Welcome to Chicago! We are delighted you are here (or considering a vacation). Whether you’re traveling for work or leisure. We realize how intimidating it might be to visit a new city for the first time. There are logistical problems, such as determining public transit options. Navigating the grid system, and determining the best communities to stay in. Then there are cultural questions: What is the ideal time to visit? What should you be accomplishing using your spare time? Where should you go? Is Deep Dish all that it’s cracked up to be? Is Malört that horrible, or are the residents being dramatic? We’ve compiled a list of what you should know as a newcomer to Chicago based on our own experience and polled our visiting friends.
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1. Take the “L” to and from the airport.
Avoid traffic and costs by foregoing the cab or ridesharing when you arrive. Our regular Chicago Transit Authority “L” (short for “elevated”). Trains provide direct service to both Chicago airports. With the Blue Line serving O’Hare and the Orange Line serving Midway International Airport. When we visit other places without such convenient airport access. A $2.50 charge from Midway or $5 from O’Hare for regular service downtown in under one hour seems like a bargain to us.
2. Buy a three (or seven-day CTA pass.
You don’t need to rent a car if you’re living close to the town. Fares, but, can be a little difficult to keep track of. You could put a dollar number on a Ventra card and then try to do the arithmetic every time you pay $2.50 on a train and $2.25 on a bus. Or does that count as a $0.25 transfer if it was within two hours of your last ride? It’s far easier to get a three-day pass for $15, which includes 72 hours of unlimited riding. If you’re staying for a longer period, a seven-day pass on a fresh Ventra card will cost you only $20. Well worth it if you’re going to be here that long. All are available from Ventra vending kiosks at any airport and any CTA station. As well as numerous shops and pharmacies.
3. If you drive, download the ParkChicago app.
If you are driving into the city and want to use your car while you are there. Download the ParkChicago app to your phone for all of your street parking needs. Create an account using your license plate number and a credit card. And then pay in the app using the zone number posted on signs where paid street parking is allowed. Rates vary by location (many residential streets will be marked permit-only. While a few unmarked streets are free to park on—check for signage before making assumptions).
4. While you’re at it, download all of these applications to assist you navigate.
Google Maps, Apple Maps, and Waze will provide you with accurate instructions. The Uber and Lyft applications can get you a ride at almost any address and at any time of day or night (most rideshare drivers work for both services, in our experience). Transit is our favorite for real-time arrival forecasts for “L” trains and bus routes. And if you’re a worried navigator, you can tell the app where you’re headed and it’ll alert you when your stop is near.
5. Learn the basics of the grid system.
Unlike many other cities, Chicago’s streets are organized around a stable grid layout. Here’s a short and dirty version. The grid’s zero point is located at the intersection of State and Madison Streets, right amid the Loop. Street numbers stretch out from there along the north-south and east-west axes. With every eight blocks (outside of the Loop) equaling one mile. Angle streets and river branches, as well as historical peculiarities and six-corner crossroads. Add to the confusion, the grid serves as a stable base for navigating. Also, if nothing else, remember that east is always towards Lake.
6. Tipping is customary for most services. Here’s how you do it.
In the United States, tipping is traditional for service in a variety of scenarios. And conventional rates in Chicago may be greater than you’re used to abroad.
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At sit-down restaurants, when a server takes your order at your table and looks after your requirements throughout your meal. You should tip at least 20% of your total cost for excellent service. If you’re out for drinks, a dollar a drink is usually enough if you order from the bar. More if the drinks are complex concoctions.
