Safe to leave MDW with a 4 hour layover?

I have a flight tomorrow that has a 4 hour layover at MDW. While I've transitioned at MDW several times I have yet to try to go to Chicago from MDW or return.

What is a realistic time to get from MDW to downtown on the L?

What is a realistic time to get back once I'm downtown in the worst case scenario (aka 15 minute wait time)?

How bad is security at MDW? I'll only be taking my laptop so I won't have a lot of stuff.

I also have status with DL and AS, but don't know if I can skip ahead at MDW since they I don't know if they even fly there.

I may just scrap the whole thing but if I can even get an hour in Chicago it would be worth it. If anyone has any suggestions I'd appreciate it.

This is probably better asked in the Chicago forum, but I believe it is about 35 minutes to the Loop. But about a ten minute walk down the never-ending passage between the transit station and the terminal.

I realize that four hours at MDW may seem like an enternity, but waiting is not as bad as the stress that you'll have trying to get to and back from the Loop in four hours if you're delayed. (And this is from someone who has done similar "runs" in Sydney, Paris, San Francisco and Las Vegas.)

The good news is that the train takes about 30 minutes (MDW station to most Loop stations). Add to that the 15 minute walk from MDW's food court and a ten minute wait for the train (depending on the time of day) and you've got to allow 55 minutes "door-to-door" on the outbound. Security lines haven't been all that bad lately (if you use the "expert" lanes), but figure at least 15 minutes for ID check, shoes, etc. If you want to be at the gate 20 minutes before take-off, that means a total of 90 minutes on the return, or 145 minutes of your 240. That leaves less than two hours drive us locals crazy as you stare at "them thar big buildin's"

You'd have time to walk around a little, not enough for a decent lunch or dinner.

I suppose that if you only wanted to have a look at Chcago you could stay on the train and ride around the loop and head back to MDW. (You really can't see much from the train.)

Some folks might suggest taking a cab or a rental car. I'd be very wary of this given the unpredictable nature of Chicago traffic.

There are no elite lines nor lounges at MDW. The food court isn't all that bad. (It's all local based restaurants, including McDonalds.) I recommend either the burger or the fish sandwich at Illinois Bar and Grill.

I can't think of things close to MDW but think of things closer to there to see. Once in New Zealand, I hired a cab to show me the city with a limit of 60 minutes. We agreed that the meter would run until $ x. We stopped at a few places including a few places that he said he hadn't seen recently.

Absolutely.. When you get off, just head straight down towards baggage claim but instead of going downstairs on the escalators, walk up the ramp in the middle and hop on the Orange Line. You'll be downtown in minutes, and when you're done, hop back on and it'll take you right back to MDW.. I would allow about 30 minutes for each way, plus figure in check in time.. So count on having about 2 hours to kill downtown, there's plenty of stuff to check out..

As often as the CTA breaks down in Chicago I would be very careful. If you have to catch a taxi the ride back to Midway it can take even longer on the Stevenson expressway due to traffic which can happen at any time of the day due to construction south of Weber road and just everyday normal nutzo Chicago traffic.

You also have to calculate time to get thru security to get back to your gate.

Here's a helpful link..

http://www.transitchicago.com/maps/rail/rail.html

You're going to be on the Orange Line.. So follow it from the airport icon all the way up to the "loop" (Thats why the call downtown Chicago the loop). Pay attention to the stop names so you have a good idea where you're going to hop off.. It's a very easy train to ride because it just goes in a big circle, and eventually you'll end back up at MDW airport.. You can ride it all day on one fare if you want..

CTA trains tend to break down on older lines such as the Blue Line or Red Line. The Orange Line tends to be more reliable.

I've left for a flight 1 hr prior to the flight and made it just fine. If the security lines aren't bad, you can definitely do 2.5+ hours in downtown Chicago, just know that the L doesn't have a set schedule (they do but it seems that they don't follow it on the loop) and that the trains come approx. every 15 mins.

You are really taking your chances if something were to happen with the train.

This happens to us one time in NYC via ISP. One of the train in front of us got derailed off it's track. They took us around it via a school bus. It took us nearly 4 hours to get to the airport and barely made it on our flight.

It's a good thing we watched the news before we check out of the hotel. We ended up leaving hotel early to give us some extra time but still cutting it close.

You can come up with a scare scenario for any situation. How often do the trains break down, derail etc.? Very rarely. As long as making your flight is not an absolute must happen situation ( and we could construct scenarios where your incoming flight is delayed 4 hours and you miss it anyways ) , then I don't see any problem with spending an hour downtown.