The Weekender: Chicago Edition

Liz Doupnik
The Weekender: Chicago Edition
9 Start slideshow

This weekend, we’re gearing up to scoot out of the city and hit up the windy city, Chicago. Though it’s our first time visiting, we’re old pros at packing for a weekend away in a hurry.

We’re implementing some of our major packing rules and including versatile dresses, light accessories, and one or two statement items (hey, you can never be too careful!). With a city that offers so much to do – and in so little time – we’re bringing along pieces that can easily transition from the plane to evening plans.

We’re definitely going to try to check out the beach and bringing along a basic bikini that can be layered under a simple sundress. Read on to see what else we’re bringing with us!

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Heading out of town this weekend? We know we are. Check out what we're bringing with us for a weekend in Chicago.

Photo: Zoltan Tombor, Grazia Italy/

Traveling light is never easy. Try donning a comfortable midi-length cotton dress that with a simple change of shoes will take you from the airport to the night club.

Tank Midi Dress, $58, at Topshop

Lugging around a laptop, book and other plane necessities can get cumbersome. We suggest a colorful tote that will add an extra punch even when you reach your destination.

Vivienne Westwood Ethical Fashion Africa, $245, at Yoox

We plan on exploring this weekend. Forget wearing heels, we want to enjoy our adventure! Update a classic flat with a floral option, they spruce up even the most basic of outfits.

Brooklynn White Shoe, $55.20, at Bass Shoes

Keep accessories simple -- who wants to haul all your goodies around with you for just a weekend, honestly?

DANNIJO Elsa Ring, $70, at Revolve Clothing

We love versatile (and lightweight) little dresses taking us from daytime fun to a relaxing dinner.

Linen Sun Dress, $70, at American Apparel

We love large-framed sunglasses for our travels. We feel like we're in an old movie!

Burberry BE4066, $230, at Sunglasses Hut

Throw a wedge in your bag -- you'll feel extra festive and ready for a night out on the town.

Jeffrey Campbell Interest Wood Wedge, $200, at Urban Outfitters

We totally plan on checking out the beaches in Chicago and are throwing one of our favorite bikinis into our bag.

The Abbie Triangle Top, $22, at Victoria's Secret

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