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This past fall while in town for the Chicago AIDS run, I hopped on Metra and headed up to Highland Park to surprise a friend of mine while at work. I hadn't been up to Highland Park before, so I took the opportunity to walk around for a couple hours to explore the downtown area and a wealthy neighborhood nearby (adjacent to Lake Michigan).
Rather cool mid century modern home with views from the back looking right out over Lake Michigan! The home was for sale if you're interested.
And returning back into downtown Chicago after the slightly less than one hour commute.
Nice tour, many of Chicago suburbs have layouts like a lot of LA's burbs. South Pasadena, Covina, Claremont, Upland, Orange , and San Marino comes to mind, but there are many others as well. What they all have in common are central walkable downtown area, with train service to downtown.
Metra is a great way of accessing Highland Park but if you really want to do things right and you are visiting Chicago, I would suggest driving up the North Shore. Obviously I'm not suggesting this for our current winter season.
From downtown, you take North Lake Shore Drive to where it ends at Hollywood. This is a pleasure in and of itself as high rises dominate the lakefront along with Lincoln Park and the beaches and harbors. There is so much to see inland a short distance from LSD (including Wrigley) but too much to keep you from getting on up to the North Shore; save for another day. From there, it is Sheridan Road and up through the northern most city neighborhoods and on to the North Shore. Sheridan connects everything. IMPORTANT NOTE: from Evanston on up to Lake Forest (or Lake Bluff, if you want to go to the last NS suburb) there are no boring stretches. Everything is either the institutions mentioned below or magnificent homes. This is an unbroken stretch of oppulence (short of a minor stretch that is Highwood mentioned below).
First is the most famous suburb (if one calls it a suburb; more of city) is Evanston and, of course, the beautiful lakefront campus of Northwestern University plus the oldest vintage estates that line the lakefront. Evanston shares with its western sister, Oak Park, a great architectural heritage. Check out downtown Evanston a few blocks to the west; arguably the best suburban downtown in Chicagoland and one of the best nationally. You won't run out of places to eat.
From Evanston, it is on up to Wilmette and the spectacular Bahai temple. Sheridan exits Wilmette with the only high rise cluster on the North Shore (short of downtown Evanston).
From there it is through Kenilworth and Winnetka and through the ravines that wind downward to the level of the lake and up again and its into Glencoe. Not too far west from Sheridan in Glencoe (Lake Cook Road) takes you to the Chicago Botanic Gardens, gorgeous in any season and quite extensive. Well worth the stop.
Then you are actually in Highland Park and if it's summer there is the Ravinia Festival. Ravinia is located between Sheridan and Green Bay Road and offers some of the best outdoor musical and other entertainment during its summer season. Sheridan will then take you northward to downtown HP where the pictures were shot here. I mentioned an arch in a post above. HP's Metra Tracks have an arch over them, ostensibly to join the two parts of DT HP.
North from DT HP takes you to the grounds of old Fort Sheridan along the lakefront. When the fort was decommissioned, it was turned into upscale housing, some new and much a renovation of existing vintage architecture. Fort Sheridan, IMHO, shares with SF's Presidio the title of what was once the most beautiful military bases in the nation.
North of Highland Park is Highwood, a small enclave, the only area without true wealth along the North Shore lakefront from Evanston to Lake Bluff. Highwood is mostly about taverns....and great Italian food, a throw back to the days when the community was heavily Italian.
After Highwood, you are in the crown jewel of the North Shore, Lake Forest. Here the lake front estates dominate like no other community. The only down side is that many are far back and hard to see from Sheridan. Still there is plenty to see. There is a New England quality in Lake Forest, actually true of whole North Shore. Check out DT LF where Market Square dominates as one of the first planned commercial retail developments in the nation.
Of course LSD and Sheridan make for a long day trip when doing the length and stopping along the way. Easy way back to the city is Hwy 41 and Edens Expressway. That will allow you a stop, if desired, at the Illinois Holocaust Museum in Skokie (Skokie had the largest number of holocaust survivors of any community in the nation). If you stop at the museum, Old Orchard shopping center is virtually next door and offers a wonderful out door mall setting so different than enclosed malls.
There is plenty to see in suburban Chicago and those who just make it downtown often miss a lot. Same thing for the neighborhoods within the city.
That's not a bad price for such a home. I mean 2.5 acres of lakefront property with a 5 bed 7 bath home on it is nothing to bat an eye at. The killer thing on that property would be the $108,000 a year in property taxes...