Chicago is served by two international airports as well as a major Amtrak station and bus station. Chicago's central location makes it easy to get to fast. It's within a one-day drive of more than half the country and with over 2900 daily flights flying here is a breeze.

Chicago has a great public transport system with the famous El (Elevated Train), tied-in underground/subway/metro lines, and buses 

 By Air

O'Hare International Airport (ORD) is one of the world's busiest, which makes it reachable from most corners of the world but prone to flight delays and congestion.

Midway International Airport (MDW) is the smaller, less congested, close-in airport.

If you find yourself with extra time at either airport, spend some time enjoying the artwork and entertaining your kids. In Terminal 1 At O'Hare, that includes a two-story Brachiosaurus skeleton in Concourse B and the kinetic neon tube sculpture "The Sky's the Limit" in the tunnel between Concourse B and C. Terminal 2 houses the Butch O'Hare Grumman F4F-3 airplane memorial exhibit about the heroic World War II naval aviator for whom the airport is named. O'Hare also has an outpost of the wonderful Chicago Children's Museum where your kids can pretend to check baggage, fly a plane and otherwise exhaust themselves while you sit on a nearby bench. At Midway, stop to have your picture taken with Chicago's famous Blues Brothers in Concourse A and spend some time admiring the artwork throughout the airport.

By Train

Amtrak trains from around the Midwest run into the beautiful art deco Union Station at Jackson and Clinton (site of the famed baby carriage scene in the movie "The Untouchables").

By Bus

Greyhound buses operate out of a station at 630 W. Harrison, just outside the downtown area. Megabus does not have a station building, but stops outside Union Station on Canal Street just south of Jackson Boulevard.  Megabus reservations must be made in advance on their web site.

By Car

Chicago is served by several major expressways, all of them crowded during rush hours and some of them crowded all of the time. If you plan to drive into the Loop, give yourself plenty of time to allow for traffic challenges. Please note that Chicagoans like to call their expressways by name. I-290 is the Eisenhower.  I-94 carries different names depending which stretch you’re on—it could be the Bishop Ford, the Dan Ryan or the Kennedy. I-55 is the Stevenson.  I-90 is the Edens and so on. Trust your GPS to get you where you need to go. The cheapest parking can be found in the underground lot at Millennium Park. Don’t risk parking in a tow zone. Chicago’s towing companies are very aggressive. Your car won’t be there when you get back. 

Hiring a vehicle at O'Hare is a quick and easy affair. Arriving passengers will find offers and services from various car rental firms there. It is only a short distance from the desks of the car rental agents to the car rental service centre where the hire cars are picked up and returned. You could also  find different private options for specialized transportation service in moving communities door to door between the city and the airport or viceversa.

Getting Downtown

Public Transit*
All of the arrival points are served by Chicago's public transit system of elevated trains, subways and buses. A one-way ride on the CTA is $2.25 ($5 if boarding a train at O'Hare). The CTA Orange Line trains run between the downtown Loop and Midway. The Blue Line serves O'Hare. If you are traveling from O' Hare to downtown the cheapest and often quickest way is to take the Blue Line el also known as the CTA. As of January 1, 2013, it's $5 per person, the only fare in the whole system that has an upcharge. There's no extra charge for luggage. Or if you plan on using the el and buses a lot in Chicago you can get a visitor pass (1, 3 or 7 days) and the ride from O'Hare is included. The trip takes about 45 minutes to downtown Chicago.

 *More details listed below.

Cabs
Cabs also are readily available, but much more expensive. City of Chicago employees  supervise taxi operations at the airport; they can answer questions about destinations, estimated fares, etc.  Plan to spend about $30 for a cab ride from Midway to downtown and about $45 from O'Hare. Only use approved taxis. Don't accept rides from limo drivers or others soliciting at the airports. It's illegal and you're likely to get ripped off.

City cabs traveling to the suburbs charge meter and a half rates. Instead, call a suburban company (the most popular is American Taxi) for fixed rates by suburb.

Shuttle buses

Several  companies offer shared van rides from the airports that stop at downtown hotels. It’s a little less expensive than a cab ride for a single rider, but it can take longer than a taxi, as you may travel to several other hotels before arriving at your destination. 

Car rental
Car rental is available at both airports. Unless you will be spending most of your time outside of the downtown area, renting a car is not recommended. You won’t need it to get around downtown and parking is very expensive. The underground parking garage at Millennium Park is less expensive than most lots.

 Chauffeur Car Service
An alternative to taxis, bus, train & any public transport, car chauffeur car services are useful for getting to the airport from the outer boroughs where taxis are harder to find, or if you prefer to have transportation reserved in advance. Some options to hire a private car service in  Chicago: Omega Shuttle, illiniShuttlle, NBC-Chicago or the new online system to hire private transportation worldwide.

Getting Around

Chicago is laid out in a simple grid system with the intersection of State & Madison as the zero point. A standard block has 100 address numbers, so 800 N. State St. is eight blocks north of Madison and 1900 W. Madison is nineteen blocks west of State. Ask a local where they live and they are likely to give you coordinates--2600 North and 700 West. There are some angle streets, such as Milwaukee, Elston and Archer,  that are exceptions to the rule.

Addresses that end in an even number will be on the west or north sides of the street. Odd numbered addresses will be on the east or south side of the street.

Walking

Chicago is a very walkable city. Grab a map from your hotel and wander the city streets or stroll along the lakefront. The city is clean, beautiful and bedecked for the season with colorful flower boxes in the summer and cheery white lights in the winter.

Subway/Elevated Trains

The CTA (Chicago Transit Authority) runs the subway and elevated, or L, trains and city bus service. 
Subways and elevated train lines are color-coded. Beware that several train lines can share one station, particularly downtown. Be sure to look at the color coded signs at the station entrance then look for the matching color on the front of the train to be sure you’re boarding the right one. Ask the station attendant or a fellow rider to point you to the right set of stairs so you catch the train going in the direction you want to go.

Green Line runs west and south, all on elevated tracks.
Red Line runs north and south, sometimes underground and sometimes on elevated tracks.
Blue Line runs west and northwest to O'Hare, sometimes underground and sometimes on elevated tracks.
Orange Line runs between Midway Airport and the Loop, all above ground.
Brown Line runs north/northwest and into the Loop, all above ground.
Pink Line runs west/southwest and into the Loop, all above ground.
Purple Line runs an express to Evanston during rush hours, all above ground.
Yellow Line connects at the northernmost city station, Howard, and runs to north suburban Skokie.

Most areas of the city can be reached by CTA bus.

Get help planning your trip by visiting www.transitchicago.com or calling the information hotline at 312-836-7000. Buy transit cards from vending machines at most train stations or order a CTA Visitor Pass before you visit. Visitor passes offer  unlimited rides for one price:
1-Day Visitor Pass for $10.
3-Day Visitor Pass for $20.
7-Day Pass for $28.
The 3- and 7-day passes are sold in special "Visitor Pass Vending Machines" at certain CTA rail stations, at retail outlets and online at transitchicago.com. To make your life easier, order online before your trip. There is no charge for shipping, but allow 10 days for shipping. The pass activates the first time you use it and is good for the number of consecutive days shown on the front of the card. As an example, a 3-day pass is valid for 72 hours from the time of first use. The expiration date and time is printed on the back of the card after the first use.

Buses

The CTA operates an extensive system of buses and serves most parts of the city, although it can be a little confusing to figure out which bus you need from the signs at the bus stop. It’s best to visit the CTA trip planner website at http://www.transitchicago.com/visitors/ or call 1-312-836-7000 for help planning your route. At the bus stop, ask a fellow passenger. Most Chicagoans are happy to help confused tourists. And let the driver know where you’re going so he or she can let you know when your stop arrives. CTA buses use the same fare cards used for trains. Buy them at train station kiosk or online before you arrive.

During the summer (Memorial Day to Labor Day) a free trolley operates from 10 a.m.-10 p.m. between Navy Pier and the Red Line subway station at Grand Avenue and State Street.

Boats & Ferry Service

In spring, summer and fall, Chicago Water Taxi operates along the Chicago River between Michigan Avenue and Chinatown, with stops at Madison (near Union Station and the Metra station) and at LaSalle and Clark streets. Fare is $2 each way to Madison, $4 to Chinatown.

In the summer, Shoreline Sightseeing operates a lake taxi from Navy Pier to the Museum Campus and a river taxi from Navy Pier to Willis (formerly Sears) Tower. Fare is $7 for adults, $4 for children or less, depending on the route. A one-day unlimited ride pass is $22 for adults, $11 for children.

Bicycle

Chicago B-cyle, a public bike rental program, operates along the lakefront from kiosks at popular tourist spots, including the Museum Campus, Navy Pier and North Avenue Beach. Use your credit card at the kiosk to unlock a bike, ride to your destination and return the bike to a kiosk there.

Taxi Cabs

Cabs are plentiful downtown and in the popular tourist locations. Look for a cab stand near hotels and main museum entrances, or hail one on the street. Simply stand at the corner and raise your hand. The next available cab will pull over. Enter and exit a cab only from the curb side door, never from the street side door. 

Suburban Trains

Metra provides commuter train service to/from downtown and many suburbs. There's a $7 pass for unlimited rides on the weekends (with up to 3 kids per adult free).  A discounted 10-ride pass may be shared between people.  Visit http://www.metrarail.com/ for details.  Please note that the conductor will charge $3 extra for one-way cash fares purchased on the train, if the origin station was open for ticket sales at the time of your departure.

Suburban Buses 
Pace provides suburban bus service. Visit http://www.pacebus.com/ for details.