Wednesday Round Up: Chicago + Travel Style

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Hey hey everybody! Sorry the absence but I was off enjoying a long weekend and a much needed break. I hope you all got some time off for President's Day or at least took advantage of some of the sales ;)

For today's post I thought I would share a little of my trip and some of  my new travel essentials. Ready?



A few weeks ago I decided I was long overdue for a trip away without Reese, and one without D too. D gets out of town a few times a year and typically ends up at his cabin. I don't have that option so I don't get to be gone for a weekend unless he and I are going somewhere. My cousin, who is from Chicagoland, was living in New York City for almost 10 years and moved back to Chicago a little over a year ago. With having a newborn last year I got out there once to see her, but she has been here a couple of times. I definitely owed her a visit and this four day weekend was the perfect time.



I got some cheap tickets and away I went. I was flying alone so I really wanted to be compact and not have to check a bag. I was doing this on the cheap the best I could overall as Chicago is an expensive place. I took an Uber the airport on Friday morning and got there a little later than I intended. Thankfully not too much later as it seemed that everyone was going to Mexico at the same time. Seemed almost like a class trip so it took a while to get through security. I did check in before so at least there was not that wait.




I got into about 9:30 AM and by the time I got a car and up to her apartment it was about 10:30. We sat around and chatted most of the afternoon. We made some lunch and then headed into downtown to check out a restaurant called The Dearborn. Really cool place. Textured subway tile, a great big bar back, high top tables. Delicious apps and drinks. We just did the apps and drinks, but it ws a gorgeous place. Clearly an after work crowd. Then we stopped for a quick drink at The Violet Hour a little speakeasy I had tried to go to several times and failed. It's a little pretentious but the cocktails are legit.






After we headed back home to get cleaned up for our nighttime plans. She wanted to show me this improv show at The Annoyance Theater. They do a show on Fridays called 'Hitchcock Tales' where by a suggestion from the audience they create an entire improv play. We met up with two of her male friends there as well. The play was honestly hysterical. I have never seen anything like that before and it was totally worth it. After, we went out to Boystown area and literally bar hopped. I have not done that in years. We had full intentions of not staying out until bar close, but whoops, we did :) 





I slept in really late the next day because I was up for 24 hours. Saturday was a lazier day because I am not as young as I used to be. Eventually we got moving and we headed out to my favorite pizza place in the city Michael's on Broadway. Seriously, best pizza in the whole city. It's in the neighborhood I used to live and one guy that works there still remembers D and I when we go. Such a great place. We also bopped over to the boutique Alice & Wonder, I love that place and wanted to take advantage of actually being in town to see it.






That night we went to The Purple Pig a tapas place that boats a novel sized wine menu. We orderd about 4-5 plates and it was so amazing! On the priceier side, but worth every penny. We ended the night at The Green Mill, a jazz club that was rumored to be an Al Capone spot back in the day. 









Sunday I was flying out, but really late. My cousin's mom and her aunt came into town and we got to see a play that was still in previews. It was a small theater but a really interesting way to see a show. After the playwright came out to answer questions. It was fascniating and honestly a great way for the playwright to get some feedback. I finished my trip in true Chicago style with an Italian meal at Sapori Trattoria. Delicious pasta, comfortable atmostphere and great service that isn't pushy. Couldn't think of a better way to cap off a wonderful weekend!






Like I said before I wanted to carry on my bags and not check. Anything to save a buck, really. I knew I would need more than my suitcase and a big purse to make it happen. I decided I would look for a bigger backpack and found this Herschel Supply co. Mine is actually green but this black one is sleek. It is really big and has a separate soft section for your laptop, which I absolutely love. Next, I did some reading about ways to pack to save space. One tip I saw was to get a big wristlet of sorts to put your cash, ID, and plugins in instead of your purse. I had a gift card to Kohl's and I have really loved Lauren Conrad's line lately, especially her accessories. This little scalloped wristlet worked perfectly. I put some of my cards and plugins and little lipstick for the flight and stuck that in my backpack. For a purse I needed something that was a space saver. I feel in love with this bag from Target. First, the navy is just a gorgeous, muted navy that caught my eye. Second, for being skinny it can really hold a lot. Enough to run around and go out in. That went in the suitcase but hardly took up any room. Last, but not least was my flying outfit. I prefer comfort but style. I wanted a new pair of black leggings and agnoized over the right pair. I really love Gap's leggings but needed it to be thick enough to wear in public. I really loved how comfortable these were and definitely the high waist. Also, the ribbing is like a velour and was so soft!  I also snagged this hoodie from American Eagle that is long and actually made for leggings. Really soft inside and the ribbon strings were a great touch. I capped the whole look with these sneakers from Target. I have been eyeing them forever and finally snagged them. I got tons of compliments and bonus? They slide on an off super easy without untying. Perfect for flying.

Travel



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What do you think? Do you have any flying trips or travel go-tos? Share in the comments below!


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Also linking up with Jersey Girl Texan Heart and Shopping My Closet today!


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