Chicago is safe, 24 hours a day. The violence you read about is largely confined to the South & West side of Chicago. Many, many people use the CTA to get to and from Midway airport at all times of the day and night.
MIDWAY AIRPORT TO DOWNTOWN:
After you deplane, find a baggage cart as soon as you can. I know your suitcase has rollers etc. etc. Get the cart. It is a lot easier to push a cart than it is to drag a suitcase. The “L” terminal is a long way from the concourse. Think 15 to 20 minutes to get to the “L” train, at a good clip.
You need a Ventra ticket to get on the train. Kiosk’s are readily available to purchase tickets. You DO NOT want to purchase a Ventra card. Locate # F on the kiosk, single ride Ventra ticket, push that, and follow instructions. This whole business works better with a credit or debit card. The cost is $3.00 and it includes 2 transfers embedded in the ticket. You tap the ticket to get thru the turn style. Don’t buy your return ticket. No need to get ahead of yourself. You may catch a ride with another Classmate etc. etc.
The train leaves approximately every 20 minutes, on the half hour. It will take you about 35 minutes to get to the Harold Washington stop. Get off the train there. Make your way to street level. Hail a cab to 511 N Columbus drive. Approximate cost is $9.00. At the Harold Washington stop, in a cab, you’re less than 10 minutes from the hotel.
For the die hard’s who want to go all the way on public transportation, go to the CTA website and figure it out. You will need to get to the Red line, get off at Grand/State and take a bus to the corner of the hotel. The reason I am not offering a full transit explanation is because when you finally get off at Grand/State, you can easily wait 20 to 35 minutes for the bus to arrive. Bus transit schedules, advertised, are highly unreliable.
DOWNTOWN TO MIDWAY AIRPORT:
Take a cab to 1167 S State street, The Roosevelt stop. Look for the signs for the Orange Line, leading underground. This is also a Red Line stop. Make sure you get on the Orange line going to Midway. Purchase ticket as above. Plan on a 35 minute return ride to get to Midway. Pick up the cart again, proceed to your terminal. TSA lines can run 20 to 35 minutes. If you like to arrive an hour early, I would plan, in Toto, for 2 hours to get to the airport, get thru TSA, and make your way to your gate from the Roosevelt stop. A shared cab ride could be much less stressful.