The Windy City, Our Second Home

Chicago is special for us.  It was our first vacation destination back in 2006 when we first started dating and we have some really special memories from that trip.  We try to go back every chance we get. 

Chicago, July 28, 2006
Chicago, May 19, 2007

Chicago, June 14, 2008
Chicago, April 24, 2011

Looks like we didn't make it to Chicago in 2009 when I was studying for the bar exam or in 2010 when we got married and went on our honeymoon.  Oops!  But we had the chance to get there this year during a long weekend in March, so we hit the road with no plans other than to eat at our favorite restaurant, Avec, which is always on our Chicago itinerary and was even referenced in our wedding vows.  We also wanted to try XOCO, a Rick Bayless restaurant.  So off we went! 

Chicago, March 3, 2012

Upon arriving in Chicago, we headed to XOCO for lunch.  Rick Bayless is Alessandro's hero.  He is a chef who specializes in cooking authentic Mexican food with a high-end spin.  Bayless lived in Mexico for a period of time and still travels regularly to Mexico searching for authentic dishes that he can recreate and modify in his own way.  Bayless has three restaurants on the same street right next door to each other in Chicago:  XOCO, Frontera Grill and Topolobampo.  We'd like to visit each one.  Topolobampo is the fancier of the bunch and reservations for the place book far out in advance, so we would have to make a reservation and then book a future trip around the reservation.  

XOCO is a casual lunch place that serves tortas (Mexican sandwiches) and caldo (Mexican soup).  XOCO is uniquely ran, in a methodological kind of way, and I was very impressed by the way that every single worker knew their role, which allowed the long line out the door to dwindle down in only about a half an hour.  That place was efficient!  Here's how it works:  when you walk in, you stand in a long line which will eventually lead you to the register to place your order.  The restaurant is small and narrow, (sorry, no pics, I was shoulder to shoulder with other patrons), and the kitchen is right behind the register and you can see fresh churros being made...it's pretty cool.  As you reach the front of the line, a host will ask how many are in your party, and you aren't allowed to place your order until the host finds a table for you.  You place your order at the register, and you have to anticipate whether you'll want dessert or not because this is your one chance to place your order!  We ordered a ton of food because, "you're only in Chicago once," which isn't true at all, but ended up becoming our mantra that weekend.  After you place your order, you sit down at your assigned table and then someone brings your food to you.  They wait until you are done with your meal before bringing out the dessert.  It was a well-run ship that place!  And the staff was memorably friendly. 

So for our lunch, we had the Carnitas Caldo, which was a slow-cooked pork soup with masa dumplings, roasted chile and topped with arugula and avocado.  It was really good, but so spicy that I couldn't really eat it.  

Alessandro had the daily torta special, which was goat barbacoa.  It was a sandwich with braised goat, tomatillo sauce, avacado and cilantro.  

I had the chicken milanesa torta, which was topped with black beans, cheese, pickled jalapenos and served with tomatillo-avacado salsa on the side.  

For dessert we had a perfectly cooked churro and authentic hot chocolate.  Both were extremely indulgent and topped us off.  Neither of us wanted to eat ever again after that meal.  

After lunch, we checked into our hotel, which was the Doubletree-Magnificent Mile.  We priceline-named our own price on that bad boy and snagged a room for $60/night!  We love Doubletrees because they make the best chocolate chip cookies and every guest receives one upon check-in.  My mom gave Alessandro a canister of Doubletree cookies for Christmas, and it was by far his favorite gift.  He dreams about those cookies.  And, if you have never tried priceline's name your own price feature, you should give it a try.  We have used it 9 times, and have only gotten 2 hotels that we wish we wouldn't have.  So I'd say that is a pretty good success rate considering how much moola has been saved.  

Here we are at our hotel about to head out to go shopping, which was only two blocks away.

Alessandro and I never go shopping together because, well, he doesn't like shopping and I like to shop alone.  The last time we went shopping together was last summer, which I wrote about here.  Ironically, that story also has to do with tortas and lots of eating, so I'm starting to see a trend in our activities. 

But, for some reason, Alessandro was in rare form this particular weekend.  He wanted to go shopping since "we're only in Chicago once."  My goal of the shopping trip was to buy Alessandro a new pair of jeans.  He was still wearing the jeans he wore 6 years ago when he was 20 pounds heavier, so I have been desperate to get him into a pair that fit.  

It was a successful shopping trip, and we came back with lots of goodies...all for Al!

He got the following:
  • A new hat from Nordstrom that he found on clearance for $13...booyah!
  • A starter shaving kit from The Art of Shaving
  • A white tea mix and tea pot from Teavana (which is actually for both of us)
  • A new pair of Levi jeans!
  • And a box of Vosges truffles "because that was the only thing [he] asked for for Christmas that [he] really wanted and didn't get," said jokingly...he's not really that spoiled.  (Read more about Alessandro's love for Vosges truffles here, and today is the last day to vote for his truffle, so please vote for it here!)   

He absolutely loved The Art of Shaving store.  I could tell that he really wanted to buy something, but he was hesitant because the stuff was pretty expensive.  So I "pressured" him into buying the starter shaving kit, which was only $25.  That ended up being $25 well spent.  I think he actually looks forward to shaving now with that kit and is always talking about how smooth his face feels.  And I have to admit that the Sandalwood scent of the product smells really good, and I typically hate the smell of shaving products.  I think Alessandro has his eye on the full shaving kit someday.  

Shopping took a lot out of us, so we wanted just a low-key dinner, and ended up at a pub down the street from our hotel called Elephant & Castle.

We had janky service and we didn't really like our food very much.  We ordered Guiness, chicken pot pie and shephard's pie.  Alessandro compares every chicken pot pie he ever eats to KFC's chicken pot pie, which I have heard from numerous other sources is delicious (albeit kinda gross actually).  So he was underwhelmed to say the least.  

On our way home from the restaurant, I got a Dunkin Donuts coffee, which made my night complete.  I don't know why, but DD coffee always completes me.  

Stay tuned for Day 2 of Chicago this week, which was the BEST day ever because we discovered an awesome market with more delicious Mexican food and drinks and also finally got what we came for:  an amazing dinner at Avec. 

What are your favorite Chicago destinations?  We need to know!

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