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
(More Details Coming Soon!)
THURSDAY, MAY 21
Arrivals and Check-Ins
Afternoon- Welcome Happy Hour
Edgewater/ Andersonville Bars
FRIDAY, MAY 22
10:00am - Chicago Architecture Center River Tour (Optional)
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
Evening - Friday night in Andersonville
SATURDAY, MAY 23
Morning
Check out the Field Museum
Evening - Dinner and Drinks
Where: Sweethearts Bar; Lonesome Rose Andersonville (https://www.sweetheartschicago.com/)
5310 N Clark Ave, Chicago
When: 6:00pm - 9:00pm
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
Garlic Rice
Sweets
Churros
Birthday Cake
SUNDAY, MAY 24
11:00am - 12:30pm - Stop by for lunch (Pizza Lobo Andersonville)
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