My wife and I are going to take a trip to Chicago for 5 days later this month. I don’t know if a live travel agent with an office downtown could have gotten me a better deal or not, but I decided to book the trip myself. I used the major travel sites: Expedia, Travelocity, Orbitz, HotWire, Priceline, Hotels.com, Kayak, Hipmunk, and American Airlines Vacations.

I wanted two non-stop tickets on American Airlines from Austin to Chicago, leaving in the morning, and returning in the late afternoon. And I wanted a downtown hotel, I did not want to stay at O’Hare.

Checking prices on a daily basis I learned that none of those agencies charged the same price two days in a row. They also had different prices from each other: one might have a special sale on a given property that the others could not match. Regardless of which service I used, I always got a better price buying a package deal than booking air and hotel separately.

In the end, I booked the trip at a site I had previously not heard of, bookit.com. I found that their price for the days of our trip were better than all the others. Was this a fluke, or will it give me a better price on another trip? Let’s find out.

I’m going to check the price on a 5-day trip from  Austin to Seattle, depart June 13 and return June 17, fly American Airlines, and stay at a nice downtown hotel. Let’s see what kind of prices I get with this highly unscientific survey.

Expedia:

American Airlines, Leave Austin 8:35 a.m., Arrive Seattle 12:35 p.m. with a stop in Dallas. On return we’ll leave Seattle at 3:05 and arrive Austin at 10:40 p.m. We’ll use these flights for all the itineraries. We’ll stay at the Sheraton Seattle, total cost $1,957.

Travelocity:

Traveloicity did not have availability for the same flights as Expedia. So I did the best I could. leaving Austin at 8:25 a.m. arriving Seattle at 2:55 p.m. That’s not bad, but I did not like my return options, all of which left at sunrise. I selected a flight that left at 7:30 a.m. and got into Austin at 2:55 p.m. I booked the Sheraton Seattle: total cost: $1,830.91 Compared with Expedia I saved $160, but also had to be at the airport on my departure day by 6 a.m., thus losing half a day in Seattle.

American Airlines Vacations:

American Airlines could not book me on the same flights as Expedia, so I tried to match the Travelocity itinerary. I could not match that either, so I booked a flight that would leave Austin at 10:05 a.m. and arrive Seattle at 3 p.m. For the return I would leave Seattle at 3:05 p.m. and arrive Austin just after midnight at 12:10 a.m. American did not offer the Sheraton Seattle so I chose the Westin Seattle instead. Total cost: $1,863.69. Not a bad deal, we’d arrive home late, but I preferred that to an early morning flight from SEA.

Orbitz

I booked the same flights as I did with American Airlines Vacations. I was however able to book the Sheraton Seattle. Total cost: $1,628.24.

Bookit.com

I was able to book American Airlines, leaving at 10:05 and arrive 3:00 p.m, returning Sunday at 3:05 arriving 12:10 a.m. I was able to book the Sheraton Seattle: Total Cost: $1,587.27.

Hotwire

Same flights and hotel as bookit.com, total cost: $1,676.99

Kayak.com

This site booked hotel and air separately. I found the AA flights I wanted and it sent me to aa.com to purchase them. Then it opened another window for the hotel. On aa.com I booked a 9:25 departure, arriving Seattle at 2:15 Return flight left at 3:05 p.m. and arrived at 12:10 a.m. Cost for tickets is $882.40. Sheraton Seattle was $281 per night plus tax, for $1,014.52. Total cost: $1896.92

Priceline.com

I used the standard Priceline, not the name-you-own-price version where you really do not know what property you will get. I booked American Airlines departing 12:20 p.m. arriving 5:55 p.m. Return is the 3:05 to 12:10 a.m. that so many others have offered. I was able to book the Sheraton Seattle. Total cost:  a stunning $1,393.70, by far the best deal I have found.

What does this prove?

Not much. It shows that this specific trip booked at this time of day resulted in Priceline giving me the best price. If I check again tomorrow evening, or change the itinerary by 1 or 2 days, it’s very likely that all of the prices listed above will change. Will Priceline still come out ahead? Bookit.com had the lowest price for my Chicago trip, and by booking it in the morning I save over $300 compared to booking it the prior evening.

Does each service offer the same features? Some offer a price guarantee while others do not, that could be part of the price difference.

I did find that the best days for booking a vacation are Tuesday, Wednesday, and Thursday. Prices go up on Friday and do not drop much until the following Tuesday.

If you are planning on taking a trip and you have the time, checking all of the services on a daily basis will help you to save money in my opinion.