September 14, 2011

Chicago: the wind is out of my sails

I planned to write this post after a trip, but now that the trip is likely not happening here’s what might have been:
Once upon a time I was going to move to Chicago.  I was going to do the cliché “move to New York as a bright-eyed twenty-something thing,” except it was going to be awesome(r) because it was Chicago.  I was going to boost my career and bravely face the cold, cold winters whilst rocking some thermal underwear.  I was going to eat my way through the ethnically diverse city.  I was going to become friends with Rick Bayless.  I was going to learn to make mole in his kitchen (not a euphemism) that was second only to his.  I was going to learn to like baseball, because that’s what people in Chicago do.  I also was going to become friends with Oprah.  I’d say “Oprah, girlfriend” without sarcasm.  I’d become one of her favorite things. 
I envisioned many moments of clarity happening for me.  I’d find the perfect career.  I’d balance that and a party girl lifestyle.  I’d have friends – lots of them.  I’d have shoes – lots of them.  I would return to Tennessee for holidays, impressing everybody with my posh wardrobe and carelessly beautiful hair.
Did I mention the eating?  I’d do oh-so-much eating. 
These plans were just starting to take shape about five years ago.  Four years, three months and two weeks ago, I had the first date with the love of my life.  Six weeks later we were engaged.  Six months later we were married.  Within that first year of marriage, I became a stepmom, homeowner and mom.  I never looked back.
Well, sometimes I look back a little bit.  I peek at Chicago and sigh.  It’s the life I could have had.  The single version of me would have thrived there.  The current me: full-time PR flack, full-time mom, 30-something, wife, girl who stresses about everything – she has no place there.  This is the life I chose; the life I want.  Nashville is home, and I’m happy here.  But…
I need to visit.  Often.  I need to feel the cold wind on my cheeks as I trudge through the snow toward the Christkindlmarket.  I need to feel the scorching sun on my shoulders as I walk many blocks – after taking three trains and two buses – to get to the real Little Italy.  I need to stroll into places like The Violet Hour like I belong there.  I need to confidently march to the El, knowing the right color or route or whatever without help of a map.  I need art.  I need shopping.  Did I mention the food?
Husband and I were planning to head there next month for two measly nights, the first trip we’ve taken alone since our honeymoon almost FOUR years ago – which, I should mention, was in Chicago.  In January.  (Yes, he loves me.)

However, those powerful people who set the travel prices have other plans.  We can’t afford it.  We can’t justify one weekend costing $1,000+, and that’s before we factor in the lots and lots of eating we’d do. 
Sad thing is I’d already planned the trip.  Here’s what we would’ve done:

Oh Southwest, gone are the $39 each way days.  I love this flight: a quick, nonstop jaunt from Nashville to Chicago, then the train ride from Midway to downtown Chicago is always fun for me.  The anticipation builds as I watch the city come into focus.

Cape Cod at The Drake
During our blustery January honeymoon in Chicago, our first meal was here.  We each had an amazing bowl of clam chowder, served with warm bread, and I can’t imagine not starting off every trip this way, no matter the temperature outside.

Whitehall Hotel
This boutique hotel is among my favorites in the city.  It’s located at the top of the Magnificent Mile, near the Gold Coast, and it’s cozy. 

Frontera Grill
If I’m in Chicago, I’m eating here.  Period.  Rick Bayless is a genius and I can count on a perfect meal here, every time. 
The Art Institute of Chicago
Husband is an art buff, and I always learn to look at art differently when I’m with him. 

Navy Pier
Ferris wheel and fireworks = perfect romantic moment.
Tavern on Rush
So far, this restaurant has my favorite steak in Chicago.  I had a memorable meal there, which ended with fresh lemon sorbet served in a hollowed lemon. 

The Motel Bar
This kitschy bar is decorated like a retro hotel, and the ‘room service’ includes old fashioned drinks and quirky bar snacks, like Old Bay seasoned potato chips.   

This is one of my favorite shoe stores.  While it’s not unique to Chicago, I always make a stop – and an indulgent purchase – when I visit.
Red Apple
I’m 25% Polish, and grew up eating and loving Polish food.  I’ve always wanted to visit Avondale and haven’t yet made it.  This trip was going to make that happen for me, including a big, hearty meal at Red Apple.

American Girl store Obligatory shopping trip for my little girl.

Lula Cafe in Logan Square
I must have these ice cream sandwiches.
This is the part where I should say “it’s ok.”  That hubs and I have a weekend together and no matter where we spend it, we’ll be happy.  But it’s not.  I had my heart set on Chicago.  On having that experience with him.  I’m disappointed and whiny and pouty and overall not a happy girl. 

That said…where should we go?  We’re probably going to road trip it.  Asheville and Louisville are contenders.  Any other recommendations?

And what’s your favorite Chicago spot?  You know, for the next time.