From Chicago Union Station to Midway Airport
All Amtrak trains serving Chicago arrive at Union Station. The best way to travel between Union Station and the airport is by the CTA rail. Trains are fast and run frequently, and the entire journey (including all waiting and walking) takes approximately 1 hour 5 minutes. Beware that private shuttles run much less frequently than CTA trains do (about once an hour compared to every 10 minutes), and so on average you are not going to save much time by taking a shuttle despite paying at least 10 times as much as the train fare. Moreover, trains run until late at night, and trains do not risk getting stuck in Chicago traffic. Unless you have a lot of heavy luggage, a train ride is a more sensible option in most cases. The two maps you will need for this journey are the Downtown Chicago map and the CTA rail map.
First of all, you need to get to the CTA station (the Quincy station on the Orange line). The Quincy station is located three blocks (400 m) east of Union Station (map). Exit Union Station to Adams or Jackson and walk east across the Chicago river towards the Willis Tower (formerly Sears Tower). The entrances to the CTA station are located between Adams and Jackson underneath the elevated structure crossing both streets (on which the trains run). The entire walk takes about 7 minutes.
Now you are at the CTA station. The fare is $3. Follow the signs "To Orange line" to the correct boarding platform and buy a single-ride ticket from the farecard machines (cash, debit or credit cards). Pay your fare, pass through the turnstiles to the platform, and board any Orange line train. Beware that several other CTA lines also serve the same platform, so check the color destination signs on the arriving train to make sure you are taking the correct line. Travel to the Midway station and get off the train. The travel time from Quincy to Midway is 32 minutes; trains run every 8-12 minutes daily.
Finally, you need to get from the CTA station to the terminal. Take the pedestrian overpass to the parking building, pass through the building, and follow the signs to the terminal. The entire walk takes about 10 minutes.
The total travel time from Union Station to Midway should be about 1 hour 5 minutes including all walking, waiting, and riding the train.
The last Orange line train leaves Quincy at 01:25 daily.
If you have any questions, please check the "Frequently Asked Questions" page first. If you carefully read all of the above, checked the FAQs, and still have a question, please feel free to contact me.
Reverse directions: from Midway Airport to Chicago Union Station