What to Wear in Chicago in Spring

One of the most common questions asked by tourists coming to Chicago is what to pack. While the answer for winter visitors is easier (pack what you’d want to wear in Siberia, because February in Chicago can feel like it), in spring it’s a little more complicated – namely due to the wildly fluctuating weather.

If you can, check the weather forecast the day before you leave, and adjust your packing accordingly. If not, plan on bringing lots of layers. You basically need to be prepared for anything from 80-40 degrees and from sunny and humid to grey and rainy..or even snowy. Here’s how.


touristsIn Chicago, layers are your best friend. If you have no idea what the weather will bring on a given day, I suggest ladies wear  jeans, a tank top or t-shirt with a sweater or cardigan over it, a scarf around the neck, and a medium-weight jacket (a trench coat is perfect), with a large purse (stocked with hat, gloves, sunglasses and umbrella). As you need to peel off the layers, you can carry them in the bag.

For men, jeans with a t-shirt underneath a long-sleeve Oxford shirt with either a light jacket or wool sweater will usually work.

These outfits also work well if you aren’t sure what you’ll be doing that day. They’re casual enough for bumming around but nice enough to be appropriate for museums and most restaurants.

If the forecast calls for warmer days, ladies can bring dresses and skirts. Wear them flipflops, or with a cardigan and jacket, tights and boots if the temperatures drop.


Chicago is a stylish city, though because most people are very active, you’ll often seen people in workout gear and tennis shoes on the street. For walking around sightseeing during the day, there’s no shame in wearing comfortable shoes like sneakers, jeans, and casual tops like t-shirts and sweatshirts. If you plan on dining out at night though, be prepared to step it up a notch. If you’re not comfortable in heels (for ladies) and loafers (for guys) and aren’t going anywhere fancy, you’ll blend in if you wear cute ballet flats (for ladies) or trendy sneakers like converse, or even flip flops (for guys).

On colder days, many women wear knee-high boots – either with tights and dresses/skirts or tucked into skinny pants – and on rainy days, wellie boots are popular.

Dressing up

dinnerMost Chicagoans dress more trendy than fancy, meaning that at most mid-range restaurants, bars and nightclubs, you’ll see fashionable tops worn with jeans or casual but chic dresses paired with flats, heels, or boots. Guys out on the town most often wear clever t-shirts and jeans (at more casual spots) or dark color trousers with button-front shirts.

At all but the swankiest of restaurants, you’ll won’t be required to wear a tie or suit, but you won’t necessarily be overdressed if you wear one. My general rule is that if I expect to spend more than $150 for dinner for two, I’m going to dress up a bit. More than $200, and I want the night to be an event – which means a dress, fancy heels, and sparkly jewelry for me, and a suit for my husband. Though it’s a uniform not required by the restaurant (and in fact, I’ve seen people in jeans at the most expensive places), I don’t feel out of place.

How to minimize your luggage

For a spring weekend in Chicago, there’s no reason why you’d need to bring more than a carry-on bag worth of clothing. If you don’t know what the weather has in store, I suggest packing according to your plans. If you’re just here to sight-see and you don’t intend to go out at night or eat at anything but the most casual places, ladies can just bring 1-2 pairs of jeans, one casual skirt, one pair of tights and boots, sneakers, flip flops, a scarf/wrap, 2-3 cardigans or sweaters, a light coat, and a handful of t-shirts.

If you do plan on hitting the town or want to be prepared for more options, add 1-2 dresses (either one fancier and one more casual, or two that could be dressed up or down with accessories). Throw in a pair of heels, one trendier top, and make sure that one of your pairs of jeans is a little more chic and you’re set. Just be sure to bring some accessories that can help you dress up or down, and use a small clutch as your wallet (so you can take it out and use it as a purse when you are dressed up). Men, add in loafers and a suit – or even just a nice pair of dark pants and a shirt without the jacket – and you’ll be prepared for anything.

Photos by (nutmeg), B*2