A weekend in Chicago always feels like an excuse to overpack, but these are my tried-and-true travel must-haves. My Away suitcase fits everything, and I like to have the right mix of joggers, denim, and a Rails dress for date night. I also bring a few different bags for every occasion. Linking everything here for you! LTKStyleTip LTKOver40 LTKTravel

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All Night Festival Bag *Micro 2L | Women's Bags,Purses,Wallets | lululemon | Lululemon (US)
Kari Mini Dress | Evereve
Dolce Vita Women's Raj Knee High Boot, Dark Brown, 9 Wide | Amazon (US)
Venice High Rise Jogger | Athleta
Sutton Sweatshirt | Evereve
UEU Women Oversized Striped Crewneck Sweatshirt Long Sleeve Color Block Pullover Tops Casual Loos... | Amazon (US)
Shop The Bigger Carry-On suitcase in Coast Blue | Away: Built for modern travel | Away
Travel Kit | Vuori Clothing (US & Canada)
Everywhere Backpack 22L | Lululemon (US)
Parker Long Short | Evereve
Parker Long Short | Evereve
Anessa 31` | Evereve
Ladder Lace Trim Blouse | Evereve
Ellisa Sleeveless Sweater | Evereve
Nolita 19 In Signature Canvas | Coach (US)
327 Sneaker | Evereve
CeCe Stripe Open Stitch Sweater Vest in Classic Navy at Nordstrom, Size Xx-Small | Nordstrom
AE Dreamy Drape Stretch Super High-Waisted Baggy Wide-Leg Jean | American Eagle Outfitters (US & CA)
Good Legs Straight | Evereve
Melanie Belt | Evereve