Ryan’s Chicago Birthday Weekend

When: Thursday May 21, 2026 to Monday May 25, 2026

Where: Chicago, IL (The Windy City, Chi-Town, Urbs in Horto, City of Big Shoulders, Fresh Coast)

Contact Ryan: 617.640.0232

Itinerary

THURSDAY, MAY 21

• Arrivals and Check-Ins

• Afternoon- Welcome Happy Hour

  • Edgewater/ Andersonville Bars

FRIDAY, MAY 22

• 09:30 am - Chicago Architecture Center River Tour (Boat leaves by 10; Ryan has tickets for you)

  • The dock is located on the Riverwalk just East of the DuSable Bridge (Michigan Avenue) at the bottom of the stairs. Look for the black awning on the northeast corner of Michigan and Wacker. You can use 112 E. Wacker for a GPS locator.

• Afternoon - Explore Chicago on your own

• Evening - Friday night in Andersonville

SATURDAY, MAY 23

• Morning and Afternoon

  • Explore Chicago on your own

  • Some suggestions

    • Check out the Field Museum and the debuting Pokemon Fossil exhibit

    • The Cubs play the Astros at 1:20pm at Wrigley Field

    • Visit Hollywood Gay Beach

      • Ryan has towels, sunscreens, coolers, coozies, etc you can use.

    • Lincoln Park Zoo

    • Lincoln Park Conservatory (free but reservation needed)

    • Ravenswood Spring Vintage and Artisan Fest

    • Bears at the Baths - Steamworks

• Evening - Big Birthday Party

  • Where: Sweethearts Bar; Lonesome Rose Andersonville (https://www.sweetheartschicago.com/)

    5310 N Clark Ave, Chicago

  • When: 6:00pm - 9:00pm

  • Dress Code: Nice, but not dressy; Summer fun

  • Menu

    • Starters

      • Chips & Salsa

      • Guacamole (vegetarian)

      • Chile Con Queso (vegetarian and vegan options)

      • Truck Stop Nachos (vegetarian)

      • Ranch-Hand Salad (vegetarian)

    • Taco Bar (Corn Tortillas, Onion, Cilantro, Limes, and Chef’s Choice of Garnishes)

      • Carnitas, Chicken, Tinga de Garbanzo (vegetarian)

    • Sides

      • Roasted Corn off the Cob

      • Black Beans

    • Sweets

      • Birthday Cake

• 9:00pm - POP’d! Disco Dancefloor Divas at Meeting House Tavern

SUNDAY, MAY 24

• 11:00am - 12:30pm - Stop by for snacks (TBD - maybe Ryan’s Apartment)

• 12:00pm-8:00pm - Belly Up Afternoon (Jackhammer) (https://2bearstaverngroup.ticketspice.com/belly-up-afternoon-iml)

  • Note: I would not recommend planning to come to Belly Up if you do not identify as a gay guy. It may be more scandalous/ sweaty/ overwhelming sensorily that you’d like for a normal Sunday afternoon

SUNDAY, MAY 24

• Most people will be departing, but there will be activities if anyone is sticking around!