We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Flights from Chicago to SJD are really expensive, any help?

Which Cabo San Lucas hotels are on sale?
dd/mm/yyyy dd/mm/yyyy
See hotels
Washington DC...
Level Contributor
106 posts
198 reviews
Save Topic
Flights from Chicago to SJD are really expensive, any help?

My wife and I want to fly to Cabo to attend a wedding. We are planning to fly 4/13/2012 - 4/17/2012 (leave Friday, return on Tuesday). We could leave 1 or 2 days earlier if we had to, then return 1 or 2 days earlier. I've tried LOTS of different combinations, but I can't find a flight cheaper than $640 per person. Even when I try booking a package with our hotel, it doesn't make a big difference in price.

I tried USA3000, but it says flights aren't available those days when I try flying from Rockford, IL. And from O'Hare, it's the same price as any of the big search sites. I even tried flights from Milwaukee and it's actually more expensive by a little at the moment. I tried Apple Vacations, and it was the same as the big sites.

Is this just about the cheapest price I am going to get? Or can someone make a recommendation on something else to try? Thanks.

Jeffersonville...
Level Contributor
379 posts
8 reviews
Save Reply
1. Re: Flights from Chicago to SJD are really expensive, any help?

Indianapolis seems to be the least expensive airport in this region to fly out of. I'm in the Louisville area and we are looking at driving the 2 hours to fly from Indy. There are four of us going to Cabo in June and we can make the drive, park the car for a week, and still pocket about $400 dollars.

It's about $680 to fly from Louisville. Chicago seems to be in line since we connect there.

Edited: 20 December 2011, 18:28
Lodi, California
Destination Expert
for Cabo San Lucas
Level Contributor
24,343 posts
53 reviews
Save Reply
2. Re: Flights from Chicago to SJD are really expensive, any help?

Since you have a bit of time to be checking, try posting your desired flights on a site like Yapta.com and let them do the checking along with what you are doing. There are carriers that also refind (e-certs) if you do book and the fare goes down.

Washington DC...
Level Contributor
106 posts
198 reviews
Save Reply
3. Re: Flights from Chicago to SJD are really expensive, any help?

I will try that.

Also, any suggestions on what date I should have this booked by? Meaning, what approximate date should I have this booked by so it doesn't skyrocket even more?

Colorado Springs...
Level Contributor
65 posts
1 review
Save Reply
4. Re: Flights from Chicago to SJD are really expensive, any help?

I've watched ticket prices go up $400 a piece over the past two months...we used miles this year and for us it was $165 for our flights from Denver. Normal ticket prices right now are ranging $600-$800+ out of Colorado.

Weston, Connecticut
Level Contributor
2,066 posts
9 reviews
Save Reply
5. Re: Flights from Chicago to SJD are really expensive, any help?

How long have you been looking?

If I were you I would set a farewatch on the flights and wait. I would also apply for a Chase Sapphire card IMMEDIATELY which will get you 50K points (miles) to use when you charge 3K on it - use it for everything you buy.

At least that will be enough for one ticket with miles.in case the fares don't move.

There's no good way to predict how and when the fares are going to move, I've seen some crazy last minute fluctuations both down and up.

Booking as a package won't help, published air is published air, despite what some people will tell you, it can NOT be discounted - it's not even commissionable, meaning a travel agent (or Expedia, Travelocity, etc.) can't get it one penny cheaper.

Bulk air is another story but there isn't much available and it's often more expensive than the best published fareds anyway.

Weston, Connecticut
Level Contributor
2,066 posts
9 reviews
Save Reply
6. Re: Flights from Chicago to SJD are really expensive, any help?

Just FYI - Apple Vacations is rarely the best deal going. Not even close.

Washington DC...
Level Contributor
106 posts
198 reviews
Save Reply
7. Re: Flights from Chicago to SJD are really expensive, any help?

I've been looking for 6 weeks now. I've got my alerts set, but nothing special has come up yet. I'm not going to do the credit card thing, for credit reasons.

I'm not sure how packages work exactly, but the price for the exact same flights and hotel was slightly cheaper when I set it as a package versus buying them separately - just telling you what I saw when I put it together. Granted, it's still more expensive than I thought this trip would be so I'm trying to find an alternative.

I'll just wait and keep searching.

Colorado Springs...
Level Contributor
65 posts
1 review
Save Reply
8. Re: Flights from Chicago to SJD are really expensive, any help?

In reference to your question about when you should book, I booked last month for our trip in April. I usually start looking a few months out just to get an idea of what the going prices are. Flight availability is also something that changes quite a bit. The flights we're booked for are full and new flights are now scheduled. Sometimes flights drop after the new year, but then you risk getting a flight to match your schedule. I find a lot of the flights out of Colorado have 8-10 hour layovers or next day arrival, which who wants to lose a day of vacation sitting in an airport? So as soon as I find the flight that has the times and dates I want, I buy. I've been doing this a while and that is what works best for us. Unfortunately flights to Cabo always book up, because well it's a great place to go and they are never in short supply of happy beach goers to fly down there.

Colorado Springs...
Level Contributor
65 posts
1 review
Save Reply
9. Re: Flights from Chicago to SJD are really expensive, any help?

oh, BTW, $640 PP isn't that bad a price...cheapest I've ever gotten out of Colorado is $450 and that was in 05. If we wouldn't have used miles, our tickets would've been in the $600 range. :)

Washington DC...
Level Contributor
106 posts
198 reviews
Save Reply
10. Re: Flights from Chicago to SJD are really expensive, any help?

yup, this is why I think i'm just going to bite the bullet and book it. Flight and hotel for 4 nights together is coming out to just under $2,000. The wedding party has a 5% off code to use on American Airlines, but it's still more expensive getting it all separately.