The weekend in Chicago started with a 6:12 train from Quincy to Chicago’s Union Station.  Let it be known that travel is the only time I will get up that early and be even slightly happy about it. On the upside, trains are a great way to travel.: you don’t have to worry about what you pack, there is no need to stop for gas or worry about the state of a car, and you get to see more of the towns and country since train tracks typically follow a different path than highways. The ride from Quincy to Chicago featured a lot of flat countryside and cute small towns but the blankets of snows and frozen streams made it worth it for me to not sleep the entire 4 hours. Something so simple as watching outside the window is one of my favorite parts of travel. It’s all about seeing things, for better or worse, and just observing what else is out there. It reminded me of the purpose of the project and made this night owl OK with starting a vacation day that early.

My first moments in Chicago after getting off the train were memorable for one incredibly obvious reason: cold, cold, COLD. I thought I was ready for it with my pea coat and scarf and Tuscan leather gloves, but I was just wrong. The wind hit me immediately and my hair went everywhere. The whole “Windy City” thing is not an exaggeration. I always try to play it cool and not come off like a noob tourist, but I failed miserably here.

After I got over myself and we got in a cab, I was actually able to notice the city and I fell in love.  I am absolutely a city girl. I don’t discriminate or anything when I travel, but cities are just at the top of my list because there is so much more to explore and experience. I looked around in Chicago and saw all the huge 50+ story buildings and the river running through the urban setting and was hooked. A little background, I work in downtown Houston and just love the setting and the way it makes me feel like I am at the center of something important. Chicago seemed like that downtown times 50 so I was definitely a happy girl.

Kori and I stayed at theWit and were lucky enough to be able to check in when we got there at noon. That seriously saved the day. We were able to drop our bags, freshen up, and get fresh cookies! theWit is a DoubleTree hotel so we definitely had those delicious chocolate chip walnut cookies for “breakfast” before we bundled up and hit the streets. The first thing we did was catch another cab, to go a few blocks around the corner. We didn’t realize that until the weekend was over. I’m pretty sure the cold kept us from considering our options clearly. Whatever. Neither of us mind talking to strangers so it all worked out. The day in the city was loosely planned which is just the way I like it.  The first stop was supposed to be for an actual meal and we eventually got there after refusing to wait an hour for brunch and getting lost trying to go around the corner to find a better alternative. It’s a good thing I actually like to wander around in the city or else my hangry side might have taken control.

We ended up at Giordano’s for the obligatory slice (whole pie) of Chicago deep dish. We were able to escape the lunch rush there by being in our early twenties, wanting to day drink and finding seats at the bar. That is also one of my travel preferences if I can swing it. The bartender, bless his heart, was busting his butt serving all the tourists, even the obnoxious milkshake couple. Mini-rant: if the bartender tells you that they do not have chocolate milkshakes, do not then proceed to ask him to make you one out of ice, half and half, and chocolate syrup. Everyone will judge you and your fellow patrons will hate you as you take all the time of the single bar keep. Oh, and don’t then stick your knife in the shake and ask him to remake it when the consistency is not to your liking. Maybe if they had asked for alcohol in it I would have given them a pass, but they were just too much. People who are rude to waiters/bartenders: I can’t. End rant.  Back to the food, my first taste of Chicago deep dish was interesting. I am actually still not sure if I like it. Yes, it was absolutely delicious with the cheese, sausage, onions and peppers (all my favorites), but I couldn’t get past the sauce on top. It’s that simple.  Of course that didn’t stop me from putting away two slices and a few ciders. It was a good girls lunch and I was glad to get one of the super touristy things off the list so we could move on to better things.

Obligatory Chicago stop #2: the Bean in Millennium Park. Our restaurant was a block from the park but we made a detour for coffee. Having a shot of espresso is something I always try to do after lunch when traveling. It keeps you going for the rest of the day and settles the stomach. An Intelligentsia coffee location was on the corner near the park so we gave it a shot. If you ever thought Starbucks was pretentious, you should never go here. The baristas wore vests and ties like professional hipsters and you could see them pouring and serving the coffees with different techniques than your typical café. I’m not the type of person to be turned off by things like that so naturally I was in awe. The place was packed and the reason became completely obvious after one sip. Any place that allows you to enjoy coffee that is not overly sweet or flavored is doing it right.

 

The drinks were the perfect hand warmers as we crossed the street and walked through the park. The Bean is perfectly situated between the lakeshore and those tall buildings I love. There was a decent crowd of people around but the good thing with the bean is that it doesn’t matter who else is in your shot. It’s a huge reflective metal object in the middle of a city park, seeing what else is around is pretty much the point. I am happy with the shots we were able to get, but mostly I was just happy to have another way to appreciate the urban setting.

 

From here, the day went totally off the tourist rails and adopted a spirit that was absolutely Kori and I. We made our way to Nordstrom on Michigan Avenue and tried on Louboutin pumps for size (literally), managed to resist the urge to buy them on the spot, got free make overs from Dior and bought way too much makeup before escaping the urge to shop and heading over to Eataly. Thanks to this market, restaurant and overall showcase of everything delicious and Italian, we made dinner out of Nutella crepes and red wine. Any place that lets me walk around with my glass in my hand is immediately at the top of my list. You add in food and kitchen gadgets and I won’t want to leave. The only thing that really pulled me away was the prospect of going to a restaurant with tequila taps ON THE TABLE called El Hefe. We didn’t make it in time for dinner before it turned into a club, but that was probably for the best. I might have died of happiness and a little alcohol poisoning if we had been able to go, but make no mistake, it is at the top of my list for my next trip to Chicago. Tequila is pretty much my drink of choice. Pineapple juice is my favorite thing to mix with it. If you don’t know, now you know.

 

Missing out on tequila heaven didn’t stop the rest of our plans for the night. The Signature Lounge on the 95^th floor of the Hancock Building was obligatory Chicago stop #3. It was a little smaller and the décor was more dated than I expected but absolutely none of that matters once you see the view. That is the real draw of the place and it does not disappoint. A city lit up a night from almost 100 stories up? Be still my heart. The drinks surprisingly lived up to the view. It would be easy for them to overcharge for subpar drinks but that is not the direction they went with their cocktail menu. They had one that mixed bourbon, cider and spice liqueur so I was beyond content. I’ve been really into mixing hard cider with Fireball. It’s my number 2 drink of choice. The one I had here tasted like straight apple juice and that was completely fine with me. I felt the alcohol just fine after I downed that first glass.

The Signature Lounge was a great way to start the night but the main event came later with cheaper drinks and a much lower elevation. We ended up at Public House on N. State Street and it was everything. It was just our speed: a little high brow with the look of it and the bookshelves, and the crowd was well-dressed but obviously chill. Kori was able to find the only group of girls dancing and of course we all immediately became best friends. It was a perfect night out pre-birthday with one of my best friends in a great city. The pickings weren’t too bad either- yet another reason I’m already planning on going back to Chicago. Our time was only cut short when I made the fatal error to bar hop and we failed to find a place that was better. We also didn’t want to wait in line in the cold after dancing in heels for a few hours. We even tried the bar on top of our hotel but we were both just done. No regrets.

After sleeping through several alarms and plans to start the day early, we managed to get ready and headed to WildBerry Pancakes and Café for brunch. We may have waited an hour for a table but the lattes with Intelligentsia espresso, the namesake Wildberry pancakes, and the duck hash were definitely worth it. So good, yet so bad, and so off my typical meal plan but whatever, this was the last day of vacation and Sunday Funday! Actually, that was my only complaint: no booze. I let it slide though. There will be other trips to have a boozy HBIC brunch. The rest of the day involved shopping with some sweet finds before heading to the airport to catch my flight back to Houston.

Chicago made it to the top of my list of favorite cities. I fell in love with it the same way I did with Paris, Florence and Venice while traveling last summer. My only regret is not having more time to explore more of the neighborhoods. I would also bite the bullet and go during the short summer despite bigger crowds and higher priced rooms. Less layers to pack means more space to bring stuff back! I could totally see myself living in Chicago, but for now I will just set up an alert for low airfare from Houston and hold out for another visit with an equally awesome travel buddy.