Webthe journey from milwaukee to chicago can take as little as 1 hour 25 minutes and starts from as little as $18. 49. The earliest bus leaves at 3:20 am and the last bus leaves at. Webthere are 3 bus stops in chicago. You can board the greyhound at chicago (cumberland farms), chicago bus station, chicago train station. You can easily find the location of. Webthe trip from chicago to milwaukee takes as short as 1 hour 30 minutes and could cost as little as $17. 99. The first bus departs at 5:55 am and the last bus departs at 9:45 pm.
