10 Chicago Travel Tips For Your Dream Vacation To This City

Chicago is the third most populous city in America. With a high-income economy and upscale markets, the quality of life in Chicago is high. Due to its advanced infrastructure, Chicago was ranked first on the Time Out City Life Index in 2018. Chicago is a tourist-friendly city. It has everything a tourist could ask for! When you go to a new place, many things should be kept in mind. To make your journey pleasant, we have shortlisted 10 Chicago Travel Tips.

Top 10 Chicago Travel Tips

When you are traveling to a new place, it is important to know some traveling tips related to that place. Here is a list of all the essential Chicago travel tips that will come in handy during your visit to this fantastic city:

1. Take advantage of affordable transportation facilities from the airport

Take advantage of affordable transportation from the airportTake advantage of affordable transportation from the airport


Chicago has two international airport terminals, namely O’Hare and Midway International Airport. Both airports serve international and domestic carriers. Once you get to Chicago, you can either take a regular CTA train or a taxi. Additionally, for all those business travelers who want to avoid the hustle and bustle of the city on peak days and want to reach the city as quickly as possible, you can opt for a new express train that was recently launched by the Governor. This train will take you from O’Hare International Airport to downtown, although it costs a little more than other regular trains.

Must read: Chicago Travel Guide: Explore the best sights of amazing architecture and beautiful landscapes!

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2. Get a CTA Pass to get around the city

cta passcta pass

If you’re planning to stay in Chicago for at least three days, be sure to take advantage of the CTA Pass. If you are new to this city then this is the best option. CTA Pass offers a variety of payment options to suit everyone’s needs. Fares for CTA trains and buses are paid using rechargeable cards. The fare is deducted whenever you use their transportation services. CTA cards also come with plans that offer unlimited access. For example, if you buy a three-day pass, you get unlimited access for the next 24 hours. You can purchase these cards at Ventra vending kiosks at the airport or any L station.

3. Know Chicago’s grid system

Know Chicago's grid systemKnow Chicago's grid system


Chicago has a unique type of system called the grid system. Basically the entire area of ​​Chicago is divided up into a grid. The city center is located in the middle of the city’s business district, where State and Madison Streets intersect. The business district of downtown Chicago is known as the Loop. Keep in mind that there are eight blocks in a mile, with street numbers indicating the north-south and east-west axes. Also know that the higher the address number, the further away you are from the intersection.

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4. Download apps that help take advantage of transportation

Download apps that help take advantage of transportationDownload apps that help take advantage of transportation

In this advanced generation, mobile phones can be of great help to you if you know how to use them. When you’re in Chicago, you can download some apps that will help with transportation. You can download Google Maps or Apple Maps to help you find directions. Additionally, you can download the transit app for L trains and bus routes.

5. Download the ParkChicago app if you plan to drive your own vehicle


In the smartphone generation, this is a very useful app if you are planning to drive alone in the city. This app informs you about parking status and car parking payment methods. All you have to do is use your credit card to create an account with the help of license plate number. Also keep in mind that rates may vary by neighborhood.

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6. Try to reach the destination in advance

Try to reach destination firstTry to reach destination first


Since Chicago is a new place and figuring out the direction system of this city is not an easy task, you need to give yourself enough time to reach a particular destination. Since Chicago’s directions and street names confuse most newcomers to the city at first, it is advised that you always plan your trip ahead of time.

7. Prefer to pay with your card but also keep some cash with you

Prefer to pay with your cardPrefer to pay with your card


This is one of the most important Chicago travel tips that you should keep in mind. Opt for card payments whenever you travel. But there are some places in Chicago where cards are not available and you can only pay through cash. For example, when you are going to summer street festivals or to local vendors to taste local street food delicacies, you will have to pay in cash.

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8. Check the weather online before going out

Check the weather online before going outCheck the weather online before going out


It is believed that the climate of the United States goes from cold to hot in a matter of hours. In the summer, you may be walking around town in 30 degree Fahrenheit temperatures and that same day in the evening, you’ll find yourself shivering in the cold and wishing for a hoodie. So it is also advisable that whenever you travel in Chicago, check the weather and dress accordingly with some extra layering.

9. Head to Downtown Chicago

Move over downtown chicagoMove over downtown chicago


Downtown Chicago is undoubtedly the center of some major areas such as business and entertainment. But it is recommended that you explore other parts of the city as well! The city’s neighborhoods are a great place to get acquainted with the culture of this place as the atmosphere here is much different from the usual hustle and bustle of the city.

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10. Pick up some swear words

pick up some swear wordspick up some swear words


When traveling in Chicago there are a few things that will make your trip even better. For example, there are some words that are only used by Chicagoans and it would be better to know them before you start exploring the city. The first term is ‘The Loop’ which is the district center for businesses in Downtown Chicago, bounded by the river on the north, west and south by Roosevelt Roads. The other word you should know is ‘L’ which is short for ‘elevated’ and is used for trains.

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According to a survey in 2017, Chicago comes in second place as the most visited city in the US with 55 million visitors, including both domestic and international. In general, the city is much cleaner, greener and friendlier than other cities. Thus, it is a good idea to come and visit this vibrant city. By following these Chicago travel tips, you can make your travel experience better and more convenient. So, pay attention to these tips when you book a trip to the USA.

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