Packing for a trip to Chicago

Can anybody humor me and tell me what to pack for a short weekend in Chicago? The plan includes two nice dinners and a matinee of Hamilton. Weather is projected to be in the 60's day, 50's night. It's a girls' weekend type of event. I am swamped by work and can't even think what to pack. Also, it has been in the 80's and 90 percent humidity all month where I live, which probably clouds my thinking further.

Some random finds of things from my closet are below. Feel free to ignore the finds and opine freely. I suppose I need two plane outfits, one dinner outfit, one play/dinner outfit, and one bopping-around-in-the-morning-before-play-and-dinner-outfit.

P.S. This is a type of thing I am really bad at.

Weather forecast:
https://weather.com/weather/tenday/l/USIL0225:1:US

ETA: added some more finds

Custom Find

by Scarlet

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Bloomingdale's

BASLER Roll-Sleeve Anorak

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Nordstrom

CeCe Scalloped Hem Shift Dress

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Bloomingdale's

BASLER Fitted Sheath Dress

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Custom Find

by Scarlet

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Bloomingdale's

BASLER Leaf-Print Sheath Dress

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Boden

Tresco Stripe Jumper

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Bloomingdale's

BASLER Studded Jeans

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Bloomingdale's

BASLER Eyelet Sleeve Tee

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Nordstrom

Rag & Bone / Jean The Dre Slim Fit Boyfriend Jeans

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Gap

Camo floral fringe scarf

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Nordstrom

Superga 'Cotu' Sneaker

$64.95

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Nordstrom

Paul Green Molly Lace-Up Pump

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Nordstrom

Paul Green Logan Bootie

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Zappos

Onitsuka Tiger by Asics Mexico 66

$85.00

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Amazon

The North Face The North Face Dipsea 78 Racer Sneaker Women's

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Yoox

Furla Handbag

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Nordstrom

Rebecca Minkoff Leather Camera Bag with Guitar Strap

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6 years ago

mtnsofthemoon

Veteran

I am by no means an expert but these are some things I have learned from YLF and real life. I spent a extended weekend in Chicago this summer to visit our son who was doing a research internship at UC.

Pack 1 Jacket/ multi use (save space and weight). Do you have something that can work on the plane, evenings and with outfit for the evening dinner/play?

Your shoe choices look great to me. Comfortable, neutral and hit day and evening needs.

I personally wear the same outfit coming and going on a flight.

I would recommend layers if possible for a) the plane and b) day and evening weather possibilities.

the 2 pant selections seem perfect in respect to color and wearing more than once. I would suggest more tops than bottoms that can mix and match.

the sweater and t-shirt (white one) seem like great options.

Your dresses are so pretty - do you plan on a dress for the dinner/play evening? If you are a color gal I suggest the green print dress as your items for day and touring around may be more neutral?

Hope this is helpful. Sounds like a fantastic girls weekend and I will say I am VERY Jealous you are going to see Hamilton. L.A. prices are out of this world ;-( and out of my reach....I am crushed.

Zibbets

If you're staying downtown, you will see people wearing lots of business professional wear, lots of black, fashionable clothing with good walking shoes. It's still warm there today, but cooling very soon. You will may want a jacket in the evening. Much like NY, you'll see people wearing everything in Chicago, so gear to how dressy your venues are.
Your finds look good. LOVE the red scalloped-hem dress. Olive jeans will be great for daytime.

Have fun and be sure to take a picture at the bean!

3style

Having lived 13 years of my life in Chicago I think that I can be a useful judge. I would recommend either of solid dresses plus a bolder accessory. I'm a floral print gal but I wouldn't ever wear it to the theater in Chicago for fear of looking like a tourist. Also, white sneakers are considered commuting shoes and aren't really worn as a fashion statement by anyone over twenty. Streets can have dirt or mud pretty readily if it rains in the summer, so I would suggest black or other darker heels. Basically, people other than college students will be dressed like it is nearly October, even if it is warmer than usual. Go for the longer of the jackets. The wind can be gusty even in the fall. The white top and sweater honestly read more New England than Chicago. The basic look that will blend in is more along the lines of Eileen Fisher. So simpler and bolder. Either pant option is okay, but you might want something more trouser like and less denim if you are planning to go to dinner in pants rather than a dress. Hope this helps.

Scarlet

Mtnsofthemoon, thank you for this well-thought out response. It helped focus my thinking right away. I am nervous about being away from my kids, but SO excited to see Hamilton. I had totally discounted the possibility in New York. It should be affordable to everybody, shouldn't it.

Zibbets and 3Style, fascinating! I hadn't considered how Chicago will have its own style. I am excited to see it. I will investigate some darker options of things I have, although my wardrobe is pretty limited at the moment. I have a pair of dress slacks, which might be a nice break from the dress if I can identify a good topper. Also for daytime footwear I can try my ankle boots. I nearly forgot I have any in this unending summer we are having. And I forgot about the wind in the Windy City, ha! Good reminder that I might feel cooler than I anticipated.

BASLER Slim Ankle Trousers - 100% Exclusive

AGL Block Heel Pump

Kate Spade New York inked texture oblong twill scarf

Tilly V-Neck Sweater

Jeanie

Layers are the best advice I can give. I like the pants/sweater and scarf combos you have above. Not sure what you are doing in the days. Whenever we go to Chicago we stay downtown and shop all day then go out in the evening. It can start out cool in the morning but as you walk and shop you can warm up and want to peel off some layers. For shopping I like jeans, tshirts or sweater and scarf with a jacket over. Loafers or fashion sneakers for all the walking. You can take the scarf off and tie it on your purse when it warms up. Dresses and slacks are great for going out. It can get really cool at night if the wind kicks up. It's so fun to go the theatre and dress up so wear what makes you happy. I like your red dress. Sounds like it will be such a fun weekend! It's always hard to leave the kids but is good for the soul.

DonnaF

Just lost my post! My DD lives in CHI and complains that it is in the 60s one day and in the 80s the next and that she can't always depend on the weather forecasts. I would check them until and on the day you leave. She said it was well into the 70s on the evening of her birthday (11/14) a couple of years ago -- so there's temperature averages and then what you will really experience.

We're going to CHI in November to see her and HAMILTON!!! on her birthday. The cost of our two roundtrip airline tix is less than the three Hamilton tix -- but still way less than what we would have to pay in San Francisco. I planned to pack all cold weather clothing and layer up but now am wondering if I should also pack a few flimsy weight items so I don't swelter to death.

Jeanie, yes good reminder to layer. It's hard to remember how after this long summer. Thanks for spelling out how you do it.

I am thinking red dress for fancier dinner, and some version of slacks for theater and fancyish dinner.

I wish I could wear my trench instead of the parka, but it's a little small right now.

DonnaF, Thank you for persevering with your post! The weather forecast does indeed look frenetic. I would have thought November in Chicago is reliably chilly. Go figure.

I'll try to post what worked or didn't work, unless it's too embarrassing I have to throw something together.

Going to check Angie's plane outfits for inspiration.

JAileen

I don't have any advice whatsoever, but I wish I were visiting Chicago! Have a good time!

Angie

(website)

Fashion Stylist

Sounds like you're sorted. Looking fab. Have a great trip. Much love to you.

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