You know how obsessed I am with creating packing lists so it’s high time for a new one – this time it’s a Chicago packing list for a winter weekend. If you follow me on Instagram, you already know that my husband Craig, our daughter Aubrey and I took a post holiday trip to Chicago last week with one goal in mind…eating! Therefore, we didn’t really think about the fact that we were scheduling our trip during one of the coldest times of the year to visit. Boy were our Texas acclimated bodies in store for a shock!
You ladies in cold climates already know this but let’s just say that what to wear in Chicago in winter can be summed up in one word: LAYERS!
On the day of our arrival, the high was 9 degrees with a wind chill of -15. Heat wave! After checking our forecast for the week, I packed up a few of the pieces from the Winter 2017 GYPO Style Challenge to create a mini capsule wardrobe for our four day weekend in Chicago.
Although this post isn’t about what to do in Chicago, let me recommend the following: The Art Institute of Chicago, Portillo’s for Italian Roast Beef and Chicago dogs, Sky Deck (go out on the platform, I dare you!), the Lincoln Park Zoo (it’s empty on a cold day!), Second City (world class improv, one of our favorite things we did), Museum of Science and Industry (fun and interactive) and of course shopping on the Magnificent Mile.
Aubrey and me chillin’ (literally) in Chicago!
That smile is actually a look of terror! I HATE heights, hate, hate, hate, loathe entirely. One of my 2018 goals is to feel the fear and do it anyway, so, thanks Sky Deck, mission accomplished!
The frozen tundra a.k.a. Lake Michigan.
A fun night of improv at Second City.
20 Piece Chicago Packing List – Winter Weekend
This 20 piece Chicago packing list will give you plenty of dress up/dress down options that will work for everything from a walking tour of the city to dinner and drinks out. In addition to these 20 pieces, I also brought a work out outfit (wishful thinking – that didn’t happen!), two pairs of pajamas and of course, bras and undies.
Tip: Pin this post for future reference. It’s a great packing list for any cold weather destination!
1. Tunic Sweater (any solid color)
3. Gray Sweater
5. Gray Jeans
7. Black Parka
10. Plaid Blanket Scarf (coordinate with tunic sweater)
11. Faux Fur Scarf
13. Pom Pom Beanie
16. Cross Body Purse
17. Pendant Necklace
19. Wool Socks
20. Leggings or Tights (for layering)
Mix and Match Outfits
Each sweater is styled two different ways for a total of six outfits – one version for comfortably (and warmly) touring the city, the other version is dressier and appropriate for going out to dinner.
Parka + Gray Sweater + Layering Top + Blanket Scarf + Gray Jeans + Tights + Black Boots
Wool Coat + Gray Sweater + Layering Top + Fur Scarf + Leggings + Necklace + Leopard Boots
If you liked this Chicago packing list but missed out on signing up for the Winter 2017 GYPO Style Challenge, have no fear, we’re getting ready for round 2 of styling our 31 days of winter outfits and it’s now ON SALE for just $29! Let me be your personal stylist for the remainder of winter. You’ll get a shopping list of winter trends and classics (including all the pieces in this post) plus a new outfit idea in your inbox every day for 31 days. Learn more and sign up HERE.
I Feel Pretty Link Up
It’s the day of the week at GYPO where we celebrate what makes us feel pretty. Whether it’s a new outfit, hairstyle, or makeup, the I Feel Pretty link up is about anything and everything that makes your life prettier. Even if you’re not a blogger, you can still play along. Just tell me what made you feel pretty this week in the comments.