July 4th in the Windy City

Finally getting back into the swing of things after a fun-filled long weekend in Chi-Town. Matt was conveniently able to schedule a work trip in Chicago for the first half of the week, and I flew up Wednesday evening to meet him. It was my first trip up since my sister got married, and was great to see her and her *husband*. Because I arrived around 5pm, I decided to take the train into the city so my sister wouldn’t have to get stuck in rush hour traffic coming to pick me up. The train is always an adventure…after sitting next to three, obnoxious, drunk high schoolers, and at one point, thinking the train car was about to be held up by a homeless man begging for money for a much-needed prescription, I was ready to get off ASAP.

We had a glass of wine and some app’s and then headed to Bill and Giuliana’s new restaurant, RPM Italian.  I was praying I would see B & G, and maybe even baby Duke, but no luck. However, the meatballs made up for the disappointment. After dinner, we stopped at a local bar, Barcito, for my sister’s favorite drink in all of Chicago; The Booty Collins. Who knew green tea infused vodka could taste SO good? We were enjoying our drinks outside when we were approached by a 10-year old selling a bunch of random items. Whitney and I couldn’t resist buying the light-up Minny Mouse ears. We were definitely channeling our inner Tamra and Vicki. The boys clearly wanted nothing to do with it (however, they were the ones who actually purchased the ears for us…just saying!)

Thursday was the 4th of July, the day we had been waiting for all year. My brother-in-law’s family has a big 4th of July party at their house every year, so we got up early and made a delicious banana pudding (our Dad’s famous recipe) to take up there. They live in a suburb of Chicago, about 40 minutes outside of the city. I hadn’t seen his family since the wedding, so it was great to see them all again. They go all-out for this party, and it was a great day. Bob’s dad is a hoot, and he and his buddies drink out of these giant glasses every year. I’m hoping that since I’m now considered family, I’ll have one of my own one day…

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Later that night, Matt had surprised me with a nights stay at The W Lakeshore in the heart of the city. We were sad to have to leave the Stanton’s party early, but were really excited to be able to have a vacation within a vacation. The W is right on the lake and happens to have a bar on the 14th floor with large windows that look right out to Navy Pier. We got into the city in just enough time to quickly check-in,  race up to the 14th floor, grab a drink, and position ourselves to watch the fireworks.  The firework display over the lake were amazing, and it was such a great treat! After the fireworks, we went down to our room to find that the lake view room we had paid extra to upgrade to, didn’t exist. Our room looked out onto a lovely parking garage. Grrrr. After a long day of drinking Pinot Grigio, sassy CMH was in full effect and my little fingers quickly dialed the front desk. They explained that they had overbooked – so annoying that hotels do this. Its simple. You know how many rooms you have, and you know how many guests you’re expecting. After being put on hold twice, and speaking to a rude employee, I was fired up. I threatened to walk down to the front desk, but was assured it would be best if I just stayed in my room. The manager finally called up to our room and first offered $50 off our bill (umm, seriously?).  After arguing some more, he said he could comp 1/2 our room price…again…not good enough. We wanted the lake view room, like we had paid for. The worst part is that I had called earlier that week, and the day of to ENSURE we would have our room, and they promised we would. After more  negotiating, we finally landed with a free night’s stay at one of their hotels in the future. Disappointment city. Get your stuff together, W! All in all, it was a night away with my boo, and it was much appreciated (despite my aggressive attitude for part of the evening)

We were feeling very lazy on Friday and so we headed to my sisters club for the day. This place is amazing. It has a gym, multiple restaurants, bars, pools, amazing locker rooms, a spa, indoor driving range and tennis courts. The pool was absolutely packed, but we were lucky enough to spend the day kicked back and enjoying the sun. Later that night, Bob’s sister came into the city and joined us for dinner at one of my absolute favorite restaurants in the city, Mercadito.

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If we didn’t already have enough excitement for the weekend, we decided to cram in one more event: a horse race! About 45 minutes outside of the city is a beautiful horse track that has races almost every day of the week during the warmer months. We met up with some of my sisters friends and took the train to Arlington Park. The train is a perfect option because you can drink mimosas onboard and it drops you off right in the parking lot of the track. We paid a little extra to have a suite and it was well worth it. The park is absolutely gorgeous and it doesn’t feel like you’re in Chicago anymore. There are 11 races total during the day with 30 minutes between each race. It’s such a fun process to research the horses, and then place your bets. I tried every strategy I could; colors, numbers, names, jockey record, etc. and didn’t have much luck. All in all,  I only lost $9 , and it was well worth it for a great day at the races!

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Chicago will always have a very special place in my heart. The vibrancy and energy of the city is undeniable. If I’m being honest, I wanted to dislike Chicago for taking my sister away from the South. But I’m so thankful that she has such a wonderful life there, and that we’re always welcome to come visit whenever we want. I’m also very thankful for my brother-in-law; I really hit the jackpot with him! I don’t know many other people who would specifically leave an ice cream surprise snack  the freezer for me OR secretly purchase this special suit…

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3 thoughts on “July 4th in the Windy City

  1. Pingback: Hemingway, Helgeson & Hewitt…old pals | The Dilworth Darling

  2. Pingback: 2013…A Year in Review | The Dilworth Darling

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