Traveling Light: Essential Packing List for Chicago (in a backpack!)

I was devastated when I saw the forecast for Chicago.

(That’s a bit of an overstatement, but I’m okay with that).

After a few weeks of delightful weather in Charlotte, we were headed North to Chicago, which hadn’t quite gotten the memo that spring had arrived.

Snowflake and raindrop icons appeared on my phone’s screen, indicating we were in for a wet, chilly weekend in the Windy City.

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Well, what can you do? You simply have no choice but to give your warm weather clothes one last longing look (and maybe whisper quietly to them, “I’ll see you soon“), and dig out your sweaters and boots.

It helped that we had just visited New York a few weeks earlier, and faced with a similar forecast and luggage restrictions, I consulted my NYC Packing List.

Looking for more packing list inspiration? Discover what's in my suitcase each season: Spring | Summer | Fall | Winter

If you’re new around here, my packing lists are all assembled with the same goals in mind: to travel light so I can move around my destination unburdened, to avoid paying for baggage, and to feel at ease during my trip – both by wearing comfortable clothing that suits the weather and by wearing garments from my wardrobe that “fit in” with the local style.

Since we were visiting yet another big U.S. city, it would have been easy to just pack the same things over again – but I decided to keep just the core staples from that trip (woolen pants, sturdy boots, toasty parka) and swap in a few new colors, textures, and silhouettes.

I grabbed the items below, plus a dress that I ultimately decided against bringing after reading how casual Chicago style is, and packed them in my backpack.

Here’s a look at everything that went inside:

CHICAGO PACKING LIST

Cashmere Sweater℅ | Wool Turtleneck | Cropped Sweater | Parka | Wool Trousers℅ | Fleece-lined Jeans | Pajama Bottoms* | Pajama Top | Crossbody Bag* | Cashmere Scarf* | Gloves | Beanie* | Belt | Sunglasses | Lug Sole Boots℅

WHY I PACKED THESE ITEMS FOR CHICAGO

Tops

Cashmere Sweater℅ | A camel cashmere sweater is a classic – but it turns into something more when paired with modern wool trousers. This one is a particularly good value.

Wool Turtleneck | I own a few of these base layers from this Scandi brand, and they almost always make an appearance when traveling to cold destinations. They’re made in a soft 100% merino wool and wear like a second skin, adding much-needed warmth without the bulk.

Cropped Sweater | Cotton isn’t usually my first choice for cold weather, but with insulating wool underneath, this one is thick enough to handle a dip in the mercury.

Outerwear

Parka | Yes, “The Amazon Coat.” Though not really my style, this big, puffy coat is super warm and has a million (or six) pockets. I scored mine secondhand, but even new it’s hundreds of dollars cheaper than similar options.

Bottoms

Wool Trousers℅ | These pants are soft and warm already, but I like to toss a pair of leggings underneath for an extra dose of cozy.

Fleece-lined Jeans | Not my favorite pair of jeans in my closet, but an essential pair to have. This pair runs large – size down for a better fit.

Pajamas

Pajama Bottoms* | When traveling with only a personal item, I try to bring my lightest pajamas. A pair of silk pants feels luxurious but takes up almost zero space in my bag.

Pajama Top | A simple silk tank is lightweight and perfect for a hot sleeper like me.

Accessories

Crossbody Bag* | Until I find another bag that holds my phone and camera, and is ready to thwart would-be pickpockets, I’m bringing this nondescript crossbody bag with me just about everywhere.

Cashmere Scarf* | An ultra-luxurious cashmere scarf with minimal branding that fits in my coat pocket? Yes, please.

Gloves | A soft, supple pair of leather gloves with built-in tech compatibility.

Beanie* | I’m a reluctant hat-wearer, but it was necessary. At least this one’s cashmere!

Belt | A no-nonsense belt that doesn’t trigger the metal detector at the airport.

Sunglasses | Since discovering this brand a few years ago, I’ve largely given up my Ray-Bans. These fit my face way more comfortably, and they have a truly fantastic warranty (ask me how I know!).

Shoes

Lug Sole Boots℅ | This pair has become my go-to this season, not just because they look effortlessly cool, but because they are sturdy, warm, and waterproof. I honestly can’t believe I made it this far without them!

Not Pictured

Undergarments | A couple of pairs of underwear and my favorite compression socks℅ were all I needed for this overnight trip – taking up hardly any room at all! As for bras, it’s not recommended to wear them two days in a row, but I make an exception for these quick getaways.

Makeup + Toiletries | Everything in this category (minus any liquids) went right into my handy catch-all case. I kept my makeup routine ultra-simple: just a tube of eyebrow gel, a tube of mascara, a bullet of lipstick, and a bit of foundation squeezed into a smaller container. I also tossed my medication organizer, nail set, hairbrush, a few extra hair ties, and my travel curling iron (below) in the bag.

Travel Curling Iron | I tossed this teeny-tiny curling iron into my toiletry bag but didn’t end up using it thanks to my beanie.

Jewelry | I wore the same pieces both days to avoid needing to pack anything delicate: a wheat chain necklace, a floral necklace℅, several rings℅, and a pair of simple solid gold studs that I could wear in the shower.

CHICAGO OUTFITS

Alyssa stands on a platform over the L tracks wearing all black — Wool Turtleneck | Cropped Sweater | Parka | Fleece-lined Jeans | Crossbody Bag* | Belt | Lug Sole Boots℅ | Wheat Chain Necklace | Floral Necklace℅ | Rings℅

Alyssa wears wool pants and a camel sweater with a big coat in front of The Bean — Cashmere Sweater℅ | Parka | Wool Trousers℅ | Crossbody Bag* | Cashmere Scarf* | Beanie* | Belt | Sunglasses | Lug Sole Boots℅ | Rings℅

Alyssa is seen through a hotel window wearing all black — Wool Turtleneck | Cropped Sweater | Wheat Chain Necklace | Floral Necklace℅ | Rings℅

FINAL THOUGHTS ON PACKING FOR CHICAGO IN EARLY SPRING

“Early spring” in Chicago is really the same thing as “late winter.” Temps can still be icy, although when the sun decides to come out, it bounces off the buildings and warms the city’s bones a little.

Packing warm layers is essential for this time of year, and having an easy-to-remove coat makes a big difference when entering heated buildings. I’ve taken to wearing my crossbody purse inside my coat to make this song-and-dance a little less awkward.

Overall, the city’s style leans incredibly casual, just like my research indicated. Even at elevated restaurants, jeans were the norm (although they leaned more dark and tailored than light or distressed) – but that’s not to say there weren’t diners who dressed for the occasion. It would have been my preference as well, but something had to give in my limited backpack space, and the dress (and accompanying fleece-lined tights) had to go. Still, it was nice to not feel out of place in my black denim.

Overall, this packing list served me quite well for a March weekend in Chicago – it was comfortable, warm, and stylish without drawing unnecessary attention. I’d pack it all again if I had to, although I sincerely hope I don’t need to. I don’t know about you, but I’m ready for a little warmth!

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How do you feel about traveling to cold-weather destinations? Is it exciting, or does it feel like a drag?