The windy city is one of the highlights of the Midwest and is considered by people across the country as one of the best cities the US has to offer. Visiting a new place is always challenging because it comes with cultural differences, weather conditions, and transportation concerns that can make things complicated. But since you want to enjoy your first trip to Chicago, it is important that you have a plan in mind so you can enjoy your trip and get to know a city that so many people love. 

Getting to Chicago 

The very first part of planning any trip should be the way you plan to travel to your new adventure. For many people that means hopping in a plane and flying to the city that overlooks the Midwest. For others, a road trip may be a better option depending on their location and their plan for the rest of your trip. One benefit of a road trip is that it means you will already have transportation once you are in the city as well. But flying can be much quicker and help you to have a more comfortable time while you are traveling to the area. It is really just dependent on what you are looking for in your first Chicago experience. 

Activities to Do 

You also want to make sure to plan a few great activities that will get you into the spirit of your Chicago vacation. One option is to take advantage of the city’s location on Lake Michigan and take a boat ride on the lake. You could also take a tour of the city by bike or sign up for a food tour that will take you to some of the best restaurants in the area. Chicago is full of museums and cultural and sporting events that can be part of your plan to get a full view of what Chicago has to offer the people who visit it. 

Places to Eat 

Choosing the best places to eat is an important part of any great trip, and this is especially true in Chicago. Most everyone knows that there are amazing options like deep dish pizza and Chicago dogs to keep you full while you are in Chicago. And while those are essential to the full Chicago experience, you also want to make sure that you are checking out a variety of local restaurants that serve a huge number of different cuisines. For example, check out Little India to gain access to a huge variety of Indian food options that can expose you to the incredible variety that Indian cuisine has to offer. 

How to Get Around 

You also need to think about the transportation you will use once you are in the city. Even if you drive, you may find that you would prefer to use alternate methods to get around town. The public transit system is pretty strong in Chicago and you can easily use the train or bus to get around town if needed. You can also use taxi services or rideshare options to get from place to place. And if you do decide to drive, just make sure that you have money for parking throughout the city. If you’re driving your car you want to make sure that you stay cool as well. Window tinting can block 98% of solar heat, making your vehicle more efficient to keep cool. 

Your Budget 

Any trip you plan needs to have a budget to make sure that you don’t get caught up in the city and overspend on things you don’t need. That’s why it is important to plan your trip with your budget at the front of your mind. Various elements of your stay in Chicago will cost money but if you shop around you can keep your budget tight and make sure that you do everything you hoped to. Your budget should include all elements of your trip from the cost of lodging and travel to food and entertainment. 

Your Lodgings 

Without somewhere to stay, your trip won’t be much fun for anyone involved. So, you need to choose the type of lodgings that make the most sense for your trip and what you are trying to accomplish. You have a few different options that can all come together to make your trip into something great. For example, you could use a service like Airbnb to select a more personal place in the city, another option is a great hotel with a level of amenities that makes you feel comfortable and luxurious. Just make sure you are choosing a living situation that will meet your needs for the length of your trip. 

When to Travel 

Depending on what you want from your trip, different times of year will be the best option for your needs. During the summer the city really lives up to its name by having nice windy days that are generally not too hot. The winter tends to be a messier time weather wise, but it is not as busy or as expensive as visiting in the summer. You really just want to choose the right time to visit so you can have more fun and see as much of the city as possible

How Long to Stay 

Chicago is a big city, and it can take a while to soak it all in. However, you can make a shorter trip work if you are ready to hit the ground running and see many things on a tighter schedule. A big part of deciding how long to stay is simply thinking about your budget and what you can afford to take off of work. If you know that, you will be in a great position to get things rolling and have an amazing stay. 

Chicago is an amazing city with tons to offer anyone who takes the time to visit. Planning your trip should be a fun experience that gets you ready to make the most out of your time in Chicago. Make a list of priorities and let it guide you as you explore and learn more about the city.

Read this next: Why a Boating Trip to Chicago Should Be Your Next Summer Vacation

Enter your email to stay up-to-date with Chicago Boat Rentals!



Join our mailing list to receive the latest news, promos and updates from our team!

You have Successfully Subscribed!