Urban Safari

Life in the concrete jungle can be dangerous. Let our Urban Safari Field Guide help you learn the ropes of the big city.

Top Chicago Instagrammers

Now that Instagram is hurdling toward the front of the social media race, here are some Chicagoan’s worth following.

A How-To Guide to Being A Chicago Tourist

Millions of people journey to Chicago every year, but many have not done the proper leg work necessary to ensure a pleasant trip. Here are some pointers to make sure you don’t end up like so many Windy City wanderers before you.

An UPchicago Summer Bucket List

There are some things you just have to do during a Chicago summer. This year, we’re making them happen. Here are our picks for the ultimate Chicago summer bucket list.

Get Your Polar Plunge On

Get Your Polar Plunge On

I stood on the frozen sand of North Avenue Beach two winters ago, looking out on the ice glazed lake. I remember going into complete warrior mode. Inspired by the hundreds of soliders beside me, we were all braced for the same, insane, arctic challenge. It was my first Polar Plunge.

Do boys ever become men?

October is always a ladies month in my mind. I mean the city lights in Chicago are pink for breast cancer awareness — even NFL players are wearing pink shoes and gloves in tribute.

Get Guilty Gurl

Get Guilty Gurl

No matter how tempted I might be to initiate sarcastic banter with the innocent, I’m better off sticking to People Watching than People Talking — also known as conversations.

The Loop Ness Monster

The Loop at lunch is pretty much the same every day.

The V Party

With a craving for chicken and waffles, sweet tea, and a burger and fries from Merlotte’s – I, Caitlin, am addicted to True Blood. If I don’t catch up on these seasons soon, I may be unable to people watch again.

Kayak Chicago

Chicago isn’t exactly a hiker’s haven, and the amount of outdoorsy activities can sometimes seem limited. Kayak Chicago is a great way to feed the outdoorsman inside you, offering great water activities for the nature-loving city dweller.


Starbucks is a people-watching heaven, and last week I remembered what it was like to be in retail hell.

My Little Monsters

The thing about people watching at Lolla is that — well– I guess it’s that because there are so many people to look at or so many people who tried to look bizarre — it all kind of cancels out and becomes this entirely over stimulating mess.

The Warrior Dash

When a college friend of mine called and asked me to run a 3.17 mile race with him I quickly agreed. Little did I know, the race was the Warrior Dash.

The Joni Mitchell Punk Movement

I get pretty bummed when I forget my headphones in the morning. A mistake like that rules out Groovesharking all day and listening to music on my commutes. However, it does amp up my listening and people watching skills and the only thing better than people watching is eavesdropping.

Morning Routines

Your morning routine is probably something you take for granted every day, but maybe stop and look around next time. You may notice someone who will change the way you look at your day.