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International Mr. Leather (IML) Chicago 2027

Memorial Day contest weekend, Congress Plaza Hotel headquarters, and private brotherhood sanctuary.

📍 Destination: Chicago, Illinois

📅 Dates: May 27 - June 01, 2027

👥 Capacity: 18 Mature Men

💰 All-Inclusive: $3,650

The Experience Overview

International Mr. Leather (IML) in Chicago in 2027 takes place over Memorial Day weekend from May 27 to June 1, 2027 (with the main weekend events running May 29 – June 2, and Memorial Day itself on Monday, May 31, 2027). Stay in our reserved block at the official host hotel, Congress Plaza Hotel (520 S Michigan Ave), with reserved contest seating, access to the annual Leather Market, official club takeovers, and curated wellness recovery.

What Is Included:

5 nights at official host hotel Congress Plaza Hotel (520 S Michigan Ave); Reserved premier IML Contest tickets; Official International Leather Market pass; Private curator tour of Leather Archives & Museum; Curated cohort dinners and daily recovery sessions.

Dress Code & Gear Notes:

Full dress leather, boots, vests, and club colors. Formal leather elegance requested for contest evening.

Investment & Reservation

Total Voyage Investment

Cohort: 16 spots open

All-Inclusive Voyage Investment

$3,650

Deposit required to secure space: $750

Duration 7 Days / 6 Nights

Target Cohort Men 40, 50, 60+

Cohort Capacity 18 Mature Men

Wellness Focus Sensory Retreat & Longevity

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Available Add-Ons & Upgrades

Master Leather Polishing & Conditioning Service +$150

Black & Blue Ball / House of Leather VIP Chauffeur Transfer +$220

Day-by-Day Journey

Voyage Itinerary

👁️ General Itinerary (Public View)

Day 1 (May 27): Arrival & Host Hotel Welcome at Congress Plaza Hotel

⏰ 16:00 - 22:00

Check into our reserved floor at the historic Congress Plaza Hotel (520 S Michigan Ave). Join the LLL brotherhood for a private welcome toast and gear unboxing.

Day 2 (May 28): Private Tour of Leather Archives & Museum + Lakefront Mobility

⏰ 09:30 - 16:00

Explore the world’s premier repository of leather and kink history, followed by an afternoon mobility walk along Lake Michigan.

Day 3 (May 29): International Leather Market & Contest Preliminaries

⏰ 11:00 - 23:00

The main contest weekend begins. Shop hundreds of master artisans at the Leather Market and attend the IML Contest preliminary judging rounds.

Day 4 (May 30): IML Contest Finals & Black and Blue Ball / House of Leather

⏰ 17:00 - Late

The centerpiece of Memorial Day weekend: the crowning of the 49th International Mr. Leather, followed by legendary late-night parties.

Day 5 (May 31 - Memorial Day): Victory Brotherhood Banquet & Decompression

⏰ 18:00 - 22:00

Celebrate the newly crowned titleholders and reflect on the weekend with our private celebratory steakhouse dinner in downtown Chicago.

The Brotherhood Cohort