“Chicago is an October sort of city even in spring.”
— Nelson Algren, Newsweek, August 13, 1984 (photo via)

No matter how many times I do it, I always get excited about taking a plane trip.

Some people only like the destination part of a trip – cough*Daniel*cough – but not me! The planning, the packing, the journey to get there, the destination itself – I love it all. (Minus the unpacking and the laundry to do when you get home.)

In less than TWO WEEKS, I’ll be in Chicago for an extended family weekend with my cousin and sister, and I really couldn’t be more excited about it. I wish Daniel could come too, but I can’t wait to explore the city with my girls! I’m the type of person that as soon as I know a specific place I’m visiting, I start planning every minute of my trip, from packing lists to the food to the must-see destinations. And, in true Pinterest fashion, I’ve been busily pinning lots of pictures of “Chicago style,” few of which actually include clothing items I already own…*oops*

I’m still working on an outfit packing list, but here’s a few pieces of inspiration. I am a packing fiend – I love figuring out how to maximize what I pack while minimizing the amount of space it takes up. Anyone else out there like that, or am I alone in my fiendish-ness?

   
   
(From top left to bottom right: 1. pin, source; 2. pin, source; 3. pin, source was Sevenly, image no longer available; 4. pin, source; 5. pin, source; 6. pin, source)

I’ll keep you posted on my outfit choices!

I was feeling extra hipster this weekend so I checked out this article:

(Pin photo via Condé Nast Traveler, article source here)

I’m not really that hipster, you guys. I could lie and be all, “Oh, I don’t want to look like a tourist,” but the truth is I really don’t care what’s considered “touristy.” I’ve been to Chicago before, but it was nearly 10 years ago when I went with the Oklahoma Baptist Youth Choir and Orchestra (which makes me sound stupid old), so it’s been awhile. We visited a lot of popular places, but I enjoyed them, so who cares?

The biggest differences between that trip and this trip are: (1) more freedom as far as itinerary, (2) staying in the city as opposed to outside of it, and (3) I’M A GIANT FOODIE NOW. It’s a little sad how excited I get about food. I’m at the mercy of the people I’m traveling with, of course, but I’m hoping we can visit some neat little local places instead of stuff we could easily get back home.

Even though I’ve been to a few of these already, here’s my top 5 hopefuls for the trip:

• Shedd Aquarium – the largest indoor aquarium in the world
• John Hancock Observatory – the best 360 view of the city
• Pequod’s Pizza in Lincoln Park – called “the deep-dish pizza locals actually eat”
• Any of Thrillist’s 10 Best New Burgers in Chicago
• Millennium Park – lots of cool packed into one city block

If you’ve been to Chicago before – what was your favorite place you visited?

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