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July 19, 2025
Chicago, IL

Madeleine & Rob

Things To Do

There's no better time and place than summer in Chicago. Some of our favorite things to do are listed below! For any restaurant recommendations, please reach out to Rob!
Riverwalk

Riverwalk

11 E Riverwalk South, Chicago, IL 60601

Take a stroll along the Chicago river and grab a coffee, wine or beer at one of the many restaurants. Stop by City Winery on the Riverwalk and enjoy the same views our families did during the moment Madeleine said "yes"!

Chicago's First Lady

Chicago's First Lady

112 East Wacker Drive, Chicago, IL 60601

Experience the city’s legendary architecture from the best seat in the house—the river. Bar, snacks, and restrooms on board. Lori Gialessas' favorite activity when her sons aren't being accommodating with their boat, which (Rob swears) happens rarely.

Lakefront Trail and Oak Street Beach

Lakefront Trail and Oak Street Beach

Chicago, IL

Walk off your Saturday morning hangover on the Lakefront Trail, but be weary of Rob's brother and brother-in-law biking recklessly on the path. Access to the Lakefront Trail are at Oak Street, Division Street, and North Avenue. Walk east until you see the large body of water! Or enjoy the afternoon at Oak Street Beach, one of Chicago's many beaches (yes, beaches exist on lakes for all the coastal elites).

Lincoln Park Farmer's Market

Lincoln Park Farmer's Market

1817 North Clark Street, Chicago, IL 60614

Perfect for a Saturday morning stroll to enjoy one of Chicago's best parks. The Division Street Farmer's Market is a closer, albeit smaller alternative in the area.

Visit Wrigley Field for a Cubs Game!

Visit Wrigley Field for a Cubs Game!

1060 West Addison Street, Chicago, IL 60613

Dare to attempt the 1:20 pm start time and make our 5:00 pm ceremony? Could be fun. Could drive us mad. Maybe come in early for Friday's game or stay late for Sunday's?