Things To Do This Memorial Day Weekend: May 23rd – 26th

Another weekend in May has come and gone. However, this long weekend is one that you certainly must savor. This Memorial Day weekend in Chicago, celebrate the 9th anniversary of Squasht Boutique. Put your taste buds to the test at Mole de Mayo in Pilsen. Bike all 30 miles of infamous Lake Shore Drive—car-free. Celebrate the Chicago born genre of House Music in Millennium Park. These fun events plus more things to do this holiday weekend in Chicago.


Squasht Boutique

Thursday | May 23rd | 5:00 p.m. – 8:00 p.m.

Squasht Boutique | 2556 W Chicago Ave. | Free

Squasht Boutique-Chicago Shopping-Featured on The Haute Seeker
Image | Squasht Boutique

Celebrate the nine year anniversary of Squasht Boutique, the local women’s boutique located in the Ukrainian Village. Grab a friend and shop some fabulous finds, discounted items and more. Oh, and don’t forget the nosh and champagne cocktails by Jo Snow Syrups. More details available on the Facebook page.

Roots Chicago Grand Opening

Thursday – Sunday | May 23rd – 26th | Time Varies

Roots Chicago | 605 N Michigan Ave. | Free

Roots Chicago-Chicago Shopping-Featured on The Haute Seeker
Image | Roots Chicago

Roots Chicago invites you to a long Weekend at The Cabin. The outdoor lifestyle brand opens its first flagship store in Chicago this weekend. To kick off the opening weekend, they will be celebrating with local musicians, stylist, influencers, beverages, shopping of course, and more. For event details, visit the event page here.

Food + Drink: 

Mole De Mayo

Friday – Sunday | May 24th – 26th | 12:00 p.m. – 9:00 p.m.

W. 18th St. and Paulina | Free

Mole de Mayo-chicago festival-featured on The Haute Seeker
Image | Star Events

Mole de Mayo 2019 kicks off this Friday afternoon in Chicago. One of the city’s most highly anticipated festivals of the season, the festival continues to draw thousands of locals and visitors to Chicago’s historic Pilsen neighborhood for a mole showdown. The outdoor festival features local restaurants, an open Mercado/Market, three stages of full of live music, plus lucha libre wrestling. Learn more about this free event taking place this Memorial Day Weekend by visiting the event page.

2019 Mayfestiversary

Friday – Sunday | May 25th – 26th | 12:00 p.m. – 10:00 p.m.

Begyle Brewing | 1800 W Cuyler Ave. | Free

Craft Brew-2019 Mayfestiversary-Featured on The Haute Seeker
Image | Dove Tail Brewery & Begyle Brewing

Two local Chicago craft breweries collide for an epic weekend celebration. Begyle Brewing and Dovetail Brewery celebrate their 3rd annual Mayfestiversary. The two-day festival celebrates spring, the neighborhood, good food, music, and beer. Check out everything from special tappings, to a full list of Chicago food trucks, and music performances by visiting the event page here.


18th Annual Bike the Drive

Sunday | May 26th | 6:00 p.m.

Grant Park | 350 E Monroe St. | Free

18th Annual Bike the Drive-Flyer-featured on The Haute Seeker
Image | Active Transportation Alliance

Bike 30 miles car-free along Lake Shore Drive during the 18th annual Bike the Drive event. The event benefits Active Transportation Alliance which is a non-profit, member-based advocacy organization that works to make bicycling, walking and public transit safe, convenient and fun. To participate in the event, visit the website here.

Arts + Culture:

Outpost Artist Alley – 2019

Friday – Sunday | May 24th – 26th | Time Varies

Outpost Artist Alley | 1636 W 18th St. | Free

Pilsen Outpost-artist alley-featured on The Haute Seeker
Image | Pilsen Outpost

Discover emerging artists this weekend in Pilsen. The lively arts and culture hub on the Southwest Side of the city is home to Outpost Artist Alley. The 2nd annual event is dedicated to showcasing and sharing the original artwork of artisan vendors. The event will also feature musicians and businesses located in the Pilsen neighborhood. Support local artists this weekend. For more details on this event visit the website.

The Chicago House Music Conference and Festival

Thursday – Sunday | May 23rd – 25th | Time Varies

Millenium Park | 201 E Randolph St. | Free

House Music Festival-Chicago DCASE-featured on The Haute Seeker
Image | House Music Festival by Chicago DCASE

The House Music festival is an event that kicks off this week in Millennium Park. The House Music Festival festival celebrates the Chicago born genre and features an industry gathering, DJs and live performances, all showcasing the various sounds and styles of house music. Admission is free to both the festival and conference. For more details on this event, visit the website.

The festivals don’t end with just this weekend guide, be sure to check out The Ultimate Festival Guide for more fun things to do this summer!

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