When visiting a big city, I hardly ever rent a car anymore. It’s just too expensive when you consider the cost of the rental, gas, parking at the hotel, parking at the locations you plan on visiting, and tolls. I’ve gotten around just fine during trips to San Francisco, Los Angeles and New York City without a rental car so I decided to not rent a car for our trip to Chicago (besides all the other reason I just mentioned, the hotel where we were staying charged $60 a night for parking!!!!)
I always look at two different scenarios when thinking about traveling without a car – getting from the airport to our hotel and then getting around town to see the things we are going to see.
Here’s how we did in Chicago:
Getting back and forth to the Chicago Airports
The Chicago Transit Authority runs trains, or the ”L’ for short, between downtown and both major Chicago airports. The trains in Chicago are designated by colors. The Blue Line trains go from O’Hare Airport, through downtown and to the Forest Park area. The Orange Line trains go from Midway Airport around “The Loop” of downtown and then back to the airport. Click on the link here to see the entire Chicago Train Map.
Getting to the train station at the airport was easy, as the signage was clear about where to go. Make sure to follow the signs to “trains”. As a New York area native, I know there’s a difference between a train and a subway and it took me a second to realize that, while in Chicago, we needed to take the train (even if it looked like a subway).
At the airport, follow the signs to CTA/Trains to City
The fare for a ride on the ‘L’ costs $2.25 for a single use Pay As You Go (PAYG) ticket, except when you are taking the train FROM O’Hare Airport, which costs $5. Note that the return trip to O’Hare only costs $2.25. To board a train, first you need to buy a “Ventra” ticket. You can buy a single use Ventra card that costs $3 (or $5 at O’Hare Airport) or you can buy a reusable Ventra card for $5. With this card, you can load money onto it to pay your fare and if you register the card online, you are then able to use the $5 fee to pay for a fare. If you are planning on taking taking multiple rides, you can get a one day use ticket added to your Ventra card for $10.
When we got to the station at O’Hare the ticket machines had a long line. I saw a sign on the wall saying “Skip the line and use your contactless bank card at the entrance.” I just wrote about this type of payment system for the London Underground and now the same system was in place in Chicago…and I didn’t bring my contactless card with me. Luckily the small print said that you can either use a contactless bankcard OR a Mobile Device. I opened up Apple Pay on my iPhone, tapped it on the turnstile and I was let through. Then I tapped it for Sharon. Note that you can not purchase an all day ticket with your mobile device, only a single ride Pay-As-You-Go ticket.
The Kimpton Hotel Allegro was located very close to the Clark/Lake station for the Blue Line train. I had purposely picked a hotel close to a train station when choosing the hotel for this trip, knowing it would make the trip easier (it was also a good way to narrow my search so I didn’t spend forever trying to find a hotel in Chicago). The ride from O’Hare took about 40 minutes. The train filled up more and more as we got closer to downtown and the seating wasn’t particularly set up for people with luggage. Even with only having our carry on bags, it was a struggle to get through the mass of people to the exit at our 
stop but as I said before, the native New York/New Jersey came out and, “Excuse me!, this is my stop,” might have been said at a somewhat increased volume. Maybe it was a breech of etiquette for Chicago, but we did get off the train.
At the end of our trip we were only 2 blocks from the Orange line stop at Wells/Washington. I used my iPhone again to pay for tickets and it was a straight 25 minute ride to Midway Airport This ride was much nicer, as the train was only partially full and we were able to ride around part of the Loop during the beginning of the ride and look at the surrounding buildings.
Getting around Chicago
We only had one and a half days in Chicago and the first half day consisted of lunch and seeing Hamilton (and going to a Tiki bar after the show). Since I picked a hotel located in the Loop, we were close to many of the places we wanted to visit for our stay, It didn’t take long to notice that Chicago is a very walkable town. *weather permitting
On Saturday, the day we did all the things, I managed to log six miles of walking on my iHealth app.
We walked for most of the trip except for when we called an Uber for the ride from the John Hancock building back to Millennium Park. For those concerned about these things, I never felt unsafe at any time in the touristy areas we walked around.
Even if my wishes came true and I was able to go and see a Cubs game, it’s possible to take the ‘L’ to Wrigley Field (or any of the other sporting venues) in Chicago. The CTA gives a listing of how to do so on this page.
Do I wish I had rented a car while in Chicago? Heck no! We had wonderful weather for our trip so walking around town was enjoyable. Public transportation to and from the airports was inexpensive and easy to navigate. The option to call for an Uber/Lyft was always there, if needed. We’re going back to Chicago this November, we’re not renting a car for that trip either and that’s the best endorsement I can think of.
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