Astonishing Chicago Vacation by Lake Michigan

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Chicago vacation is more than some ordinary city travel. It is the style, it is the culture, and it is the entertainment. The Wind City is perfect place for romantic city getaway, family vacation or friend convention. Chicago with its phenomenal attractions and beautiful locations on the shore of Lake Michigan will astonish you on every step.

Since Chicago is a kind of “never sleeps” town, travel planning is essential. I am confident that everybody can enjoy the stay in Chicago. However, it all depends on arrangement process as Chicago vacations is more than just choice of resort or hotel in some small Caribbean island. With around 45 million visitors each year, Chicago is one of the most visited cities in US, so are its attractions. Therefore, every step in a big city will cost some money, the only question is, how useful you will spend it?

Vacation planning processes consist of several factors: travel time, flights, accommodations, ground transportation, attractions and, the most important, budget. With the right planning process, you should be able to enjoy more for less money.

Travel Time

It is better to start planning city vacation at least two months before the travel time. It will give you more options to choose from and will save you money. In such a big city like Chicago, reservations are made even a year in advance, so as sooner you will start as better chances you will have.

Attractions & Entertainment

Before you start to plan Chicago vacation, you should to determine the purpose of it. It is very important, as Chicago has so much to offer, and unfortunately, you will not have time to see everything. It is also important for your travel budget. If it is Chicago family vacation, then you should look through and decide which attractions you would like to see. If it is romantic weekend getaway, then you should choose which restaurant to book and cruise line to take. If it is convention with your friends then you need to locate the best Chicago clubs. If you are looking for cultural aspiration in Chicago, then you should choose which museums, theaters or musicals you would like to visit. Here I point out some ideas, but there can be thousand of them.

Astonishing Chicago Vacation by Lake Michigan

Flight & Accommodation

I reviewed this subject a lot in Flight to Chicago and Hotels in Chicago page. However, I would like to say that from my point of view vacation package do not consist only of a flight + hotel or flight + hotel + car. I think that the vacations are when all the parts are planned, and you just can relax and take pleasure in.

Ground Transportation

You have great offer of ground transportation in Chicago. Right choice of it will save huge of your travel budget. If mainly you are visiting some Chicago attractions, then better you choose some shuttle or limo service to/from the airport and for the rest of the time use public transport or taxi. If you will visit some places outside Chicago, then probably it is better to rent a car. However, you need to consider how long this driving will take, and you should rent a car only for that time. When you will determine the purpose of Chicago vacation, then it will be very easy to calculate the best transport choice.


Budget planning is essential for any city vacation, as every step on it will cost something. As an example I can refer to a hotel choice. If you will pick the hotel, which seems to have cheaper rate, but every day you will need to drive two hours by car or use public transport, in the end you probably will pay the same as to a hotel closer to your targeted locations. This is one of the common mistakes made by travelers when traveling to big city.

When you plan your Chicago vacation, it is better to design some travel plan. There you can indicate all travel steps – starting from home and finishing at home. Here are some planning questions you should ask yourself:

  • Why I am traveling to Chicago?
  • Which attractions I would like to visit?
  • How I will get from my home to the airport? If you drive by car, how much the parking will cost?
  • Which airline can bring me to Chicago?
  • How I will get from airport to my hotel? Maybe your hotel has shuttle service from Airport.
  • Do I need to rent a car? If yes, does my hotel have free parking space?
  • What kind of dining places are around my hotel?
  • What are the costs of taxi and public transport services?
  • How I will get back to the airport from the hotel?

This is just an idea of Chicago vacation planning, but there are much more questions you should ask yourself or let a travel agent ask you. If a travel agent does not ask questions like this, forget about him, you will just spend more on your vacation then you have to, and you will not get the enjoyment that you deserve.