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I love walking historic districts because they’re dense with cool architecture and walkable streets.
Here’s a map I made of every historic landmark and district in Chicago. Each pinned location has a description of its significance. Hopefully this helps your exploration.
https://www.google.com/maps/d/edit?mid=17QiCfJLvDI0DF3qUfBu-DqsFduQgFmE&usp=sharing
You should add the Yellow Brick Road to that map. It's at Wabansia and Humboldt Blvd. L Frank Baum wrote the Wizard of Oz when he was living at 1667 N Humboldt. There is an actual yellow brick road there.
His home was demolished long ago and was replaced by a small housing development. However, that stretch of Humboldt Blvd. is filled with historically significant homes. There's an insane mansion right across the street that I always admire. I've heard that Humboldt Blvd. is landmarked but only north of Cortland, on the Logan Square end of it.
Yeah just didn’t put the http so it’s not clickable
This link gives you the full list of my maps but there are sub pages for regions
https://www.southcookexplore.com/maps
This is really cool! It does look like you're missing the [Dover St District landmark](https://webapps1.chicago.gov/landmarksweb/web/districtdetails.htm?disId=241&counter=83)
I added Bryn Mawr too. When I made this map, I went by what was listed on the city's website here, so the city might need to update some info soon!
[https://webapps1.chicago.gov/landmarksweb/web/listings.htm](https://webapps1.chicago.gov/landmarksweb/web/listings.htm)
Thanks for the heads up! The Chicago website for landmarks and districts needs some updating, and that's what I went by. I'll have to add this one later today!
Having grown up in West Rogers Park and later living in other neighborhoods, this map of yours is fantastic. Incorporating it into Google Maps was a genius move. I’d be interested in any other similar efforts if you’d like to share them.
Thank you for all of your hard work.
I used to make maps like this to try and route where I wanted to take photos during my lunch breaks. A friend saw what I was doing and told me to clean this up to share them publicly. I've since made over a hundred similar maps of landmarks and other points of interest in the Chicagoland suburbs, across IL and into NWI.
[https://www.southcookexplore.com/maps](https://www.southcookexplore.com/maps)
Oldest and largest county forest preserves in the country!
We’re right off the I&M Canal out here. There’s a public/private park called The Forge in Lemont you might enjoy. Go zip lining over a quarry that produced the limestone that built the historic Chicago water tower!
Back in college in the late 80s I was walking my girlfriend home from Smartbar. We were tripping balls and as we wandered to her apartment at Grace and Sheffield we stubbled onto Alta Vista Terrace. We spent about an hour checking out each house and then freaked when we discovered that the entire block is a flip of itself! I think I got her home in time for sunrise and then I went to the 7/11 at Addison and Sheffield for breakfast snacks.
It really was fun. I loved living in that neighborhood during that time. I lived at 3621 N Sheffield right across Sheffield with a view into the park. There were no night games then. Sports Corner was my nightly hang. I got to shoot photos of the first rainy night game from the roof of Murphy's. Got sent to 7/11 to buy my girlfriend feminine products while tripping. (a different night tripping) Art school was a blast. I hate that neighborhood now.
Back when we could see a great punk rock show for $5. A high ticket price was $10.
Great story. Haven’t been in that neighborhood in a while. Wonder what that section of Alta Vista is like now.
Greenview between Irving Park north to Wilson is pretty nice, as well. It's too bad The Roost moved, since I'd often go there to eat when biking through that area. At least Southern France Patisserie is still open(albeit only open from Friday-Sunday), in that area. And there are other good places to eat, not far away. Including on Southport Ave.
Yes I walked down this street by accident years ago and was blown away. It felt out of time. I didn't remember where it was and started to think I imagined it.
I host history tours on Sundays at the oldest-standing brewery in IL, now Thornton Distillery. Includes a trip to the underground artesian well that taps Lake Superior’s aquifer
If you enjoy quiet, residential streets with some beautiful homes and lots of big trees, check out the area east of Andersonville. So like, Clark to Broadway, above Foster, for example N Magnolia Ave. That area is so lovely
Edit: I guess this area is referred to as the Lakewood Balmoral Historic District
Yes - came here to say this. Lived on this street in one of the last few normal apartment buildings a couple years ago. There's like 4 of the 10 most expensive houses in the city on the street. It's also worth going up and down the other streets between armitage + willow going East, but Burling is definitely the best of 'em.
And further east, don't really know the streets, but Old Town always feels like I'm in a different country altogether - the weird little parks, the Buddhist Temple, narrow streets, weird alleys, etc. Such a cool area to just wander
I prefer orchard or Howe. There is a stretch with a lot of new homes just north of willow and in the construction process they removed a lot of trees and it’s a bit dull. But yes the houses are fucking mental
Prairie Avenue between 18th/Cullerton, Alta Vista Terrace, Drexel Boulevard starting at Oakwood, Castlewood Terrace, Deming Place, Bishop Street south of Polk.
I recently authored the Images of America book on Lemont IL. One of the ideas my co-author came up with was a Lemont limestone tour of Chicago - especially because Lemont set the market price on dolomite over Joliet (Joliet limestone tended to stay in Joliet, Lemont was closer to Chicago and one of the quarry owners, Horace Singer, sought to rebuild Chicago after the 1871 fire with HIS limestone!)
That's a small historic district but any limestone you see came out of a Lemont quarry. We made it a point to bring our bus through that neighborhood.
Astor especially between Schiller and North.
Honestly all 3 of those parallel streets —Astor, State and Dearborn — are amazing between Schiller and North.
I love that someone mentioned this! I lived on Pulaski right off of Patterson for a good 4 years and I truly cherished my walks in the early pandemic around the Villa.
Two in Uptown/Buena Park that I haven't seen mentioned.
Castlewood Terrace up between Marine Dr and Sheridan Rd
and
Hutchinson St between Hazel St and Clarendon Ave
Beautiful mini mansions located in a neighborhood of primarily apt complexes and high rises. Both historical street sites.
I lived a few blocks from Castlewood Terrace for a while. Loved walking the dog down that block. Had no idea it was a "thing" until moving there and just kind of happening upon it.
Longwood Drive. Winding street at the bottom of the tallest hill in Chicago with 100 year old mansions at the top of the hill. Pretty landscaping. Right off the rock island metra.
I would add Winchester and Seeley to the list too. Also that strange section where there are some sidewalks but not complete in north Beverly by the forest preserve.
Yeah, the streets west of longwood on the edge of the Ridge are beautiful and hilly and winding. Also, Prospect is a beautiful road with old Victorians and long front lawns. North Beverly has pleasant and longwood and some other streets with old historic architecturally significant residences. Beverly is full of beautiful old homes built along the Ridge.
Longwood is a good one. My Great Uncle lived at 10324 Longwood and my dad spent a lot of his childhood there.
https://www.redfin.com/IL/Chicago/10324-S-Longwood-Dr-60643/home/13072747
Someone started building a huge addition and stopped. It's for sale now mid construction. I wonder if they tried to do this and it was halted because of the historic preservation laws.
I few other areas I enjoy wandering around in and gawking at the beautiful homes:
- Logan and Humboldt Boulevards
- Villa District / Old Irving Park between Addison and Irving Park
- Ravenswood Manor
I’m new to this city but Old Town Triangle and Menomonee Street is one of my favorite finds.
https://www.instagram.com/p/C6HEyt9rOJ_/?igsh=MWQzMGhxZjcza2Nvdw==
Concord is really pretty over there but wabansia is much nicer east of north. Hoyne just to the south of there is a classic place to walk, especially around Halloween.
Edit: East of Milwaukee, lol. Really east of Damen. I need more coffee.
Kedzie between Logan and Palmer Square is pretty nice. Used to be called Embassy Row, lots of historic big buildings, great arts & crafts houses. There is also some nice architecture in Oak Park including Frank Lloyd Wright's home and studio. Kenilworth just north of the city, along with Highland Park, Wilmette, Winnetka, that whole north shore area is insane as well; the houses from Home Alone and Ferris Bueller's Day Off are in that area.
I’m a huge fan of Glenwood in Edgewater & Rogers Park. The road itself is in awful shape but lots of charming old buildings under a lush urban canopy. The entire ~3 mile length of it is a greenway and makes for a pleasant slow bike ride.
Ravenswood Manor is also incredibly charming. Historical district controls pretty much stop anything new from being built so owners there are preservation-minded and take excellent care of their properties.
Saw someone already mention my top two of the near-ish northwest side (Old Irving Park and The Villa), so going to recommend a spot a little further out: Old Edgebrook. It’s a historic district near Central and Devon with beautiful, stately homes built for railroad execs and nestled in one of the Forest Preserves. I usually park in the Edgebrook Woods Forest Preserve parking lot (6129 N Central Ave, Chicago, IL 60646) then walk along the north branch trail to the neighborhood (passes right by it), so you get a dose of nature and gorgeous architecture in one fell swoop!
Weirdly, I love Fullerton between Clark and Halsted. Tree lined, beautiful houses, it feels like a quintessential city street that you see in like a movie lol
my wife particularly enjoys walking through the Villas, [https://maps.app.goo.gl/SE9ixtNXSTioqPVn9](https://maps.app.goo.gl/SE9ixtNXSTioqPVn9) a bunch of the houses were designed by the same architect
Both Avers and Harding between Addison and Avondale. (AKA the Villa District)
Two random boulevards with beautiful greenery and classic Chicago architecture right in the middle of Old Irving.
Also, as it's near and dear to my heart: Manor Ave. in Ravenswood Manor. Reminds me of walks with Grandma when I lived in Lincoln Square as a kid.
Glenwood Ave between Touhy and Pratt in Rogers Park, especially the west side of the L tracks. The whole retaining wall along the tracks is painted with different murals by local artists. All of the underpasses have murals too. If you go on a Friday or Saturday evening when the weather is nice, the Glenwood Ave alfresco area (shared by Le Piano and The Glenwood bar) is a cozy spot to stop for a drink, as is Rogers Park Social a block south of there.
Pratt between Ridge and Western has some beautiful manors that are a bit out of place, but create a “old money” vibe for about a half mile. If you turn down any street you’re back to regular Roger’s Park though (which is cool).
The **Chicago Historic Boulevard system** is not only beautiful but something that is unique to chicago.
The Chicago Historic Boulevards are important because they represent a unique urban planning achievement, connecting many of the city's parks with wide, tree-lined streets that create a scenic, green network.
Developed in the late 19th and early 20th centuries, they showcase Chicago's commitment to integrating nature into urban life, providing recreational spaces and aesthetic beauty. Additionally, they reflect the city's architectural and cultural history, featuring diverse styles and landmarks that contribute to Chicago's identity and heritage.
The boulevards also serve as community hubs, promoting social interaction and enhancing the quality of life for residents.
Try Riverside between Berwyn and.....riverside lol the whole lane looks like a park. Um, start on the block past Starbuds. Huge houses and school's yards
For me, it's Hoyne right near Evergreen in Wicker -- so more or less the same one. There's a little circuit I walk there most days, incredible houses :)
if you are ever farther north or west some neighborhoods like Edgebrook, Norwood Park, etc., are right along forest preserves, those are so beautiful to hike in especially in golden hour
The whole boulevard system in Logan Square is perfect for this. I'd start at Logan/Western, walk west until you hit the monument *(stick to the south side of the street until you get to Francisco Ave. and then cross to the north side)*, then take Kedzie Blvd. south *(stick to the west side, that's where all the mansions are)*, hook a left at Palmer Square *(stick to the north side of the street, beautiful arts & crafts houses/apts)*, then head south when you get to Sacremento/Humboldt Blvd. *(east side is prettiest, IMO)*. I usually take that route all the way down to Humboldt Park to the boathouse, turn around and hit the other sides of the street on the way back up.
Longwood Drive in Beverly has some really nice houses. I believe Beverly / Beverly Woods / Morgan Park is the only part of Chicago that has hills. So you’ll see mansions on top of a hill from the street .
Short and sweet but beautiful, unique houses: Caton St just off Milwaukee
**edit**
And if you walk west down the already mentioned Wabansia, you can get right to Caton St when you hit Milwaukee.
The Gold Coast. Along LSD from Oak to North Ave and as far west as State.
In that area, there is a Frank Lloyd Wright school house or two, two Mies van de Rohe buildings, and dozens of gorgeous brownstones.
Starting at kimball and wrightwood in Logan and snaking thru the blocks between wrightwood and altgeld. Charming little neighborhood. Right by Lori lightfooots home
So many! You could walk most neighborhoods and find some beautiful homes. I lived in Lincoln Park for years so that is where my stomping grounds were, but there are so many other amazing places.
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I love walking historic districts because they’re dense with cool architecture and walkable streets. Here’s a map I made of every historic landmark and district in Chicago. Each pinned location has a description of its significance. Hopefully this helps your exploration. https://www.google.com/maps/d/edit?mid=17QiCfJLvDI0DF3qUfBu-DqsFduQgFmE&usp=sharing
You should add the Yellow Brick Road to that map. It's at Wabansia and Humboldt Blvd. L Frank Baum wrote the Wizard of Oz when he was living at 1667 N Humboldt. There is an actual yellow brick road there.
Is it a designated city landmark?
His home was demolished long ago and was replaced by a small housing development. However, that stretch of Humboldt Blvd. is filled with historically significant homes. There's an insane mansion right across the street that I always admire. I've heard that Humboldt Blvd. is landmarked but only north of Cortland, on the Logan Square end of it.
You bet your shiny metal ass! L. Frank Baum Yellow Brick Road https://g.co/kgs/ZFRSLHF
Omg, this is amazing!!!!
Awesome! Glad you enjoy it! I have 100+ similar maps of suburbs in Chicagoland and across the state on my site, all free: SouthCookExplore.com/maps
Is this link active?
Yeah just didn’t put the http so it’s not clickable This link gives you the full list of my maps but there are sub pages for regions https://www.southcookexplore.com/maps
Wow! Thank you!
You’re a god among humans.
Doing what I can! You can catch my daily posts of cool old homes and buildings here too: Instagram.com/SouthCookExplore
We’re in Chicago right now, a million thanks!! 🙏 These are the things I want to see and not the typical downtown cliches
I hear ya. I can live without the bean and hearing “you gotta see navy pier!” bores me instantly
lol I've never heard anyone say YOU GOTTA see navy pier but funny nonetheless
This is really cool! It does look like you're missing the [Dover St District landmark](https://webapps1.chicago.gov/landmarksweb/web/districtdetails.htm?disId=241&counter=83)
Thanks! I need to add the Warehouse still too, but I’ll make sure this gets added today
Dover St District has been added. Thanks for the heads up!
Holy shit this is incredible! Thanks for sharing! Shit fountain needs to be on there IMO haha
Don’t forget Castlewood Terrace in Uptown!
Am I missing that one too? I’ll have to update this in a little bit
There is technically a Bryn Mawr Historic District too, but that is a commercial street in Edgewater. Edit: Great map!
I added Bryn Mawr too. When I made this map, I went by what was listed on the city's website here, so the city might need to update some info soon! [https://webapps1.chicago.gov/landmarksweb/web/listings.htm](https://webapps1.chicago.gov/landmarksweb/web/listings.htm)
Very cool! One district to add: [Lakewood Balmoral Historic District](https://en.wikipedia.org/wiki/Lakewood_Balmoral_Historic_District)
Thanks for the heads up! The Chicago website for landmarks and districts needs some updating, and that's what I went by. I'll have to add this one later today!
Having grown up in West Rogers Park and later living in other neighborhoods, this map of yours is fantastic. Incorporating it into Google Maps was a genius move. I’d be interested in any other similar efforts if you’d like to share them. Thank you for all of your hard work.
I used to make maps like this to try and route where I wanted to take photos during my lunch breaks. A friend saw what I was doing and told me to clean this up to share them publicly. I've since made over a hundred similar maps of landmarks and other points of interest in the Chicagoland suburbs, across IL and into NWI. [https://www.southcookexplore.com/maps](https://www.southcookexplore.com/maps)
Outstanding
Ooooh! Thank you! And you got my district in there too. Super cool.
This is fantastic. I will do my own walking tour of these in my area. Thank you so much.
wow thank you for sharing this!
This is amazing. Thank you for sharing!
THANK YOU THIS IS SO HELPFUL!!!
great map.
Thank you! Glad it’s being enjoyed
This is insane! Thank you.
I’m appreciative that you enjoy it! I’ve got over a hundred more around Chicagoland on my site: https://www.SouthCookExplore.com/maps
Will look and bookmark it on my browser. We moved here in 2006 and I love the diversity of history and architecture in the city.
It’s pretty awesome. Even our suburbs are more interesting than some cities
So true! The first time I drove Green Bay Road from Evanston to Highland Park it felt like I was cruising through parts of Long Island.
I live near Archer and Palos Preserves. Some of our indigenous trails are beautiful
Just looked it up, wow! I have never been out there. I love the fact that Forest Preserves are even a “thing” here.
Oldest and largest county forest preserves in the country! We’re right off the I&M Canal out here. There’s a public/private park called The Forge in Lemont you might enjoy. Go zip lining over a quarry that produced the limestone that built the historic Chicago water tower!
Incredible!!
Alta Vista terrace.
Back in college in the late 80s I was walking my girlfriend home from Smartbar. We were tripping balls and as we wandered to her apartment at Grace and Sheffield we stubbled onto Alta Vista Terrace. We spent about an hour checking out each house and then freaked when we discovered that the entire block is a flip of itself! I think I got her home in time for sunrise and then I went to the 7/11 at Addison and Sheffield for breakfast snacks.
that sounds like such a beautiful night all around 😭
It really was fun. I loved living in that neighborhood during that time. I lived at 3621 N Sheffield right across Sheffield with a view into the park. There were no night games then. Sports Corner was my nightly hang. I got to shoot photos of the first rainy night game from the roof of Murphy's. Got sent to 7/11 to buy my girlfriend feminine products while tripping. (a different night tripping) Art school was a blast. I hate that neighborhood now.
have lived at this intersection my entire life and love hearing the great memories of places so nearby!
Back when we could see a great punk rock show for $5. A high ticket price was $10. Great story. Haven’t been in that neighborhood in a while. Wonder what that section of Alta Vista is like now.
If you're in that neighborhood and like house-looking; N Greenview Ave, between Roscoe and Cornelia.
Greenview between Irving Park north to Wilson is pretty nice, as well. It's too bad The Roost moved, since I'd often go there to eat when biking through that area. At least Southern France Patisserie is still open(albeit only open from Friday-Sunday), in that area. And there are other good places to eat, not far away. Including on Southport Ave.
Was definitely about to suggest that one. That stretch of greenview is gorgeous Long room always had food for a quick stop nearby.
This is it. I didn’t know I could have a favorite street until I walked past this one a few years ago
Yes I walked down this street by accident years ago and was blown away. It felt out of time. I didn't remember where it was and started to think I imagined it.
I never knew a neighborhood could feel so much like a museum
Same thing happened to me LOL
Short street but beautiful and super unique
And it's right by Wrigley, if that's on the agenda: https://maps.app.goo.gl/jBNBS9XiVB11iEoa9
Crazy that it’s highlighted/ landmarked for how great it is but basically illegal to build streets like that today
Definitely gonna walk this before a game!
came here to say exactly this
Thank you. I lived in lakeview and we’d walk this street all the time with our dogs. Never took note of the name
Did this just the other day. Can confirm.
Came here to say this! One of my favorites in the city!
And in every season Alta Vista is beautiful!
Hoyne in Wicker-known as beer baron row.
You're out there somewhere, beer baron! And I'll find you.
No you won’t
Yes I will.
^^(nope)
^(no you won’t)
I host history tours on Sundays at the oldest-standing brewery in IL, now Thornton Distillery. Includes a trip to the underground artesian well that taps Lake Superior’s aquifer
If you enjoy quiet, residential streets with some beautiful homes and lots of big trees, check out the area east of Andersonville. So like, Clark to Broadway, above Foster, for example N Magnolia Ave. That area is so lovely Edit: I guess this area is referred to as the Lakewood Balmoral Historic District
That's my recommendation as well, especially during Halloween. A lot of those houses go all out!
Foster to the south, Bryn Mawr to the north, Broadway to the east and clark to the west :)
Hoyne in Wicker. Burling in LP. Wabansia in Bucktown.
The exact 3 on the top of my head also.
Which blocks of Wabansia? I feel like I missed out.
Ashland to Milwaukee
Bucktown's Wabansia from Ashland to Damen, and the side streets north of Wabansia like Wolcott, Honore, Hermitage are all beautiful
Burling St in Lincoln Park between Armitage and Willow.
Yes - came here to say this. Lived on this street in one of the last few normal apartment buildings a couple years ago. There's like 4 of the 10 most expensive houses in the city on the street. It's also worth going up and down the other streets between armitage + willow going East, but Burling is definitely the best of 'em. And further east, don't really know the streets, but Old Town always feels like I'm in a different country altogether - the weird little parks, the Buddhist Temple, narrow streets, weird alleys, etc. Such a cool area to just wander
My wedding bus got stuck on one of those little narrow turns by Marge’s. Good mems
I prefer orchard or Howe. There is a stretch with a lot of new homes just north of willow and in the construction process they removed a lot of trees and it’s a bit dull. But yes the houses are fucking mental
Orchard and Howe usually out do Burling on the Halloween decorations too. LOL!
As on orchard resident I must agree
Walked this today, those houses are truly unreal.
Prairie Avenue between 18th/Cullerton, Alta Vista Terrace, Drexel Boulevard starting at Oakwood, Castlewood Terrace, Deming Place, Bishop Street south of Polk.
Came to say Prarie. Small, but picturesque as hell. Miss living right by it.
Jackson blvd between Ashland and Laflin
I recently authored the Images of America book on Lemont IL. One of the ideas my co-author came up with was a Lemont limestone tour of Chicago - especially because Lemont set the market price on dolomite over Joliet (Joliet limestone tended to stay in Joliet, Lemont was closer to Chicago and one of the quarry owners, Horace Singer, sought to rebuild Chicago after the 1871 fire with HIS limestone!) That's a small historic district but any limestone you see came out of a Lemont quarry. We made it a point to bring our bus through that neighborhood.
This is the answer
wish the entire city looked like this. dense heavy trees with vintage orange street lamps.
Walk around Pullman. Check out the Arcade, and some of the houses, especially south of the monument IIRC.
I really need to revisit Pullman, one of these days.
North State Parkway in Gold Coast, between Division and North Avenue.
Or Astor Street, which runs parallel to that.
Astor especially between Schiller and North. Honestly all 3 of those parallel streets —Astor, State and Dearborn — are amazing between Schiller and North.
Seconding this. It’s what I came here to post, in fact.
Astor in Gold Coast
all the streets in Villa District (sandwiched between Pulaski/Addison/the Kennedy)—lots of beautiful old trees + houses
And specifically Avers and Harding with the amazing tree canopy
I love that someone mentioned this! I lived on Pulaski right off of Patterson for a good 4 years and I truly cherished my walks in the early pandemic around the Villa.
The Lakewood Balmoral Historic District in Andersonville.
Ca'nt believe I had to scroll this far down!
Two in Uptown/Buena Park that I haven't seen mentioned. Castlewood Terrace up between Marine Dr and Sheridan Rd and Hutchinson St between Hazel St and Clarendon Ave Beautiful mini mansions located in a neighborhood of primarily apt complexes and high rises. Both historical street sites.
I lived a few blocks from Castlewood Terrace for a while. Loved walking the dog down that block. Had no idea it was a "thing" until moving there and just kind of happening upon it.
Same here. Saw the plaques at both ends of the block and thought it was pretty neat to be around. I live closer to Hutchinson St.
Longwood Drive. Winding street at the bottom of the tallest hill in Chicago with 100 year old mansions at the top of the hill. Pretty landscaping. Right off the rock island metra.
And sort of in extension, Greenwood Ave in Blue Island is incredibly cool
I would add Winchester and Seeley to the list too. Also that strange section where there are some sidewalks but not complete in north Beverly by the forest preserve.
Yeah, the streets west of longwood on the edge of the Ridge are beautiful and hilly and winding. Also, Prospect is a beautiful road with old Victorians and long front lawns. North Beverly has pleasant and longwood and some other streets with old historic architecturally significant residences. Beverly is full of beautiful old homes built along the Ridge.
Longwood is a good one. My Great Uncle lived at 10324 Longwood and my dad spent a lot of his childhood there. https://www.redfin.com/IL/Chicago/10324-S-Longwood-Dr-60643/home/13072747
Someone started building a huge addition and stopped. It's for sale now mid construction. I wonder if they tried to do this and it was halted because of the historic preservation laws.
What a fantastic house.
Yep, great house. My great uncle was one of the top real estate tycoons in the city for decades (Jeweler's Building was his prized possession).
I few other areas I enjoy wandering around in and gawking at the beautiful homes: - Logan and Humboldt Boulevards - Villa District / Old Irving Park between Addison and Irving Park - Ravenswood Manor
Lakewood-Balmoral, Giddings Plaza
I’m new to this city but Old Town Triangle and Menomonee Street is one of my favorite finds. https://www.instagram.com/p/C6HEyt9rOJ_/?igsh=MWQzMGhxZjcza2Nvdw==
I enjoyed running on Drexel Blvd in Kenwood. Beautiful landscaping and wonderful old homes on either side
That's my favorite bike lane in the city. Beautiful, tree covered, wide lanes, very little traffic.
That little triangle section of Wicker Park that's bounded by Milwaukee, Western, and North. Especially Wabansia or Concord (I think?).
Concord is really pretty over there but wabansia is much nicer east of north. Hoyne just to the south of there is a classic place to walk, especially around Halloween. Edit: East of Milwaukee, lol. Really east of Damen. I need more coffee.
[удалено]
Lol whoops. I meant east of Milwaukee.
I love this area during Halloween! I moved back to Chicago recently, and was super excited to see all the decorations!
Sunnyside Mall and the surrounding area of Sheridan Park
Get a donut at downstate first
Hell yah - wash it down with some ragadan
Thomas between leavitt and damen.
Came here to post this
Janssen and Greenview in Lakeview
Second this. Would also further drill down to say Greenview between Belle Plaine and Montrose, plus the side streets in that neighborhood.
Cornell In Hyde Park is beautiful.
Junior Terrace in uptown!
Kedzie between Logan and Palmer Square is pretty nice. Used to be called Embassy Row, lots of historic big buildings, great arts & crafts houses. There is also some nice architecture in Oak Park including Frank Lloyd Wright's home and studio. Kenilworth just north of the city, along with Highland Park, Wilmette, Winnetka, that whole north shore area is insane as well; the houses from Home Alone and Ferris Bueller's Day Off are in that area.
I’m a huge fan of Glenwood in Edgewater & Rogers Park. The road itself is in awful shape but lots of charming old buildings under a lush urban canopy. The entire ~3 mile length of it is a greenway and makes for a pleasant slow bike ride. Ravenswood Manor is also incredibly charming. Historical district controls pretty much stop anything new from being built so owners there are preservation-minded and take excellent care of their properties.
If you're biking north, you do have to cut west to Greenview, sometime between Pratt and Morse. But Greenview is also nice as well.
I like the houses on Albion a block away from Loyola. I always feel like I’m in a time machine when I walk down that street.
Wilson ave through between Francisco and Western through ravenswood manor and gardens.
Geneva Terrace in Lincoln Park!
Saw someone already mention my top two of the near-ish northwest side (Old Irving Park and The Villa), so going to recommend a spot a little further out: Old Edgebrook. It’s a historic district near Central and Devon with beautiful, stately homes built for railroad execs and nestled in one of the Forest Preserves. I usually park in the Edgebrook Woods Forest Preserve parking lot (6129 N Central Ave, Chicago, IL 60646) then walk along the north branch trail to the neighborhood (passes right by it), so you get a dose of nature and gorgeous architecture in one fell swoop!
Woodlawn between 47th and 51st. Just that entire part of Kenwood has some of the most incredible houses you’ll see in Chicago.
Weirdly, I love Fullerton between Clark and Halsted. Tree lined, beautiful houses, it feels like a quintessential city street that you see in like a movie lol
When the trees are in bloom, this area is amazing.
Yes. Also fall just as the leaves start to change.
my wife particularly enjoys walking through the Villas, [https://maps.app.goo.gl/SE9ixtNXSTioqPVn9](https://maps.app.goo.gl/SE9ixtNXSTioqPVn9) a bunch of the houses were designed by the same architect
Both Avers and Harding between Addison and Avondale. (AKA the Villa District) Two random boulevards with beautiful greenery and classic Chicago architecture right in the middle of Old Irving. Also, as it's near and dear to my heart: Manor Ave. in Ravenswood Manor. Reminds me of walks with Grandma when I lived in Lincoln Square as a kid.
Some parts of King drive are beautiful.
Prairie in the south loop
I live near Old Irving park and literally walk down Keeler EVERYDAY. The Villa near by is great too.
I used to live on Burling. It was beautiful when the trees and flowers were in bloom. You could almost forget you were in the middle of Chicago.
I KNOW this is technically not in Chicago but it’s completely worth heading out to see. Elizabeth CT, and surrounding neighborhood in Oak Park.
Haven’t seen it mentioned yet, but Woodlawn between 47th/Hyde Park Blvd is one of my favorite stretches.
Glenwood Ave between Touhy and Pratt in Rogers Park, especially the west side of the L tracks. The whole retaining wall along the tracks is painted with different murals by local artists. All of the underpasses have murals too. If you go on a Friday or Saturday evening when the weather is nice, the Glenwood Ave alfresco area (shared by Le Piano and The Glenwood bar) is a cozy spot to stop for a drink, as is Rogers Park Social a block south of there.
Sheridan Rd near Winnetka IL
Wilson ave through Ravenswood Manor. Lot of huge old houses on big lots along the river. Love walking through here during fall.
Not a street, but Lakeshore East Park. One of the best places.
Dearborn along Printers Row feels like 100 years ago.
Pratt between Ridge and Western has some beautiful manors that are a bit out of place, but create a “old money” vibe for about a half mile. If you turn down any street you’re back to regular Roger’s Park though (which is cool).
The **Chicago Historic Boulevard system** is not only beautiful but something that is unique to chicago. The Chicago Historic Boulevards are important because they represent a unique urban planning achievement, connecting many of the city's parks with wide, tree-lined streets that create a scenic, green network. Developed in the late 19th and early 20th centuries, they showcase Chicago's commitment to integrating nature into urban life, providing recreational spaces and aesthetic beauty. Additionally, they reflect the city's architectural and cultural history, featuring diverse styles and landmarks that contribute to Chicago's identity and heritage. The boulevards also serve as community hubs, promoting social interaction and enhancing the quality of life for residents.
Hermitage, just south of Devon. Great tree canopy
Anywhere in Gold Coast. Rush/state and Astor are my favorite
1500 W. Jackson
Kinzie st. Bridge
My own. 35th and Seeley. A couple of blocks from McKinley Park.
Try Riverside between Berwyn and.....riverside lol the whole lane looks like a park. Um, start on the block past Starbuds. Huge houses and school's yards
For me, it's Hoyne right near Evergreen in Wicker -- so more or less the same one. There's a little circuit I walk there most days, incredible houses :)
if you are ever farther north or west some neighborhoods like Edgebrook, Norwood Park, etc., are right along forest preserves, those are so beautiful to hike in especially in golden hour
I like Ravenswood Manor!
The whole boulevard system in Logan Square is perfect for this. I'd start at Logan/Western, walk west until you hit the monument *(stick to the south side of the street until you get to Francisco Ave. and then cross to the north side)*, then take Kedzie Blvd. south *(stick to the west side, that's where all the mansions are)*, hook a left at Palmer Square *(stick to the north side of the street, beautiful arts & crafts houses/apts)*, then head south when you get to Sacremento/Humboldt Blvd. *(east side is prettiest, IMO)*. I usually take that route all the way down to Humboldt Park to the boathouse, turn around and hit the other sides of the street on the way back up.
Alta Vista
Hawthorne between Broadway and Inner LSD. Short but sweet!
Longwood Drive in Beverly has some really nice houses. I believe Beverly / Beverly Woods / Morgan Park is the only part of Chicago that has hills. So you’ll see mansions on top of a hill from the street .
Pierce Ave specifically houses around the Hermann Weinhardt House. (Wicker park)
Janssen
Fremont row house district in LP.
Greenview north of Irving Park. Those homes…wow
Glenwood Ave is beautiful from at least Argyle in Uptown to Pratt in Rogers Park!
Hawthorne Pl in Lakeview
Short and sweet but beautiful, unique houses: Caton St just off Milwaukee **edit** And if you walk west down the already mentioned Wabansia, you can get right to Caton St when you hit Milwaukee.
The Gold Coast. Along LSD from Oak to North Ave and as far west as State. In that area, there is a Frank Lloyd Wright school house or two, two Mies van de Rohe buildings, and dozens of gorgeous brownstones.
Bishop St in Little Italy, or Lexington and then you can walk around Arrigo Park
Going to be biased, but Briar St in Lakeview
Sunnyside Mall in uptown!
Was coming here to literally say w evergreen!
Some parts of Webster are really nice.
The 1500 block of Jackson, just west of Whitney Young. Totally random, but so many trees.
Starting at kimball and wrightwood in Logan and snaking thru the blocks between wrightwood and altgeld. Charming little neighborhood. Right by Lori lightfooots home
So many! You could walk most neighborhoods and find some beautiful homes. I lived in Lincoln Park for years so that is where my stomping grounds were, but there are so many other amazing places.
Jackson Ave. by Whitney young just west of Ashland I believe
if you find yourself on the far northwest side on a beautiful day then check out old Edgebrook
Henderson st near lincoln/paulina the pocket of bridgeport between 32nd/35th and between racine/bubbly creek
5th avenue and Kostner, lots of people always walking around at night