Updated: December 2017

Midway Airport to Downtown Chicago via the CTA Orange Line:

Flying into or out of Midway International Airport is often much easier than dealing with the craziness associated with Chicago O'Hare. I recently (October 2011) flew into Midway Airport (MDW) from Portland, Oregon. My wife and I were out in Chicago to enjoy a long weekend. I had not been to Chicago for over a decade and the last time I visited I had driven in from the Milwaukee region. Taking the Chicago Transit Authority (CTA) "L" train is the easiest way to get to and from the airports. I decided that we would take the Orange line into Chicago and if it was easy enough we would take the same line back out to the airport on our departure and skip the cab ride. We arrived into Chicago Midway on a Saturday afternoon and proceeded to follow the signs at the airport that say "CTA Trains" and "Trains to City". Both are visible as you walk through the airport and leave the security area. The Midway orange line station is literally right next to the airport and it's connected with an enclosed walkway. It takes a few minutes to walk, but be prepared to either take the elevator or carry your bag down a few flights of stairs to get to the actual train.

Midway to Downtown Chicago:

Near the L train station at the airport is an area where you can buy tickets from machines. There are often CTA agents in the area if you have questions, but don't rely on that. I had never bought a subway ticket before in Chicago so this was all new to me and it worked out fine. Just remember that the machines don't give change. I used cash thinking I could get a few tickets for the $10 and it ended up giving me 1 ticket with $10 worth of credit. I did use it on the trip, but beware. The ticket machines also accept debit/credit cards. After buying our tickets at the airport train station, we got on the train that was heading into downtown. There is really only one choice as this is the end of the Orange line and all passengers must unload as they arrive so the train should be nearly empty when you get on. The CTA train fare from Midway to downtown was $2.25. Compared to the $25 rate that we were quoted to take a taxi, this seems like a decent bargain. The train itself takes about 25 minutes to reach the "Loop" in downtown and when riding in a cab, you could be looking at over 30 minutes depending on traffic to get to the same destination. The Orange line has 7 stops before you can get access to change over to another line. At the Roosevelt stop we got off and went over to the Red Line to continue our ride up to Chicago stop. There are multiple on/off points as you reach the downtown "Loop" as it's called. Watch the map on the inside of the L car to see where you need to get off. You can check out all the trains, maps, and timetables online at http://www.transitchicago.com/riding_cta/airports.aspx. Eventually the Orange line makes the complete "loop" and heads back to the airport. Be prepared to lift your luggage as you head out of the L stations. Not all offer up escalators, although most have elevators, but you have to look for them. We ended up carrying our bags up or down a few flights of stairs, but I don't recommend this option.

Orange Line L Tickets and Fares - How Often to the Trains Run?:

The CTA trains run all day (except for a few late night/early morning hours), every day. The Orange line runs from Midway to downtown and back from around 4 AM to 1AM daily. Check their schedule online for specific times. You will see trains every 5 to 7 minutes during "rush hour" and 10 minutes most other times of the day. Sometimes, the wait could be 15 to 20 minutes during the really early or late hours of the day. FARES - As we mentioned above, you will need to get your Transfer Card at the station and put a $$ amount on it. The base fare is $2.25 for the rail, so make sure you have the correct change if that is your plan. You can also buy 1 day, 3 day, and 7 day passes if you are going to use the system for more than a few days. The full day fare is less than $6 so it's a great deal compared to cabs. Keep your transfer card as you get on and off the trains. When it gets low on funds, just put it into the slot on the machine and add "funds" to it. Easy to do and you can check the value left on the ticket at any time when at the machines. The signs and maps within the above ground and underground stations are easy to follow and read. Just remember what the name of the station is at the end of the specific lines. For example, the Red Line ends at Howard (north of the city) and goes to 95th/Dan Ryan at the southern end of things. When you enter a station and look for the Red Line, check to make sure you are heading in the direction you want to go. Each station for the Red Line will show a track for the Howard direction or the 95th/Dan Ryan direction. It's easy once you get the hang of it. Transfering between lines at a station is just as easy. Follow the signs that lead to the other line. There are attendants at most stations that can answer your questions.

Taking the L Train from Downtown Chicago to MDW:

Ok, the trip back to Midway on a Monday during rush hour was a bit hectic. We started at the Chicago station on the Red Line and headed towards the Loop at about 4 PM. The trains were already crowded and it was hard finding any room to just stand up with our bags. When we made the transfer at Roosevelt for the Orange Line it only got worse. It was now about 4:15 and the first Orange train that came our way was fully loaded. A few passengers got off and twice as many tried to get on. My wife got into the front door of the car and I ran to the back door just in time. At this point we were expecting things to lighten up a bit with space as we headed towards the airport. It only got worse as more and more people got on the trains versus got off. I never had a place to sit the entire ride - this made it uncomfortable. I would avoid this time of day to ride the L train if you have luggage. There is no place to put it on most trains and you'll end up standing next to your bags trying to maintain your balance for 20 minutes. A taxi may have been a better option, although we passed a few streets and highways on our route to the airport which were totally bumper to bumper with traffic. I guess you'll need to choose your poison. I would say DO NOT take the Orange Line during peak hours if you have children with you. It's too crowded and congested. Spend the extra $25 to $30 for the cab and relax before you get to the airport.

Midway Train heading towards the airport - Orange Line.