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CA $559 Cheap Flights from St. Thomas (STT) to Chicago (ORD)

View CA $559 flight on Sat, Dec 26, 2026Opens in a new window

Popular airlines from Cyril E. King Airport (STT) to Chicago O'Hare International Airport (ORD)

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Cheap flights from St. Thomas (STT) to Chicago (ORD)

Prices were available within the past 7 days and start at CA $559 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frequently asked questions

How much does a flight from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find one-way and return flights from STT to ORD with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when STT to ORD ticket fares go up or down.
What is the cheapest month to fly from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest months to fly from STT to ORD are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
Only one airline offers direct flights from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.). United operates 7 direct flights from STT to ORD every week.
What is the cheapest airline that flies from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
JetBlue Airways offers one of the cheapest connecting return flights on this route, with a layover in Luis Munoz Marin Intl. (SJU), starting from about CA$638. King) to Chicago, IL (ORD-O'Hare Intl.), with tickets starting from around CA$912 for flights that can be booked for departure within the next year. American Airlines is one of the cheapest airlines offering nonstop return flights from St. Thomas (STT-Cyril E. These prices are per adult, for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, United typically offers the lowest fares. American Airlines offers the most daily flights from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 18 connecting flights per day from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.). Some common connection points include Luis Munoz Marin Intl. (SJU), Miami Intl. (MIA), and Charlotte-Douglas Intl. (CLT).
What is the earliest flight from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) typically departs around 7:00 AM. This seasonal service is active in July and is operated by airlines such as Cape Air, Silver Airways, and United. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) on a Sunday, with around 19 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include American Airlines, Cape Air, and United. Sundays offer notably more flight options compared to other days of the week, so if flexibility is key, this could be a great day to fly.
What are the most popular departure times for flights from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) are between 12pm and 3pm. Many major carriers, including American Airlines, United and Delta, offer flights during this window. Many travellers prefer this time as it allows for a relaxed morning before heading to the airport and an afternoon arrival at your destination.
How long does it take to fly from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
A nonstop flight from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) typically takes around 5 hours 48 minutes. This route covers a distance of approximately 3,409 kilometers. If you opt for a one-stop flight, your travel time will be longer, usually around 8 hours 18 minutes. Flights with two or more stops can take significantly longer, averaging about 17 hours. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some extra time when planning your trip.
Can you fly business or first class from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
Yes, you can fly business class or first class between STT and ORD. You can fly business class with American Airlines.First class cabins are available on Spirit Airlines, Delta, and United.
How do I earn miles on a St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago, IL (ORD) from St. Thomas (STT)?
If you're planning to travel to Chicago from Cyril E. King (STT), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Luis Munoz Marin Intl. (SJU), Miami Intl. (MIA), or Charlotte-Douglas Intl. (CLT) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your St. Thomas (STT-Cyril E. King) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Cyril E. King
Destination airport
O'Hare Intl.
Distance
3388 km
Average flight time
6 hours 34 mins

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St. Thomas to Chicago Flights

The easy way to book your flights from St. Thomas to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from St. Thomas whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 12 airlines that cover this route. There are nonstop flights to O'Hare Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from St. Thomas to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Cyril E. King, STT to O'Hare Intl., ORD 

Sort your search results by price to find great deals on your flight from St. Thomas to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from St. Thomas currently is just rising to .  

Here are more money-saving tips: 

  • Fly in when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from St. Thomas 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

St. Thomas to Chicago Flights

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