Flights From Chicago To St Thomas Island

Are you planning a trip to St. Thomas Island from Chicago and looking for the best flights? Look no further! In this comprehensive guide, we will provide you with all the information you need to know about flights from Chicago to St. Thomas Island. From the various airlines to the best time to book, we’ve got you covered. So, sit back, relax, and let us help you plan your dream getaway to this beautiful Caribbean destination.

Exploring the Airlines

When it comes to flying from Chicago to St. Thomas Island, there are several airlines to choose from. Let’s take a closer look at the major carriers and lesser-known options:

Major Carriers

Major carriers such as American Airlines, United Airlines, and Delta Air Lines operate regular flights between Chicago and St. Thomas Island. These airlines offer a wide range of flight options, including economy, premium economy, and business class. They also provide various amenities such as in-flight entertainment, complimentary meals, and Wi-Fi on select flights.

American Airlines, for example, offers direct flights from Chicago O’Hare International Airport (ORD) to Cyril E. King Airport (STT) in St. Thomas Island. Their flights provide a comfortable travel experience with spacious seating and a selection of entertainment options. United Airlines and Delta Air Lines also offer similar services, making it convenient for travelers to choose the carrier that best suits their needs.

Lesser-Known Options

In addition to the major carriers, there are also lesser-known airlines that operate flights from Chicago to St. Thomas Island. These airlines may offer competitive prices and unique services:

Spirit Airlines: Spirit Airlines is a low-cost carrier that operates flights from Chicago to St. Thomas Island. They offer affordable fares, but it’s important to note that additional fees may apply for services such as baggage and seat selection.

JetBlue Airways: JetBlue Airways is another option for travelers flying from Chicago to St. Thomas Island. They provide a comfortable flying experience with spacious seating and complimentary snacks and beverages.

While lesser-known airlines may not have the same brand recognition as major carriers, they can often provide cost-effective options for budget-conscious travelers. It’s worth exploring these airlines to find the best deals and potentially save money on your flight.

Flight Duration

Knowing the estimated flight duration from Chicago to St. Thomas Island is essential for planning your trip. While the exact duration may vary depending on factors such as the airline and weather conditions, here’s an overview of what you can expect:

Direct Flights: Direct flights from Chicago to St. Thomas Island typically have a flight duration of around 4 to 5 hours. These flights offer a convenient and time-saving option, as there are no layovers or stops along the way.

Connecting Flights: If you opt for a connecting flight, the total travel time will be longer. The duration of the layover will vary depending on the airline and the chosen route. It’s important to consider the layover duration when planning your itinerary to ensure you have enough time to catch your connecting flight.

Considerations for Connecting Flights

When booking a connecting flight, there are a few factors to consider:

1. Layover Time: Check the duration of the layover to ensure you have enough time to comfortably make your connection. It’s recommended to have a layover of at least 1-2 hours to account for any potential delays or unforeseen circumstances.

2. Airport Facilities: Take into account the facilities available at the connecting airport. If you have a longer layover, it can be beneficial to choose an airport with amenities such as lounges, restaurants, or shopping areas to make your wait more enjoyable.

3. Baggage Handling: Confirm whether you need to collect and recheck your baggage during the layover. Some airlines have agreements in place that allow your checked bags to be automatically transferred to your final destination, while others may require you to collect and recheck them.

By considering these factors, you can make an informed decision about whether a direct or connecting flight is the best option for your journey from Chicago to St. Thomas Island.

Best Time to Book

Booking your flight at the right time can make a significant difference in the cost. Here are some tips to help you find the best deals on flights from Chicago to St. Thomas Island:

Book in Advance

Generally, booking your flight well in advance can increase your chances of finding lower fares. Airlines often offer discounted prices for tickets booked several months ahead of the departure date. Aim to book your flight at least 2-3 months before your planned travel dates.

Be Flexible with Travel Dates

Flexibility with your travel dates can also help you secure better deals. Consider flying on weekdays instead of weekends, as flights tend to be less crowded and more affordable. Additionally, traveling during off-peak seasons, such as late spring or early fall, can result in lower airfare prices.

Use Fare Comparison Websites

Take advantage of fare comparison websites such as Skyscanner, Kayak, or Google Flights to compare prices from different airlines. These platforms allow you to input your travel dates and destination, and they will provide you with a list of available flights and fares. Be sure to check multiple websites to ensure you’re getting the best deal.

Sign Up for Price Alerts

If you have flexible travel plans and are not in a rush to book your flight, consider signing up for price alerts. Many travel websites and airlines offer this feature, which notifies you via email when the price for your selected flight route drops. By monitoring price fluctuations, you can seize the opportunity to book your flight at the lowest possible price.

Consider Travel Packages

Another option to explore is travel packages that include both flights and accommodations. Travel agencies and online platforms such as Expedia or Travelocity often offer discounted rates when you book a flight and hotel together. This can be a cost-effective solution, especially if you’re planning to stay in St. Thomas Island for an extended period.

By following these tips, you can increase your chances of finding affordable flights from Chicago to St. Thomas Island and save money for other aspects of your trip.

Choosing the Right Airport

When flying from Chicago to St. Thomas Island, you have several airport options to consider. Let’s take a closer look at the airports in both cities:

Chicago Airports

Chicago is served by two major airports:

O’Hare International Airport (ORD)

O’Hare International Airport is one of the busiest airports in the United States and offers a wide range of domestic and international flights. It is located approximately 17 miles northwest of downtown Chicago. The airport is well-connected to the city center via public transportation, including the Chicago Transit Authority (CTA) Blue Line and various bus routes.

Midway International Airport (MDW)

Midway International Airport is another option for travelers flying from Chicago to St. Thomas Island. It is located approximately 10 miles southwest of downtown Chicago. While Midway has fewer international flights compared to O’Hare, it offers a convenient option for domestic travel. The airport is also easily accessible via public transportation, with the CTA Orange Line providing direct service to downtown Chicago.

Cyril E. King Airport (STT)

In St. Thomas Island, the main airport serving international flights is Cyril E. King Airport. It is located approximately 3 miles west of the capital city, Charlotte Amalie. The airport offers various ground transportation options, including taxis, car rentals, and shuttle services.

Proximity to City Centers

When choosing the right airport, consider the proximity to the city centers and your final destination in both Chicago and St. Thomas Island. If you’re staying in downtown Chicago, O’Hare International Airport may be more convenient due to its proximity to the city. On the other hand, if you’re planning to explore the southern suburbs of Chicago, Midway International Airport might be a better option.

In St. Thomas Island, Cyril E. King Airport is centrally located, making it easily accessible from various parts of the island. However, it’s a good idea to check the distance between the airport and your accommodation to plan your ground transportation accordingly.

Direct vs. Connecting Flights

When booking your flight from Chicago to St. Thomas Island, you’ll have the option to choose between direct and connecting flights. Let’s weigh the advantages and disadvantages of each:

Direct Flights

Direct flights offer the convenience of a non-stop journey from Chicago to St. Thomas Island. Here are some of the benefits of choosing a direct flight:

1. Time-Saving: Direct flights are typically shorter in duration since there are no layovers or stops along the way. This means you’ll spend less time traveling and more time enjoying your destination.

2. Convenience: Direct flights eliminate the hassle of navigating through a connecting airport and the potential stress of making a tight connection. You can simply board the plane in Chicago and disembark in St. Thomas Island without

any interruptions.

3. Reduced Risk of Delays: With direct flights, there is a lower risk of experiencing delays caused by factors such as missed connections or weather conditions. This can provide peace of mind, especially if you have a tight schedule or important events planned upon arrival.

Connecting Flights

While direct flights have their advantages, connecting flights also offer some benefits:

1. More Flight Options: Choosing a connecting flight opens up a wider range of flight options, allowing you to select the schedule and airline that best suits your preferences and budget. It may also give you the opportunity to fly with an airline that offers specific amenities or services you desire.

2. Potential Cost Savings: In some cases, connecting flights can be more affordable than direct flights. If you’re flexible with your travel time and are willing to make a stop along the way, you may find significant cost savings on your ticket.

3. Break the Journey: Connecting flights can provide an opportunity to break up a long journey and stretch your legs during the layover. Depending on the duration of the layover, you may even have the chance to explore the connecting city or airport if time permits.

Factors to Consider

When deciding between direct and connecting flights, consider the following factors:

1. Time Sensitivity: If time is of the essence and you want to reach your destination quickly, a direct flight may be the best option. However, if you have a more flexible schedule or if you enjoy the adventure of exploring new airports, a connecting flight can add an extra layer of excitement to your journey.

2. Layover Duration: Take into account the duration of the layover when choosing a connecting flight. If you have a short layover, ensure that there is sufficient time to make the connection without feeling rushed or risking missing the second flight. On the other hand, a longer layover can provide an opportunity to relax, explore, or even book a mini layover tour in the connecting city.

3. Traveler Preferences: Consider your personal preferences and travel style. Some travelers prefer the convenience and efficiency of a direct flight, while others enjoy the flexibility and potential cost savings of connecting flights. Think about what matters most to you and choose accordingly.

By weighing the advantages and disadvantages of both direct and connecting flights, you can make an informed decision that aligns with your travel needs and preferences.

Baggage Allowance

Understanding the baggage allowance policies of airlines operating flights from Chicago to St. Thomas Island is crucial to avoid any surprises or additional fees. Here’s what you need to know:

Checked Baggage Allowance

The checked baggage allowance refers to the number, size, and weight restrictions for bags that are placed in the aircraft’s cargo hold. The specific allowance can vary depending on the airline and ticket class. Here’s a general overview:

1. Major Carriers: Airlines such as American Airlines, United Airlines, and Delta Air Lines typically allow one checked bag per passenger on domestic flights within the United States. The maximum weight allowed is usually 50 pounds (23 kilograms) per bag, and the maximum linear dimensions are around 62 inches (157 centimeters).

2. Low-Cost Carriers: For low-cost carriers like Spirit Airlines, the baggage allowance may differ. They often charge additional fees for checked bags, and the weight and size limits may be more restrictive. It’s important to review their baggage policies and consider any additional fees when comparing prices.

It’s worth noting that some airlines offer baggage fee waivers or different allowances for passengers with elite status, certain credit cards, or specific ticket classes. Be sure to check with the airline or review their website for the most up-to-date information on baggage allowances and any potential fees.

Carry-On Baggage Allowance

In addition to checked baggage, airlines also have specific policies regarding carry-on baggage. These are the smaller bags that passengers can bring into the cabin with them. Here are a few general guidelines:

1. Size Restrictions: Most airlines allow carry-on bags with dimensions of around 22 x 14 x 9 inches (56 x 35 x 23 centimeters). However, it’s important to check with the specific airline as some may have slightly different size restrictions.

2. Quantity Allowance: Generally, passengers are allowed one carry-on bag and one personal item, such as a purse, laptop bag, or small backpack. The personal item should fit under the seat in front of you.

3. Security Regulations: Keep in mind that carry-on bags are subject to security screenings, and certain items may be restricted or prohibited. Familiarize yourself with the Transportation Security Administration (TSA) guidelines to ensure a smooth and hassle-free security screening process.

It’s crucial to pack within the size and weight limits specified by the airline to avoid any additional fees or the need to check bags at the gate. Be sure to check the baggage policies of the specific airline you’re flying with to ensure compliance with their requirements.

Flight Costs and Budgeting

Understanding the average cost of flights from Chicago to St. Thomas Island and budgeting accordingly is essential for a smooth travel experience. Here’s what you need to know:

Average Flight Costs

The cost of flights can vary depending on factors such as the time of year, the airline, the ticket class, and how far in advance you book. As a general guideline, here’s the average cost range for flights from Chicago to St. Thomas Island:

1. Direct Flights: Direct flights from Chicago to St. Thomas Island typically range from $400 to $900 round trip, depending on factors such as the season, availability, and the airline. Prices tend to be higher during peak travel times, such as holidays and school vacations.

2. Connecting Flights: Connecting flights can offer cost savings, with prices ranging from $300 to $700 round trip. However, keep in mind that the total travel time will be longer due to layovers.

It’s important to note that these are general price ranges and can fluctuate based on various factors. It’s recommended to use fare comparison websites and sign up for price alerts to track the latest deals and secure the best price for your travel dates.

Budgeting Tips

To help you budget for your trip, consider the following tips:

1. Set a Travel Budget: Determine how much you’re willing to spend on your flight, accommodations, meals, activities, and other expenses. This will give you an overall budget to work with and help you allocate funds accordingly.

2. Compare Flight Prices: Use fare comparison websites to compare prices from different airlines. Look for deals and promotions that can help you secure a better price. Be flexible with your travel dates if possible, as prices can vary significantly depending on the day of the week and the time of year.

3. Consider Additional Fees: Take into account any additional fees that may apply when booking your flight, such as baggage fees or seat selection fees. These can add up quickly, so it’s important to factor them into your budget.

4. Save on Accommodations: Consider staying in budget-friendly accommodations such as guesthouses, hostels, or vacation rentals. These options can often provide more affordable alternatives to traditional hotels while still offering comfort and convenience.

5. Plan Meals and Activities: Research local restaurants and activities in St. Thomas Island to get an idea of their costs. By planning your meals and activities in advance, you can estimate how much you’ll need to budget for each day.

6. Allocate a Buffer: It’s always a good idea to allocate a buffer in your budget for unexpected expenses or emergencies. This way, you can handle any unforeseen circumstances without compromising your travel experience.

By setting a budget, comparing prices, and being mindful of additional fees, you can effectively manage your expenses and make the most of your trip from Chicago to St. Thomas Island.

Airport Facilities and Services

Being aware of the facilities and services available at the airports in both Chicago and St. Thomas Island can enhance your travel experience. Let’s explore what you can expect:

Chicago Airports

Both O’Hare International Airport and Midway International Airport offer a range of facilities and services to accommodate travelers:

O’Hare International Airport (ORD)

O’Hare International Airport is known for its extensive amenities. Here are some of the facilities and services you can find at ORD:

Dining Options:

From fast-food chains to sit-down restaurants, O’Hare offers a wide variety of dining options. Whether you’re craving a quick snack or a full meal, you’ll find something to satisfy your appetite.


O’Hare features numerous shopping opportunities, including duty-free shops, luxury boutiques, and souvenir stores. Take advantage of your time at the airport to browse and purchase items such as clothing, electronics, and local products.


Several airlines and independent lounges provide comfortable spaces for passengers to relax and unwind before their flights. Access to these lounges may be available for purchase or granted to eligible passengers, such as those with premium status or certain credit cards.

Midway International Airport (MDW)

While Midway International Airport is smaller in size compared to O’Hare, it still offers a range of amenities for travelers:

Dining Options:

Midway has a variety of dining options, including fast-food chains, coffee shops, and restaurants. Whether you’re in the mood for a quick bite or a sit-down meal, you’ll find plenty of choices to satisfy your hunger.


Midway features a selection of shops where you can purchase last-minute travel essentials, souvenirs, and more. Take a stroll through the airport to discover bookstores, gift shops, and specialty stores.

Relaxation Areas:

While Midway may not have dedicated lounges like O’Hare, there are designated seating areas throughout the airport where you can relax and unwind before your flight. Find a comfortable spot and enjoy a moment of tranquility.

Cyril E. King Airport (STT)

Cyril E. King Airport in St. Thomas Island offers a range of facilities and services to enhance your arrival or departure experience:

Transportation Services:

Upon arrival at Cyril E. King Airport, you’ll find various transportation options to reach your destination on the island. Taxis, car rental services, and shuttle buses are readily available outside the terminal. Consider your transportation needs and choose the option that best suits your plans.

Duty-Free Shopping:

Like many international airports, Cyril E. King Airport features duty-free shops where you can purchase a variety of products, including alcohol, tobacco, perfume, and cosmetics. Take advantage of duty-free prices to save on your favorite items.

Restaurants and Cafes:

If you’re feeling hungry or in need of a caffeine boost, Cyril E. King Airport has several dining options. Grab a quick snack, enjoy a meal, or savor a delicious cup of coffee before or after your flight.

Amenities for Passengers with Disabilities:

Cyril E. King Airport is committed to providing accessibility for passengers with disabilities. The airport offers services and facilities such as wheelchair assistance, accessible restrooms, and designated parking spaces. If you require any specific assistance, reach out to the airport in advance to make arrangements.

Overall, whether you’re departing from Chicago or arriving in St. Thomas Island, the airports offer amenities and services to make your travel experience more comfortable and enjoyable.

Travel Tips and Recommendations

When traveling from Chicago to St. Thomas Island, it’s helpful to have some insider knowledge and recommendations to ensure a smooth and enjoyable trip. Here are a few tips to enhance your travel experience:

Best Time to Visit

St. Thomas Island enjoys a tropical climate throughout the year, with warm temperatures and occasional rainfall. However, certain months offer more favorable conditions for a visit:

1. High Season: The high season in St. Thomas Island runs from December to April, coinciding with the colder months in northern regions. During this time, the weather is typically dry and sunny, attracting many tourists. However, prices for flights and accommodations are generally higher, and popular attractions may be more crowded.

2. Shoulder Season: The shoulder seasons, which fall between the high and low seasons, can be a great time to visit. From May to June and November to mid-December, you’ll find fewer crowds and more affordable prices. The weather is still pleasant, with warm temperatures and a lower chance of rain.

3. Low Season: The low season in St. Thomas Island occurs during the summer months, from July to October. While this period may bring more rain and the possibility of hurricanes, it can also offer significant cost savings on flights and accommodations. If you’re willing to take the risk and plan accordingly, you can enjoy a quieter island experience.

Must-See Attractions

St. Thomas Island is known for its stunning beaches, crystal-clear waters, and vibrant culture. Here are a few must-see attractions to include in your itinerary:

Magens Bay Beach:

Considered one of the most beautiful beaches in the world, Magens Bay Beach offers a picturesque setting with soft white sand and calm turquoise waters. Spend a day relaxing, swimming, and enjoying the breathtaking scenery.

Charlotte Amalie:

Explore the capital city of St. Thomas Island, Charlotte Amalie, known for its colonial architecture, historic sites, and vibrant shopping district. Visit attractions such as Fort Christian, Blackbeard’s Castle, and the famous Main Street for a taste of the island’s history and culture.

Trunk Bay:

If you have the opportunity, take a day trip to nearby St. John Island and visit Trunk Bay. This stunning beach is part of the Virgin Islands National Park and offers pristine white sand, crystal-clear waters, and an underwater snorkeling trail.

Local Cuisine:

Indulge in the flavors of St. Thomas Island by sampling the local cuisine. Try dishes such as conch fritters, johnnycakes, and fresh seafood. Don’t forget to savor a refreshing cocktail made with local rum, such as the famous Painkiller.

Respect Local Customs

When visiting St. Thomas Island, it’s important to respect the local customs and culture. Here are a few tips:

1. Dress Code: While the island has a relaxed atmosphere, it’s still important to dress appropriately, especially when visiting religious sites or local communities. Opt for modest clothing that covers the shoulders and knees out of respect for the local traditions.

2. Greetings: It’s customary to greet locals with a warm “good morning,” “good afternoon,” or “good evening” when entering shops or restaurants. This simple gesture is appreciated and helps to create a friendly atmosphere.

3. Tipping: Tipping is customary in St. Thomas Island. It’s customary to leave a gratuity of around 15-20% of the bill at restaurants, and a small tip for taxi drivers, hotel staff, and tour guides is also appreciated.

By following these tips and recommendations, you can make the most of your trip to St. Thomas Island and experience the beauty and culture of the destination.

Booking Your Flight

Now that you have all the necessary information about flights from Chicago to St. Thomas Island, it’s time to book your flight. Here’s how to make the process as seamless as possible:

Online Booking

The most convenient and popular way to book flights is through online platforms. Follow these steps to book your flight online:

1. Choose a Reliable Travel Website: Select a reputable travel website or airline website to search for flights. Websites like Expedia, Kayak, or the official websites of airlines like American Airlines or United Airlines are reliable options.

2. Enter Your Travel Details: Input your departure city (Chicago) and destination city (St. Thomas Island) along with your desired travel dates. Consider the flexibility of your travel dates to find the best deals.

3. Explore Flight Options: Browse through the available flight options, considering factors such as flight duration, layovers, and price. Utilize filters and sorting options to narrow down your search and find the flight that suits your preferences.

4. Review Fare Rules and Restrictions: Before finalizing your booking, carefully review the fare rules and restrictions of the selected flight. Pay attention to cancellation policies, change fees, and any other terms and conditions that may apply.

5. Select Your Seat: Once you’ve chosen your flight, you’ll typically have the option to select your seat. Consider factors such as legroom, proximity to the exit, or window preference when choosing your seat.

6. Provide Traveler Information: Enter the required traveler information, including full names, contact details, and any special requests or requirements you may have. Double-check that all information is accurate before proceeding.

7. Make Payment: Proceed to the payment page and provide the necessary payment details to complete your booking. Ensure that the website is secure and reputable before entering any sensitive information.

8. Confirm Your Booking: After completing the payment process, you will receive a confirmation email with your flight details, itinerary, and booking reference number. Save this information for future reference and present it at the airport during check-in.

Travel Agent Assistance

If you prefer a more personalized approach or need assistance with your booking, you can also consider reaching out to a travel agent. Travel agents can provide expert advice, help you navigate the various options, and handle the booking process on your behalf. They may also have access to exclusive deals and discounts.

When working with a travel agent, communicate your preferences and budget clearly to ensure they find the best flight options for you. Be prepared to provide them with your travel dates, preferred airlines, and any other specific requirements you may have.

Booking your flight from Chicago to St. Thomas Island is an exciting step towards your dream getaway. By following these steps and considering the available options, you can secure the best flight for your travel needs and embark on a memorable journey to this beautiful Caribbean destination.


Planning a trip from Chicago to St. Thomas Island involves several important considerations, from choosing the right airline and airport to securing the best deals and understanding baggage policies. By following this comprehensive guide, you now have a detailed understanding of the various aspects involved in booking flights from Chicago to St. Thomas Island.

Exploring the airlines provides you with a range of options, from major carriers to lesser-known airlines, each with their own advantages and services. Understanding the flight duration, whether opting for a direct or connecting flight, helps you plan your itinerary and manage your time effectively.

Knowing the best time to book your flight allows you to take advantage of lower fares and avoid peak travel times. Choosing the right airport ensures convenience and accessibility, considering your proximity to city centers and transportation options.

Deciding between direct and connecting flights requires weighing the benefits of time savings versus potential cost savings and flexibility. Understanding baggage allowances helps you pack efficiently and avoid additional fees.

Estimating flight costs and budgeting appropriately allows you to plan your overall trip expenses and allocate funds accordingly. Familiarizing yourself with airport facilities and services ensures a comfortable and enjoyable travel experience.

Lastly, our travel tips and recommendations provide insights into the best time to visit, must-see attractions, and respecting local customs. And when it comes time to book your flight, you are equipped with the knowledge to navigate the online booking process or seek assistance from a travel agent.

With this comprehensive guide, you can now confidently plan and book your flights from Chicago to St. Thomas Island. Embrace the beauty of the Caribbean, relax on the stunning beaches, and immerse yourself in the vibrant culture of St. Thomas Island. Bon voyage!

Related video of Flights from Chicago to St. Thomas Island: A Comprehensive Guide

Also Read