Did you know it's possible for a family of four to fly to six destinations for less than $100 per trip – all on Southwest Airlines? It's not all too complicated or time-consuming to master the system and leverage rewards points to enjoy stress-free and cost-effective travel. It simply requires employing a few simple strategies. With a little know-how, you can be boarding a plane alone or with a companion just about anywhere in the U.S., Mexico and Caribbean on points or a small fee in no time. Here are three tricks for flying (nearly) free with Southwest this year.[See: 2015-16 Best Airline Rewards Programs.] Earn Rapid Rewards PointsThe first step to fly nearly free on Southwest is to sign up for the airline's Rapid Rewards frequent flier program and accumulate points. The most obvious way to do this is to choose Southwest flights and earn points for each of those flights. Though you may only earn an average of 2,000 points on most flights when you are paying for low-cost tickets to quickly accumulate enough points for award flights, fortunately, there are plenty of techniques that allow you to earn miles without ever setting foot on a plane. The quickest and easiest way to collect points is to sign up for the affiliated Southwest Airlines Rapid Rewards Premier card. After spending a minimum of $2,000 on each card within three months, you will be awarded bonus Rapid Rewards points. Several times each year, they offer a 50,000 bonus per card. Be sure to wait until these bonuses are active. And keep in mind that the cards do come with a $99 per year fee, charged in the first billing cycle and, even on award trips, you'll incur an additional $5.60 mandatory government fee charged for each leg on all U.S. flights. Before you decide to invest in the affiliated credit card, ensure you'll be able to easily pay off your credit cards each month. Do not use credit cards to pay for purchases you cannot afford and thus are unable to pay off monthly, as the high interest rates attached to these cards can be steep.Beyond sign-up bonuses, the easiest way to continue to earn significant points is to use the cards for your everyday expenses – think: meals, utilities, gas, groceries, sports fees, gifts – and pay your bill on time each month. After all, why not earn a return in the form of miles on money you would already be spending?You should also sign up for Southwest's Rapid Rewards Dining program, which lets you earn points when you dine at select restaurants. Register your credit cards with the program and points will be added to your account anytime you dine at a participating restaurant.Another easy way to earn points for activities you may already be doing is shopping on Southwest's online shopping portal. By using affiliated e-commerce sites, you earn between one and 20 times the points per each dollar you spend. You can also earn points when switching mobile phone services, cable providers, renting cars or even subscribing to magazines and newspapers. And if you pay using your affiliated credit card, you'll earn even more points.[See: 8 Ways You're Annoying Passengers During the Holidays.]Get a Southwest Companion PassTo maximize your Rapid Rewards points and travel with family members and friends for free, seek out the coveted Companion Pass. This pass allows you to bring one person free on any flight you book with Southwest – either with money or points – from the time you earn the pass until the end of following year. You can even switch companions up to three times.To reach Companion Pass status, you need to accumulate 110,000 Rapid Rewards points. While the benchmark may sound intimidating, in reality, it's quite simple. You can easily sign up for a Southwest credit card from Chase. By signing up, you'll earn a 50,000 point bonus and if you meet the $2,000 minimum spend, you'll net you another 2,000 points (1 point per dollar spent), bringing you to 104,000 points. To secure the remaining 6,000 points needed, use the cards for your everyday shopping, dining and travel expenses until you reach 110,000 points. Collect these points as early in the year as possible, so that you can use the pass for the maximum period of time since it's valid through the end of the following year.Stretch Your Miles FurtherAfter you've earned the Companion Pass, collected miles and are ready to start taking advantage of free travel, there's an art to making your hard-earned miles last as long as possible and covering multiple family members. The number of miles or points required to book a Southwest flight is based on the price of the fare; therefore, it's best to only book your flights with points when Southwest is having a fare sale. It's important to regularly check Southwest throughout the year to understand the value for the flights and routes you are most interested in. That way, you can better assess whether you're snapping up a good deal before booking. Southwest also allows you to cancel or change flights with no penalty (your points are reimbursed to you) apart from the difference in fare price, so it doesn't hurt to book a flight, knowing you can switch your ticket later if the fare drops.[See: 10 Outrageous Fees Every Traveler Should Know About.]Should you need more points, the Chase Sapphire Preferred card is a good third card to have in your wallet. The card earns Ultimate Rewards points, which can be transferred to the Rapid Rewards program. The card regularly offers a 50,000-point bonus upon sign-up (and spending a minimum of $4,000 in the first three months of opening an account). Plus, the card allows you to earn double points on meals and travel, making it easy to accumulate points for everyday expenses. Best of all, you'll be awarded an additional 5,000 points for adding an authorized user to make a purchase in the first three months of creating an account.With these strategies in hand, it's easy to maximize points and get the most out of membership to enjoy nearly free travel around the U.S.