Through our research into Chicago weddings and conversations with planners across the city, we've learned that choosing from the diverse selection of wedding venues in Chicago means understanding the trade-offs between lakefront locations with stunning views, historic downtown spaces with architectural character, and neighborhood gems in areas like Wicker Park or West Loop. Chicago offers everything from classic hotel ballrooms to converted industrial lofts to outdoor spaces along Lake Michigan - but each comes with specific considerations around weather backup plans, parking logistics, and seasonal timing. Daniel Kim, a planner who's coordinated over 250 Chicago weddings, told us that couples often choose venues based on beautiful summer day tours without fully considering what that same space feels like during unpredictable spring weather or how winter conditions affect guest comfort and access.