From Midway Airport to Chicago Union Station
All Amtrak trains serving Chicago depart from Union Station. The best way to travel between the airport and Union Station is by the CTA rail. Trains are fast and run frequently, and the entire journey (including all waiting and walking) takes approximately 1 hour. 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 CTA rail map and the Downtown Chicago map.
First of all, you need to get to the CTA station (the Midway station on the Orange line). From the terminal just follow the signs "Trains to City". Pass through the parking building and take the pedestrian overpass to the station. The walk from any gate to the station takes about 10 minutes.
Now you are at the CTA station. The fare is $3. Buy a single-ride ticket from the farecard machines (cash, debit or credit cards). Pay your fare and pass through the turnstiles to the boarding platform. Take any train and travel to the Quincy station on the same Orange line. The travel time from Midway to Quincy is 27 minutes; trains run every 8-12 minutes daily.
Finally, you need to get from the CTA station to Union Station. Union Station is located three blocks (400 m) west of the Quincy station (map). Simply walk west along Adams or Jackson towards the Willis Tower (formerly Sears Tower) and the Chicago river. You will see an entrance to Union Station just after you cross the river. The entire walk takes about 7 minutes.
The total travel time from Midway to Union Station should be about 1 hour including all walking, waiting, and riding the train.
The last Orange line train leaves Midway at 01:00 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 Chicago Union Station to Midway Airport