Chicago in a day (and a half)

There’s nothing more exciting than visiting a new city! A little over a week ago, the hubs and I were given the opportunity to visit Chicago together and we jumped at the chance.  The only catch was, we only had a day and a half to take in the entire city! Would we be able to see all that Chicago has to offer? Would we survive the frigid weather (our house is never below 70*)? Would I be able to pack everything I need into one carry-on? So many questions, so little time. Check out our whirlwind Chicago trip below, and then get to planning your own weekend getaway to “The Windy City”.

View of downtown from BP Pedestrian Bridge

Eric and I stayed our first night at the Hampton Inn Majestic in the Chicago Theatre District.  The location is prime.  We were about 2 blocks from Millennium park, and even in the freezing cold 30 degree weather it was super close.  This historic hotel has all the modern amenities and decor that I love, while still retaining original pieces like the original gold mail chute. Also, it’s right next door to the theatre playing Hamilton.  We weren’t able to catch a show on this trip, but its definitely on the bucket list.  Fun fact, the hotel is off West Monroe street, which also happens to be the name of the town I was born in, and where my dad’s family lives.  Hamilton and I were both very excited by this!

Eric and I both love vacation spots that allow for a lot of walking, and Chicago did not disappoint.  Walking was much more convenient than having a rental car in this town. Our first stop was The Gage, near Millennium Park.  We made reservations, which I highly suggest.  It’s a bustling town full of people that are not deterred by cold weather!  I love a restaurant that serves brunch.  I ordered the Irish Breakfast, which included 4 different versions of pork (not complaining) and Eric had the Eggs Benedict with Gage Potatoes.

Irish Breakfast – Gage

Now we are fueled and ready to take on the town!  The Bean, or as it’s properly known “Cloud Gate”, is something I’ve wanted to visit since it was first built.  It was just as enormous and gorgeous and reflective as I hoped it would be! I always love seeing the surrounding area of a famous site, because it can sometimes be surprising.  All my Texas people, remember your first trip to the Alamo? When you realized that its directly across the street from about 15 cheap gift shops? That was super disappointing.  Cloud Gate is actually positioned above and behind a quaint skating rink and restaurant called Park Grill, it was seriously adorable, like out of a movie.


Jumping Bean

(Found these in our Dropbox – my husband is obsessed with me)

After visiting Cloud Gate and taking a trillion pictures, along with every other person in town, we continued our trek through Millennium park.  The park is full of magnificent installation art, including the Jay Pritzker Pavillion and the BP Pedestrian Bridge.  It’s not a regular bridge, it’s a cool bridge (“Mean Girls”, anyone?).  The BP Pedestrian Bridge is covered in stainless steel, that not only compliments the whole aesthetic of the city, it also assists in drowning out traffic noise. We also checked out Buckingham Memorial Fountain.  It is one of the largest fountains in the world, during warmer seasons a light, music and water show happen every hour for 20 minutes.

View from above of Cloud Gate, Jay Pritzker Pavillion and BP Pedestrian Bridge
View of Jay Pritzker Pavilion from back lawn
Buckingham Memorial Fountain with view of downtown

The food in Chicago was amazing, and I can’t pick a favorite.  So, you should probably just eat at every restaurant we went to.  Eric and I had dinner at the historic Italian Village, its three restaurants in one, all varying degrees of fancyness.  Eric picked The Village, because he knew I would love the Tuscan Village aesthetic.  Y’all, this place was so beautiful on the inside, it was so romantic.  Mood lighting does not make for great food pictures, but order anything on the menu and it will be amazing! We sat at the back table on the right, so I had a view of a Tuscan city during our meal, and I couldn’t be happier.

The Village - Oldest Italian Restaurant in Chicago
The Village – Picture Courtesy of The Italian Village website

We ended our night at Cindy’s Rooftop at the Chicago Athletic Association.  The rooftop has an incredible view of Millennium Park.  While the restaurant is indoors, the outdoor section has multiple fire pits and heat lamps that make it enjoyable to be outside.

Blurry pic from Cindy’s Rooftop

Day 2 began with walking to our second hotel, the Hampton Inn Chicago Downtown West Loop (that’s a mouthful).  This hotel is brand spankin’ new, as in less than three months old! The interior is fantastic, the rooms are decorated to look clean and fresh and even the bathroom door has an uplifting message on it!  I can’t say enough good things.  Also, shout out to both Hampton Inn’s for letting us check in so early, so we could make the most of our time in Chicago!

I love this – can someone get this for me in an 8×10?

Eataly.  Just go.  Eat + Italy, the name alone lets you know it’s an amazing place.  Eataly is a slice of Italy in the middle of Chicago.  It has a fresh seafood restaurant and 5 different Italian restaurants on the second floor.  As in homemade in-house pasta and mozzarella style Italian food.  They also have a market including meat, fresh made pasta, beer and wine.  But the first floor is where the magic is.  The first floor has a Italian coffee shop, an Italian hot chocolate shop, a deli, the cutest pastry shop and a NUTELLA bar!  Y’all it’s a place dedicated JUST to Nutella, I didn’t know how much I loved Nutella until I walked into Eataly.  Eric and I split a Nutella and strawberry crepe.  Then we each got a panini from the first floor deli.  We each had a half of each sandwich, because sharing is caring and everything tastes amazing, and now I want to go back because I want more food.


The majority of this day was devoted to walking the Magnificent Mile, or Mag Mile if you’re a local.  Unfortunately, I didn’t remove the security tag from my scarf before I packed, so I set off the alarm in every single store.  After about store 5 Eric said I wasn’t allowed in anymore stores, something about not wanting to be seen with a suspected thief ;).  So, we made our way to the Navy Pier, where all are welcome.  Navy Pier is definitely kid and family friendly.  It has a children’s museum, shops, restaurants, pirate ship rides, a theater and a Ferris Wheel.  The theater is called the Shakespeare Theater and I really feel like they missed an opportunity to call it the ShakesPier Theatre.

Navy Pier

Our next stop was easily my favorite part of our entire trip.  We almost didn’t go for various reasons, and despite my multiple bruises and visible limp afterwards, it was totally worth it! The Chicago Skating Ribbon.  Here’s the deal, there’s a skating rink right across the Pedestrian Bridge, with a view of Cloud Gate (remember that from earlier?), so you gotta wonder what makes this one any better.  The answer is everything.  For one it’s a winding ribbon that varies slightly in elevation.  Which means there are parts where you can just coast or speed down.  Also, all the skates looked pretty new and there’s a hot chocolate stand in the skating area, in addition to a rock climbing wall.

Only experienced Ice Skaters can stand completely still

I also learned that I have incredibly strong bones. When I fell (we all knew it would happen) I didn’t even attempt to catch myself and just landed right on my face and stomach, completely sprawled out.  And after the initial phase of thinking that surely both my hips and knees were broken and that this is where I would die, I was able to get back up.  We skated for another hour, and all I had were a few bruises and a fun new swagger to my walk.  This is a story of perseverance, use this whenever you need a burst of motivation, you’re welcome.

My Husband (multiple times): “You look like you’re about to fall”

Me: “No, this is just how I look when I skate”.

Hey, look! It’s the spot where I almost broke all my bones!

 While skating we realized that we were in the Central Time Zone, and that we had about 30 minutes to find a place to watch the Super Bowl! So we booked it, as fast as my gimpy little legs would take me, to the Haymarket Pub & Brewery.  Y’all such a fantastic choice for so many reasons.  For one, the food was amazing.  The Riot burger was literally the best burger I’ve ever had in my life.  The burger patty is made in house from sausage, not to mention there is pulled pork and apple bacon on top.  Eric said his Mr. Potato Head Burger was better, but he’s wrong.  The second great part, we got to watch the Super Bowl with former Chicago Bears: Charles Hurd, Marcus Robinson and Fabien Bownes.  Like actually watch with them, they were at the table next to us and we talked the whole game as if we were all old friends.  Shout out to my hubs for making me watch so much football that I was able to have an intelligent football conversation with an NFL player, while drinking.  Have you been hugged by an NFL player? Because I have! Thirdly, the camera guy brought his service dog, Jack.  Jack sat with me the entire second half and we are now best friends.  Best Super Bowl Ever, aside from the actual outcome of the game.

Fabien Bownes, such a great guy!
Jack Jack, also a great guy!

Chicago you are beautiful and wonderful and we already miss you! Did I mention that your people are super friendly?  Thanks for all the memories!!



p.s. HUGE thanks to my fellow Skimm’bassadors for all the great recommendations!

Not a fan of The Skimm yet?! Check it out: TheSkimm


Coming Next Week:

My must haves for Chicago’s super cold & windy weather,

that can fit in a carry-on


4 thoughts on “Chicago in a day (and a half)

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s