Every time I told someone I was taking Derek to Chicago to celebrate his 30th birthday, I was met with the same response:  Why Chicago?

In fact, after the 5th person or so asked, I began to wonder if I had made some sort of Birthday-ruining mistake by planning this trip. Chicago was a place Derek and I had always talked about wanting to visit one day, so I thought his birthday would be the perfect time to cross it off the bucket list. But I think he even began to second guess the trip with all the nay-saying in the background, so we stepped into this little vacation cautiously excited.

Well, to everyone who wondered “why Chicago”, this post is for you. The city blew our socks off. Literally, and figuratively (Chicago definitely lives up to its nickname, The Windy City!). We decided that it was as if Manhattan, New York and Pasadena, California had a baby. It had the hustle and bustle of NY, on a smaller, more manageable scale. And the cleanliness and feel of Pasadena. With fresh tulips growing in planters all throughout the city and some of the kindest people I have ever met.

It’s huuuuge. We could have spent an extra 2-3 days there and probably still have left several things undone. We didn’t do everything we wanted to, but that’s because we chose to walk as much as we could to take in the scenery and fully engulf ourselves rather than rush from place to place. We racked up over 10 miles of walking in one day!

So here’s a rundown of our incredible Chicago trip.

FOOD

Of course, I’m starting with the food because, duh. In all honesty, we ended up eating appetizers and finger food for about 80% of the trip. It wasn’t that we didn’t want to man vs. food it, it’s just that we walked soooo much that by the time we finished, we would find ourselves skipping lunch and heading straight to happy hour because it was usually already pretty late. But here are some of our absolute favorites from the trip.

LOU MALNATI’S PIZZERIA

Lou Malnati’s Pizzeria was our first Chicago deep dish, and it did not disappoint. We ordered the Malnati Chicago classic and added pepperoni at our waiter’s suggestion. It was amaaaazing.

KIM AND CARLO’S HOT DOG CART

We stumbled upon Kim and Carlo’s Hot Dog Cart on our 3 mile (one way) walk to Soldier Field one day, and we ended up coming back two days later because it was that good. Classic Chicago dogs are a must, so that’s what we got! They’ve got a sign on their cart that reads “You must dance for ketchup!” because in Chicago, ordering ketchup on your hotdog is almost offensive.

PUBLIC HOUSE

Admittedly, my dessert game was weak on this trip and I only indulged once. But I made it count with this insane cake shake from Public House. I literally could not stop laughing when our waitress brought it out because I couldn’t believe how absolutely absurd it was. Our seasonal shake was strawberry, with a rainbow lemon cake on top. It was deliciously awful for us and I loved every bite.

GIORDANO’S

Giordano’s was another must and our Chicken, Sausage, Deluxe deep dish was on point!

PORTILLO’S

And we stopped in at the famous Portillo’s for more Chicago dogs. We meant to go back and try their italian beef which is supposed to be amazing, but we never made it. However, I just heard that they’ve actually got a location out here near me, so it looks like we will be making a trip to one soon!

P.S. If you’re thinking that all we ate this entire trip is pizza and hot dogs, you’re basically correct. When in Chicago!

ATTRACTIONS

CLOUD GATE AT MILLENNIUM PARK

Cloud Gate, better known as the Bean, is an obvious but necessary, stop. Millennium Park as a whole is really incredible, and this tourist attraction is one I don’t recommend skipping because it really is very cool to see in real life.

360 CHICAGO OBSERVATION DECK

360 Chicago Observation Deck is a thrill that I definitely recommend. The attraction Tilt, allows you to tilt outward over 1,000 feet above the Magnificent Mile and the view is absolutely breathtaking.

Not into tilting? That’s okay! Grab a cocktail and enjoy the view.

PINSTRIPES

Pinstripes was a bowling alley we stumbled upon and it was fantastic! They had luxury couch seating, table service, and private bowling lanes. Not to mention some delicious calamari and bruschetta which are not pictrued.

SECOND CITY

When I found out that Second City had a comedy show about the website Derek and I met on almost 9 years ago, I knew we had to go. #DateMe: An OkCupid Experiment was vulnerable, hilarious, relatable, and down right perfect. If you’re a comedy fan, I highly suggest you check out this theater and this show!

SAFEHOUSE

We happened upon SafeHouse on accident, which seems to have been a bit of a theme for us this trip. We were hungry and started yelping places nearby, and I saw that the food and atmosphere looked good, so we walked over. When we got there, we thought we had the wrong address, because there was no restaurant in sight.

I ended up opening a door to a room that looked like a real estate office, with one women sitting inside reading a book, and I awkwardly said, “Is there a restaurant here…somewhere?” I felt ridiculous, but to my surprise she replied, “I might be able to help you with that, and had us come inside.” She then asked us if we knew the password (we didn’t) and made us show her our best disco moves before finally letting us through a secret door that led to a downstairs area.

All of a sudden, we were transported into a spy-themed restaurant and we became aware of the fact that security cameras upstairs showed the entire restaurant our embarrassing entrance and disco. It was hilarious and amazing.

The waiters give you name tags to become a spy, along with a mission card—allowing you to walk around the place solving riddles.

And the food was delicious. I had a burger with Brie and bacon jam and ommmmg.

To leave, we had to find a secret doorway, put a dollar in a payphone and wait for it to ring, then enter a secret code. I mean, come on! It was such a happy accident and we had an absolute blast.

THE FIELD MUSUEM

Since The Field Musuem has dinosaurs and mummy tombs and is so gorgeous on the outside, we decided to check it out.

I would say the musuem is a must for anyone who loves science/history. It houses the most complete T-Rex found to date, along with over 30 million other specimens and artifacts.

When I entered the Egyptian tomb, I couldn’t breathe and started to cry, so you know there’s some serious history in the place.

It was remarkable, and definitely worth checking out.

NAVY PIER

Go to the pier, pay the outrageous $15 per person price tag to ride the ferris wheel, and take in the beauty that is Chicago.

 

THE EXPERIENCE

Chicago is rich in history, from its architecture to prohibition and underground crime scene back in the 1920s. We were lucky enough to find ourselves completely engulfed in this culture, often times by total accident. Walking through the city with no destination in mind led us to some gorgeous places.

And walking through the city with Yelp in hand and a vague idea of where to go, also led us to some awesome spots, like these:

THE DRIFTER

You have to walk into a Pub, go downstairs, and find the secret doorway in order to get into The Drifter—but once you do, you’re completely transported into the prohibition back in the 1920’s. Specialty drinks are printed on tarot cards and they have sporadic performers throughout the night. We even saw a burlesque show which was craaaazy!

THREE DOTS AND A DASH

This was another accidental find. We were actually looking for somewhere to eat, and Yelp showed some delicious food here, so we went looking. But once we hit the spot the directions said it was at, there was nothing there and I was sooo confused. Luckily, Derek saw people standing in the alley and decided to walk over, and to our surprise, people were walking into some random back door and we decided to follow.

The door took us to a set of stairs leading down, with skulls hanging overhead. When we got downstairs, we had been completely transported yet again into another world. This time, it was a tiki paradise!

Three Dots and a Dash is definitely worth visiting—that is, if you can find it!

OVERVIEW

Why, Chicago? Because it’s beautiful. It’s full of life. It’s rich in history. It’s welcoming. It’s everything you could possibly want in a city.

And I cannot wait until we return!