questionslooking for a good deal on a flight/car rental…

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I have had excellent results using kayak... give it a try, you'll be presented with lots of options. But not SWA... as noted they only book through their own site.

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@thunderthighs: I am my employer :) That is a good idea though that I did not even think of.

@bnbsouthworth: Thanks for the info. All this is really helpful. I did notice that SW stands out with the baggage perk (smart on their behalf).

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You might even try some of the consolidators like kayak.com or travelocity. Look for surrounding airports. Sometimes it is cheaper to go in one airport or airline and out another. Not usually, but you might find a deal. Sign up or fair trackers that will notify you when a price hits your threshold. Cheapest lights usually found looking on Tuesdays. Cheapest days to fly are usually Tues/Wed/Sat.

My Mom flies Spirit from FL to MI all the time. Haven't noticed they're any worse than the others.

Make sure you factor in the cost of baggage. SW privce includes luggage. Most of the rest don't. Airtran might.

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Check to see if your employer has any Employee Discounts.

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Airlines vary their prices based on booking volume and capacity. If you are flying during a time that historically has high flight loads (holidays, long school weekends, etc) you can expect the prices to increase; if it's a less popular travel date the price will go down to fill the planes. Tuesdays and Saturdays are typically less expensive days to fly. Airlines will keep their capacity close to the belt to maximize profit but if the prices seem high I personally would wait and watch a bit. If you see it go up (usually in small increments at first) you may want to jump on it. Good luck! Ps, follow the airlines on Twitter, some of them post special sales there.

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@okham: Thanks for the link. I will check it out. We are going to go for 4 days (2 before and 1 after) so we have allotted time to do things. My husband grew up in Chicago so he is excited. I have only been there once during the brutal winter so it will be nice to enjoy things a bit more.

@videowallart: Thanks for the heads up on Spirit Airlines and the link.

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swa only books through swa.com

carrentals.com for the car

cannot speak as to timing questions

avoid spirit airlines like the plague

have fun

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With the price of gas going up, you might be better buying sooner. I've had good luck through Expedia, but definitely check in the airline's sites as well; many of them have best price guarantees. But the Expedia will have good package deals, so it may balance. And if you have time to sightsee at all, check into the citypass; we used it in atlanta and saved a bunch.

http://www.citypass.com/chicago

Good luck!