Chicago vacation outfits

Discover Pinterest’s best ideas and inspiration for Chicago vacation outfits. Get inspired and try out new things.
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Chicago in September: Travel Tips | Chicago vacation, Chicago vacation outfits, Chicago travel

Visiting Chicago in September? Read our visiting tips from a local: Weather insights, what to wear (outfit guide, packing list), crowds, and the best things to do!

How to Spend 3 Days in Chicago | Chicago summer outfit, Chicago outfit, Chicago summer

I just recently traveled to Chicago, Illinois! I have always wanted to visit the Windy City (in the summer, because who likes -30-degree temperatures and many feet of snow?) but I have not gotten the chance until now! I brought the sunshine and warm weather with me from New York for my week in Chi-Town. Thursday 5/23 I walked eight miles my first day in Chi-Town. I saw it all! We started off at the River Walk, a brand new beautifully landscaped and designed seating and bar space along the…

My Packing List for a Quick Chicago Trip - What to Pack for a Spring Trip | Chicago outfit, Chicago travel outfits, Chicago vacation outfits

Last weekend I took a trip to Chicago with some friends, and although it might be late in the season for a "What to Pack for a Spring Trip" type of post, I thought it might be fun to share it anyway!

Chicago in August – Summer Outfits, Packing Tips, and Itinerary Ideas in 2025 | Chicago travel outfits, Chicago summer outfit, Chicago fashion summer

Planning a summer trip to Chicago? Discover what to wear in August with this seasonal guide to summer outfits, smart packing tips, and top things to do. Whether you’re exploring the Riverwalk, Millennium Park, or a festival by the lake, this guide helps you build your itinerary with must-see attractions and weather-ready style essentials.

Chicago in July: Visiting Tips | Chicago travel, Chicago vacation, Chicago summer

Visiting Chicago in July? Check out our complete guide with essential tips from a local: What to wear in July (outfit tips), how to avoid the summer crowds, the best things to do, and many more Chicago travel tips for July.

20 Baddie Summer Outfits You Can't Miss in 2025 | Casual summer outfits, Top summer outfits, Summer brunch outfit

Get ready to turn heads with these stunning baddie summer looks. Save these outfit ideas for endless style inspiration all season! 💁‍♀️🌟

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