Tips to travel with a first-time Chicago visitor should know

11 min read
30 January 2023

Tips to travel with a first-time Chicago visitor should know

Welcome to Chicago! We're happy you're here (or thinking about a trip, at the very least). No matter if you're there for the business or for pleasure, We know that it's not easy to move to a different place for the first time. There are logistical obstacles to overcome, such as finding the best transportation options for public transport, navigating through the system of grids, and knowing which neighborhoods are the best to live in. Then there are the cultural considerations: When is the most appropriate time to go? What do you want to do during your visit? Do you think that deep dish is the all-encompassing dish it's claimed to be? We've taken our lessons learned as Chicagoans and asked our fellow travelers to prepare you for what you'll need to be aware of as a newcomer.

There are several places to discover and learn more about this place. So, if you’re visiting and taking flights from Seattle to Chicago, then take a stroll of the entire city and find out what’s hidden in those tiny bustling streets. Also, book your tickets with Lowest Flight Fare to avail impressive deals.

Chicago tourist tips and tricks for visitors who aren't familiar with the city.

1. Utilize"L" or the "L" to and from airports.

Avoid the hassle and costs, and avoid the cost of a taxi or rideshare once you arrive. The regular Chicago Transit Authority "L" (short meaning "elevated") train provide the direct connection to two Chicago airports, which are for the Blue Line serving O'Hare and Orange Line for Midway International Airport. A $2.50 cost at Midway as well as $5 for O'Hare for regular downtown service within less than an hour feels like a bargain for us, especially when traveling to cities with the convenience of airport access.

2. Take advantage of a three-day (or seven days) CTA pass.

There's no need to rent cars if you're staying near to the city. In this day and age of smartphones, it's no wonder that the CTA is easy to navigate, even for novices. However, the fare structure can be a bit difficult to track: It is possible to put a dollar amount on a Ventra card, then attempt to calculate each when you spend $2.50 on the train or $2.25 on a bus. Or maybe it was an $0.25 payment if it happened less than two hours after your last trip? It's much easier to purchase an all-day pass that is priced at $15 for 72-hours of unlimited travel. If you're planning to stay longer and need a pass for seven days, the new Ventra card costs only $20, which is a great deal when you're spending that long time in the area. The cards can be bought at the Ventra vending machines at any airport, or any CTA station and also at a variety of pharmacies and supermarkets.

3. If you drive, you must install ParkChicago. ParkChicago app.

If you're traveling to the city and would like to park your car while you're there, Download ParkChicago (parkchicago.com) onto your mobile phone to meet all your parking needs on the streets. Set up an account using the license plate number of your vehicle and connect a credit or debit card and then pay through the app with the number of your zone printed on the signs, such as this one that indicates where paid street parking is offered. The rates differ depending on the area. (Many residential streets are only marked with permits, whereas some streets that are not marked are free to park, check for signs before you make a decision.)

4. While you're at it, install these apps to assist you to navigate around.

Google Maps, Apple Maps or Waze can provide you with accurate directions. Uber and Lyft apps will be able to find the right ride almost at any location and at any time of night or day (most riders are employed by both companies, in our experiences). Transit Stop is our favorite to provide real-time arrival forecasts for buses and L trains. Routes. If you're an anxious navigator, you can inform the app where you're heading, and it will notify you a heads-up that the stop you're waiting for is coming up. Find more transportation apps that we like here.

5. Learn the basics about the grid structure.

Contrary to the majority of cities in the world, Chicago's streets are laid out on a solid grid system. This is the most basic version that the junction between State and Madison Streets, smack in the middle of the Loop and the zero point on the grid. Street numbers spread out from here on north-south as well as east-west axes. Every 8 blocks (outside the Loop at the very least) equals one mile. There are angle streets as well as rivers, as well as historic quirks that can cause confusion, as well as six-corner intersections, however the grid is solid and provides a solid base for moving across. If you're able to, do not remember anything else, east always points toward the Lake.

6. Take your time to get to where you want to go.

In a city that has nearly 3 million inhabitants delays are likely to occur, whether it's on the L or the expressway (which is also, of course, is known as our controlled-access highways a.k.a. motorways, freeways, interstates or freeways). If you're trying to make an appointment that has a strict date and time, be it an appointment, dinner reservation, or a theatre curtain, allow more time than you'll need in order to ensure your safety.

7. Tipping is commonplace for various services. Here's how to tip.

If you're in the United States, tipping is standard for service in a variety of circumstances, and the typical rates in Chicago could be higher than the rates you're used in the US. In sit-down dining establishments with servers taking orders at the table and attending to your needs throughout your meal, it is recommended to give at minimum 20 percent of the total cost for excellent service. If you're going out for drinks at a bar, a dollar for each drink is typically acceptable, especially for drinks ordered from the bar. It's more if it's complicated drinks.

If the establishment is able to accept credit cards, you are able to include the tip on your total at the time you pay the bill. Numerous coffee shops and restaurants also have payment systems that allow you to add a gratuity automatically to the bill with a debit or credit card and calculates the percentage automatically for you.

In the aftermath of the COVID-19 virus, certain bars and restaurants are able to add a charge to your bill to cover reduced revenue and the increased cost because of the epidemic. This is not an alternative to tips, so you must still be prepared to include a tip on your bill.

Other circumstances may require cash tips: Pay an attendant at the valet parking counter two dollars each time they take your car back, and give the bellhop or skycap with one or two bucks for every bag they manage. The housekeeping staff in hotels should be given a tip of around $5 per day during your stay. This tip can put in your room after you have checked out.

8. There are times when you'll need cash in other scenarios as well.

Although it's becoming more common, however, there are still a handful of cash-only establishments in the city that don't take credit cards. Among them are the best dive bars and inexpensive dining establishments. It's also beneficial to have cash available if looking to attend any of the street fairs or festivals in the summer, or to buy something at craft or art fairs and other small shops can accept credit cards using services such as Square However, it's still recommended to carry cash in case of need (and to keep away from the high charges which are typically charged by ATMs at events that are located on site).

9. Prepare yourself to get your bag or purse checked at large locations.

If you're a commuter for work or tourist, unless you're driving your car wherever you go, you'll likely carry an item like a bag, purse or briefcase that you can carry things around. Security measures in certain big locations like ballparks and stadiums or concert venues, as well as music festivals, will result in the agent asking for an in-depth look inside your bag prior to going into the venue; this is a standard procedure. Certain venues will not allow big bags or certain items to be inside, as well as they will not be able to store any items at the entrance or in the restroom. If you don't won't be forced to travel back to your vehicle or hotel, and then missing a portion of your party, It is best to confirm the rules before you go.

10. Stay away from the chains and choose to stay at the local hotel...

You can choose to stay at a Hyatt or a Hilton wherever you travel. If you're in Chicago, spend to one of the top hotels in Chicago. Unique hotels like Chicago Athletic Association, the Chicago Athletic Association or the Ace Hotel. You can also look around the city's top boutique hotels, treasures including those at the Freehand, Hotel Lincoln or the Robey.

Take some time to explore the splendid attractions of this place, and make your trip worthwhile. While booking your flights from Boston to Bermuda, don’t just fool around restaurants and tall buildings. Instead, take a good note of what’s under the table. 

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