I'm not a fan of MDW. It's a smaller airport, and I'm sure it's conveient to Chicagoans, but for the traveler making a connection, it's definitely a downer. It's better than Houston Hobby (its equivalent there) in that there's at least several places to get food, but the only way I can get online is to go to the business center and rent an office with an Internet connection for $3 for the first 5 minutes and 48 cents a minute after that. Otherwise, it's a really boring wait - and on the trip over, the layover was almost 4 hours. Unfortunately, it was the cheapest way to get from MSP to DTW.
This is the second of three trips this month, and it's looking like next month will have at least one and maybe two - including the possiblity of being in New York over Christmas. Whee. At least the trip next week is personal, not business.