Chicago is a dynamic city. The third-largest city in the US, it has a thriving business community and is full of culture, history, and adventure. There’s so much to do in Chicago that you won’t want to miss out on anything when you go there for work or leisure. 

But how can you plan for all the different experiences that Chicago has to offer? How can you get the most out of your trip? And what if something goes wrong? This article has ten tips for planning a successful trip to Chicago, whether it is for business or pleasure.

Plan Your Trip Dates

Your next step is to plan your travel dates. There are a few different factors to consider:

  • When do you want to go? It’s important to decide when you would like to leave and return from Chicago because this will help determine what airline tickets cost and whether or not your business trip can coincide with a vacation.
  • How long do you want to stay? If there’s no chance of overlapping with another trip, then think about how long you need in Chicago before heading back home. If there is room for overlap, then look into what activities might be available during that period. So both trips can be maximized for enjoyment and productivity (we’ll discuss this later).
  • What’s my budget? Once we know when our trip will take place, we can start figuring out how much money we have available every month or quarter toward travel expenses. This way, we don’t end up with less than ideal options because all other aspects of planning went smoothly, but our finances didn’t hold up as well!

Purchase Your Air Travel Tickets

This is the most important step of all. You don’t want to be stuck in a seat next to some guy who smells like he hasn’t showered since June. And if you’re flying internationally, you must get your tickets early. It is because there are fewer seats available at a lower price and those are the ones you want!

Now that we’ve covered how to purchase your tickets, let’s talk about what happens after that point. If you have elite status with any airline, check to see if there are any type-specific perks (for example, first-class passengers get free drinks). 

If there aren’t any promo codes available for flights on your route and time frame (which is unlikely), then just look up when flights tend to sell out and buy accordingly. So as not to miss out on one of those last few remaining seats before they’re gone forever.

Book a Hotel Room 

Once you’ve selected your meeting location, the next step is booking a hotel room. You should choose a hotel that’s close to your meetings so you won’t waste any time traveling back and forth. 

A great gym is essential for staying in shape on the road. Some of the best fitness amenities include a sauna and steam room, as well as personal trainers who can design an exercise regimen just for you. Once you’re feeling energized, head over to one of Chicago’s many world-class restaurants. 

You can also try something new at one of its many food tours run by locals who know where all the good spots are hidden!

Research the City

Before you start packing, there are a few things you’ll want to research about your destination. Chicago is a big city, so you must learn more about where you’re going before making any decisions about what to do or where to eat.

Chicago is also very diverse and has many different neighborhoods, each offering something unique and fun for travelers of all types. If you’re not sure what part of the city would best fit your needs, check out our guide on how to choose between Chicago’s neighborhoods!

Get a Reliable Cab Partner

There are many ways you can get a cab in Chicago. If you want to get to the city from the airport or vice versa, you can check the numerous car services to Midway Airport.

When you need a solution for a city ride, you can hail one on the street, call a taxi service, or use an app. If you’re planning to travel from place to place, the latter two options may be more convenient for you. However, if there’s no public transportation available to your destination or if public transportation isn’t reliable (for example, during bad weather), then getting around by cab might be the best option for you.

Research Your Business Contacts

In the world of a business trip, nothing is more important than knowing your audience. When you are meeting with someone new, or even someone familiar, it’s important to do some research. So you know what they like and dislike. This will help you plan an effective itinerary for the day and make sure that everyone has a good time while getting work done!

Prepare for Your Meetings

  • Be prepared for the meeting.
  • Be prepared for the weather.
  • Be prepared for the traffic (in this case, Chicago is pretty much an exception to all rules).
  • Be prepared to meet people from all over and learn about their cultures and customs, which can be very different from your own.

Prepare for the Weather in Chicago

The weather in Chicago can be unpredictable. It can be hot in the summer and cold in the winter, so it’s important to pack for all seasons. If you’re going to Chicago during these months:

  • April – May (spring): The weather is great! You’ll want to pack shorts and sandals, but don’t forget a sweater for those chilly nights.
  • June – August (summer): Be prepared for high temperatures and humid air at night! Make sure your wardrobe has plenty of roomy T-shirts and shorts with lots of pockets for your cell phone, cash, and credit card. 
  • September – November (fall): This time of year is typically mild until October hits. Temperatures begin dropping then as leaves begin falling off trees across Illinois’ natural habitats.  

Plan Your Work Space at the Hotel

There are some things you should bring on your business trip to Chicago:

  • Laptop and charger
  • Wireless mouse and keyboard (in case the Wi-Fi is finicky)
  • A Laptop Stand to elevate your laptop if it has a touchscreen or a trackpad.

Set up Mobile Internet Access 

Use a mobile hotspot. If you don’t have cellular data, you may be able to turn on your phone’s hotspot feature and connect other devices to the internet through your phone. Be sure to check with your service provider before doing so. Some providers charge extra for tethering, while others do not allow it at all.

Use a VPN (Virtual Private Network) service. A VPN provides a secure connection from your device to another network, such as the internet or another private server or network.  

Begin Packing for Chicago

Pack for the weather. Chicago is known for having four seasons, and if you’re not prepared, your trip can end up being miserable. The best way to prepare is by looking at the weather forecast before you leave home and packing accordingly.

Pack extra clothes in case you get stuck in traffic. Traffic can be pretty bad around downtown Chicago during rush hour (from 6:30 am to 9:00 am), so it’s always a good idea to have an extra outfit on hand just in case!