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Your main concern should be safety if you are going to the south side at night.
Train and then uber. Traffic is still terrible at that time.
Train than uber, or blue to red at Jackson, red to closer to Kenwood !!
If the El is ever an option, take it. The only time the Kennedy doesn't suck is between 3a and 5a.
Train then uber
Southside suburbs or southside Chicago? Not trolling at all- but google that shit and check transit vs car. Grew up where I80 meets 355, and google works really well for commute estimates.
Train from ORD. Depending on your destination can stay on train. I hope South Loop, not South Side?
Uber
Chill out friends, I'm going to The Kenwood neighborhood and I live there. Just never had a flight land this close to rush hour before.
P2: yeah I usually trust google with traffic, but I've had it be wrong the last few times, so wanted to see what other people do
Look at 294-290 or 294-55. Longer in mileage, but has often worked for me in terms of traffic flow.
Took blue, home in 55 minutes 😎