What to Wear in Chicago in Summer

chisummerPacking for a trip to Chicago can be challenging, and while it’s much easier for a summer trip than for a visit in the spring, it can still be difficult to cover all your bases, especially if you only want to bring a single carry-on bag.

Weather in Chicago in summer doesn’t fluctuate as wildly as it does in spring and fall, but there can still be a large variance in temperatures over the course of your visit and you’ll want to pack for a few contingencies.

If you can, check the weather forecast the day before you leave, and adjust your packing for the forecast, plus a swing of about 10-15 degrees in either direction. This means if the forecast calls for days of 75 degrees, expect that it could be as cold as 60 or as hot as 90.  It’s been known to be nearly 100 degrees in October…and likewise, it’s been below 50 degrees in July before as well. Chicago summer also brings thunderstorms, so be sure to bring an umbrella or raincoat.

Chicago style

As in other seasons, in summer, layers are your best friend. Even on hot days, it can get cold indoors – where AC is set to nearly Arctic levels – and a cool breeze often kicks up along the lakefront and in early morning/late evening.

For an outfit than can take you from day to night, no matter what the weather, I suggest jeans or khaki pants and t-shirts for men, and dresses (with a cardigan in your purse) for ladies. Shorts are popular options for both men and women in the summer; capri pants are a nice compromise for women.

During the hottest days of summer, and especially at the many summer weekend festivals, comfort rules. For walking around sightseeing during the day, go with sneakers or flip-flops. At night, dress it up a bit with nice shoes, like loafers for men or strappy sandals, ballet flats or heels for women.

Summer style in Chicago is pretty casual but trendy, but if you plan on going to a nicer restaurant or for a romantic night out, you’ll want to dress up a bit more. Men can get by with a button-up Oxford shirt and khakis, trousers, or even nice dark jeans with loafers; a suit and tie isn’t required except at a small handful of places. A simple dress, some heeled sandals, and a wrap (for when it gets cooler) is a great summer ensemble for women.


For a long weekend, I suggest ladies bring 1 pair of jeans, 1 pair of shorts or capri pants, 1 casual skirt, 2-3 tank tops or t-shirts, 1 dressier shirt, 2 cardigans, and 1-2 dresses that can be dressed up or down. For footwear, a pair of sneakers, a pair of flipflops, and a pair of heels or nicer sandals will cover all bases.

For men, 1 pair each of jeans, khakis, shorts, and trousers, 1 pair each of flipflops, sneakers, and loafers, 1 button-up shirt, 1 hoodie sweatshirt, and 3-4 t-shirts will keep you clothed for any situation.

Photo by xispo