How to plan a trip to Chicago?

Chicago, also known as the “Little Apple” for its downtown full of skyscrapers reminiscent of New York, is one of the most interesting cities in the United States because it has a great cultural offer. For this reason, at Passporter we want to help you plan a trip to Chicago in the best possible way to make the most of your stay. Our experience was wonderful, but we would have liked to know certain details that would have made our trip even better.

In this post we have set out to give you these little tips of information that will help you organize your trip. We tell you how to get to the city, the best areas to stay, where to eat and the main tourist attractions that you can’t miss. We have also prepared many practical tips that we learned on our trip.

1. Prepare the necessary documentation for traveling to Chicago

To travel to the United States for tourism purposes from anywhere in the world, you must have the following documents and have applied for a visa, also known as an ESTA:

1. Biometric passport: all travelers, including minors, must have a valid passport for at least six months from the date of entry into the country. It must also have a machine-readable chip.
2. Travel Authorization ESTA: this is a type of visa for stays of less than 90 days. The application is made online through the official website of the U.S. Embassy, and it is recommended to apply at least 72 hours before of your trip. Once approved, the ESTA is valid for two years. The processing fee is 14 euros.
3. Visa: if your stay will be longer than 90 days or if you are traveling for reasons other than tourism or business, you will need to apply for a specific visa. If you are traveling from Spain, you will need to do so in person at the U.S. Embassy in Madrid.
4. Return ticket: it is necessary to have a return ticket to ensure that you will leave the country. In case you don’t know what day you will return, there are agencies that will buy it and then cancel it and refund your money.

Another important aspect to keep in mind when arranging your trip to the United States is your driver’s license. You will need to apply for an international driving permit, which is valid for one year in most countries around the world. The fee to process it is 11€.

In the United States, before granting you permission to enter the country, they check if you have previously been in any of the countries that are banned there, such as Cuba, Iraq, Iran or Syria. In the case of having traveled to these countries or having dual citizenship, it is possible that they may put you some impediment to travel or request to have an interview at the embassy.

Travel Tip: To organize your trip we recommend using Passporter totally free. You can be inspired by the experiences of other travelers, choose the places that interest you most, create the travel route with a geolocated map, upload all important documents such as reservations and invite your friends so that everyone can participate in the organization of the trip.

2. Choose the date to plan your trip to Chicago

The best time to travel to Chicago is during the spring and fall. During these months the temperatures are mild and there are fewer people, allowing you to enjoy the city’s outdoor attractions and events. We traveled in June and the weather was perfect, we just had to bring a thin jacket in case it cooled off at night.

Summer is popular among tourists for its festivals and outdoor activities, but it can be quite hot and crowded. And in winter it gets very cold and it might snow. Still, being a city, the weather is not an impediment to visiting the main points of interest.

3. Find out how to get to and around Chicago

Chicago’s main airport, and where you’re likely to land if you’re flying from Europe, is O’Hare International Airport, although Midway International Airport is also close to the city.

Some airlines such as British Airways or American Airlines have regular, direct routes between major European capitals. Other airlines such as AirLingus offer trips with a stopover, which can be in Ireland, England or directly in the United States. Ticket prices vary widely, but usually range from €400 to €1,000 depending on the season. On the Passporter App you can compare prices and buy your tickets directly through Skyscanner.

Once at the airport, you can get to the city on the “L” Train, which for $5 will take you downtown in less than 45 minutes. The train runs 24 hours a day and is the fastest and cheapest option.

There are also buses that arrive at different points in the city and can take between 25 and 90 minutes depending on the route. The schedule is more limited and the frequency is usually every 10 to 15 minutes. If you prefer a more comfortable option you can take an Uber or cab, whose price is around $50, or hire transportation from the airport.

To get around the city you can choose between the subway or the bus. Our favorite option was the subway because the tracks are elevated and are not under the ground, so you can see the whole city. Being such a big city the transportation network is very complete and efficient, you will be able to move from one place to another without problems. In these cases, having internet on your mobile is very useful to have access to Maps platforms that will tell you what transport to take at any time depending on where you go.

4. Compare and find accommodation with Passporter

There are several good areas to stay in Chicago, but in general, it is recommended to avoid the south side, which tend to be the most troubled areas. These are the best neighborhoods to stay in:

• The Loop: this is the heart of the city. Being the central area, it is very close to the main points of interest, but it is also the most expensive area.
• River North: it is a lively and trendy neighborhood with a great nightlife.
• Magnificent Mile: this is the main avenue, an area of upscale shopping, first-class hotels and restaurants. As you can imagine, it is one of the cheapest areas.
• Wicker Park: it is a neighborhood with a bohemian atmosphere, perfect for young people and lovers of indie culture.

Compared to European prices, accommodation may seem a bit expensive, however, you should know that it is quite inexpensive compared to other American cities. You will be able to find good options to stay at an affordable price.

Through the Passporter App you will be able to compare accommodation and find the best option with Booking. In addition, you will be able to keep your bookings in an organized way.

5. Choose the activities you want to do in Chicago

Chicago is a city with a lot of life and cultural offerings, which means that, in addition to the typical points of interest such as museums, parks and monuments, there are many events that change every week. Concerts, Farmer’s Markets, theater, festivals, dance meetings… During the summer many of these activities are free. There is so much to see and do that you’ll have to spend time planning your trip to Chicago.

Our recommendation is that you use the Passporter App to write down all the points of interest you want to visit and the activities you’ll be doing during your stay. Plus, you can get inspired by the experience of other travelers who have visited the city before you.

Here are the must-sees in Chicago, but we encourage you to expand your search with Passporter and get the most out of the city.

• Chicago River Cruise: enjoy the stunning architecture of the city from the water. The price starts at 25€.
• “The Bean” in Millennium Park: this is a silver bean-shaped sculpture. It is an icon of the city and a perfect place to take pictures. Admission is free.
• Willis Tower Skydeck: panoramic views of the city from one of the tallest buildings. The price is around $30.
• Art Institute of Chicago: one of the world’s foremost art museums. Admission is $40.
• Navy Pier: entertainment area, restaurants and views of Lake Michigan.
• Chicago Theatre: a historic performance venue to enjoy shows.
• Lincoln Park Zoo: a free zoo in the middle of the city.

With Chicago’s CityPASS you’ll get access or discounts to most of the city’s attractions for about $50. We tell you much more in this post: What to see and do in Chicago

6. Where and what to eat in Chicago

Chicago’s cuisine, like that of the rest of the United States, is famous for a wide variety of fast-food options. However, the city’s signature dish is the Deep Dish Pizza, a pizza that is made in a pan and has such depth and quantity of ingredients that you almost have to eat it with a spoon. Is it worth a try? Definitely.

While you’ll find that burger, sandwich and hot dog restaurants abound, you can also find more sophisticated and elaborate options. In the end, it’s a great city with a great culinary offering.

Just a reminder that in the United States tipping is not mandatory, but it is common, being an unwritten rule. In addition, the prices of the cards do not include VAT. Also keep in mind that the United States is generally more expensive than Europe, so don’t be surprised if you have to pay $5 for a coffee.

7. Organize a trip with friends to Chicago

Chicago is a great destination to travel with friends because of the great cultural and nightlife offerings. In summer you can attend festivals like Lollapalooza and enjoy the atmosphere of its bohemian neighborhoods and lively atmosphere at night. The only barrier you will have to overcome is the organization. When you’re traveling with a lot of people it can be a challenge to get on the same page, so we encourage you to use the Passporter App to plan your trip to Chicago: Group travel: The best way to travel with your group of friends.

With the Passporter App you can also plan your travel itineraries from start to finish and discover the experiences of other travelers. You can read about the best places to visit in Chicago, but also about transportation, necessary documentation and many other details. Add your friends and create together your travel itinerary with the stops you are going to make and the points of interest you are most interested in. Later you will be able to share your experience through the pictures you take during the trip.

8. Tips for planning a trip to Chicago

• The currency of the United States is the dollar.
• We recommend that you take out cash or pay with an international card during your stay. Avoid exchanging money at the airport or exchange houses where the cost may be higher.
• Investigate safe areas and neighborhoods to stay in.
• There is a 6 to 9 hour time difference between the United States and Spain.
• Remember that in the United States measurements are in miles, gallons and pounds.
• Consider purchasing Chicago’s CityPASS to save on admission fees.
• Chicago’s water is safe to drink. The city treats and monitors Lake Michigan water to meet water safety and water quality standards set by the U.S. Environmental Protection Agency.
• Pack appropriate clothing for the weather, especially if you’re traveling in winter.
• Book flights and accommodations in advance for better prices.
• Find out about events or festivals during your visit.
• Be covered for medical emergencies: travel insured. Choose a good travel insurance, such as for example the one provided by Mondo.
• Sign up for Passporter and discover our Chicago travel itinerary. Using passporter to plan trips is free and helps you get inspiration from other travelers 🙂

9. How to prepare what to see on your trip to Chicago

Download the Passporter App and discover all its possibilities.

• Get inspired by other travelers’ experiences, photos and itineraries.
• Organize your trip by the categories that suit you best: dates, number of days or typology (beach, mountain, restaurants…).
• Add your friends so they can see and modify all the plans and information of the trip.
• Create your own itinerary of your destination with everything you feel like visiting each day.
• Add the stops that interest you the most, including your accommodation, restaurants, museums…
• Book your flights, accommodations, transfers and activities through a single app.
• Save all your documents in the app to always have everything at hand: reservations, boarding passes, important documentation…
• Make any modifications you need and you’ll be all set for your trip
• Share your experience with other users. Upload photos of the places you have visited on your trip to the app and inspire other travelers with your experience. In addition, you will be able to share your experience on how to plan your trip to Chicago.

If you have doubts about how to do it, you can check our post: How to create your travel itinerary with Passporter.

10. Frequently asked questions about a trip to Chicago