Airfare Insights/Info needed

I have been looking at flights for Dec/January and cannot find any direct flights from Chicago to Montego Bay. We started flying out of Chicago when Milwaukee no longer offered direct flights. I am wondering if anyone has any insights on this subject, specifically - is it possible that direct flights may be added later in the year? How far ahead would I be able to book just airfare on the charters such as funjet or apple that fly direct? I would sure appreciate any help - as my husband is ADAMANT on flying direct after having a problem with missed connections one year.

Direct flights are hard to find coming from the upper Midwest US. But on www.matrix.itasoftware.com, I found these from Chicago:

http://matrix.itasoftware.com/view/c...4-5b25d2c556ee

Try searching for flights out of Midway and Rockford. They both have them in season.
Also try Airtran out of Midway.
Both Frontier and Apple charter NS flights that time of year also.

We are out of Madison and like NS also

will have to give Air Tran a try next time.

We are from the Green Bay area, so I hear you on flights from MKE. After 10 years of Christmas/NY travel (to MBJ and other caribbean islands annually), here is what I know:
1. Usually can get a charter flight from MKE, but you are bound to their travel dates. Usually a 7 day stint, with Sat-Sat service or Weds-Weds. As we usually go 10-14 days, this is not an option for us.
2. We have found direct from CHI (O'Hare), but not every year. I start looking in February when flights start to open, and truly check daily on matrix (site listed above), Kayak.com and direct websites like US Air.
3. This year, I found a one stop from CHI to MBJ on our way south, and a direct back from MBJ to CHI on US Air (so they do exist!!!). Decided not to book, as I really wanted to fly from MKE rather than drive to Chicago.....
4. We just booked our flight for this Christmas - flying from Milwaukee to MBJ. One stop, 1.5 hour layover. VERY reasonable for the holidays when I booked ($650/pp),
Good luck, happy hunting!

I got Airtran out of Midway this May for 385 total nonstop both ways. Can't beat that.

Sun Country outta MSP (Minneapolis) runs WED SAT and Sunday NS flights beginning in December or so through early April... That 41/2 hour drive may be a tad far.... But like the others said the charters out of Chicago may be an option too. I much prefer the NS flights too. Get on and go. Not fun to miss a connection, lose luggage etc...

Wisconsin Gal ??

wont the airlines let you stack two, 7 day trips, to get your 14 days???...
most used to????maybe not anymore??
Apple sometimes would have air only 7 day travel, sat-fri or wed-thur, and they let us put 2 together


(I think American has non stops out of ORD)

American comes out of ORD direct and you should be able to book at least 6 months out. Frontier also goes direct and can be booked on line. Air Tran is new coming out of MDW took over southwest gates I'm trying them this time so I'll let you know. Sometimes United will do a direct during peak seasons. You just have to keep checking til you see what you want. And as mentioned above they only fly certain days like Sun to Sun

I'm going Monday to Sunday on AirTran out of midway in July nonstop ,they're out there keep looking!