River Bend

Timberland in Chicago | The Modern Otter

Chicago is probably my second favorite city in the US. Nothing against the others, I just love the vibe. Like a cleaner NY... but without the grid layout and thin crust pizza.

Fantastic food, really interesting architecture, and water is always just around the corner. 

I think that's my favorite part: walking along the river. The city is building a river walk (pictured here), and every time I visit it creeps a little further along. I like to grab a glass of Rosé at this wine bar on one of the banks. People pull up in their boats or kayaks and just sit out for an afternoon. How wonderful is that?!

Timberland in Chicago | The Modern Otter
Timberland in Chicago | The Modern Otter
Timberland in Chicago | The Modern Otter

Take the architectural boat tour if you visit Chicago! It sounds cheesy, but it's really cool and a great way to see the city. I was met up with a few friends from Canada, so it was a must on our list. 

It said 0% chance of rain, but the clouds said otherwise. I packed my waterproof Timberland jacket just in case, and I'm glad I did! The skies opened up right in the middle of the tour!

It's super thin though, so I just rolled it up and stuffed it in my bag when the sun came back out. 

Timberland in Chicago | The Modern Otter
Timberland in Chicago | The Modern Otter


A few places I always hit up while in the city:

-Girl And The Goat (if you can get a reservation): order the pig face, cauliflower and duck tongue. Those are my favorites and they're not as scary as they sound. 

-Little Goat: If you can't make it to Girl And The Goat, go across the street for brunch. Order a cinnamon roll for the table. 

-I met up with Drunk on Shoes and Walk in Wonderland at SoHo House Chicago. It's a member's only club so you need to know someone or put your name a very long wait list, but there's a great lounge that's open to the public, a spa, and right across the street is the most "Instagramable" matcha latte around... or so I'm told. 

-Anywhere in the West Loop really. It's wear all the best restaurants are and the coolest scene. Like the East Village meets Williamsburg in NYC. 

Short but sweet trip. I'll be seeing you again real soon, Chi Town.  ;)


Timberland jacket / Gap chinos / Club Monaco tee / Sebago boat shoes