Chicago Travel Guide: Read the essential things to know when visiting Chicago for the first time in 2023. You'll find useful Chicago travel tips to make the most of each visit, integrate like a local, and make your visit stress-free and enjoyable. Know Before You Travel to Chicago, Illinois I have compiled the necessary information. Find out when to go, where to stay, areas to avoid, how to get around, and the best things to do in Chicago.
First Time Visitor to Chicago
1. Take the "L" to and from the airport.
Avoid traffic and surcharges and skip taxis and carpools on arrival. The Chicago Transit Authority's regular train "L" (short for "elevated") provides direct service to both Chicago airports. The Blue Line serves O'Hare and the Orange Line serves Midway International Airport. $2.50 from Midway and $5 from O'Hare with a scheduled downtown flight within an hour feels like a steal when traveling to other cities that don't have easy airport access.
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| Chicago Travel Guide |
2. Get a 3-day (or 7-day) CTA pass. If you live near
cities, you don't need to rent a car. CTA navigation in the smartphone era can be easily operated even by beginners. However, tracking fares can be a little tricky. You can add $1 to your Ventra card and count every time you spend $2.50 on trains and $2.25 on buses. What if it's been less than two hours since your last ride? Much easier to buy a 3-day pass for $15 for unlimited rides for 72 hours. If you want to stay longer, just buy a 7-day pass with the new Ventra card for just $20. Definitely worth it if you spend a lot of time here.
All of these can be purchased at airport Ventra kiosks and CTA stations, as well as many supermarkets and pharmacies.
3. If you drive, download the ParkChicago app.
If you're driving into town and want to use your car while you're here, download ParkChicago (parkchicago.com) on your phone to get all the information you need to park. Create an account with your license plate, link your credit card, and pay on the app using the zone number printed on signs like this where metered street parking is available. Prices vary by district. (Many residential streets are marked as allowed, but some streets without signs are actually parking lots. Check the signs carefully before deciding.)
Google Maps, Apple Maps, or Waze will give you reliable directions, and the Uber and Lyft apps will find you at just about any address, day or night (in our experience, most ridesharing services works for both services). Transit Stop is our favorite for its real-time arrival predictions for L train and bus routes. Sensitive navigators can pinpoint their destination to the app, which alerts them when stops are approaching.
5. Get an overview of the grid system.
Unlike many other cities, Chicago's streets are generally laid out on a reliable grid system.
Here's a quick version. Grid zero is the intersection of State Street and Madison Street in the middle of the loop. Street numbers run north-south and east-west from there, with every 8 blocks (at least outside the loop) equaling 1 mile. Winding roads, streams and historical curiosities are here and there, creating chaos and hexagonal junctions, but the grid is a solid foundation for getting around. Also, if I don't remember anything else, the east is always towards the lake.
6. Allow enough time to go where you want to go.
In a city of about 3 million people, even if you're traveling on the L or motorway Delays are almost inevitable. When you're trying to set deadlines—meetings, dinner reservations, theater curtain calls—you're giving yourself more time than you think each event needs.
7. Tipping is standard for many services. Method is as follows.
In the United States, it is customary to tip for service in a variety of situations, and standard rates in Chicago may be higher than what you are accustomed to seeing elsewhere in the country.
In sit-down restaurants where waiters take your order at your table and attend to your needs throughout the meal, you should tip at least 20% of the total bill for good service. $1 a drink is usually enough if you order from . Even more so for complex cocktails.
If the establishment accepts credit cards, a tip can be added to the total amount when signing the bill. Many restaurants and cafes now also have payment systems that automatically add a tip to your bill and allow you to calculate a percentage using your credit or debit card.
If not, you must pay the tip in cash. A few dollars when the attendant picks up the car, and for the bellboy or skycap, he tips a dollar or two each time he handles a package. Hotel housekeeping staff are required to tip approximately $5 per day for the duration of their stay. This chip can be left in the room upon checkout.
8. Cash may also be required in other circumstances.
There are still some cash shops in town that don't accept credit cards, although they are becoming rarer. So are your favorite pubs and cheap restaurants. It's also a good idea to have cash on hand if you plan to attend a summer street festival or shop at a craft market. Many small retailers now accept credit cards through services like Square, but it's a good idea to have some cash on hand just in case (and large amounts to pay at on-site ATMs).
9. Be prepared to search for purses and bags in key locations.
Whether you are a business traveler or a tourist, you probably carry a purse, handbag, briefcase, or tote with you when you are not driving your car anywhere. Security measures at some major venues, such as concert halls, music festivals, etc., require staff to scan your bags before you enter. It's common practice. However, some places don't allow oversized bags or certain items at all, and nothing is held at the gate or cloakroom.
10. Experience the local sports culture.
From the Bulls dynasty led by Michael Jordan in the 1990s to the recent championships of the Blackhawks, Cubs and Sky, Chicago boasts strong sports teams and wildly passionate fans. Most stadiums are easily accessible by train or bus, and single-game tickets are relatively affordable if you book in advance (for example, you can get White Sox tickets for as little as $8), rooting for one of the many local teams with a dog and an old fashioned in hand is great way to spend an afternoon in Chicago.
If you're not particularly into sports, it still helps to know when the local teams are playing for the bypass. If you're traveling north on the Red Line and the Cubs are in town, be prepared for a crowded train or bus and possible delays. There's even a handy website for quick reference.
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