sunshine Artist’s Top 100 Fine Arts Fairs. This juried event features the work of 200 national exhibitors and is attended by more than 40,000 art enthusiasts.

Southport Art Fest 2025
2025-07-12 10:00 - 2025-07-13 19:00 | Southport Art Fest, W. Waveland Ave. & N. Southport Ave., Chicago, 60657, United States
I’m back, Southport!
For the fourth year in a row, I will be a vendor at the Southport Art Fest – my own neighborhood show! I can’t wait to share my art with you all again this year. I hope to see many familiar faces and meet lots of new friends too!
DETAILS:
Saturday, July 12th
Sunday, July 13th
Located on Southport Ave, between Grace and Waveland

Saugatuck Village Square Art Fair 2025
2025-07-26 10:00 - 17:00 | Saugatuck Village Square, 428 Butler Street, Saugatuck, MI, 49453, United States
For my third year in a row, I will be vending at the Saugatuck Village Square Art Fair! I am thrilled to be back for this summer weekend, and I hope to see you there!
DETAILS
Saturday, July 26th 10am-5pm
Village Square in Downtown Saugatuck
Coinciding with the Saugatuck Venetian Festival, this art show is the perfect daytime activity to round out a weekend of summer loving’!

Printer's Row Art Fest
2025-08-09 10:00 - 2025-08-10 17:00 | Printer’s Row, 728 S Dearborn St, Chicago, Illinois, 60605, United States
Find me this August at the Printer’s Row Art Fest!
DETAILS:
Date: August 9th-10th
Time: 10am to 5pm both days
Location: On Dearborn from Polk to Harrison
728 S Dearborn St, Chicago, IL 60605
From their website:
Chicago’s historic Printer’s Row neighborhood sets the stage for one of the city’s most vibrant and exciting art festivals! Now in its sixth year, the Printer’s Row Art Fest brings together 95 talented juried artists from across the country, showcasing an incredible variety of artwork—including paintings, street art, jewelry, photography, sculpture, woodworking, and more.
Enjoy fantastic art, live music, personalized poems, and nearby restaurants, cafés, and bars to keep you fueled as you shop and stroll.

Downers Grove Fine Arts Festival
2025-09-06 10:00 - 2025-09-07 17:00 | Downers Grove, Downers grove, Illinois
Early this fall, I’ll be heading out to the Chicago Suburbs for the Downer’s Grove Fine Arts Festival!
DETAILS:
September 6th and 7th · 10am-5pm both days
Downtown Downers Grove in the middle of Main Street
From their website:
The Downers Grove Fine Arts Festival will be celebrating 48 years this fall. The festival is held in the middle of award-winning, historic, Downtown Downers Grove which is located 22 miles from Chicago’s loop. Direct access to the BNSF rail line brings patrons from around the region and the City of Chicago to the festival. The festival is currently scheduled to be held in the middle of Main Street. Live music, boutiques, cafes and a children’s art area will complement the high caliber of art that will be present at the show. The show is a community favorite and will be open from 10am-5pm on Saturday and Sunday. In addition, enjoy our boutiques, cafes and a children’s art area that will complement the high caliber of art that will be present at the show.

Flowers for Dreams Wedding Showcase
2026-01-31 14:00 - 18:00 | Flowers for Dreams HQ, 1812 W Hubbard St, Chicago, IL, 60622, United States
Flowers for Dreams Wedding Showcase

What: An immersive wedding showcase with fully designed table scapes, ceremony set ups, and even bridal bouquets that guests can “try on” for inspo! I will be painting a bouquet live throughout the event, and will be showcasing several paintings as well!
When: Saturday, January 31st – 2-6pm
Where: At the Flowers for Dreams Headquarters – 1812 W Hubbard St
How: Tickets are free and can be reserved here!

West Loop Wedding Walk
2026-02-01 12:00 - 17:00 | the Arbory, 2219 WEST GRAND AVENUE, Chicago, IL, 60612, United States
West Loop Wedding Walk

What: A traveling wedding show of sorts! 12 different West Loop Venues will be decked out with vendors and designs to give you inspo for your big day. A shuttle bus will take couples between each venue throughout the event, and you’ll be able to chat with vendors, try yummy food, and have a great time! I will be stationed at The Arbory and will be painting live throughout this event!
When: Sunday, February 1st – 12-5pm
Where: 12 different venues in the West Loop
How: Tickets can be reserved here! Use code VENDOR for 50% off tickets!

Valentine's Day Market
2026-02-07 11:00 - 15:00 | Harold Washington Library, 400 S State St, Chicago, IL, 60605, United States
Made in Chicago Valentine’s Day Market

What: I’ll be participating in this one day pop-up art market downtown at the iconic Harold Washington Library’s Winter Garden! Put on by the Design Museum of Chicago and Chicago Public Libraries.
When: Saturday, February 7th – 11am-3pm
Where: Harold Washington Library – Winter Garden
How: It is free to attend, no tickets needed. More info can be found here!

Committed Wedding Show
2026-02-15 12:00 - 15:00 | Fairlie, 339 N Bell Ave, Chicago, IL, 60612, United States
Committed Wedding Show

What: This Wedding Show is all about sustainability practices in the wedding and event space, and is hosted by the Sustainable Events Collective. Each vendor at this event is committed to eco-friendly practices within their category. This is an excellent market to attend if you’re looking for ways to reduce the environmental impact of your wedding while also making your big day spectacular! I’ll most likely be painting live at this event:)
When: Sunday, February 15th – 12-3pm
Where: Fairlie Chicago – 339 N Bell Ave
How: Info can be found here, and I have several free tickets to give away, too! If you’d like to snag one, respond to this email and I will add you to the list!!

Grand Rapids Market
2026-03-01 10:00 - 18:00 | Grand Rapids Downtown Market, 435 Ionia Ave SW, Grand Rapids, MI, 49503, United States
Art Print and Patter Pop Up
When: Sunday, March 1st · 10am-6pm
Where: Grand Rapids Downtown Market · 435 Ionia Ave SW, Grand Rapids MI 49503
