Your Ultimate Guide to Packing for A Trip to Chicago in Early Fall
Chicago is one of my favorite cities to visit. The atmosphere, the city... there is so much to do when I visit Chicago and it always feels like there is never enough time to fit everything into one trip!
In one week, I will be in Chicago with my boyfriend, Noah, and his family for what has become an annual trip in September. Since last year, we have traveled to Chicago in early September to watch the opening Bears football game.
This year, we are staying in the Windy City for three days and it already feels too short! I know that my boyfriend's mom has a packed itinerary for us when we arrive, starting with shopping, a tour of Prince: The Immersive Experience, attending both Cubs and Bears games, and more.
With that being said, our trip will consist of a good bit of walking, so packing with comfort in mind is at the top of my list. I want to look cute while being comfortable, which isn't asking for too much right? Below, you will find the outfits that I plan to pack for our trip! I am 100% investing in packing cubes to save space in my carry-on, for items I will buy in Chicago. So, here is what I am taking with me to Chicago...
Travel
First and foremost, let’s talk about what to wear while traveling. The only correct answer is sweats and/or comfy clothes. For Friday and Monday, I will be sporting the same outfit (sorry not sorry) to travel in.
*The images are all linked to my LTK. :)
Friday
Friday will consist of early morning travel, shopping and sight seeing, followed by dinner with family Friday evening. Maxi dresses are such an easy and comfortable item to pack for trips. Paired with a cute and comfortable sandal will ensure that walking around town will be easy and pain-free.
*The images are all linked to my LTK. :)
For dinner Friday, I’ll be sporting some comfy and chic faux leather leggings, with a basic top and a light jacket. The weather shows that the low will be around 60 degrees, so better safe than sorry! Would you believe me if I told you that these boots are from Walmart?! They’re so cute and comfortable!
*The images are all linked to my LTK. :)
Saturday
On Saturday, we’re going to see a Cubs baseball game at Wrigley Field and I’m excited! It’s funny, because I don’t care to watch baseball on TV, but something about seeing a game in person is a million times better. Comfort is once again the goal, so wearing a onesie bodysuit with an oversized button up is the way to go. My legs might look like sausages, but I’ll be comfortable!
*The images are all linked to my LTK. :)
After the game, we’ll venture out and about for dinner and I’m absolutely feeling the denim on denim trend. Throw in some simple tan booties and my look is complete! The belt bag is from Amazon and it’s so practical to carry, especially when you’re in a city or running errands.
*The images are all linked to my LTK. :)
Sunday
Bear down!! 🐻 Sunday will be the best day of the entire trip, because we will be attending the opening home game of the season against the 49ers. I’ll be sporting an outfit similar to the one I wore last year… a bears jersey and jeans is an easy, staple look for an early fall game. We can’t forget the clear purse, per stadium guidelines!
*The images are all linked to my LTK. :)
Lastly, Sunday dinner will consist of a comfortable dress paired with sneakers and a classic shoulder bag. It seems fitting to bookend my outfits with dresses. I’m excited for this trip!
*The images are all linked to my LTK. :)
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