A Girl's Guide to Chicago

by Kelly Russell

  As I leave my building to walk outside, I wonder who Leah invited and if it would be the same girls from last time. I’m hoping Mary is coming again. I had fun with her and Leah last time. We are not meeting ’til around six, so I have plenty of time to meet the girls. I take my time to wander in and out of a few stores along Michigan Avenue.

  Each store has exploded into fall fashion season. I browse through so many cute sweaters and jackets, but I don’t have time to shop now. Maybe I will do a little shopping this weekend. I’m trying to be wise and use the extra money in my paycheck to pay down my credit card balance; however, I think shopping for a few fall staples is okay. I’ve been getting all my fashion style tips from Kourtney, and she says that you always need a few nice staple pieces each season.

  I quickly hop on a bus going south-bound on Michigan Avenue. It’s five minutes to six, and I walk into the Chicago Athletic Association and toward the elevator that goes up to the rooftop. The doors open, and I get into the elevator and hit the top-floor button to Cindy’s. When I arrive, the doors open again, right onto the rooftop.

  I say hello to the host and tell her I’m meeting a friend. She gives me a friendly smile directs me to where Leah is seated. This time, I’m the first of the group to arrive, and I’m not soaking wet from the rain.

  “Hiya!” She greets me as I sit down across from here.

  “Hey, how are you?”

  “Good, just been busy with work. Everything is going well, but this new freelance job makes me go through a lot of people to get things done. But, that’s corporate life for you.” As she finishes her sentence, we hear someone walking over and look up to see Mary is making her way over.

  “Hey, guys. How are you? I haven’t been here in a while.”

  “This is my first time here,” I admit to her.

  “Oh, it’s great. The food, the cocktails, everything is great.”

  I glance over the menu. “Is anyone else joining us, Leah?”

  “No, just the three of us tonight.”

  I’m okay with this. I really like the other girls, but smaller groups are more fun, and I really like the company of Leah and Mary. We each order a cocktail and chat for ages. They are just so cool because they know so much about everything in the city. They have seen and done so much, and they know all the newest spots. I wonder if, in a few years, I will be like them?

  The server comes by, and we order another cocktail and decide to share the shellfish platter. However, our server doesn’t come back with our cocktails. Instead a young man comes to our table with three of the same cocktails on a tray.

  “Hi, Leah!”

  “Oh, my gosh, hi!” She stands up to greet him as he hands Mary and me our cocktails. “Ladies, this is Mike. He is the manager here at Cindy’s.”

  “Hi, ladies, nice to meet you all. I saw that Leah was sitting over here, and I wanted to bring you one of our signature cocktails that will be on our new fall menu.”

  “Wow! Thank you so much.”

  “You’re very welcome. I hope you enjoy. It was nice to meet you ladies and please feel free to come back and ask for me anytime.”

  “Okay, we will.”

  “Wow Leah, how nice of him.” I take a sip of my cocktail. It is delicious, and he’s right, it is perfect for fall.

  “Yeah. I’ve known him for a while. I’ve been coming here quite a bit with my friends. He’s a really nice guy.”

  Before our shellfish platter arrives, we all get up from our table to look at the view. I look out over the glass balcony. Millennium Park is right across from the hotel. The leaves are changing to bright yellow and orange colors throughout the park. The lake is beyond the park and is still blue even early in the evening. This view is stunningly exquisite, and I cannot help but take a few photos.

  Our seafood arrives, and we eat and chat and enjoy the cocktails. Before we realize, it’s just before nine, and we are all a little tipsy from our cocktails. We start to wrap up our evening since we all have work in the morning. It’s been a fun night, and I’m bummed for it to end. I enjoy having a few girlfriends who you can spend having endless hours of conversation.

  Before I head to bed, I send the girls all a text telling them I had a nice evening and hope to see them soon. I scroll through my social media and check my blog email. There’s an email that was sent to me at four-thirty this afternoon.

  Dear Kelly,

  I hope this email finds you well. I recently met you at an event at Swarovski, and I wanted to invite you to our Chicago Fashion Week Runway Show. The event is on Friday, October 10th, at the main tent in Millennium Park. Your invite includes two VIP tickets to the show, an amazing goodie bag filled with tons of great products, and tickets to the after party at Underground nightclub. Please see the attached materials to read about all the events we are hosting for Fashion Week.

  We hope to see you there!

  Kristy Vick

  Director of Special Events

  Please see attached

  Wow! Wow! Wow! I cannot believe I got an invite to runway show. I didn’t know there is a Chicago Fashion Week! I can’t wait to tell Jillian about it tomorrow. I have no doubt she’s invited to cover it as well. This is a huge highlight for me. I cannot believe that all my blogging and hard work is paying off. I’m so proud of myself for pushing to do something new. Jillian is right. It’s still hard to believe that just nine months ago, I was this super shy girl moving to the city. I did not know anyone or anything about living here, and now I’m going to this special event.

  Jillian is always in the office before me, so I leave a little earlier for work so I can tell her about the exciting news.

  “Morning! I really have to tell you something.”

  “Morning, ah okay, what is it?”

  “Well, last night I got an email with an invite to the “Chicago Fashion Week Runway Show.” I have two free VIP tickets!”

  “Cool! I’m going too. My editor told me about it a few days ago.”

  “Really? Yay! This is going to be so much fun. I need to read about the Chicago designers that are headlining so I know who to look for.”

  “It’s all on the website, I can send it over to you.”

  “Okay, thank you! That would be great.”

  “Wait, Kelly. What’s going on? Come over here.” I hear Amy calling my name from the other side of the wall.

  “Okay, be right there.” I head over to tell her my news.

  “So, tell me. What are you so excited about?”

  “Well, I’m invited to Chicago Fashion Week! I have two VIP tickets for the event in October. It includes drinks and apps obviously, but also a huge gift bag and tickets to the after party at Underground.”

  “How cool! So, who are you going to bring?”

  “Well. Jillian is already going, and I would love all you guys to come. But, I only have one extra ticket.”

  “Well pick me. I definitely want to go with you.” I knew Amy would want to go with me. She went to school for fashion design, and I know designing is her dream.

  “Okay, you can, and we will just figure it out with the other girls.”

  “Figure what out?” Kourtney has just come into the office.

  “Kelly is invited to Chicago Fashion Week. She has two VIP tickets to go to the event. She said I can be her guest, and we will figure out tickets for you and Natalie.”

  “Well, let’s just buy VIP tickets and go. We can tell Mark that it’s for work. You know researching models for events coming up.”

  “Oh my gosh, yeah. That’s such a good idea. I will buy two tickets today.”

  “Perfect! I cannot believe we are all going to Chicago Fashion Week! I’m so excited!”

  September is a busy month for fashion in Chicago. Vin let me leave for a few hours to attend a blogger’s brunch at Summer House Santa Monica in Lincoln Park. It’s a gorgeous place to host a brunch. The restaurant is bright and pretty and has an atrium roof. The decor makes me feel like it’s summer every day. Gilt C
ity is hosting the brunch to go over some fun and exclusive restaurants, spas, bars, and events that they are partnering with this fall season. They are hoping we will help spread the word or purchase some of the event or restaurant deals. I love the idea of getting a good deal to some of the best places in the city since it is expensive to go out all the time. As I look at the upcoming events, the fall wine tasting at Eataly really catches my eye.

  Over the next week, I have an event to go to almost every night, and by Friday I’m exhausted! After work, I’m ready to go home and catch up on some TV or just watch a movie. I almost forgot that I promised my Mum that I will come home for the weekend. It’s been awhile, so I’m taking the early train on Saturday morning.

  After a weekend at home, I walk into work on Monday feeling somewhat refreshed. I don’t have much going on this week, and I’m looking forward to not having plans. I take a few minutes to enjoy my coffee and catch up on the Chicago news. I like to find out what new places are opening and read about the latest hot spots. I’ve downloaded this app on my iPhone called Checkli so I can add things to my growing list of all the places I want to try.

  I see that today is officially the first day of fall. Summer is officially over. I absolutely love the summer. My first Chicago summer has been amazing. But I enjoy the fall season too, and I’m really looking forward to seeing how the city celebrates the holidays. I remember all the holiday lights and falling in love with the city that first time I visited all those years ago.

  I look at my calendar to see which day is October 10th, the day of the Fashion Show. I have about two weeks until then. I look at tomorrow, it’s the 23rd. The 23rd? Why does that date sound familiar? Do I have something planned for tomorrow? I look at the calendar on my phone and see that it’s Vin’s birthday. Oh no! I totally forgot! The office should really do something for him. I instantly send a message to James.

  Hey!

  Hi, what’s up?

  So, tomorrow is Vin’s birthday. I almost forgot. Should I order lunch for him or something? What do you think?

  Yeah, he would like that. Order pizza or something.

  Okay, sounds good. I will also pick up a cake or dessert.

  Okay, thanks.

  I stop by Vin’s office later in the day to see what he’s been up to. “Hey, Hey! It’s almost your birthday! Did you do anything fun to celebrate over the weekend?”

  “I went out with the guys, but I didn’t tell them it was my birthday.”

  “Really? Why not?”

  “Guys don’t do that.”

  “They don’t? Hmm okay, well I hope you had fun anyway.”

  “Yeah, it was okay.”

  “So, what are you doing tomorrow night for your actual birthday?”

  “I don’t have plans.”

  “Oh. Well, we haven’t hung out for a while. We can go to dinner or something if you like?”

  He looks up at me. “I would really like that.”

  “Okay good. Me too.”

  Vin says it would be fun to go all out for his birthday dinner. I’m not sure what that means exactly, but he tells me he’s been wanting to go out for a steak dinner for a while. He tells me Mastro’s is his favorite and is best steak restaurant in Chicago. So, I make a reservation using OpenTable for seven.

  Since it’s still balmy for the end of September, I wear a silky green dress and my favorite pair of wedges. I bought this dress over the summer and haven’t had a place to wear it. I grab a wrap just in case it gets chilly and head out the door. It’s only a twenty-minute walk, but I decide to cab it there instead since it’s almost seven and I don’t want to be late.

  I get out of the cab and walk toward Mastro’s. Vin is already outside waiting for me. We greet each other with a quick hug and walk into the restaurant. A host takes us to a cozy booth in the bar area. The bar area is very dark and intimate. There is an older guy playing soft music on a grand piano, and the back of the bar is illuminated with bright, colorful lights, so all the bottles glow.

  When Vin said he wanted to go all-out for his birthday, we really do, starting with the seafood tower. When the appetizer comes over, it’s almost the size of our table. The seafood is fresh and delicious. I can never eat a whole steak by myself, so I tell Vin if he orders a steak I will have just a few pieces. We get the biggest filet Oscar-style, the twice baked potato, and a side of the lobster mac and cheese.

  Even my lemon martini is over the top. I sip on it, which is served with dry ice and the whole shaker on the side. That is pretty much another martini and a half. After we finish our appetizer and drink half our first cocktails, we both start to relax a little more. I decide now is an appropriate time to ask Vin a few personal questions about himself. I feel like our conversation is flowing naturally in that direction. He has just shared with me his dreams for the future of the agency.

  “I know that you are truly passionate about your company, and you should be, but do you have any other dreams or goals? Do you think about ever getting married or having kids?”

  “Hmm, yeah, I guess so. I mean yes, I want to eventually get married. But it’s not something I’m thinking about right now.”

  “Yeah, of course, you have a lot going on. I’m just wondering really.”

  Our food comes out. The steak and sides look unbelievably amazing. Our sides are brought out on a sizzling hot plate. The server asks if we need anything else. I cannot imagine needing anything else, and Vin and I continue our conversation.

  “So, where are your parents and your sister? Do they celebrate your birthday with you?”

  “Well, tonight my sister is working. She’s a server at Weber Grill just down the street. My parents right now live in New York City. They also own a condo here in Chicago, so they come visit a few times a year.”

  “Wow, that’s cool. Do they like New York?”

  “My Mom does, she loves it. They also lived in Paris for ten years. They moved right after I finished high school.”

  “Really? That’s amazing. I’ve never been to Paris.”

  “I’ve been a few times obviously to visit them. It’s a nice city.”

  “Well, I’d love to go someday.”

  “Wait, you never went to Paris when you lived in London?”

  “No, we only went to Ireland, Wales, and Portugal.

  “Well, I moved around a lot as a kid.”

  “You did?”

  “Yeah from Indiana to New York and Connecticut and then to Illinois.”

  “Wow, that is a lot of moving. After my parents decided to stay in the United States, we just stayed in the same place in the suburbs. They tried to move us a few times, but my brother and I thought where we lived was everything. Sometimes I wish now they would have made us move just to try somewhere else. I was very shy in school, and so the thought of moving to a new place terrified me. I’ve definitely come out of my shell a lot more over the years, and especially since I’ve moved to the city. I feel like a completely different person.”

  “You’re definitely not the quiet girl you were when you started at the agency.”

  “Nope. I’m not.” I put my fork down and my plate. “Everything was delicious, but I seriously can’t eat another bite.”

  “Well, we can’t not order the butter cake. It’s the best dessert. Seriously, you have to try it.”

  “Okay, then. It’s your birthday. Let’s order the butter cake.”

  We order the butter cake, and Vin is so right. This cake just melts in your mouth, and it’s so delicious. It would have been wrong to not order it.

  We finish our dessert and drinks and ask for the bill. I get the check, and I look at the total. It’s $198.68. Whoa. I want to pay for dinner, but including tip, over two hundred dollars is a little out of my price range. I just sit looking at the bill, trying to figure out how to pay.

  “Kelly, you definitely don’t have to pay for this. I got it. I picked this place.”

  “I really want to pay. I feel bad if you pay on your birthday.” />
  “It’s okay. I didn’t expect you to pay for tonight. It’s just nice to go out and have dinner with you.”

  I feel myself turning a little red. I feel awful that he is paying. Especially after he treated me on my birthday. “Well, only if you’re really okay with it.”

  “Yes. My treat.” He throws down his credit card.

  For the fashion show, I shopped at H&M for the most perfect outfit. I'm wearing leather leggings, a long creamy-white tunic with an asymmetrical cut and lots of frilly layers. It’s a little chilly out, so I'm also wearing my leather jacket. I have never bought a fun top like this one, and I love it. I feel very trendy and cool.

  I arrive at the tent in Millennium Park just before six. Amy is already waiting for us. Ten minutes later all of us are together. Everyone looks great, and we have really gone all out with our outfits for tonight. The tent is enormous. Huge spotlights shine all around the outside. I’m so excited to see what it looks like inside. We walk over to the VIP line and give our names. Once inside, the VIP section is crowded, and I can see that the runway area is currently roped off.

  We find an area to hang out, and soon a waiter comes by with champagne. Fancy little appetizers are passed around to all the fashion-goers. We all sit in our little corner, watching everyone who walks in. Most of the people who enter our VIP area all seem to know each other and greet one another with that European double-kiss thing. It’s definitely a scene and so much fun to watch.

  We chat amongst ourselves and check out everyone’s outfits. There is definitely a variety of styles from the simple black dress to outrageous, colorful outfits. Photographers walk around among the guests and ask to take photos of who they think is best dressed. At six forty-five, a voice on the microphone tells everyone to head into the main tent. Suddenly, everyone rushes to claim their seat. It’s a little crazy, but we make it to our reserved seats in the second row. It’s not a bad view for our first fashion show.