If you’re here, you’re looking at the vibrant Windy City for your vacation, and we’re here to tell you that you’ve picked one of the hottest destinations in the country. Chicago is a lot of things, but boring is not one of them.

You’re bound to find architecture that is both stunning and creative no matter where you turn. The food scene is as sumptuous as sin. The zany museums make for an intriguing visit, and the nightlife is thriving. And for the easy-breathers, well, there’s always Lake Michigan.

While planning your trip to Chicago, do not forget to look for visitors medical insurance or travel insurance to safeguard yourself and your traveling companions in case of mishaps or trouble.

Visitors Medical Insurance for Travelers in Chicago - FAQs

Chicago is a large and thriving city, filled to the brim with interesting things to do. While exploring such a destination is fun, trouble can find you any time. The stress of an accident or healthcare emergency only precedes the large financial distress that may follow. This is where a good visitors medical insurance plan comes in - to protect you from the financial burden.

Why buy visitors medical insurance before traveling to Chicago?

Healthcare facilities in the U.S. are expensive, especially so on a short-term basis. A good visitors medical insurance policy for when you’re traveling can help take care of the costs of any treatment of physical injuries or ailments while you’re there. This saves you a lot of administrative running around.

What should I look for in my Chicago visitors medical insurance?

Your Chicago visitors medical insurance will ideally include benefits for emergency medical expenses, emergency medical evacuation and repatriation, acute onset of pre-existing conditions, the return of mortal remains, and more.

Traveling without stress is worth buying visitors medical insurance and saving yourself from the possibility of financial ruin.

Trip Cancellation Insurance for Travelers in Chicago - FAQs

Travel comes with the slightest undercurrent of anxiety and unpredictability. If your flight, long-awaited tour, or extravagant event is delayed or canceled, the huge financial loss only intensifies this stress. In case that happens, well, what can one do without a safety net in place?

Why should I get trip cancellation insurance for my Chicago travel?

Can you ever predict when your airline decides to reschedule or cancel a flight, or when your hotel bookings accidentally get deleted? Not really, but this is where your trip cancellation insurance comes in. It can save the day by recouping your expenditures and protecting you from huge financial loss.

What should I look for in my Chicago trip cancellation insurance?

With trip cancellation insurance, you can be reimbursed for any of your trip-related, prepaid, non-refundable expenses—as long as you cancel for a reason explicitly listed in your policy’s certificate wording. Make sure to review the fine print before purchase so you know what your coverage is. The benefits vary by plan, but most standard trip cancellation insurance plans include the most common reasons for cancellation, including flight delays or cancellations, you or an immediate family member falling sick, weather-related delays or cancellations, getting called for jury duty, and more.

With a good travel insurance policy, you can recover from emergencies. Check your plan’s certificate wording carefully to see what is (and isn’t) covered.

Chicago’s Most Famous Places for Travel

Millennium Park

Millennium Park is one of the indispensable destinations of Chicago that make the city what it is. With treasures like the 33-foot (about 10-meter) Cloud Gate (aka The Bean), the gorgeous Lurie Garden, and the bizarre Crown Fountain, it is definitely a place worth exploring. The range of activities offered in the park is crazy—from rock-climbing activities to concerts—and entry is free.

360 CHICAGO Observation Deck

Towering 1,000 feet (over 300 meters) above the Magnificent Mile, the Deck offers fantastic panoramic views of the whole city, including the blue water of Lake Michigan and the gorgeous skyline. If you’re one for thrills, you’ll adore the TILT, which offers a bird’s eye view of the city and an unparalleled adrenaline rush!

Food Heaven

In Chicago, you cannot go wrong with the food. Everyone knows about the city’s love-it-or-hate-it deep dish pizza, the Italian beef sandwiches, and the hotdogs, but keep an eye out for more. The cuisines are diverse and created by fusion as well. From Michelin-star restaurants to local breweries, from Polish to Puerto Rican food locales, Chicago is a total cornucopia.


The Museum of Science and Industry is home to rare artifacts of scientific intrigue. The Field Museum contains relics of a holistic nature, such as Sue the T-Rex and the large ancient Egyptian exhibit. The Art Institute of Chicago offers a hefty expanse of historic pieces, including works by Monet and Van Gogh, and each with its own tale to tell.

Lincoln Park Zoo

One of the oldest zoos in the U.S., the Lincoln Park Zoo houses almost 200 species of animals and birds from all over the planet, including endangered species. The gardens are extensive and lush, making it a beautiful place to spend an entire morning. Complete with a well-stocked gift shop and multiple dining options, you need not look elsewhere.

Key Guidelines for Travelers in Chicago


It is a well-known fact that Chicago winters are no joke, but if you’re planning on visiting for the holidays anyway, there are several precautions you must keep in mind. Temperatures can go as low as -3 degrees Fahrenheit (about -19 degrees Celsius). Chilly winds and ice storms are not uncommon. Tourist spots and many events may be subject to cancellation or delay because of the weather, and public transport may not be as efficient. Remember to keep warm, and plan your vacation accordingly.

Road Safety

Heavily populated cities like Chicago always experience terrible traffic, and Chicago is no exception. Road blockages and delays are common. Crowded areas are accident-prone, and the roads can be incredibly dangerous if you’re driving during the winter season. It is always best to avoid rush hour (between about 6 a.m. to 8 a.m. and 4 p.m. to 8 p.m.). If you’re unfamiliar with the city and are planning on driving, you may want to take certain precautions, like predetermining your routes and leaving plenty of time.


While Chicago is pretty safe overall, the risk of crime is not something you should ignore. Pick-pocketing is very common, especially in tourist spots and on public transportation. Sometimes, it even takes place in groups. It is advisable to be vigilant about your belongings. Muggings are also fairly common in some places around the city. It is best to do your research about which neighborhoods should be avoided (locals around will be helpful with that information) to avoid damage or loss of life and property.

Before You Go to Chicago - Do This!

  • Prepare for The Weather: Chicago experiences pretty extreme climates. If you’re traveling for the winter holidays (or even spring), make sure you have enough layers to keep warm. Summer, on the other hand, can be very warm. Remember to pack accordingly!
  • Make Reservations Smartly: Chicago is packed with some world-class restaurants and iconic places to eat, but there’s a good chance you won’t get to try any of them if you don’t book in advance. It is advisable to make timely reservations.
  • Entertainment Galore: Whether it’s comedy clubs, theaters, or jazz bars, you’re in a city of entertainment and leisure, among other things. Chicago certainly has a great sense of humor and a lively vibe. Make the most of it.

Travel smart with good travel insurance coverage to soothe your mind during your stay in Chicago. Enter some basic information about your trip, compare a vast variety of options, and pick the plan that best suits your own personal needs.

Did you know?

Prices are regulated by law.

You cannot find a lower price anywhere for the same product.

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Why buy insurance from Insubuy?

Same Price. Better Service.®

There are many advantages in purchasing from Insubuy and no disadvantages.

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Visiting USA?

Healthcare costs are very high in the U.S.

Buy U.S. based visitors insurance and enjoy your trip.

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Traveling abroad?

Did you know that your insurance may not cover you abroad or that it may only provide limited coverage?

Purchase travel medical insurance that includes emergency medical evacuation.

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New immigrant to USA?

You are not eligible to enroll in Medicare for the first 5 years.

Purchase new immigrant medical insurance to bridge the gap.

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Going on a vacation?

You could lose your non-refundable trip costs if you had to cancel your trip.

Buy a trip cancellation insurance package plan and be worry-free.

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Are you an exchange visitor to USA?

The U.S. Department of State requires all J visa holders to purchase compliant insurance.

Buy J visa medical insurance to meet your requirements.

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Traveling to Europe?

Schengen countries require most non-US citizens to purchase Schengen visa insurance.

Make an instant purchase online and get instant visa letter.

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Traveling frequently throughout the year?

You don't need to purchase travel insurance for every trip.

Purchase annual multi trip travel insurance for your travels.

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International student in the U.S.?

Most schools require international students to purchase health insurance.

Purchase international student health insurance that meets most school requirements.

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