Done with the holidays and already suffering the relentlessly long winter despair, I took the chance last weekend to head down to Chicago in search of lasting inspiration and motivation among the museums, restaurants and urban streets.

Yes, it's only Chicago and yes, cold weather and bone-chilling wind permeates the city to our south just the same. But, I love parts of Chicago and just as I hoped, I had a great time and came back ready for more in Milwaukee.

I kind of know my way around Chicago. I visit regularly to see friends and shows but I've never been a resident. So, when I'm there, I rely heavily on friends to guide me through the many neighborhoods to restaurants, stores and bars.

On this visit, we ate dinners at the Green Zebra in West Town and Ping Pong in Lakeview, grabbed lunch at assorted diners and had drinks in Lincoln Park and Little Armenia.

To some extent, Milwaukee's and Chicago's nightlife aren't that different. Every neighborhood throws a certain vibe and draws a particular crowd.

As a larger city, Chicago's bar, restaurant and club options are vastly greater. Yet, more doesn't inherently imply unheard-of, ingenious creativity. It often means just a longer list of options; some with a greater level of experimentation.

In either city, you can hunt down a $2 beer or splurge on a $20 martini. You can head to dive bar for a beer and darts or sip infused vodka cocktails on a trendy dance floor. All within blocks, you can dine at a chain staple, locally-owned fusion eatery or hole in the wall serving ethnic tradition.

And of course, we share the Midwestern sense of low-key and casual.

Yet despite so many similarities, there's still something dynamically dissimilar about Chicago and Milwaukee nightlife.

After retracing my weekend, I think it ultimately comes down to one simple yet huge difference: at 10 p.m. on any given weeknight, restaurants in Chicago are alive and pumping while Milwaukee eateries are generally dead quiet and closed.

Are we not a big enough city?

Granted, Milwaukee is about one-fifth the size of Chicago and has only one-eighth the exterior metropolitan make up. But take Portland, Denver or Atlanta; all comparable in size to good old Milwaukee and you'll find the same Chicagoan-style culture pulling residents out and about every night of the week.

Are we not a fun city?

There's no question our summer, packed with festivals, concerts and activities, rank at the top of any fun list out there. We have NBA, MLB and AHL teams coupled with two urban Universities. We're home to Harley and Summerfest, dozens of local breweries and an ongoing list of art fairs, gallery nights and ethnic festivals; all things categorically meant for fun.

Or are we just not a young city?

The median age in Milwaukee is 30 whereas Chicago's is 31. So statistically, we should be right in the running.

And regardless, I don't even think I can justify the "young" reasoning. Sure, there are college kids out on campus but Chicago neighborhoods are packed with 20-, 30-, 40- and 50-somethings having late dinners and drinks with friends.

There's not necessarily resolution to this question. Really, it could be any number of things. Maybe the difference is income level or maybe Milwaukee is just a much more sedate, family style city. Maybe restaurant hours guide our behavior more than our behavior guides restaurant hours.

Ultimately, though, I like Chicago's style in this respect. Not just the dense population but more so the lively, social nature of restaurants, bars and cafes all night every night.

Of course, I got a hefty parking ticket while dining late in the evening. So, Milwaukee's still definitely got something.