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The LADIESSTREET Edit

Chicago Formal Event Dresses: Wedding Guest & Black Tie Guide

by LADIESSTREET Style Team 17 Jun 2026

Chicago knows how to dress up — and so should you.

From black tie galas at the Art Institute to wedding receptions at the Drake Hotel, summer garden parties in Lincoln Park to winter formals at Navy Pier — Chicago demands elegant, occasion-appropriate dressing.

Wedding Guest Season

Chicago wedding season runs from May through October, with venues ranging from lakefront ballrooms to West Loop lofts. For wedding guest duty, think elegant maxi dresses, satin midi dresses, and floral floor-length gowns.

Shop: Wedding Guest Maxi Dresses | Evening Maxi Dresses

Black Tie & Galas

For formal galas and black tie events, a sequin maxi dress or an embellished evening gown is the move. Chicago formal style is sophisticated, polished, and timeless.

Shop: Sequin Maxi Dresses | Evening Dresses

Summer Garden Parties

Chicago summers are made for garden parties, rooftop socials, and outdoor celebrations. A floral maxi dress or a satin midi with block heels is perfect for these occasions.

Shop: Floral Maxi Dresses | Satin Midi Dresses

Find your Chicago event look at LADIESSTREET — free US shipping on orders $250+.

Sample Image Gallery

SPRING SUMMER LOOKBOOK

Sample Block Quote

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Sample Paragraph Text

Praesent vestibulum congue tellus at fringilla. Curabitur vitae semper sem, eu convallis est. Cras felis nunc commodo eu convallis vitae interdum non nisl. Maecenas ac est sit amet augue pharetra convallis nec danos dui. Cras suscipit quam et turpis eleifend vitae malesuada magna congue. Damus id ullamcorper neque. Sed vitae mi a mi pretium aliquet ac sed elitos. Pellentesque nulla eros accumsan quis justo at tincidunt lobortis deli denimes, suspendisse vestibulum lectus in lectus volutpate.
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