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)