I have to decide between flying SW into Midway or American into O'Hare. I will be with an elderly person who can tire easily. We will need to get downtown to the Drake Hotel on a Friday morning and back to the airport on a Sunday afternoon.

Can anybody advise as to the best choice of airports, taking into account ease of transportation as well as cost?

I will confess I'd rather fly American, but in this case I want to make it as easy as possible for my friend, so if Midway is a lot easier, we'll go that way.

Thanks in advance for your help - I appreciate it so much (and thank you for saving me from trying to wade through all the options).

A detailed list can be found here.

In theory, either is fine, since both have public transit and expressways that head straight into downtown. That said, Midway is slightly closer, so it can usually arrive at Michigan Ave. (and the Drake) about 5-10 min. faster than if you used O'Hare. Since you are traveling on Friday night and Sunday afternoon, you won't have rush hour to contend with on the expressways. In the end, if 5-10 min. doesn't matter to you, it really doesn't matter which airport you will use.

My recommendation is to use a limo for a comfortable and stress-free experience. You can easily arrange for one through the Drake's concierge before your flight. If too expensive, then take a taxi. If that's also too expensive, you can consider the airport van (Airport Express). No reservations needed for either. The absolute last option is taking CTA's light rail, the L, but it requires lots of walking and stairs, so I wouldn't do it for your companion's sake.

Those times of day (non-rush hour), from O'Hare downtown by taxi/limo/car would be roughly 50-60 minutes, maybe a bit more or less. Taxi/limo somewhere around $50-60 each way as I recall.

By public transportation, a problem because of construction. At the moment, you'd have to take a shuttle bus for the near-O'Hare part (O'Hare to Rosemont each way).

For MDW, taxi/limo maybe 30-40 minutes, cost perhaps $35-40. Or take the Orange line train most of the way (30 minutes, about $2 each) and cab the rest once you get downtown, maybe $8 each way. There is a decent walk to the Orange terminal at MDW, about 10 brisk minutes, all indoors.

Plus stairs, as the previous poster says.

There may have been a fare increase recently for taxis as a result of gas prices; not sure.

I have to cordially respectfully disagree with ninja and toomanybooks.

First, OP is arriving on a Friday morning, not evening. There was a time in Chicago when freeways/expressways were only jammed inbound from 6:30am to 9:30am and then outbound from 4:00pm to 7:00pm on business days. Sadly, this is changing. It's not uncommon to see major backups on Saturday afternoons.

Yesterday I drove from my home (downtown) to ORD at 10:30am. It took me about 40 minutes -- which is long. If there is no traffic, it takes 20 minutes. My record time is 17 minutes, from car on to parked in the ORD garage.

Which brings me to my next point -- while extreme traffic can certainly make the journey from ORD to the Drake in the 50-60 minute range, a more typical timeframe is 30-35 minutes.

For some reason MDW has achieved this reputation as being more convenient because it's geographically 1.5 miles closer to the city center. But when one factors into consideration the long stretch on Cicero Ave to I-55, and then the I-55 traffic, then the merge onto 94...the time difference is minimal and, in fact, I'd argue that traveling time can be faster to ORD when there's no traffic since it's all highway.

So to answer the OP's question, the airports are nearly equidistant from the Drake. And I'd fly AA over WN any day!

To answer OP's question, it depends on when you're coming in. If it's Friday late morning, like 11, it doesn't matter. If it's 8 or 9, and a savings of at maybe 15-20 minutes matters, go with MDW. Otherwise, go with your airline preference of AA at ORD. Sunday isn't going to be a big deal either way.

Now, on to the digressions!

Huh? I get 17.5 vs 11.5 when I put just "Chicago" into google maps (which ends up being right by city hall, seems fair enough to call "city center". Point being, it's not a 1.5 mile difference. To the drake, it's 18 vs 13.5.

Stevenson traffic? Compared to Kennedy traffic? And why on earth would you merge onto the Ryan from 55 if you're going anywhere downtown except the west loop? The traffic there is almost always horrible and it's almost always better to take LSD. Also, the amount of time that there's no traffic on the Stevenson is much more then there's no traffic on the Kennedy. I'd argue that MDW is going to be faster except for a rare occasion where the Kennedy is clear and there's an accident on the Stevenson, though most of the time, not by much.

UNITED959:

You have better luck on the Chicago-area highways than I do.

I especially remember a 90+ degree day with a 2.5 hour one-way trip in from ORD.

Oy. This is definitely not unheard of. Nice thing about Chicago, though, is that side streets are an option...the longest it will ever take me to get to ORD is 1.5 hours. Of course if you're at the mercy of a cab driver, it could be tough...

I can't stand WN, and usually fly out of ORD rather than MDW in order to stick with UA, even though I live much closer to MDW. However, if I were travelling with my elderly mother, MDW would be my choice hands down. The distances inside the airport are generally shorter at MDW with gates closer to the (usually working) moving walkways.

On the highways, as the foregoing spirited debate indicates, it is a crapshoot, though I tend to agree that IN GENERAL, not invariably, backups are less likely and shorter between the Loop and MDW than between the Loop and ORD.

Deciding factor for me right now would be: The Blue Line subway to/from ORD is f(*(&d up all month -- you have to take a bus for the last stop -- so more travellers will be in cars/taxis/buses at ORD than usual, at least until 8/1. I'd do MDW until that clears up. www.transitchicago.com will have status of the construction.

Not to be pedantic, but the L is not "light rail", it's heavy rail, i.e. what is commonly called a "subway", except you'll be above ground the entire time from MDW, and most of the time from ORD.

I'm not sure I'd call it the "absolute last option" but given the circumstances it might not be the best choice, unless saving money is important.

The CTA is a pretty long walk at Midway. So, if you're going to take the L, O'Hare is the way to go. But, you would still have to take a taxi from downtown to the hotel.

A taxi would be the best bet and much cheaper from Midway.

From ORD, I'd have to have a pretty darn good reason to drive (or cab/limo) to downtown. Blue line FTW.

What's the difference between "light" and "heavy" rail? Is there some definition?

During one trip where I had limited mobility and public transport wasn't a good option, I took a shuttle from the Magnificent Mile area to MDW for something like $12, which seemed like a good compromise since I was on a budget. If money isn't a concern, a taxi would be a good choice for ease of transport.

The American Public Transit Association defines the difference here. However, their descriptions are somewhat technical. In some ways it comes down to "you know it when you see it". As a general rule, heavy rail tends to be found in older, northeast cities, and light rail is found in newer southern and western cities. (But there are exceptions: Baltimore and San Francisco have both heavy and light rail, for instance.)

In the "more than you ever wanted to know" department, there is a Wikipedia article on the light rail that also discusses the differences between light and heavy rail:
http://en.wikipedia.org/wiki/Light_rail

I always think of it as more like "you know it when you hear it" because light rail is much quieter than heavy rail.