Friday, April 8, 2011

Adventures in the Windy City

This year Hubs and I took off to Chicago for our Anniversary. We love exploring new places and love big cities. Last year it was NYC, then on to Chicago, maybe next year I'll find some place warm to go since heading north isn't generally a good idea in March.

We only had 2 1/2 days there, so we had to squeeze as much in as we could. On Saturday after checking in at The Drake

and taking a quick power nap, we headed to the Hancock Building. There is a bar/lounge on the 96th floor. We headed up to grab some cocktails and watch the sunset over the city. 

From there we headed out for none other than Chicago Deep Dish. We had seen the Food Network's challenge of Chicago vs. New York pizza. We knew we would probably be squarely on the New York side, but that doesn't mean it wouldn't be delicious! We headed to Giodorno's. Half an hour into our hour wait we had to order so our pizza would be ready shortly after our table was ready. 

I thought it was delish. You can't compare it to NY Style pizza. They are so different. Deep dish was more of a pasta dish than pizza to me, I had to use a fork and knife to eat it. They are good at what they do though, good enough for us to decide we needed to try Lou Malnati's later in the trip. 

The next day we woke up, enjoyed brunch, booked a tour for the next day, then headed out on foot to explore the city. We walked down the Magnificent Mile but didn't stop to do any shopping. Our first stop was at Millennium Park. It is such a cool place next to the skyscrapers and historical buildings. Of course we had to get some pictures at The Bean:

We then walked up to the top of the Art Museam for some more pictures until my camera died. (Note to self: check that camera is charged before vacations). We hiked from there over to the Navy Pier. It was pretty empty, but it was also in the 30's. Not a ton of people out enjoying the icy wind like we were!

For lunch we went to try out Al's Italian Beef. Hubs had seen something about it on Man Vs. Food, but I didn't know anything. When they asked me if I wanted my sandwich "dipped" I had no idea what the right answer would be. It turns out, even if you say No, it'll still probably get dipped. We were not impressed with Al's, so with that, we headed back to the hotel to nap before dinner.

That night we went to Rosebud for dinner, I had no idea when I was booking the reservations, but it was on the same block as the hotel, that worked out nicely!!!! We had a fantastic steak dinner and then headed down a couple blocks to Jilly's, a piano bar I had found on Yelp. 
The description said this place would be a hit for fans of The Rat Pack. It did not disappoint. We had a blast at Jilly's. 

On Monday we had booked a tour with The Untouchables to see all the Gangster and Mob historical places around the city. We saw bullet holes left over from one killing at a cathedral (Sorry, I didn't take any notes and lost the handouts they gave us)
They took us through Capone's history along with several others. The guys leading the tour were SUPER cheesy, but it was fun and a good way to see much more of the city. (We also drove by Harpo Studios, too bad we couldn't get in for one of Oprah's final shows)

Then it was back to the hotel for another nap (we love sleeping) and to get ready for our big anniversary dinner! We had brought wine from the vineyard where we got married and stopped at Sprinkles for a red velvet cupcake to share. 

Dinner that night was a Cafe Spiaggia, again I managed to book a dinner right across the street from our hotel. Dinner was amazing. We were in our own little world, lingering over each course, just chatting and enjoying our evening. From there we went back to The Drake to have a night cap in their bar.

Tuesday was a relaxing morning of breakfast and packing and then we wandered over to Portillo's for hot dogs. These dogs are LOADED. Hubs got a traditional dog that is served with everything including tomatoes and pickles. I got a chili cheese dog. Both were amazing.

From there it was back to the hotel to collect our bags, hop in a cab, and wave adios to a spectacular city. It was another successful trip and an amazing anniversary. I can't believe it's been two years already! Seems like just yesterday I was running down the aisle to marry my man! And what kind of anniversary post would it be without gratuitous wedding pics??? Here you go!!!!!!


  1. It's really fun seeing Chicago form a tourist perspective. I need to get out and explore more or I'm really going to be sad when we move away and it isn't an option.

    And I really need to walk to Giordanos and get some pizza. Isn't it crazy that I can easily walk there? (Well to one of the locations at least...)

  2. These are great! Thanks for the tips! I will use this for my trip!