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Well, the fine folks of Chicago showed my friend Julianne and I one hell of a weekend.  Don’t believe me? Well, thank goodness I took Monday off to recover because I slept soundly until nearly 1 p.m. So much for that productive day off.

After a nearly 12-hour bus ride up to Chicago on the Megabus, I quickly checked into our hotel, showered and ran out to meet my friend and Chi-town resident Lindsey for a couple of drinks while we waited for Julianne to arrive.  Lindsey is officially my sister Becky’s friend, but Linds and I are kindred-spirits. The kind that you meet and instantly think – yes, this person gets me and we must be BFFs. First we stopped at Jilly’s on Rush for a cocktail – then we headed over to O’Brien’s for a beer.

After Julianne arrived, we made our way over to Gino’s East for some deep dish pizza.  By the time we arrived, it was nearly 9 p.m. and there was still a line around the corner.  Despite the outside host telling us that he’d hook us up…in 45 minutes, it felt like it took forever to get a table.  Once we got seated around 10 p.m., we sat down and immediately ordered beer and bread sticks for the 45 minute wait for our pizza.

When it comes to pizza – I know that there are two schools of thought – New York vs Chicago-styles.  Blog fans – I have to admit.  I am a New York-style girl.  While Gino’s East does it right, I just prefer the thinner, hand-tossed crust of New York-style pies.

If you’ve never had Chicago-style deep dish before, here’s how it goes.  First there is a crust.  It’s a flaky, almost biscuit-like crust topped with a layer of cheese, then the toppings, then the sauce goes on top.  Go figure – it’s kind of like opposite of traditional pizza.  We went with traditional crumbled sausage and cheese.  It was delicious, but not necessarily what I crave when I want pizza.

After we rolled ourselves up Michigan Ave to our hotel, we woke up early on Saturday morning and headed to the Chicago River.  Julianne and I knew that we wanted to take the Chicago Architecture Foundation’s Boat Tour.  If you do one thing the next time you hit the Windy City – DO THIS.  While we didn’t pick the optimum time to be on the river (12:30 p.m. – it was HOT!), the tour and our guide were fantastic.  If you love architecture, like I do – DO THIS.  Did I say that before?  :)

After the 90-minute tour, we decided we needed some rehydration, a snack and some shade – so we walked up the Chicago river to the Bridge House Tavern.  They had a lovely river view patio with big umbrellas for some shade as well as some interesting cocktail recipes, so it was a perfect spot.  I had the Water Cooler made with Hendrick’s Gin, Watermelon, Cucumber, and Julianne enjoyed the Lightning Bug made with Earl Gray infused Stoli, Lemonade, Orange.  As we sipped our drinks, watched the boaters, commented on the trials of kayaking – we enjoyed their cheese board.  It came with a yummy blue cheese, a cranberry stilton and a smoked cheddar with lots of bread and fruit.  A great way to spend an afternoon.

That evening, we met my former roommate Katie (she was in Chicago on business – what luck!) for dinner at Carmine’s. Holy enormous portions Batman!  Thankfully, Julianne knew what we were in for and suggested that we pick two pastas and share among the three of us.  That girl is one smart cookie, because after sharing a salad and two entrees, we were all beyond stuffed.  Carmine’s was delicious – but pretty classic Italian-American fare.  I wish we had chosen some where a little more authentic – but that will teach me to leave reservations until the last minute.

After dinner, we laughed off the dinner’s calories at Second City.  Oh – I think that I laughed for three straight hours.  If you love comedy and are in Chicago – do yourself another favor and get to Second City.  We completely lucked out and got second row seats, and lived in fear that we would be pulled into the action like another guy on our row. Thankfully, they left us to just laugh our way through the night.

Unfortunately, my MegaBus ride left early on Sunday, so I had to leave Julianne to her own devices for the rest of the day.  I grabbed my seat on the bus, turned on my iPod, closed my eyes and drifted off to sleep to the sounds of Bon Iver.

All in all – it was a whirlwind trip, but absolutely the best time spending some much-needed quality time with my college roommate Julianne.  When I first met her junior year of high school, we explored NYC together – it was only fitting that we explore another city together.  Can’t wait to explore another great city with her soon.