Chicago! Part 1–Sightseeing & Eating Our Way Through The Windy City

It’s been a little over a week since we returned from Chicago and the heat index is finally under 100 for the first time all summer! Hallelujah! What better way to spend the day than outside recapping our trip! We had such a wonderful time in Chicago and I’m happy to add it to my list of cities I love. Good food, nice people, so much to do and see! It’s a little like New York except smaller and not quite as busy. Robert and I both agreed we thought it would be a fun place to visit with children that were a bit older as there seemed to be a lot of family centered activities. Hopefully we’ll get back again someday, possibly we kiddos in tow!


We arrived on Thursday and waited at the airport for about an hour for my sisters flight to get in. Once she arrived we hopped on the train from the airport to the city. The ride was fine but took about an hour, certainly longer (although cheaper!) than a cab ride would have been. We checked into our hotel and freshened up before heading right out to a deck party in a high-rise!

Shawn's Building  Shawn 3

Shawn, my good friend from college lives in Chicago and graciously invited us to a cookout on his deck. I wasn’t quite sure what to expect, but when we arrived at his building which overlooked the river we were instantly impressed. The building itself was sleek, modern and beautiful and the views from the 28th floor where the party was held were breathtaking. Shawn had Mediterranean food catered which was delicious, orzo salad, skewers of lamb and chicken, even grilled calamari. The party ended fairly early since most of the guests had to work in the morning and we called it a night in anticipation of a full day on Friday. It was a nice, low-key introduction to the Windy City! Thanks for the hospitality Shawn!

Shawn 2
Windy but worth the view!

The next morning we had a quick breakfast at our hotel before hopping aboard Chicago’s First Lady for a Chicago Architecture Foundation River Cruise. I am usually a fan of walking tours when traveling but the boat tour came highly recommended and I knew it would be right up Robert’s boat loving alley.


The 90 minute tour was awesome, well worth the money (about 40 dollars a ticket) and so informative and interesting! It gave us a great feel for the streets and buildings along the river and helped orient us to the city we would soon be exploring by foot.

IMG_1088 Building 1

The docent knew so much about every building; everything from the architect to different design elements and fun facts. We loved this building which was designed by a female architect (Girl Power!) and won a PETA award because it uses special types of glass that not only create a pleasing wave-like aesthetic, but also keep birds from flying into the windows.


We loved the river tour and I would highly recommend to first time visitors. After we got off the boat we walked to Millennium Park. We stopped along the way at Garrett’s Popcorn for a mid-morning snack.

Garretts Bag Garrett's PopCorn

We choose to all split the Chicago Mix, a mixture of cheddar corn and caramel corn. Sounds gross but weirdly tasty. Once we got to the park, there was a magician performing by Wrigley Square. We took this opportunity to practice using our new selfie stick.

 MP Selfie

No judgment, they are pretty fun and highly useful for group pictures if you aren’t into bothering strangers. We spent some time at the Bean (err technically Cloud Gate…but doesn’t everyone call it The Bean?).

IMG_1250 IMG_1276

Inside the Bean IMG_1268

And caught the tail end of a concert at the Pritzker Pavilion.


We also walked through Lurie Garden and Crown Fountain which I loved.

IMG_1288 IMG_1290

The fountain has two glass towers at either end which project moving images of giant faces, smiling, laughing. Occasionally, the mouths open and a water spout shoots out over the fountain! It’s really neat and so fun to watch the kiddos splashing around and giggling.

IMG_1368 IMG_1371

Once we had had our fill of the park, we walked to the former Sears Tower now known as Willis Tower. The Willis Tower is not only America’s tallest building, but also home to SkyDeck, a glass box 103 stories up that without a doubt offers the best (and most stomach dropping) views of the city. The lines at SkyDeck are long but they move fast and there are fun facts and videos to keep you entertained while you wait.

IMG_1293 Willis Tower

Heights aren’t my favorite but I mustered the strength to step out into the glass box for a few photos.

Group Ledge 2 IMG_1309

IMG_1321 H and L Ledge

Once we left Willis Tower we were all starving and decided it was time to sample Chicago’s famous deep dish pizza. After getting 100 different opinions about which pizza was truly the best, we decided on Giordano’s. It had been recommended by several people but more important was the fact that it was right around the corner from Willis Tower.


We were seated immediately and waited about 45 minutes for our pizza. A few fried appetizers were necessary to tide everyone over. Oye.

 All the fried things

The pizza was… different. Far from my favorite, but I’m certainly glad we tried it…after all, when in Rome!

 Giordanos Pizza

After our late lunch we walked to the Magnificent Mile and did a little shopping and a little street performer watching.

 Street Performers

We got back to our hotel in time to rest a bit, change clothes and head out to a late dinner at Carnivale, a Latin fusion restaurant that had been recommended by a friend who lives in the city.


The restaurant was so bright and colorful, I liked it right away and wished I wasn’t still so full from lunch.

Carnivale 3  Sisters Carnivale

We started with guacamole and calamari, both of which were fantastic. The boys ordered two different types of beef, Churrasco and Arrachera, both of which were delicious. My sister Haley and I split the paella which we both agreed was just ok.

Calamari Arrachera


We returned to our hotel stuffed and sleepy, ready for the Field Museum in the morning!

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