For a list of five places to find vacation discounts in Chicago, you should try a website, called VacationHotline.net, an online travel agency that offers travel booking and research services. The site allows you to research information on a trip you are planning to take and to book the desired vacation on the website. This website also provide links to other websites, with some of the hottest deals for traveling and vacations and the deals are sorted by the type of airline you travel by to the hotels and shopping centers at the desired destination. This site is a must-see for some hot and sizzling discounts for traveling to Chicago. Prices vary from location to location and from date to date, so make sure to check and book your vacation in advance for the best deals for vacations to Chicago.

Travelocity

Another site that offers its visitors hot discounts on vacations to Chicago is a website, called Travelocity, which is always running hot deals and promotions for vacationing in Chicago and you can choose from deals on flight and hotel, deals on hotel and car and escorted travel vacations. Travel booking is also available for this site and all you have to do is choose they type of vacation you desire the number of people participating in the vacation, input the requested departure and arrival info and if it is a round trip vacation, choose the return date and time as well. The site is easy to use and services a dedicated customer staff that will help you with any questions and/or concerns about you traveling needs. Prices vary from location to location and from time to time, so check and book your vacation in advance to get the best deals to Chicago.

Orbitz

This is another great travel and vacation booking site for those who plan to vacation to Chicago and also offers some hot deals on vacations to the “Windy City.” You can use customize your vacation search option and plan your vacation that way, by choosing the type of flight you desire, the departure and return dates, if you are taking round-trip vacation to Chicago. There are many different hotels and rental car agencies to make your reservations with and there are many places of interest to see in Chicago. For the best deals on vacations to Chicago, plan and book your reservations early and enjoy!

Priceline

You can find more great deals and promotions for vacations to Chicago on a website called Priceline.com. Pricleline.com is one of the premier sites for vacation booking, including to cities like Chicago and are always running promotions for those who like, no matter the budget, so you can have a good time, without the stress of paying for a huge vacation budget.

Travel.Yahoo.com

And another great site to find cheap travel is the site called travel.yahoo.com, which is always listing vacation discounts to Chicago. Some of the prices for vacation discounts are cheaper or the same than the other major travel and vacation sites, but unlike the other vacation sites, you cannot book vacation packages on the site either, however trave.yahoo.com does provide links to other vacation sites and you can book a vacation from there. The prices of the vacation packages differ from date to date and the type of packages requested and you may save $100 on a vacation package on one day and $500 on the next, but to guarantee in buying a vacation package at the lowest prices, book the vacation packages early and if the packages are not available on the date you desire, find the next best date, with the best price, to book your vacation package.

The first thing I tell people is don't pay the asking price. That means, don't just walk up to a car rental counter and ask for the price. You will always get ding'd if you do that. Instead, find a computer that is connected to the internet and book it online.

If you are looking for a cheap rental, check out Dollar, Thrifty, Budget and Enterprise. Each of these companies provide pretty new vehicles at their locations for a low rate.

1. The first place when you reach the company's website to check is their Specials page. Depending on how long you need your vehicle, check if there are any dollar savings off a weekend, weekly or monthly rate. Most of these specials are in the form of a promo code or discount code. Take note of it before you leave the page.
2. If you work for a large corporation, check with your company and see if they have a preferred car rental agency and what the discount is. Most large corporations have corporate accounts with Hertz or Avis, and not any of the discount ones that I have listed. With the right corporate code, you may be able to get better rates with their companies or you may get special privileges. I would compare the prices with these discount companies just to see which one offers the better deal.
3. If you don't have a corporate code then ask your friends if they know of any. For example, if you belong to Costco, they have codes for Alamo, Budget, Avis and Hertz. And if you golf and belong to the USGA, you can use their special code for Hertz. (I believe the last time I looked, the code was printed on the USGA site under benefits.) Having a code will save you up to 25% off your total rental costs.
4. When you pick up your car, stay firm on your booking. Because their rates are substantially discounted, they will try to encourage you to upgrade the vehicle for an additional cost. Or if they ran out of the size that you had booked for, they will try to charge you for a larger size car. Either way, stay firm and demand that they honor your booking.
5. Check with your car insurance company and credit cards to see if there are any car rental coverages that are included. For instance, most gold credit cards offer comprehensive coverage on car rentals. This will save you up to $10 per day if you decline the coverage from the car rental agencies but remember to use the gold card to pay for the rental. Also, some car insurance policies allow you to take the coverage you have on your home vehicle and transfer it to the rental car. This could potentially save you another $20 per day.

I personally take no coverage when I rent because my AllState insurance allows me to take my coverage and transfer it to the car rental and my gold American Express card covers the liability. I have to stay firm at the counter, and decline their coverages and not flinch when they say I am responsible for the whole car in case something happens to it. I know AllState and American Express are behind me on it.