Want to visit the beautiful city of Chicago but don’t know where to start? Then you have come to the right page. In this blog, I will share with you everything there is to know to plan your trip to Chicago on your own. The only thing you’ll have to worry about is about having a fantastic time!
When Is The Best Time to Visit Chicago?
The first thing to consider when planning your trip to Chicago is to decide when you want to visit. Your trip will be completely different if you go during the summer than during the winter.
So when is the best time to go to Chicago? In my opinion, the best moment to visit Chicago is late Spring (May – June) or early Autumn (September – October). This is the best compromise between weather, how crowded the tourist places are, and accommodation prices. However, every season will have its advantages and disadvantages. Visiting Chicago during the winter will guarantee you cheaper accommodations but the weather will be quite cold. On the other hand, the summer months will mean warmer temperatures but the touristy places will be more crowded.
Book Your Flights
Once you know when you want to visit Chicago, the next thing to do is book your flights. When flying to Chicago (and the United States in general) you should always book your flights as soon as possible. This way you will get the cheapest fare possible.
Chicago is quite a big airport in the United States, so depending on where you are flying from, you might be able to get a direct flight. I booked my flights with United Airlines, which offered direct flights between Brussels and Chicago.
Good to know: If you are not flying directly to Chicago and you have a connection somewhere else in the United States your checked-in suitcase will not go directly to your last destination. You will first have to pass immigration control to enter the country. Afterwards, you will collect your suitcase and pass the customs control. Only then, you will be able to drop your bags again at a special counter so that they fly to your end destination.
Don't Forget Your Insurance
The next step will be to get some travel insurance. The health system in the US is private which means that if something happens to you, your medical bill will be no joke. In most cases, your trip will be fantastic and you will not use the insurance at all. However, it is not worth the risk and you will feel more comfortable knowing that if anything happens you will be covered.
In addition, you can always complete your insurance with a cancellation policy to ensure you will get your money back if for some unlucky reason, you have to cancel your holidays.
Book your accommodation
Now it’s time to decide where you are going to sleep and book your accommodation.
Which neighborhood is the best in Chicago? Well, the options are endless and I recommend that you choose the best fit based on your budget.
- The Loop (Downtown Chicago): Many of the things you will visit in Chicago (Grant Park, Willis Tower, the Art Institute of Chicago, etc.) are located within The Loop.
- West Loop & West Town: Chicago’s former industrial area has now become one of the trendiest neighborhoods in the city. If you’re looking for the trendiest restaurants and places to eat, then this is your neighborhood.
- Gold Coast and Lincoln Park: Lincoln Park is the biggest park in Chicago and it is a perfect area to stay for families.
- South Loop: Located in the museum district, it is also a nice area.
- Hyde Park: If you’re looking for a place to stay that is a bit more budget-friendly, you might consider the area around Hyde Park. It is a bit far from Chicago Downtown but there is really good communication with the express buses.
Apartment recommendation: Historic HP 2 BR with Fast Transit to UChicago & Downtown.
I stayed in this apartment in the Hyde Park neighborhood in 2022 and the stay was fantastic. The apartment was really big with 2 bedrooms, 2 bathrooms, a kitchen, and a living room. In addition, the neighborhood was really calm and the building was located within walking distance of Lake Michigan. You could be in Downtown Chicago in 30 minutes with the express buses.
Get your ESTA
To enter the United States you will most probably need to get your ESTA (Electronic System for Travel Authorization). This is a VISA waiver program for people with specific nationalities and your travel is for a duration of maximum 90 days.
To apply for the ESTA and check which nationalities are applicable for this visa waiver, go to the official ESTA site: https://esta.cbp.dhs.gov/
The ESTA has a price of 21$. However, once approved it is valid for 2 years starting from the day it got approved.
How much time do you need to visit Chicago?
I recommend spending in Chicago 4 days minimum but, if you can, I would go for 6 full days. I like to visit places at a slower pace and not just run from one spot to the other to tick them off my bucket list.
There is plenty of things to do and see and Chicago! You will be able to fill in your 6 days with many activities. However, if you feel that 6 days in Chicago are too many days, you can always consider doing a day trip out of Chicago.
Here are some examples of possible day trips from Chicago:
- Milwaukee, WI: Just an hour and a half north of Chicago, Milwaukee is a charming city with plenty to do, including the Milwaukee Art Museum, the Harley-Davidson Museum, and the Pabst Mansion. You can also take a stroll along the Milwaukee Riverwalk or enjoy some of the city’s famous beer.
Starved Rock State Park: Located about two hours southwest of Chicago, Starved Rock State Park is a beautiful natural area with hiking trails, waterfalls, and scenic overlooks. It’s a great place to escape the city for a day and enjoy the outdoors.
Make A List Of The Things You Want To See In Chicago
When planning your trip to Chicago, I recommend that you make a list of the things you want to see during your time there. Once this is done, I would pin the on a map so that you can group them per area that you can visit each day.
Once you are in Chicago, you can choose what to do each day based on the weather for that day. For example, when I visited Chicago, the first day I was there it was raining a lot. Because of this, we decided to spend most of the day visiting some museums.
Moving Around Chicago
There are several options that you can use to move around Chicago.
Public Transport: The best way to move around Chicago is with public transport. The Chicago Transit Authority (CTA) operates an extensive network of buses and trains that run throughout the city. In addition, you can also use the “L” train (elevated train) system.
If you’re planning on using Public Transport, then the best solution is to get a Ventra Card. The Ventra card can be charged with unlimited travel day tickets that cost 5$/day. To find the closest location where you can buy a Ventra Card, follow this link.
Good to know: You can also download the Ventra App on your phone and add your Ventra Card to Google Pay.
Walking: Walking will be your best option to explore the Loop and River North Neighborhoods since most sites are within walking distance.
Biking: Chicago has a large network of biking lanes. The bike-sharing program is called Divvy and it can be a great way to explore the city during the spring and summer months.
Chicago City Pass
When visiting Chicago, another thing to consider is getting the Chicago City Pass. Let’s face it, entry tickets to different attractions are expensive. Depending on how many places you want to visit, the Chicago City Pass might be a good option for you.
The Chicago City Pass is a pass that will allow you to visit a total of 5 attractions while saving some money.
- Every Pass includes by default access to the Skydeck Chicago (at the top of the Willis Tower) and the Shed Aquarium.
- Afterwards you can choose to access 3 additional between the Field Museum, the Art Institute of Chicago, the Museum of Science and Industry, the 360 Chicago Observation Deck (at the top of the John Hancock Center), the Adler Planetarium, and the Architecture River Tour.
- The Chicago City Pass has a validity of 9 days starting the day you visit your first attraction.
Additional Tips to Visit Chicago
Getting from Chicago O'Hare International Airport to Chicago Center
The easiest and cheapest way to get from Chicago Airport to Chicago Downtown is to take the Blue Line “L” train. This will take you from the airport to the center of Chicago in approximately 45 min. This will allow you to avoid traffic jams if you arrive at peak hours.
Remember to Tip at Restaurants
In the US, it’s common practice to tip your waiter at restaurants and cafés. The reason for this is that the standard salary is quite low and it is completed with customer’s tips. A standard tip to give is 15% and if the service is really good you can give 20%.
Money and Payments
The official currency of the United States is the US Dollar ($).
You can pay almost everywhere with your credit card so you really don’t need to carry cash with you. However, it is always convenient to have some cash available.
Useful Apps in Chicago
- Uber and Lyft: These two car applications will allow you to order a car with a driver much cheaper than a regular taxi.
- Ventra App: This app will allow you to have your public transport tickets on your phone.
Have Fun!
Now you’re all ready to have the best time possible in Chicago!
I hope you found useful this blog. Let me know what you thought in the comments.
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