You might be surprised I say this , but I ' d say at least during the day the Pink Line is fine to explore . I ' ve explored areas around Polk and 18 th before , and even around Damen , Western , and California . If you can take the # 60 bus west on 26 th , Little Village is a must explore Hispanic neighborhood , with the heart of that area between Kedzie and Pulaski . There ' s also some Hispanic shops slightly east and west of those 2 streets , plus the biggest Village Discount Outlet location in Chicago . I ' d caution NOT getting off the Pink Line at Central Park or Pulaski , the area by those 2 stops is very sketchy . If you want to explore more , you could get off at Cicero andor 54 thCermak and explore Cicero , IL , which is also interesting in its own regardi . e . Klas Restaurant which is an old school Czech restaurant , plus lots of Hispanic shops . On the Blue Line Forest Park branch , I ' ve explored by stops as far west as Medical Center , and the stops from AustinI ' d be careful not to go to this one at night , though west to the last stop which is Forest Park . I ' ve only explored this during the daytime and wouldn ' t advise going there at night , but if you walk south on Homan Ave from the KedzieHoman stop and exit from the Homan sidewest , you can walk south to where the Sears headquarters once stood . Numerous buildings are left from when Sears was headquartered here , most famously the ' old Sears tower ' that was the only part of a manufacturing building not demolished , and the power house buildingnow a charter school . If you go during next year ' s Open House Chicago weekend in October 2017 , you can explore both buildings , including the usually closed observation deck inside the ' old Sears tower '. The buildings are all centered along Arthington Street , between Kedzie and Saint Louis . Also the old company park at the northeast corner of Arthington and Homan , still stands as a public garden you can freely walk into to look at . Once more back to Cicero , IL a cool place that isn ' t too far of a walk south of the Blue Line Austin stop is the longtime Italian pizzeria , deli and gelato place Freddy ' s . It ' s on the southwest corner of 16 th Streeteast to west and 61 st Avenuenorth to south street , and be advised it ' s cash only . Along the Green Line , I ' d say any of the stops from downtown to Ashland are safe . I ' ve explored around ConservatoryCentral Park Drive , and that immediate area within Garfield Park to the south , and north to the Conservatory is safe . I wouldn ' t go too far into the neighborhood , though . Been meaning for ages to try eating at Inspiration Kitchens on Lake east of Central Park , but haven ' t yet . I ' d say during the daytime you ' d be safe getting off at Austin , and likewise safe at probably all times between Ridgeland to Harlem . Wouldn ' t recommend getting off any stops from California to Central with the exception of ConservatoryCentral Park , though . For the Red and Green Lines south of downtown , I ' ve explored all the stops to 35 th , and I ' d say even at 35 th at nightsince IIT campus security patrols around here you ' d be safe . Illinois Institute of Technology ' s campus is right by the 35 th Green Line stop , and worth a look . Also it ' s worth it to travel into Bridgeport from 35 th and take the # 35 bus west or from the Halsted Orange Line south into that neighborhood and catching the # 8 bus south , for a look . Check out Maria ' s for a good hybrid beer barliquor store , if you go to that neighborhood . 31 st Street has a bunch of interesting restaurantsbars , that I always forget about too often . Have explored around a couple of the Orange Line stops , and for the most part I didn ' t feel the creepy vibe that some parts of the ' L through other west and south side ' L lines felt like to me . I ' d highly recommend exploring Chinatown by the Cermak Red Line stop , at some point . Sorry that was a super long post , but just saying a lot of people shouldn ' t be dismissing with a broad brush exploring all areas west and south of downtown near an ' L stop . This is also very important too , if it ' s late at night , ALWAYS board the train from the first and frontmost car where the train operator is in . Almost got robbed years ago , and it greatly reduces your risk of being robbed during those late night hours if you board the train from that car . NEVER board an ' L car that doesn ' t have any riders on it , that ' s a recipe where you ' re risking getting jumped . I almost had 2 robberies occur to me years ago , one of those 2 instances being on the Brown Line right after it left Quincy and most riders got offthankfully that guy gave up trying to rob me , but it was scary since I was initially thrown against a seat . this was before the emergency blue buttons were added to all railcars , and the other instance was when I was riding the Red Line through Rogers Parkluckily another passenger came to my defense , and I wasn ' t robbed . Hence my tip about trying to board a railcar with a lot of other riders on it , to greatly reduce any chances you ' ll get jumped .