Chicago has two primary airports, O'Hare International Airport and Midway International Airport. Both are linked to the Loop by frequently running local trains. The links in the Trains section below provide detailed map and schedule information for all train lines.

There are several local train lines identified by color as well as the terminal points of the line. Rates are reasonable. A single fare is $2.75 per person and allows transfers at any station that services multiple lines. There are several stations that service multiple lines so make sure to pay attention to the line information on the train that you're boarding. The final destination in the direction of travel is displayed in white on the front of the train and the side of each car. The background color represents the color of the particular train line. There are maps of the train system in each car so you can track your progress through individual stops. Each stop is announced prior to arrival and clearly marked on station signage.

Both of Chicago's major airports are linked by local train to the Loop. The blue line services the O'Hare/Loop route. The Orange Line covers the Midway/Loop route. Maps and schedules are available via the following link.

CTA - Chicago Transit Authority

You'll have no problem hailing a taxi or booking an uber/lyft around tourist locations, transportation hubs and popular nightlife/dining venues.

Taxis in Chicago are closely regulated. Each car must sport a silver medallion on the hood and driver identification badges should be clearly displayed within the cab. The picture on the badge should match your driver. Make sure to note the driver's badge number and the cab number to report a bad experience. Rates are tracked by sealed boxes that are inspected by the city regularly for tampering.

Never accept a ride from anyone offering taxi services inside of the airport. If you want to take a taxi from the airport, follow the taxi signage at the baggage terminal to the taxi queue. An airport employee will flag down a taxi and assign the individuals in line to a taxi when it arrives. There are some fixed fare options when traveling between the airports and the Loop. These rates should be clearly posted in the cab. Make sure to let your driver know if you want to use that option before you begin your trip.

The only specified taxi queues in Chicago are outside of the airport. If you've already ventured into the city book your pickup online, have your hotel concierge turn on a taxi light or hail a taxi on the street. It's a good idea to notice if cabs frequent the area where you're staying before you need one to determine whether you should make arrangements or test your luck. If the light on the top of the car is on, the taxi is free. If it's off, someone beat you to the punch and you'll have to wait for another car that's not occupied.

Unless you're using the Airport/Loop flat rate option mentioned above, the meter should be started when you pull away from your starting location and stopped when you pull up to your destination. Rates are $1.80/mile with a $2.25 surcharge per ride. There is an additional $1.00 surcharge per ride for a second passenger and then an additional $0.50 surcharge for each additional passenger. There's also a $1.00 surcharge for rides that begin or end at an airport. If you're heading to certain suburbs, meter rates are doubled for the portion of the trip that's outside of the city limits. A tip similar in percentage to restaurant wait staff is expected for good service.

You can use the following link to estimate the taxi fare for a particular trip and to contact a dispatcher for a pickup. (surcharges not included).

Taxi Fare Finder

If you're driving or renting a car, make sure to notice and comply with all parking regulations. It's a challenge to find parking in many areas of the city but Chicago is very adept at ticketing violators. The odds are not in your favor if you try to squeak by on an expired parking receipt, use a prohibited parking area or take a space that requires a special permit.

Receipt Based Parking; Chicago has replaced metered parking with receipt based parking throughout the city. The concept is the same but instead of feeding a meter, you purchase parking for a specified period of time at a parking pay box and display the receipt on the right front hand side of your dashboard. 'Pay at parking box' signs indicate where parking is allowed. Pay boxes are currently being converted to a new format that requires you to enter your license plate when choosing the length of time that you wish to park. Converted pay boxes don't provide a receipt. Instead they transmit parking purchases to a central database that meter enforcement agents reference online. The individual pay box you use will provide instruction if there are additional actions that you should take after purchasing parking. For convenience, you can also download the Chicago Parking Application to your smart phone free of charge. The app allows you to purchase and renew parking (where regulations permit) without going to a physical pay box.

Parking rates and enforcement times vary so make sure to check the particular pay box for these details in the location where you are parking. Please note that virtually all major streets and city lots in Lakeview are receipt based parking areas and the city is extremely efficient when it comes to ticketing vehicles without a valid receipt.

Permit Parking; Many neighborhoods in Chicago require a local resident permit to park on streets. The streets in permit parking areas are marked with signs that identify the particular permit that's required for that area. Residents can obtain visitor permits for a nominal fee so make sure to let your host know if you're staying with a friend. Permits are good for 24 hours. The time period must be indicated in ink on the permit which is then adhered to the inside of the windshield directly above the dashboard on the passenger side.