$63 to Chicago: FOOD



We love our food whenever we visit a new destination. We managed to hit up all the places we wanted to in just over two days.

Pizzeria Due

It’s the second pizzeria opened by Ike Sewell, the founder of the famous franchise Pizzeria Uno. It’s a block north of the original Unos location and they say it’s just as good. They even share the same menu!

My first taste of Chicago deep dish in probably more than 15 years. The 4 of us shared a large Numero Uno®, since we were starving, not having eaten since early in the morning (it was now 2pm). They take your pizza order as you wait because it takes 45 minutes to make the pizza anyway.

When the pizza finally came, it was HUGE. Deep dish is serious. Layers upon layers of cheese, pepperoni, sausage, peppers, and onions smothered in a bright red tomato sauce. There’s no other way than a fork & knife for this.

Pizzeria Due uno chicago

Pizzeria Due

The Numero Uno pizzeria due

The Numero Uno

The Numero Uno pizzeria due

Serious meat & cheese layers

The Purple Pig

This is a highly rated Mediterranean tapas joint right in the heart of Downtown. Like most trendy tapas places, the place was tight and loud. The prices were actually pretty good, cheaper than any tapas place we’ve been to (Barbuto in NYC, Sra. Martinez & MGFD in Miami).

We ordered about 8 dishes between the 4 of us which was plenty as we were all still full from the pizza about 8 hours earlier. I’d say the highlights for me were the roasted bone marrow, fried brussel sprouts, pig ear & kale salad, and porchetta panini. I love tapas restaurants because you get to try so much and it’s just a more engaging eating experience with friends.

the purple pig tapas restaurant chicago

Crispy Pig Ear Salad with Kale & Egg, Burrata

the purple pig tapas restaurant chicago

Roasted Bone Marrow


We were tipped off about this Chicago institution as having good food but not specializing in anything particular. We figured it would be a good place to try both the Italian beef sandwich and a Chicago-style hot dog.

Everything was simple.. and delicious. Italian beef with spicy peppers was a perfect combo, the bread soaked with all the jus that the beef was dipped in. I had low expectations for the Chicago hot dog with all those non-meat toppings, but it all went together really well and was quite tasty. Their crinkle cut fries looked frozen but were fried perfectly. Throw some cheese sauce and chili (that tasted exactly like Fuddrucker’s) on the side and we were in heaven.

Click for the full size panorama of Portillo’s

portillos italian beef chicago hot dog

Italian Beef, Portillo’s Hot Dog, Fries, Chili and Cheese!

1 Comment $63 to Chicago: FOOD

  1. Pingback: $63 To Chicago - The #hustle Blog - The #hustle Blog

Comments are closed.