My Packing List for a Quick Chicago Trip – What to Pack for a Spring Trip

Spring Packing List

A couple weekends ago 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!  Perhaps you’re going somewhere soon where it’s still not that warm, or perhaps you just love looking at curated collections of clothes.  Both apply to me ?, so I figured why not!

Before I get to the clothes, let’s talk through the details of the trip so you can get the context of what I was packing for.


The weather forecast was ALL OVER THE PLACE.  Those of you who live in the area are nodding, “YUP.”  Temps were 60-ish degrees with some rain for some of our time, or 82 with humidity and sunshine, or somewhere between with drizzly patches.  What was more confusing is that the weather app would change everyday, saying it would be 75 and mostly sunny on Thursday (for example) but the next day it’d say Thursday would be 62 and raining.  It was kind of confusing to plan for, so I ended up packing a bit more than I needed.  You all know I hate overpacking, but sometimes it’s just what you’ve gotta do.


Our plans were fairly low-key: relaxing, seeing a few tourist sights (just a few–because most of us had been to Chicago several times before), eating good food, watching Hamilton (!!), and going to a Cubs game.


I was in Chicago for just 4 days, including travel.  We planned to do several activities each day, like visiting the Art Institute during the day, then watching Hamilton at night, or going to a Cubs game one day and a nice dinner that evening.  That required a couple different outfits some days which meant I needed to pack more than 4 outfits worth of clothes for 4 days.


Typically when I travel, I pack my favorites.  I prefer being in clothes and outfits that I know I love and feel comfortable and confident in.  Maybe that sounds weird or boring, but not having to worry about whether my clothes helps me to focus better on the trip itself.

SIZING: I’m 5’6″ and usually S/M or 6 in clothes, 8.5 to 9 in shoes.

Spring Packing List

Shop the Items:
tan striped tee  |  striped peplum tee yellow tee
white knot top  |  olive lace top*
denim jacket  |  utility jacket* |  grey moto jacket*  |  rain jacket*| cardigan
dress  |  jumpsuit  |  jeans* |  black jeans | lightweight sweater
metallic pendant  |  white pendantturquoise pendant* statement necklace
tan cutout earrings  |  white earrings  |  spotted earrings  |  metallic gem earrings
white sneakers*  |  nude heels* |  taupe slides  |  yellow slides

Items marked with a * means it’s a similar item and the exact one I own is no longer available.


Even though there was one fairly hot and humid day, I didn’t pack any shorts because the weather forecast didn’t indicate there would be such a hot day until we were already in Chicago.  Wasn’t too bad though!


  • Comfy Jersey Dress (I wear size XS) – Love the ease and comfort of a jersey dress like this!  You can look pretty dressed up while being really, reallyyyyy comfy.  I was excited to wear my rainbow striped dress, whether as a nice but super comfy option for walking around the Art Institute, or for going out to dinner one night.  But, I wasn’t able to wear it for either as the weather didn’t cooperate.
  • Jumpsuit – Planned to wear this to see Hamilton the way that I styled it recently HERE, but the weather didn’t work out that night.

In the widget below are several VERY COMFY dresses and jumpsuits.  Swipe through to see all the options.


  • Tan/White Striped Tee – I almost always travel in jeans, a striped tee, and a utility jacket.  I wore this on the plane to Chicago.  I wear size M.
  • Colored Tee – Went with my new yellow tee!  Should be no surprise that yellow was my color of choice. ? This is the same tee as the white one I remixed 6 ways last week, just in yellow.
  • Striped Tee – A regular striped tee would have worked, but I opted for this peplum striped tee as a casual but slightly dressier option.  My peplum striped tee is almost sold out (see it HERE–I wear size S), but my current favorite regular striped tee is available HERE.
  • White Knotted Top – Another option that’s casual but a step up from a t-shirt.  Also very comfortable and stretchy, so I knew it’d be good for being out all day exploring the city.
  • Olive Lace Tee* – Option for night out in case it would be too cool to wear my other options
  • Sweater – Brought as a warmer casual option because the forecast said it was going to be chilly and drizzly the day we were at the Cubs game.  Ended up being the hottest day, so I didn’t need this.


Completer Pieces / Jackets:

  • Grey Faux Leather Jacket* – dressier option that could pair with my lace tee, jumpsuit, or rainbow striped dress
  • Denim Jacket (I wear M) – the goes-with-everything completer (except jeans)
  • Utility Jacket* – another goes-with-everything completer
  • Cardigan – In case I needed a cozier option than the jackets.  Never needed it while outdoors, but ended up wearing it indoors while lounging around.
  • Rain Jacket* – Lightweight, easy to store in my tote, and was useful for the intermittent rain through out the weekend.  It even fit over my denim jacket and utility jacket!

I rounded up a few more options in the widget below.  Swipe through to see them all and click to shop.



In retrospect, I was extremely happy I packed my rain jacket, sad I didn’t get to wear the jumpsuit or dress, and wished I’d packed a different pair of shoes for evening, like wedges or closed toe flats.  The evenings we dressed up a bit more were both drizzly, and I felt hesitant doing tons of walking through the city through potentially slippery streets in thinner heels.  Would have felt fine doing that in wedges, though.  But, not a huge deal!

If you want to see any of my other packing posts, click HERE.  You can always find them through the menubar at the top of this blog under “Packing/Travel.”

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