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Chicago, The Windy City, houses a unique artistic culture, a bustling business capital and a remarkable dining scene. This makes for a fantastic 3-day weekend travel destination. Chicago is beautiful in the Fall and a wonderful spot for November travel. It is no secret that it can get cold in Chicago, so when traveling in November, the earlier in the month, typically the better, in terms of pleasant weather. Expect high temperatures in the 60s and low temperatures in the 40s. As the month goes on, it does get notably cooler, so to enjoy the moderate Fall temperatures, aim for travel early in November.
Deep dish pizza and Chicago-style hot dogs are obviously two of our favorite things about Chicago. Along with checking our reflections in “The Bean” at Millennium Park and sightseeing across the city at the plethora of free museums, Chicago offers a number of unique experiences for you to plan for when you take long weekend trip. Enjoy the city, eat well and look fabulous!
Shop the Chicago Vacation Wardrobe
Outerwear
Cool outerwear is a must for a Chicago vacation. To create a travel wardrobe with some edge, we chose a gorgeous leather blazer from BALMAIN to help you stand out and stay warm in The Windy City.
BALMAIN Double-Breasted Leather Blazer; $2,942
Tops
To allow for simplified mixing and matching, we chose comfortable tops in basic colors and materials. Pair them with pants of the same color for a monochromatic look, swap the pants, or wear them over the slip dress. Easy to pair and easy to wear – this is why we chose them.
Haider Ackermann Slim Fit Tank Top; $202
FRAME Le Mid V-neck Cotton T-shirt; $96
Pants
To ensure maximum versatility and comfort, we chose 2 easy-to-style pants – a pair of fitted black leather leggings and a pair of relaxed denim pants in a soft gray color. These pants can easily be matched with the tops we have selected. The black leather leggings would be a fantastic match with the nude slip dress.
Helmut Lang Stretch-Leather Leggings; $920
Dsquared2 Distressed Boyfriend Jeans; $555
Slip Dress
This nude slip dress is the perfect piece for a night out in Chicago. Top it with the leather blazer from BALMAIN and pair it with sexy black and gold heels for a look that is effortlessly fashion-forward.
Raey Deep-V Silk Slip Dress; $190* It’s On Sale Now For $114!
Shoes
Strappy sandals, sexy pumps and edgy on-trend stilettos are must-packs for a weekend in Chicago. Our selections are incredibly versatile and easy to match. Create a monochromatic gray look with sex appeal when you pair the basic grey t-shirt with Dsquared2’s grey jeans and Saint Laurent’s nude pumps – so simple, so sexy.
Maison Ernest Glamour pumps; $494
Aldo Amilmathien Snake Print Stiletto Heel Ankle Boots; $110
Saint Laurent Zoe Patent-Leather Pumps; $625
Accessories
Flashy gold jewelry with edgy details, a bright red bandana scarf and cool cateye sunglasses are perfectly packable accessories for a long weekend in Chicago. Wear one alone as a statement piece or pair them all together for a showstopping look.
Aurelie Bidermann Tangerine Ring; $221
Saint Laurent Bandana Print Scarf; $795
Wouters & Hendrix Gold 18kt Yellow Gold ‘Crow’s Claw’ Earrings; $1,507
Gentle Monster Mad Crush B4 Sunglasses; $281
Bags and Luggage
Black bags easily pair with anything, so we chose two that should suit your needs through the weekend. Load your luggage in an uber-chic carry-on from GLOBE-TROTTER, and pack a sexy black clutch for this trip to Chicago. A basic black one, like our selection from Jimmy Choo works well with this Chicago wardrobe, no matter how you style your look.
Jimmy Choo Celeste Clutch; $1,395
Globe-Trotter Centenary 20″ Cabin Suitcase; $1,440
Long weekends are perfect for getting away from everyday life. They are fun little escapes, and Chicago always seems to provide the perfect break.
Safe travels! xo, The OFT Style Guide
