By Plane: You can get into Sanatiago by plane, to the Santiago Municipal (STI) at the Aeropuerto Internacional del Cibao.
There are direct flights from New York (JFK) by Delta Airlines, and JetBlue. From Miami (Fort Lauderdale) by Spirit Air and American Airlines from Miami International Airport (MIA). Also if you are in South America there is a direct flight from Panama (PTY) by Copa Airlines. Air Turks & Caicos have a direct flight from Providenciales (PLS) and connection to Nassau (NAS), Bahamas.
To get from the Airport to the city cheaply, here is Suggestion #1.
Suggestion #2 for getting from the Airport to the City cheaply. Get to the road Las Palomas which runs through Licey, either by walking (a bit over 5km, or 1 hour at a moderate pace with baggage) or bargaining with some mototaxi or taxi at the airport (as per the first suggestion, go a little out of the airport to get cheaper taxis). From Licey there are regular gua-guas westbound to Santiago, which shouldn't cost you more than 25 pesos.
Dominican Airport Transfers  . You can book online on their automated site.
There are many Bus Lines that can take you to different cities in Dominican Republic:
Metro Bus & Metro Pack which travels from Santiago To Santo Domingo and Puerto Plata also delivers packages.
Caribe Tours travels to Dajabon, Montecristi, Sosua, Puerto Plata and Santo Domingo.
Expresso: those are the cheapest transportation to another city but this one stops everywhere during the trip to leave people so it will be slower and smaller than others..
Taxis/Cab: most of them are expensive depending where you want to get but actually they cost RD$ 150.00 aprox US$ 4.00
Coches: this one is pulled by horses it just take you around the city, it is fun and romantic, you can find them at the Monument.
Conchos: those are the cheapest public transportation for going around the city with many routes it cost actually RD$ 15.00 aprox. US$ 0.40
MotoConchos: this motorbikes can take you anywhere around the city it's fast and dangerous for just RD$ 20.00 US$ 0.55
Centro Leon (Centro Leon Santiago), Av. 27 de Febrero No. 146 (Santiago de los Caballeros, DR), ☎ (809) 582-2315, . 8-6. This is the modern center of Santiago, offering art galleries, audiovisual presentations, cinemacafe every week, a library and multimedia services. Local and international expos are present all around the year.edit
El Monumento Santiago (Monumento de Santiago), Avenida Circunvalacion (Santiago). 10-10. Is located in the highest hill in the city, called also Monumento a los Heroes de la Restauración. All the nightlife in Santiago is conveniently located around this area. Live Concerts are held in the premises. Inside has a museum and library as welledit
Calle El Sol (Calle El Sol Santiago), Calle El Sol (Santiago). This is the shopping street of Santiago de los Caballeros, here you will be close to museum, local attractions, giftshops, places to eat and drink and important monuments.edit
Monumentos a los Heroes de la Restauracion, Centro León, La 37 por las tablas, Teatro Nacional del Cibao...
Santago has many places to eat and a variety of dishes.
There are many cultural places in Santiago due to globalization, such as american food (TGI Fridays, Burger King, McDonalds, Pizza Hut, Domino's, Papa John's, Taco Bell and others.
Asian (Chinese & Japanese): Pez Dorado, Super Rico Restaurant, Expresso Jade, Sushi Ya!, Belcaire Niguri...
International: Satay, Paparazzo, Vivres, Front Door, Kaafa, Tete Club...
Seafood: Marisco Centro, Pedro's, Puerto Madero...
Steak's & Grill: Camp David Ranch, Rancho Steack House, Cukara Makara, Boceto, La Parrillita, Montezuma, Nano's....
Italian: Piccola/La Locanda, Il Toscano, Il Pasticcio, Pizzarelli.
Santiago has many Bars where you can drink anything you want. The cerveza is of the pilsner type, and it is very good. Both Presidente and Bohemia are great choices, as well as the Brazilian beer Brahma, which is sold in most places as well. For a cheap beer (as in not full restaurant prices) look for a colmado, or mini-market that delivers as well.
Search for a place called "Chico's Drinks" in el barrio "Los Jardines" - it's more of a cart run out of a guy's house, but man his mojitos and dakaris are good!
Local rum or Rón, is very cheap and very delicious. Two brands that stand out for quality for price are Brugal and Barcelo. Look for the extra añejo which is aged up to 12 years. At a bar, a rum and coke is called a Cuba Libre, a rum and sprite is a Santo Libre. Besides "Dónde está el baño" that's about all you need to know!
In most bars and clubs, the bartender will know what drink you want in English terminology, but often times, one has to put the name together into one word to get the point across - it's more Dominican that way. For example, a gin and tonic would be pronounced, "Gíntón." Keep that in mind, and be patient with the Dominicans, it will get you a long way.
Besides rum, whiskey is the other most commonly consumed hard alcohol. Johnny Walker bottles can be seen on most tables in clubs and drinking establishments, either Red, White, or Black Label.
Whatever your poison is, there will be plenty of it.
Lodging/Hotels If you are just stopping by or must wait for another flight you can stay at the Hodelpa Courtyard at less than 20 mins from the airport.
If you are going to be around the city, one possibility is Hodelpa Gran Almirante, which has a convention centre, a casino, and TGI Fridays.
In the city centre there is the Hodelpa Centro Plaza & Casino just in the right middle of the city, and if you want something near to the beautiful monument you can stay at Hotel Matum & Casino.
Hotel Aloha Sol, Calle del Sol #50, ☎ 809-583-0090, . checkin: 3:00 P.M.; checkout: 1:00 P.M.. The hotel is on Calle Del Sol in the center of the city. The hotel has 103 rooms available. One can reach the Monumento by foot in about 10 minutes. $83. edit
Hotel Colonial, Calle Salvador Cucurullo, Nos.: 109, 113, 115., ☎ 809-247-3122. This is a simple but comfortable hotel. The kitchen prepares delicious local dishes, and there is wifi access in the local and dining area. edited: I slept there for few nights. For me they seem to be spoiled by various recommendations (LonelyPlanet for example) and what they really care now about is - your money. Not bad standard tough. I am 60 % sure that I've been food poisoned after eating in their restaurant....$14 (RD$ 560). edit
Hotel Los Jardines, Av. Texas esq. Calle10, ☎ 809-276-8222, . Hotel Los Jardines is located right next to the Gran Almirante. The hotel has 65 rooms available. $48. edit
Hotel Dorato, calle salvador cucurollo (calle salvador cucurollo). Just in front of the Hotel Colonial. Cheaper and the rooms are with the same standard as of Colonial400 pesos. edit
Hotel Cucurollo, calle salvador cucurollo (calle salvador cucurollo). For people that won't get depressed fast while staying in its room.... No hot water, no internet, electricity blackouts are frequent...Rooms look like bunkers. You won'f find anything cheaper in Santiago probably - pay 200 pesos and see how most of Dominicans live on daily basis...200 pesos. edit
The Centro Historico clears out after dark and it is not smart to be there. The western half (La Joya, Gurabito, Cienfuegos, etc.) of the city is generally poorer and rougher than the eastern half, but it is unlikely that any travelers would end up there.