Packing for a Chicago Summer

Photo: Marc Furlong

Photo: Marc Furlong

Summer wedding season is in full swing, and it was a wedding in the ‘burbs of Chicago on a hot Friday in July that gave my husband and me a genuine excuse to spend the week in the city prior to the event. This way, we were able to catch the festivities of the Fourth, enjoy city strolls along shady, brownstone-lined streets and even catch a baseball game.

I’m a classic over-packer, and for this particular trip I was also a gnarly procrastinator. While this is okay for a quick weekend away, it didn’t work out too well for a week in Chicago where the weather changes hour to hour and on any given day you may deal with rainfall, sticky humidity, cool nights—and in all of this you’re trekking all over the city on foot. In an attempt to learn from my mistakes and successes this past week, here’s a few packing tips for heading to the Midwest.

1. Bring a jacket!

Via Pinterest

Via Pinterest

Don’t let the nice weather wherever you are—even in Chicago—fool you. You must bring a jacket, preferably water resistant, with you. When the weather changes so fast, you don’t want to be stuck out in the rain, literally. I find that packing a rain coat that I can roll up or scrunch into a ball inside my purse works great.

2. And with a jacket, comes an umbrella

ShedRainCompact Umbrella - Solid Colors

And umbrella is also a must, like this ShedRain compact umbrella. It fits easily in a purse or backpack, and it comes in numerous bright and fun colors.

3. Leave your heels at home

Image via Pinterest

Image via Pinterest

This is a tough decision, but you’re wasting a lot of space if you even attempt to pack heels for a trip to Chicago, or really any city or vacation where you think you’ll spend a majority of your time on foot. Think flats, flip flops, wedges and sneakers. Your feet will thank you.

4. Leave your hotel with everything you need

MICHAEL Michael KorsDevon Large Shoulder Tote

I love bringing a big bag on any trip, something like this Michael Kors tote. This way, I have room to take maps with me, a kindle or iPad, make-up, my umbrella and more. Bringing a large bag around the city gives you the freedom to take with you anything that you think you may need along the way.

5. Sunscreen


Sure, all the talk of rain and a jacket may leave you thinking that it was a dreary week in Chicago. Quite the opposite! Despite the occasional storm, the sun made an appearance daily. Just because you’re not at the beach doesn’t mean that you shouldn’t cover up. I’m a sunscreen junkie. If you can’t make room to pack the sunscreen with you on your flight due to those annoying liquid restrictions then buy some cheap sunscreen when you get to your destination.

6. Layer it up


Pack a lot of light layers—thin sweaters, tanks, long-sleeve tees. Strip down or layer up depending on how hot or cold you are, but this way at least you’ll be comfortable.


Joanna Brinjak Furlong is the marketing manager at She loves to travel and is a self-proclaimed foodie and wine aficionado. When she’s not in the office or dreaming of her next trip, Joanna can be found hiking in Los Angeles’ hills, whipping up a homemade meal or hitting a pilates class.

Written by Joanna Furlong


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