So this post has taken quite some time for me to finish. The reasons are two-fold; one, there is just SO much for me to talk about in regards to food in Chicago, and two, I got sick with a nasty cold almost as soon as I pulled into my driveway.

I can honestly say I’ve never been somewhere that had such a plethora of [delicious] food in such a small radius. You name the type of food, it’s available. They even have late night places open from 9p to 5a, for the sole purpose of feeding your midnight munchies!

That being said, I’ll do this the most economical way; day by day, meal by meal. So prepare yourself!

We arrived Friday evening after a grueling 12 hour drive. Not to waste any time, we checked into the super nice Belden Stratford Hotel (thanks, Orbitz!) and set out on our first culinary adventure. We weren’t sure what type of food we wanted, or even where to go, so we settled on our tried and true favorite, Mexican. The place was called El Nuevo Mexicano, and it was awesome! The place was small and loud with lots of talking, and great music. We each ordered a Mojito; mine regular and my boyfriend splurged for the pomegranate. The tortilla chips were nicely seasoned, and the salsa was spiced just right. I got the Combonation Vegetariana, which had a guacamole burrito, rice and bean chimichanga, and chile relleno, all served with rice and beans. I’ve had all of the aforementioned foods, but never in the specific combinations. A burrito solely stuffed with guacamole is satisfying in itself. Throw in some deep-friend rice and beans, almost like a Mexican eggroll, and a deep fried, stuffed with cheese chile smothered in sauce = heaven. I left full, with a smile on my face!

On the way home, we happened upon Molly’s Cupcakes, which was actually recommended by a friend (Serial Baker). Ecstatic over our first cupcake experience in Chicago, we ran into the store, forgetting our stuffed bellies. I’ve never seen a cupcake joint so crowded in my life! It was overflowing with people sipping huge cups of coffee, and chatting over delicious looking cupcakes. I ran up to the counter, and immediately started deliberating. Being in an extreme chocolate mood, I went for the Chocolate Decadence, while my boyfriend got the Pumpkin Spice. BEST. CUPCAKES. EVER. Mine was filled with chocolate mousse, and topped with two different types of chocolate ganache. As a chocolate lover, I couldn’t have asked for anything more! The pumpkin was also awesome; the spice and pumpkin ratio was perfect, with an almost cheesecake –like filling and icing. I really don’t think I could have asked for two better cupcakes!

Saturday morning we got up early, and trekked through the rain to the all famous Orange. A breakfast place known for its juices and frushi, I had only heard great things. Though, some of Yelp’s reviews left me a little wary. At any rate, we sat down and immediately got a water with a cucumber slice (nice and refreshing), and some orange infused coffee. The coffee was okay; it tasted more like a tea, and reminded me a  bit of a mixed drink. We then ordered some frushi, which was absolutely delicious. It was coconut rice wrapped around either kiwi or watermelon… yum! I went for the #11.5 omlette that had bacon, leeks, and brie cheese, along with toast and delicious breakfast potatoes. My boyfriend went for the chai tea French toast. Both were decent, but nothing to write home about. The French toast was a little soggy, and the eggs were good, but could have used more cheese. Overall I enjoyed the experience, but wasn’t floored.

We continued our mediocre eating day by stumbling upon Phoebe’s Cupcakes, a place I had found from the Cupcakes Take The Cake blog. I went for the red velvet, and my boyfriend got a red licorice cupcake. I couldn’t have been more disappointed! It feels blasphemous to even write about a subpar cupcake, but someone’s gotta do it. The cake itself was really good. The icing, however, not so much. It was WAY too cheesy, to the point where I couldn’t even finish it. My boyfriend’s, however, was good. I’m going to chalk it up to a bad batch of icing, but it’s definitely ruined red velvet for me for awhile. Such a shame. On a brighter note, though, they did have cupcake flavored coffee that was amazing! I couldn’t put my finger on the flavor combination, but it was just right without any milk or sugar.

We spent the rest of our Saturday at The Lawrence Arms 10 year anniversary show which was awesome, despite me feeling sick from the aforementioned cupcake. Afterwards, we stopped at The Weiner’s Circle to get ourselves a Chicago dog. I was skeptical about liking a hot dog with pickles, hot peppers, and relish, but I really liked it! It’s definitely something I would get again. The place itself was also quite an experience; the help talked back to every drunk person looking for a late night snack, and didn’t take anyone’s crap. I was actually afraid to place my order, in case I messed up. Thankfully, since I was sober, they treated me with respect. Others weren’t so lucky.

Since Sunday was our last full day, we decided to spend most of it doing touristy things like visiting Millennium Park and the Willis (Sears) Tower.  We decided to start the day off with breakfast at The Bongo Room. Now let me tell you, I’m actually not much of a breakfast person; I tend to shy away from it when given the option. But Chicago has definitely showed me how delicious it can be! We decided to share plates this time, as every thing on the menu sounded amazing, and we couldn’t decide on one thing each. Being a lover of Mexican food, I tend to judge places on their burritos. Naturally, we got the breakfast burrito, and one of their daily specials; French toast smothered in cream, caramel and caramelized apples, along with a side of Thai chicken sausage. Every single thing I tried there was phenomenal. Everyone around us had something equally delicious looking on their plates. If I had the stomach for it, I would have tried everything. It seemed like most tables each got their own dishes, and then shared one of their yummy sounding pancake options. I would go back there in a heartbeat; the 45 minute wait was more than worth it!

We ended our trip with some Chicago style pizza. I had searched on Yelp while waiting in line at the Willis Tower, and decided on Giordano’s, which was around the corner. After tweeting about it, some locals gave me a hard time, telling me I should have gone to a few other places. Unfortunately, they were too late. I’m not sure what the huff and puff was about, though, because I really enjoyed Giordano’s! We decided to get the pie stuffed with onions, peppers, and broccoli. I was never really interested in the concept of a stuffed pizza with the sauce on top. After having it, though, I’m a fan. We only got a 10 inch pie to share, and wound up bringing more than half of it home which was convenient for snacking on the 12 hour drive back!

All in all, I think I gained anywhere from 2 to 5 pounds (I was too afraid to actually weigh myself), but it was totally worth it. While we were there, we walked everywhere, and I couldn’t help but take note of all the people out for jogs. Now I understand. If you live in that city and aren’t afraid to eat, you need to work it off some how! Needless to say Chicago is vying for the top spot on my list for best cities. And when it comes to food, it’s definitely number one.

So here are the pictures of everything mentioned above. Let the salivating commence!