By Samantha McCarthy

We all do it and we all judge, usually without the other person’s knowledge. Maybe you even guess their whole life story by the way they talk, act and dress. It’s fun and free. So, where are the best spots around town?

Photo Credit: Kathleen Virginia Page

Viagra Triangle

The “triangle” where State St and Rush St come together
Chicago, IL 60610

The nickname alone is pretty telling. There’s absolutely nothing that would surprise me here. You’ve got the 40-something women who are trying too hard (hello botox, bleached out hair and collagen injected lips), the dog people (you know the one’s I’m talking about, they push their dogs in strollers and treat them as though they are small children) and last but not least, the drunks. Likely, stumbling out of one of the area’s numerous bars and restaurants. Just grab a coffee or soda at Whispers, plop down on a bench in Mariano Park, and watch the magic unfold.

North Avenue Beach

Along N Lake Shore Dr
Chicago, IL 60611

If it’s during the warmer months, head down the lake path to North Avenue Beach (Oak Street will do just fine too). It doesn’t get much more amusing than this. Here you’ll find a plethora of people doing and wearing ridiculous things. There’s the women who shouldn’t be wearing a bikini, but are anyways; men proudly walking around in Speedos; people with odd tattoos and piercings; couples spoon feeding each other picnics; the Ed Hardy types with overly tanned skin and pierced ears…the list could go on for days.

Photo Credit: Kathleen Virginia Page

Magnificent Mile

Along Michigan Avenue
Chicago, IL 60611

Feel like making fun of tourists? The Magnificent Mile is an obvious choice. Two of the best spots to people watch on The Avenue are outside the Hancock building, and just out front of the Apple store. You can spot the tourists a mile away with their cameras poised, walking slow, taking it all in. They are hard to miss, seeing as how they take up the entire span of sidewalk and you can’t get by.

The Red Line

Or, any form of public transportation for that matter. The red line just happens to be my favorite. It’s always packed, and goes through just about every neighborhood from the south side to the north side. Monday through Friday there’s the sophisticated businessmen and women heading into the loop, then the crazy Cubs and White Sox fans during baseball season.

Sunderground (Sunda + Underground)

110 W. Illinois St.
(N. Clark and N. LaSalle St.)
Chicago, IL 60654
(312) 644-0500
Website & Reviews

The Underground
56 W. Illinois St.
Chicago, IL 60610
(312) 644-7600
Hours: Thurs to Fri 9pm – 4am; Sat 9pm – 5am; Sun 10pm- 4am
Cover Charge: $20

So I made this one up, a little. Both Sunda and The Underground (Billy Dec’s fab restaurant and nightclub) are great for people watching, particularly if you like celebrity spottings. It’s all about seeing and being seen. There are always beautiful people dressed to the nines, many of which are secret train wrecks after a couple of cocktails.

What are your favorite people watching spots in Chicago? Leave your comments below, we would love to hear from you.

Samantha McCarthy is a freelance writer living in downtown Chicago.