I flew in May through Chicago and through Baltimore. Other than the gate being terrible on the way out of MBJ (because of how SW does their lineup) I have no complaints.
I have flown Southwest twice,it was a great experience and the 2 free bags are really nice.
Here's how you get an early boarding if you don't want to pay the $12.50 for priority:
Sit at your computer exactly 24 for hours before your flight. Check in online within the first minute and you'll get an "A" boarding number.
You can do it with your tablet or phone by WIFI on the beach for the way home!
My number tomorrow is A 38
Cap
linston@redplate-negril.com
We fly SW out of Midway. The direct flight is great - On the way there, we depart around 9:00 and arrive by 2:00ish which is fine by me. I like choosing our seats when we board. (We do get the eary bird check-in but I may try what captaind & Linston does next time). We got the SW Credit card & our airfare for our trip in January is now pretty much free except some taxes & fees I think.
The only issue might be the weather. Come into the city a day early and stay at one of the stay and park hotels around the airport. I'm not from Milwaukee but we have tons of them in Chicago and you can usually park for up to 14 days for the price of the room. (parking can get very high in chi)
that which does not kill you makes you stronger
We booked our flight for February for less than $500 each two weeks ago and checked yesterday and it was $688. If you see a good deal take it and don't hesitate!