Frank Sinatra said it was his kind of town. Because of the month of September, I've always believed it was my kind, too.

There's nothing like September in Chicago. The cold isn't present to freeze the tears on your cheeks, and the sweltering heat has long since blown away. It's big enough for the exciting bustle of visiting the city - but it's small enough that it isn't as overwhelming as New York can be. It's also full of mid-western friendliness. Because when I'm in New York for too long, I sometimes find I have a perma-frown on my face. You know, so I don't get mugged simply for having a stupid grin on my face and wearing my heart on my sleeve.

For two consecutive Septembers, my friend Jessica and I went for our Chicago weekend to celebrate her birthday (which, this year - is the day I'm getting married!) 

The first year, we stayed in Hotel Monaco. PEOPLE. After you check in to your room, an employee knocks on your door to surprise you. WITH YOUR VERY OWN GOLDFISH. A real goldfish. Not the crackers. We named ours Perfect. We had zebra and tiger print robes. It was the perfect amount of boutique. The walls were striped in green and white. The the headboard was a plush red. It was a perfect location.

The next year, we went a more modern route and stayed at Hotel 71. The room was enormous and the view was even better. We didn't get a goldfish, but we did get swindled by a toothless lady on Michigan Avenue that convinced me to give her fifteen dollars. That was also the year that a man at a bar we visited kicked me in the knee, and I told him that it was just like Nancy Kerrigan. What a butthead! 

I have been craaaaving a Chicago layover. 


Conveniently enough, it was a long layover on the same weekend that there was a mass exodus of the city because of the NATO Summit. We're talking riots and ridiculously heightened security everywhere. Thank you, Mr. President. 

I was flying with a girl that not only looks like Ali the former bachelorette, but is also has a completely fantastic Etsy shop. She makes gorgeous pottery. Her pricing is super affordable, and I am giving you the opportunity to support a small business! GO VISIT HER!

We ate Chicago pizza. We marveled and played at the Bean. I silently wished I could go streaking through the fountain. We walked around Michigan Avenue. 

We went to bed early because we were getting picked up at FOUR IN THE MORNING. But THAT. Is an entirely different story.

When are you going to Chicago?

Right now?




  1. FUN! I actually was born and raised in Chicago, on the southeast side of the city. Lived downtown for college and north side as a single gal =) After I got married I moved about an hour north into WI. I LOVE every single thing about my city. And you are right, September is perfect! =)

    1. That's so great! I would love to explore outside of the Michigan Ave area (clearly I don't know neighborhood names). What are some other great areas to explore?

    2. My favorite neighborhoods are Bucktown, Lincoln Square and Edgewater- Bucktown is very artsy and young, Lincoln Sq. has some german influence but also a great place relax and kick back (Welles Park, Bowmans Bar and Grill) , Edgewater is also a darling Swedish area (Ann Sathers cinnamon rolls-I DIE!) . The CTA and bus system is extremely easy to figure out and accessible from MDW. If you take the 22 Clark St. bus straight north from the loop you get a great experience of many different neighborhoods. If you head far north onto Devon Ave. it seriously transports you to a little India. Amazing!

  2. My family and I were looking for a place to go for a few days this August, and Chicago sounds perfect! Maybe we'll end up there :)
    <3 Kiersten