Seeking advice from fellow Chicago area fliers!

[thelittlethings]

I am heading to WDW around October 20th. Just my DD (6) and I for our second trip! (DH and baby brother decided to sit this one out.) I haven't booked airfare in the longest time and really don't know what a good deal is. I've been checking rates from Southwest out of Midway and it looks to be in the $140 range one way. Is that good? Should I grab it while the flight times I want are still available? Or wait and see if Southwest comes out with a Fall deal in the summer? I've looked at other airlines as well but they seem to be similar in price with the exception of added on baggage fees. I have the park tickets, Pop is booked, ADR's made... Just can't seem to wrap my head around paying $550+ for airfare! Anyone have any words of wisdom they can share? Thanks in Advance!

BTW, I did sign up for the Southwest Click N' Save emails as well as Airfare Watchdog's emails.

 

[jec6613]

I'm technically NYC area, but I'm in and out and through O'Hare at least a dozen times a year, so here's my take:

First, if you're using a flight comparison site, it won't be the best deal there, because it can't be. Direct to the airline site is always best. Midway is home to WN, as you know, but O'Hare is a major hub for both AA and UA, so you should check both of those. Since it's only 3 airlines, it's not exactly a big deal.

For October 20th, $140 OW is a decent price, but not a good price (that would be around $120 or so for a good price). Also remember to make sure whoever you pick has other frequencies, and you should try to leave as early in the day as is practical. October is early, but you can have weather issues out of the airports and earlier in the day flights are more likely to leave and be less delayed than later in the day ones.

 

[robinb]

Will you be renting a car? If so, ORD-TPA on United is $166 round trip for 10/20 - 10/27.

 

[jec6613]

Will you be renting a car? If so, ORD-TPA on United is $166 round trip for 10/20 - 10/27.

That's a really excellent price nowadays!

 

[robinb]

That's a really excellent price nowadays!

But she would have to add the cost of a car rental which makes it less attractive if she was planning to take DME.

 

[PrncessA]

We fly out of Chicago and I am always checking prices. The cheapest that I have saw flights to MCO in the last couple of years (on a airline I would fly on, i.e. NOT Frontier) is around $130 each way and that was on Southwest. You can sometimes find a slightly cheaper flight on Frontier, but they have horrible reviews and nickle and dime you for even carry on luggage let alone checked luggage. Southwest is usually the best deal to MCO.

Even when Southwest throws out their $73 sales, MDW to MCO is never $73 it is always $130 at the cheapest.

 

[StitchesGr8Fan]

From what I've seen that is pretty standard for pricing. I don't think you'll get much better.

 

[StitchesGr8Fan]

fWIW, we are flying out of Milwaukee on SW for our next trip. The cost (or in our case) point savings is with the 90 mile drive.

 

[thelittlethings]

I'm technically NYC area, but I'm in and out and through O'Hare at least a dozen times a year, so here's my take:

First, if you're using a flight comparison site, it won't be the best deal there, because it can't be. Direct to the airline site is always best. Midway is home to WN, as you know, but O'Hare is a major hub for both AA and UA, so you should check both of those. Since it's only 3 airlines, it's not exactly a big deal.

Yes, thank you, I have been mostly on the airline (southwest, aa, United, and frontier) sites themselves. Checking both midway and O'hare.

Will you be renting a car? If so, ORD-TPA on United is $166 round trip for 10/20 - 10/27.

Thank you. I checked into it today but im not planning on 7 nights, just 6. I checked other dates though because I'm not against renting a car, but by adding that cost in I'm not to sure I'd be saving that much money (or time)to make it worth it. Any ideas on car rental cost for 6 days? $170 sound about right? The magical express and disney busses just seem so practical since it's just me and dd.

Even when Southwest throws out their $73 sales, MDW to MCO is never $73 it is always $130 at the cheapest.

That's the info I was looking for! Thanks! I know they are running their nationwide sale now and my fare didn't budge. I would just hate to wait and the early flights be gone and I waited for nothing!

 

[thelittlethings]

From what I've seen that is pretty standard for pricing. I don't think you'll get much better.

fWIW, we are flying out of Milwaukee on SW for our next trip. The cost (or in our case) point savings is with the 90 mile drive.

Checked into it, thanks. It would add an hour to the drive which wouldn't bother us, but it looks like it wouldn't save me any money.

 

[AliceIn]

I am heading to WDW around October 20th. Just my DD (6) and I for our second trip! (DH and baby brother decided to sit this one out.) I haven't booked airfare in the longest time and really don't know what a good deal is. I've been checking rates from Southwest out of Midway and it looks to be in the $140 range one way. Is that good? Should I grab it while the flight times I want are still available? Or wait and see if Southwest comes out with a Fall deal in the summer? I've looked at other airlines as well but they seem to be similar in price with the exception of added on baggage fees. I have the park tickets, Pop is booked, ADR's made... Just can't seem to wrap my head around paying $550+ for airfare! Anyone have any words of wisdom they can share? Thanks in Advance!

BTW, I did sign up for the Southwest Click N' Save emails as well as Airfare Watchdog's emails.

I got United out of O'Hare for $140 each way for early June. I bought my tickets about 3 months prior to the trip. $140 is a reasonable price to Orlando.

 

[thelittlethings]

I got United out of O'Hare for $140 each way for early June. I bought my tickets about 3 months prior to the trip. $140 is a reasonable price to Orlando.

Thanks! So my current Southwest price now is probably my way to go. Looks like united right now would be $563 not including luggage and southwest would be $552 with baggage fees.

 

[thelittlethings]

Thanks everyone! Seems like you have helped answer my question! I think I'll just go ahead and book and hope a price drop doesn't happen. Hopefully I can save that money elsewhere. And hopefully Disney doesn't go all coo coo again like they did with the free dining craziness, I'm going to really need that 15% room discount now!

 

[robinb]

I just ran your real dates ast ITA (http://matrix.itasoftware.com/) and I now get $145 RT on American ans US Airways ORD-TPA for 5 people. I wouldn't check bags. You should be fine with 3-4 carry-ons.

So, that's a total of $721 airfare for all 5 people. You'll need a minivan for your crew. Dollar has a minivan for $391 (using code OI1054) all in. Your price is now up to $1112 total. Compare that to $1377 on Southwest, that's a $265 savings. It's an easy drive to WDW from TPA and might take less time that DME. You will have to leave WDW earlier for your return trip.

 

[thelittlethings]

I just ran your real dates ast ITA (http://matrix.itasoftware.com/) and I now get $145 RT on American ans US Airways ORD-TPA for 5 people. I wouldn't check bags. You should be fine with 3-4 carry-ons.

So, that's a total of $721 airfare for all 5 people. You'll need a minivan for your crew. Dollar has a minivan for $391 (using code OI1054) all in. Your price is now up to $1112 total. Compare that to $1377 on Southwest, that's a $265 savings. It's an easy drive to WDW from TPA and might take less time that DME. You will have to leave WDW earlier for your return trip.[/QUOT

I checked it out, but btw its just me and dd (6), not the all five of us. So looks like fare would be about $289, and car rental from dollar for mid-size would be $188. That's $477 compared to southwest at $552. That's only a savings of $75 that way. Would $75 be worth it to have to drive myself and daughter? Ahh, i really don't know?

 

[robinb]

I checked it out, but btw its just me and dd (6), not the all five of us. So looks like fare would be about $289, and car rental from dollar for mid-size would be $188. That's $477 compared to southwest at $552. That's only a savings of $75 that way. Would $75 be worth it to have to drive myself and daughter? Ahh, i really don't know?

No, it's probably not worth just $75 unless you're planning to go offsite for something.

 

[thelittlethings]

No, it's probably not worth just $75 unless you're planning to go offsite for something.

Okay, that's what I was thinking. This is only our 2nd trip and the first time we stayed off-site and had our own vehicle because we didn't fly. We have never stayed on property so I just thought it would be easiest for the two of us to just take Disney transportation. Thanks for your advice. Again, I haven't flown in what seems like forever and I'm definitely new to the flying to and staying on Disney property. I'm a big planner and this flying thing has been my biggest decision and headache. Thank You Again!