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Chicago is a fantastic destination...and a very large one. Your first challenge in planning your trip can be how to get from the airport to your hotel. Car rental? Mass transit? Limo? Whether flying into Chicago O'Hare or Chicago Midway renting a car from an airport location will come with hefty airport fees and taxes that can add two hundred dollars or more to a weekly rental. To avoid these fees consider two things: #1 Do you really need a car? #2 Will you be staying downtown and focusing or activities and locations there?
If you'll be traveling around the Chicagoland area, not just downtown, then yes, you will probably need a car. If traveling in a small party, without too much luggage consider booking your car through a car company such as Enterprise that offers an off-site, yet very nearby location on River Road in Schiller Park. Since it is located just outside the airport zone, you will not pay the higher airport fees and taxes. Grab a cab to the location which as of October 2013 will be about $20 for fare and generous tip. You will have your car and be on your way in the same time as it would take to ride the airport locations' shuttles to their location away from the terminal. When returning the car, Enterprise can take you to the Blue Line station about 1 mile away and you can ride it one stop further into O'Hare for your flight for $3 per person. Tickets are purchased through the Ventra ticketing machines with cash or debit/credit card. Note: the Blue Line will take you into the terminal, but it is a bit of a walk from there to the ticket counters, baggage check and security checkpoints; lots of luggage and/or trouble walking will be an issue.
If you will be staying downtown in The Loop area be aware parking a car will most likely cost $50 per day. Mass transit is a very viable option for most people. The Blue Line "L" train runs from O'Hare to the station at Clark and Lake downtown. Many hotels are located within 8-10 blocks of this station, so as long as you're able to walk that distance with your luggage you won't even need a cab. Cabs are available, but on rainy, snowy or very cold days they can be very hard to find.
The Chicago area also enjoys the services of a very large livery fleet that can take you just about anywhere in the city or the suburbs for a reasonable flat rate. This way you can avoid car rental fees, parking fees and the shortcomings of public transit from/to the airports.
If you want to make sure you get to your destination on time and in style you should hire a chauffeur service to pick you up from the airport. When searching for a Limousine service Keep These 3 Things in mind.
There are plenty of Local, National & International services available, remember that you get what you pay for, most services like Elite Limo will give you a free quote. Its always a good idea to make your reservations as far in advance as possible but usually you can get a Vehicle in as little as 1-2 hours' notice in 40 U.S. cities. You can get a single bill and single point of contact for all of your rides, worldwide.There is a 24 Hour dispatch service so you can speak to a real person anytime and Every ride is watched closely by their staff through GPS tracking of the vehicle and status updates directly from the driver via a mobile app.