Packing for a day trip in Chicago

I’m beyond excited for this weekend! I’ve been trying to take advantage of the unusually-low gas prices to reconnect with friends across the Midwest. I asked my college friend Emily if I could visit her in northern Indiana for a weekend since I’m about two years overdue, and her answer was a resounding “Yes. Brunch?! Day trip to Chicago?!”

How can you say no to college friends, brunch and Chicago?

Following the “I’m so pumped to pretend we’re still in college for a weekend and OMGBrunch” elation, I got to thinking about the technicalities, of course. We’ll be taking the train into the city Saturday morning and out of the city at night, which means it’ll just be a day trip. Which means I’ll be responsible for carrying all of my belongings on me – throughout the entire day.

So… what to pack?

I opted to bring a roomy crossbody with me for ease of carry and storage space because shopping. Mine is Jenna Kator’s Corktown.

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ID, cash, credit cards, insurance cards. Duh.

A water bottle. I like this collapsible bottle because it’s easy to store when it’s empty.

Band Aid blister stick. Nothing is worse than realizing your shoes rubbed the wrong way two hours into a day trip, and then realizing you still have eight hours left of walking with that blister. Ouch!

Face lotion and ChapStick. Pick one with an SPF. Cold temperatures are incredibly drying, so I like having lotion on hand to combat that in advance.

Snacks! Walking burns a lot of calories and stopping for bagels and coffee cake every half a mile gets really expensive! I love easy-to-tote snacks, like granola bars, apples, small bags of trail mix and bagel sandwiches. Make sure your snacks are really dense so they don’t get smashed in your bag! (Also, freeze your water bottle so it acts like an ice pack if you want something to stay cold.)

Touch-up makeup and a foldable hair brush or a comb. I mean, come on, it’s called the Windy City. Keep waterproof mascara, tissues and eyeliner in your  bag to fix teary-eyed smears, and a foldable hair brush to keep unavoidable tangles at bay.

Phone battery pack and charging cable if it’s needed. You’ll be Instagramming your way through your phone’s juice faster than humanly possible. Bring a portable battery pack and/ or a charging case if you have one!

Mild painkillers, like Asprin or Advil, just in case your feet or head start hurting.

Gloves, hat, scarf. If you’re not wearing these, they should definitely be in your bag! Hand warmers won’t hurt either!

Various sundries. I keep an “Oh s#!t kit” in my handbag filled with spare contact lenses, bandages, a perfume rollerball, dental floss, tampons, hand sanitizer, bobby pins, hair ties, oil absorbing sheets, mints, a Tide to Go pen, etc. Basically my version of the Minimergency Kit!

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I still have to figure out what to wear and pack for the entire weekend, but I’m relieved I’ve at least figured out what to bring with me to the city!

Am I forgetting anything? What do you pack for day trips in big cities? Let me know in the comments!

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