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 O’Hare airport at all times of the day and night.
O’HARE 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 CTA is in the bottom level of Terminal 2. If you arrive in Terminal 1 or 3, most common, after you get your bags you are looking at 15 minutes or more to get to the bottom of Terminal 2, walking at a decent pace.
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 every 15 minutes, approximately on the quarter hour. It will take you about 45 minutes to get to Clark/Lake. Get off the train there. Make your way to street level. Hail a cab to 511 N Columbus drive. Approximate cost is $8.00. At Clark/Lake, in a cab, you’re less than 8 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 O’HARE AIRPORT:
Take a cab to Grand/ Milwaukee, 502 N Milwaukee Ave. Look for the signs for the Blue Line, leading underground. This is NOT the same Grand Avenue, Red stop, mentioned above. Purchase ticket as above. Plan on a 40 minute return ride to get to O’Hare. Pick up the cart again, proceed to your terminal. TSA lines can run 25 to 40 minutes. If you like to arrive an hour early, I would plan, in Toto, for 2 ½ hours to get to the airport, get thru TSA, and make your way to your gate from the Grand/ Milwaukee stop. A shared cab ride could be much less stressful.