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Chicago! My Kind Of Town!

Updated on January 12, 2012

Finding More Than Wins in the Windy City!

I travel all across the country and being single and not having any kids (that I know of!) allows for me to be on the road for several weeks at a time. I found myself in the midst of such a streak as I was wrapping up a 1:1 Coaching program in Los Angeles for Bob Leonetti and Real Estate Profit Coach ( I could either fly home to Austin and then turn around and fly back out to Chicago the following Sunday night or Monday morning, or fly directly to Chicago and spend a day and a half being a tourist. I chose the later!

Its funny how things can line up when you make the right decision. I called my Choice Hotels concierge and found out that I had enough points that my hotel for the weekend would be free. Southwest Airlines let me know almost 30 minutes after booking my flight that I had just received a free flight for flying enough with them. And then to top it off, Alamo car rental ended up giving me a free rental for my stay in Chicago as I had enough rented enough times with them that this trip would be free. It definitely pays to join your hotel, airline, and hotel members rewards clubs! Having all three fall in line made me think that the week was off to a fabulous start already.

My flight from Los Angeles arrived at Chicago Midway at 4:30 pm. My luggage was one of the first ones off of the plane, my car rental took five minutes to get and my compact reservation while already free, was upgraded to a midsize rental as they were out of compacts. After a short drive to my hotel in La Grange, Illinois, I set out to find a restaurant as I was starving after my four hour flight.

I found a great Italian restaurant and I guess I suprised the waitress by ordering the antipasta appetizer and then following it up with a 14oz grilled ribeye smothered in blue cheese. The steak was moanable! Everything about the meal was fabulous and after gorging myself like a fat kid, I headed out to find the local watering hole!

I drove down a couple blocks and found the local tavern, Brixie's, that was advertising a Led Zepplin cover band that would be playing that evening by the name of Kashmir. I thought, why not! I walked in and the place was pretty quiet with just a few patrons and a half pint, female bartender who I later found out went by the name of Jacklyn Daniels (named on behalf of Jack Daniels). Jacklyn introduced herself as I bellied up to the bar and ordered her namesake.

I've always been a fan of Chicago for their sports teams and the awesome variety of great restaurants and communities in and around the "Windy City." As a young kid I was a fan of the two baseball clubs, the Chicago Cubs and the White Sox, even being nicknamed by my high school baseball coach as the "Big Hurt" after Frank Thomas. When you ad in that I was huge fan of the Chicago Bulls and watching Michael Jordan, Scottie Pippen, and Toni Kukoc bring back six NBA championship rings to Chicago. My Dad and I watched every playoff game the Bulls were in during those 6 plus years and I can remember us talking about those games over the phone when I wasn't home. It was always a dream of mine to take him to a game, but unfortunately he passed on before I had the opportunity to take him to a game.

Anyway, here I was sitting in Brixie's (Chicago's oldest licensed bar) getting ready to watch the Chicago Blackhawks game and listen to Kashmir. I started visiting with Jacklyn's freind, Stacey, a very attractive brunette, who was sitting there and we had a good time cutting up at a few jokes and visiting with each other while yelling for the Hawks who jumped out to an early lead. We and the whole bar patronage (that had swelled to a large number) were excited as the Hawks won the game to take a 3-1 series lead. They would eventually wrap up the series two night later to advance into the NHL playoffs for the first time in over seven years. Stacey left me to join Jacklyn as her Jacklyn's father in law came into the bar and the three of them spent the next hour or so visiting. I stayed at the bar and enjoyed the company of some of my new friends that I had made

As the game ended, Jacklyn headed home and I was suprised that Stacey rejoined me! As Kashmir fired up, we laughed at how long the fake wigs were on the band members and how much they were imitating Page and Plant! We listened to a few songs and it was funny that we both almost simultaneously stated that we were giong to leave. We both giggled and headed out the door. I walked her to her car and asked her if she'd like to go out later in the week and she suprised my by reaching up and planting me with a great big kiss! I returned the kiss and chuckled to myself that I love this place! We exchanged numbers and Stacey recommended that if I wanted to blow off some steam that I should head out to one of her favorite places, Pole Katz. I thanked her for the referral and promised to give her a call.

I left Brixie's laughing to myself and feeling quite confident! While I enjoy traveling, it does make it a little tough to date someone regularly. I recently had been dating an old high school friend who lived outside Louisianna, but I had just broken up with her the previous week realizing that what she needed, I wasn't able to give her. While it always hurts to end a relationship, I knew it was the best thing for the two of us.

After breaking up with Jules, I decided I would post an ad on I found myself chuckling at the idea, but why not! I had set up a date for Thursday night with a girl named Stephanie that I had met on Match and we had originally thought about heading to the Cubs game on Thursday night. Steph was planning on moving to Austin and she offered to show me around while I was in town, so I had that to look forward.

Anyway I wasn't ready to head back to the hotel after Brixie's so I decided to give Stacey's referral a try. I drove the 20 minutes to Pole Katz and chuckled as I pulled up to an obvious gentleman's club. I thought for a moment of turning around, but I decided I might as well have some fun! I'm single, hard working, make plenty of money so I could blow some in just pure fun. I walked in and sat down at the bar. Four and a half hours later I walked out with a hat, t-shirt and a $100 bar tab and two phone numbers. Let's just say that I blew off some steam and had a great time (watching beautiful women dance around topless in g-strings!). What can say! I'm a guy!

I got up the next day and watched the Bulls win game four at the local sports bar and then headed into Chicago and had a great another steak dinner inside the Loop at Graziano's. I drove back to my hotel, called and visited with my mom, and then headed back to Brixie's to quench my thirst. Jacklyn was working again and I hung out visiting with her and some of the other guests until 10pm. It was time to get some sleep and get ready for my week with my coaching student.

The week went well with Andrew as I was treated to the best deep dish pizza at Uno's in the loop on Monday night along with enjoying great food at just about everywhere I went. The best part was picking up 3rd level, mid court playoff tickets to Game 6 of the Bulls versus Boston Celtics. I called Steph up to inform her and we visited for a while with us both being excited to make it to the game. The week couldn't go fast enough! I was going to be able to make a dream of mine come true and watch the Bulls play at the United Center! Thursday afternoon came and went and I found myself pulling into the parking lot and standing outside of the arena waiting on Steph.

She showed up about a half hour later and I was plesently suprised that the brunette wearing a red Blackhawk's jersey was my date. She gave me a big hug and we visited for a second and then headed into the United Center. We were greated with the sound of the Chicago Bulls pregame band along with the increased energy that built minute by minute as game time inched closer. Steph and I were both thirsty so we grabbed a couple drinks (along with us each taking a shot of Jagermiester) and grabbed a tasty pulled pork sandwich. We listened to the band, talked some more and finished our dinner. We grabbed another round of drinks (the bartenders gave us more like triples instead of singles) and headed up to our seats.

We arrived at our seats on the third level just in time for the starting lineups. My heart was pounding as the place was rockin! We watched the first quarter (including a scuffle between Rondo of the Celtics and Heinrich of the Bulls) and then headed down between quarters to grab another round. While we were down stairs, we decided to see if we could take advantage of any open seats on the lower levels. Steph tried a couple entrances but she was denied. I waited until near the end of the 2nd quarter and then was able to walk right into the lower level and spotted four seats on the 10th row which we slid into. Steph was cracking up at how I just acted like I needed to be there and strolled on in. The seats were awesome!

We spent the rest of the game celebrating the awesome game that went back and forth and led to three overtime games. Steph is an awesome chick and we hit it off almost instantly! We shared a lot of the same opinions and interests. We were high fiving, hugging, and dancing like we didn't care who was watching. The fans around us were cracking up and having a great time with us and I got one guy to take some cash and buy us a round of drinks so that we didn't lose our seats. There was obviously some chemistry between us and we found ourselves kissing on a couple occasions during the game as the Bulls would make a run or answer a run by the Celtics. The game was not only the greatest game that I've ever witnessed (the Bulls finally one by 1 point), but Steph was one of the funnest ladies that I've ever been out with.

After the game we weaved through downtown Chicago traffic (after she passed the door test with flying colors) to a bar that Steph liked to frequent. We ordered a couple rounds, watched the highlights of the Cubs, Hawks, and Bulls games while we split a few appetizers and a burger. I felt instantly comfortable around her and it was obvious that she felt the same. We talked about her moving to Austin for her career and we discussed some of the great places to go in Austin and she stated that she looked forward to me showing her around. It was getting late, so I drove her back to her place as she had to get up at 4 am and I had an early flight that I had to make at 7 am. I walked her to her door and we enjoyed kissing each other good night for a few minutes. We both looked forward to seeing each other in a few weeks and promised to stay in touch. She told me to have a good time in Las Vegas the following week and make sure and make some memories and have some fun! What a cool chick!

There is nothing like wrapping up my week in Chicago like I did. Not that I'm a player or anything (unless you ask my to be sister-in-law, Lindsay), but I'm not ready to settle down after being divorced for just about a year. I enjoy traveling and my career. Each day and trip is a mini vacation, a day off, and each day is completely different. You never know who you are gonna meet and never know where life will take you. Life is a buffet and a playground and I'm glad to take in as much fun and life experiences as I can! Watch out Vegas cause here I come!

Pictures From The Game!

Stephanie and Me
Stephanie and Me
6 Championship Trophies
6 Championship Trophies
What is it about a good looking woman in sports jersey?  Sexy!
What is it about a good looking woman in sports jersey? Sexy!
Me and Steph celebrating after the 2nd Overtime!
Me and Steph celebrating after the 2nd Overtime!
Our Original Seats
Our Original Seats
Our Better Seats
Our Better Seats

Starting Line Up Video


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    • gmwilliams profile image

      Grace Marguerite Williams 

      7 years ago from the Greatest City In The World-New York City, New York

      Now I have to go to Chicago! I have heard the Chicago has some of the best steakhouses!

    • LorenaGerlach profile image


      9 years ago from Dallas, TX

      You go, Scott!


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