I’ve been a notorious over-packer for as long as I could remember. And, since I usually fly Southwest Airlines, I’ve never had to worry about baggage fees or anything, so that hasn’t really ever been a problem. However, while browsing Google Flights (as I too often do) back in January, I stumbled upon $39 roundtrip flights to Chicago.
I couldn’t whip my card out fast enough.
The only problem is that the flights were on Frontier, which I dislike for many reasons, but I figured, “oh well, it’s cheaper than a weekend going out in Denver! We’ll make it work.”
Frontier Airlines nickles and dimes you for every little thing. You pay extra for a seat that reclines, extra leg room, even to choose your seat ahead of time. But, the strangest part to me is that they not only charge for a checked bag, but also for a carry-on!
I was going to purchase a carry-on, knowing that would be more than enough luggage space for 5 days, but the fee for a carry-on is $35 – EACH WAY! So, that was basically tripling the price for my flight.
No thank you.
So, I selected no baggage options and figured I would pack everything in my “personal item” that would fit neatly under the seat in front of me.
Enter, my trusted OG Sack.
I’ve had this backpack for a few years and it’s gone with me so many places. It’s great for weekend trips and also as a gym bag since it has a cool strap in the front that’s perfect for holding a yoga mat.
Plus, it’s made by Denver locals who are friends of mine, so of course I want to support!
But, the bag truly is a lifesaver and is always my go-to carry on for flights because it fits under the seat in front.
So, I decided anything I was bringing to Chicago was going to fit in this bag! Surprisingly, I was able to fit a lot more than I thought! Below is a breakdown of everything I packed.
When choosing my outfits for this trip, I had to plan everything ahead of time. Usually, I just throw a ton of crap into a bag and plan my outfits later, but since I was so limited, I decided all my outfit combos ahead of time so I could maximize the pieces I brought. Then, I made sure to wear as many items on the plane as I could. Here are the clothes I brought:
1 workout outfit: sports bra, tank, and leggings. I knew I would want to work out a couple times in the hotel gym, so I planned on wearing the same outfit. I know that might sound gross, but if you give your workout clothes time to dry out, they actually don’t smell. And honestly, who cares? It’s the hotel gym.
1 pair PJs: comfy tee and comfy pants. You really just need one since you’re just sleeping.
1 suede jacket: I also wore this on the plane since it’s big and heavy and would have taken up a ton of space in my backpack.
2 pairs of shoes: This was the hardest part to choose. I brought one pair of black boots that I know are comfortable for walking around in and that I could make dressy or casual. The 2nd pair I brought was Nikes that are pretty light so I was able to pack those and wear the boots on the plane.
1 long sleeve dress: I packed one casual dress that I didn’t even end up wearing!
1 sweatshirt dress: I only really wore this one around the hotel, but the plan was to wear it with my leggings and boots. I just didn’t want to put the leggings back on again after I worked out haha – didn’t quite think that one through. It’s on sale now too!
1 big puffy coat: Essential in Chicago in January. I wore it on the plane as well.
2 beanies: one pom beanie and one waffle knit slouchy one.
1 crossbody bag: much easier to pack than a big purse.
2 pairs of sunnies: I probably would have been fine with just one pair.
A ton of random jewelry. This didn’t take up a lot of space because I packed all of it in my favorite toiletry bag ever. This bag is awesome because the bottom part of it is made for holding jewelry. It’s so genius! It even has little snaps so your necklaces don’t get tangled.
Surprisingly, I was able to pack quite a lot! As I mentioned, this toiletry bag is pretty much the best and fits a ton of stuff. I did forget a razor, toothpaste, and toothbrush though, but thankfully the hotel provided those for us 🙂
I only packed my essential makeup, and I had a few sample sizes so that helped with packing.
For makeup: I brought tiny samples of moisturizer and foundation, a sample size CC cream, concealer, blush, bronzer, highlighter, eye shadow, lip gloss, lipstick, lip balm, Kiehl’s balm, eyeliner, mascara, and a brow pencil, plus 3 makeup brushes.
For hair: I brought a round brush since I figured the hotel would have a hair dryer, my curling iron, shampoo & conditioner, a leave-in hair treatment, and dry shampoo.
For skincare: moisturizer, face wash, and deodorant.
I brought all travel size things so I could put it in one of those little plastic baggies for going through security.
The only things not pictured that I also brought were my laptop and charger, my camera, both lenses, and charger, and my phone charger. Oh and socks and underwear of course 🙂
And YES – it all fit in a backpack!
I do roll my clothes when I pack them, and that seems to help keep everything compact. If you haven’t tried that before, I definitely recommend!
So there ya have it! If I can do it, anyone can. And if you have any packing tips of your own, please share them in the comments!