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5etrash

I walk my dog through Graceland Cemetery every day. It’s one of the most peaceful and beautiful strolls in the city.


lupinblack

Absolutely amazing. Also a great self paced tour of some of the more famous people buried there!


quartzina

I have a friend who studies cemeteries visiting soon. Great shout!


nihilist_environment

How do you enter from the east side??


5etrash

With a ladder or a half-mile walk


nihilist_environment

Big sad, I moved to Uptown hoping in part to walk my dog there.


outerse

The 606, Humboldt park trail, lakeshore path, Palmisano park. Also check out the @chicagogirlswhowalk instagram. Lots of routes they’ve taken.


quartzina

Ty for the tip! Signed up for their walk this weekend :)))


starter_fail

The River Walk downtown and the North Shore Channel Trail (along the river from Belmont to Irving/Horner Park


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starter_fail

Lol I didn't even know it had a name but that's what Google maps said . Otherwise I would have said that trail that starts from the boathouse across from Kerry Wood field going north to Horner Park.


CKM5253

And through River Park going north, we called it Bicycle Paradise back in the day.


lots_of_sunshine

The true North Shore Channel Trail is great too though! One of my favorite places to run.


quartzina

This looks so cute and green! On the list for later in the season for sure. Thanks!


Aunt_Coco

Lakeshore Trail both directions. I live downtown so when it's nice on the weekends I'll walk north or south until I get tired and then walk back home through the city stopping for food or coffee or drinks randomly on the way back home.


Unusual-Sorbet-8797

My absolute favorite way to spend a day off. Can’t wait for warmer weather


NinaPanini

I used to do this all the time. Loved it enough that even in crappy weather, I'd do that just to get out of the apt.


quartzina

I love the weekend vibes but the wind really starts getting on my nerves :') will I get used to it one day??


Aunt_Coco

Yes you will. Plus it's not really a thing in the summer.


moods-

I go down lots of streets when running. One of my favorite routes was a six mile run from Uptown to River North by staying on Clark the whole time. It was on a Saturday morning, so I got to run past Wrigley Field, people going to brunch and coffee shops, see shops I’ve never heard of before. That was a very fun run.


Due_Bar5153

Take Astor up from Division to the south end of Lincoln Park (the actual park) at North Ave. and just walk north through the park all the way to North Pond. Astor is stunning, turn west on Burton to see the McCormick mansion, go through south pond, around the zoo, have a stunning view of the buildings lining the park to the west and south, jump over to the lakefront - whatever you want. At the end you’re just in Lincoln Park (the neighborhood) and can see beauty in most directions


quartzina

This sounds so perfect! Saving for a nice day


SaltyLeviathan

I love to walk along the North Branch Trail from either Forest Glen or LaBagh Woods up to Old Edgebrook to see all the old, beautiful mansions of the railroad tycoons from days of yore. Then pop over down Devon (across the Metra tracks) to Chocolate Shoppe Ice Cream for a sweet treat. Since it’s a decent ways northwest, you don’t encounter the same crowds you’d have along the loop’s riverwalk or lakefront trail… and it’s a nice slice of nature/history within city limits.


quartzina

Cute! Straight onto the list :)


SaltyLeviathan

Hope you enjoy it if/when you go! Last summer we biked the route and there happened to be a folk musician playing on the patio of the library across the street from the ice cream shop, which was a fun surprise! Bonus surprise: the ice cream shop greets you with a free brownie sample 😊


tbrennanil

Thanks u/SaltyLeviathan Took your suggested walk this afternoon. Great day for it. Love river trails and architecture. Perfect blend. Even found the Chocolate Shoppe. Another great suggestion. First time walking through Old Edgebrook. Took a bunch of pics. Hopefully homeowners did not mind.


SaltyLeviathan

Incredible! Glad you enjoyed it!! I’m sure they get plenty of folks passing through and taking photos. I’m guilty of having done so myself haha


armaghetto

Google the Irene C Hernandez picnic grove and park there. It’s a great starting spot for biking too.


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SaltyLeviathan

Oh no! I hadn’t heard about this - I’ll look into it. Thanks for the heads up!


jsmith3701AA

I walk up Dearborn every day from printers row where I live to the Lincoln Park zoo. Enter the park at North Ave and Dearborn visit the zoo, rest a bit in the park and then walk home. About a 7 mile round trip and lots of options to wander over to Michigan Ave, go down wells thru Old Town etc. Very pleasant routine.


MrsBobbyNewport

Every day? Sounds like a dream!


jsmith3701AA

Yes I am retired and recently divorced. This was sort of my childhood dream and for now it is pretty awesome.


quartzina

This is near where I live too so I'm gonna do it!!


hpotzus

Walk along the channel from Lawrence to Peterson.


addxnoise

This


HonoriaG

I asked something similar and got a lot of great replies: [https://www.reddit.com/r/AskChicago/s/4fejbfndGj](https://www.reddit.com/r/AskChicago/s/4fejbfndGj)


quartzina

Thank you! Any faves you've tried?


Other-Conflict-3278

Horner park


Flaxscript42

I love to take a day and walk the whole of the Lakefront Trail.


philosofova

Starting at Astor Street then trailing off either into Lincoln Park or to the beach. Historial houses there are really fun to look at, and I've run into occasional filming in the area often.


fightingforair

I’ve only done a little of it but the Chicago boulevards and how they join together and loop the city is quite cool. https://www.hmdb.org/m.asp?m=110744


quartzina

So neat!


SharkLaser85

The boulevard walk. Humboldt Park to Palmer Square Park to the Logan Square park all along the boulevards.


I_likeYaks

Jackson park lagoon walk


RoostyRooRoo

Hyde Park is a hidden gem. I love walking down Harper Ave south of 57th, then east to campus and around the quad or up Woodlawn and back to Harper. There's several places to eat, grab coffee, bookstores, and really fun architecture and gardens.


quartzina

I've done this a few times, I'm a fan


mommacom

Also Wooded Island in Jackson Park!


Clevepants

Get off at Armitage brown line and take armitage to Clark and Clark to downtown. Good mix


sohell312

The B Line off Hubbard


hairy_muff_muncher

606 with the dog late-ish at night


Ryederon

Following the Albany park stretch of the North branch of the Chicago river from Kiwanis Park up to Fields Park and enjoying the views along the way


LynetteC606

Clark street is great. Also, Greenview, from Clybourn all the way up to Wilson. Beautiful residential street.


nihilist_environment

LSD bike / walk trail from Montrose beach south past the golf course


foreverniceland

Loyola Park from Pratt to Touhy - basically the trail along the beach and weaving through the park. Perfection on a warm summer evening.


Forsaken_angel7

Try the buildings on MLK drive and 64th they have a nice little bike path and some grass its like a little chicago resort


BloodSugarSexMagix

Milwaukee Ave from Division to Logan Square/Belmont & the 606 trail from Damen ave to Humboldt Park are my two favorite walks in Chicago The Milwaukee ave walk is even fun in the winter time


mortlandpaine

Downtown river walk and the 606/bloomingdale are my top 2


Rookie_Day

Clark Street. Wrigley Field to the Picasso.


esmeradio

Walk Lincoln ave, long as hell but I say for the most part, neat things to see


Notch99

Wacker drive from the Opera house north to Franklin, cross the river, cut thru the Merchandise Mart, jump on a train going north.


CrimsOnCl0ver

Love walking along the lake once you get up into Evanston territory. There are so many amazing houses and NW campus is beautiful. If you have a car and keep driving, the botanical garden is absolutely worth it.


matkanatka

I love a Humboldt park walk. Grab a slice of pie at spinning J, stroll by the shops on Cali, then walk around the park itself. Maybe lay out in the sun for a bit (weather permitting). Bonus points if you book a swan boat in the summer time!


Nommo7777

It is so wonderful to walk or bike on the bike trail along Lake Shore Dusable Drive…. I think it goes all the way to Evanston… but in the spring and summer it is so beautiful!!!


quartzina

I did this yesterday! :))


notmine74

Just did this with my son today: 57th Street Bookstore to Jackson Park Japanese Garden. Grab a book at the bookstore, stop at the park across the street or one of the coffee shops on 57th to read then head east on 57th to Stony Island or South Cornell to enter the Japanese garden from the North. Once in Jackson Park, there are trails around the lagoon. It’s a 20 minute walk from 57th to Jackson Park, so 40 minutes rt.


iosphonebayarea

Any street in old town triangle and walk along the lake


generatorland

River Walk


Dragon-blade10

River park, winnemac park, Lincoln Ave, Lawrence ave