How about Lakeshore Drive from Navy Pier south to the Shedd Aquarium?
I have walked from Union Station all the way east on Jackson Blvd. to Lakeshore and south to the aquarium. I took the bus on the return. Take the time to see the Federal Reserve Bank and maybe the Chicago Board of Trade.

Thank you Tom. Altough what you suggest is a nice thing to do (we've done that trek) this time we're just looking for more of a neighborhood feel if you will. Funny Cafes and unique non chain shops. (yes my wife loves to shop) We also like to pop in an out of pubs for a quick warm up drink before heading back out walking. I realize area like this are a far cry from Michigan Avenue in terms of glitz but that's what we're trying to escape if only for a couple hours

I have eaten at Mr. Beef on Orleans. http://www.mrbeefonorleans.com/
Another place to check out is Greektown west of Union Station.

I think you mean the Fullerton area, west of Lincoln Park. For period architecture, not retail, Gold Coast, Division to North, Lakeshore Drive to N. Dearborn Parkway

Wicker Park area http://www.wickerparkbucktown.com/

Polish, German neighborhoods as well as Little Italy and China Town.

River North area http://www.explorechicago.org/city/en/neighborhoods/river_north.html

I think Lincoln Park / Old Town it is! Thank you all and Happy New Year!

I hope I am not too late to chime in but Lincoln Park and Old Town are great options. If your wife loves shopping, there are shops and pubs along Wells in Old Town. Here is a guide for shopping Old Town: http://www.destinationshopper.com/town-chicago-east-town-west-town-shopping/

However, I highly recommend Andersonville as well. This page will show you different shopping neighborhoods. I hope this help. http://www.destinationshopper.com/united-states-2/united-states/chicago/chicago-suburbs/

Have fun!

Hi Michael --

This post on my blog goes live tomorrow at 6:00 a.m. CST -- it is the first of 4 in the series.

http://www.esmetravels.com/lincoln-park-part-1/

It's a walking tour of modern homes and McMansions in the Lincoln Park area of Chicago, but it also includes information on cute neighborhood shops for furnishings and where to stop for food along the way. The starting point is one block away from the Goose Island Brewery Restaurant.

When I travel to other cities I love to find an upscale or edgy residential area for walking as I feel it gives me a better feel for the place and people. I was hoping to capture that for people who visit Chicago and want to explore it a little deeper.

What I find very interesting about this part of the city is that there's a sort-of home one-upmanship going on, and I linked to some interesting articles on that Keeping Up with the Jones phenomenon that is happening in my backyard.

Some good suggestions here. I would recommend Lakeview from Wrigley Field walking south along Clark until you get tired, maybe stopping at Bittersweet on Belmont for a snack. Another area: Lincoln Square. It's farther out, but there are a bunch of cool restaurants, and it has sort of a Main Street USA feel to it.

Chicago is just a great city for walking. When we come to Chicago we stay at the Homewood Suites on Grand and we just get out and walk everyday. We walk along Lakeshore, we walk Michigan and to Navy Pier and everywhere in between. Just pick a direction and walk. We haven't taken cabs for restaurants-we just walk and love every minute.