CHI - STT

$114 Find Cheap Flights from Chicago to Saint Thomas Island

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Saint Thomas Island departing on 10/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Saint Thomas Island

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Saint Thomas Island, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Saint Thomas Island, as well as popular online travel agencies
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Cheap Flights from Chicago to Saint Thomas Island (CHI-STT)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Saint Thomas Island that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Saint Thomas Island

Sat, Oct 18 - Sat, Oct 25
Spirit Airlines Logo
7:43 pm - 9:56 amORD-STT
13h 13m1 stop
Spirit Airlines Logo
11:01 am - 11:45 pmSTT-ORD
13h 44m1 stop
$224Spirit Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Spirit Airlines Logo
7:43 pm - 9:56 amORD-STT
13h 13m1 stop
Spirit Airlines Logo
11:01 am - 6:38 pmSTT-ORD
8h 37m1 stop
$232Spirit Airlines
Find Deal
Wed, Oct 22 - Sat, Nov 1
Spirit Airlines Logo
7:43 pm - 9:56 amORD-STT
13h 13m1 stop
Spirit Airlines Logo
11:01 am - 6:38 pmSTT-ORD
8h 37m1 stop
$235Spirit Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Spirit Airlines Logo
6:58 pm - 12:59 pmORD-STT
17h 01m1 stop
Spirit Airlines Logo
2:01 pm - 9:33 pmSTT-ORD
8h 32m1 stop
$239Spirit Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
Multiple Airlines Logo
11:36 am - 2:30 pmMDW-STT
25h 54m1 stop
Multiple Airlines Logo
4:06 pm - 9:12 amSTT-MDW
19h 06m1 stop
$351Multiple Airlines
Find Deal
Sun, Dec 7 - Fri, Dec 12
Multiple Airlines Logo
2:15 pm - 3:11 pmMDW-STT
22h 56m1 stop
Multiple Airlines Logo
9:49 am - 8:38 pmSTT-MDW
12h 49m2 stops
$500Multiple Airlines
Find Deal
Tue, Jan 6 - Fri, Jan 16
Delta Logo
6:00 am - 2:55 pmMDW-STT
6h 55m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$509Delta
Find Deal
Sun, Jan 18 - Sun, Jan 25
Delta Logo
6:00 am - 3:54 pmMDW-STT
7h 54m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$514Delta
Find Deal
Tue, Feb 10 - Wed, Feb 11
Southwest Logo
5:00 am - 2:55 pmMDW-STT
7h 55m1 stop
Southwest Logo
3:55 pm - 8:45 amSTT-MDW
18h 50m2 stops
$699Southwest
Find Deal
Tue, Feb 10 - Sun, Feb 15
Southwest Logo
7:55 pm - 2:55 pmMDW-STT
17h 00m2 stops
Southwest Logo
3:55 pm - 10:50 amSTT-MDW
20h 55m2 stops
$769Southwest
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Choose Economy Plus on United for extra legroom.
At STT, use USVI-licensed taxis with 'TP' plates.
Expert advice
Expert advice
Expert advice
Expert advice
Top routes
ORD-STT
Cheapest
ORD-STT
Most popular
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 33% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 15% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
2 days a week
There are direct flights from Chicago to Saint Thomas Island 2 days a week: Sat, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
Cheapest round-trip
$224
Overall average: $509
Spirit Airlines
Sat 10/18Sat 10/25
ORD - STT • 1 stop
Cheapest non-stop
$500
Typical prices: $525-768
United Airlines
Wed 1/21Wed 1/28
ORD - STT • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Saint Thomas Island!
Expert advice

Expert advice for your flight from Chicago to Saint Thomas Island

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Consider Main Cabin Extra for early boarding and complimentary drinks on longer flights.


Use American Airlines app for inflight entertainment; seatback screens may not be available.

United Airlines

Opt for Economy Plus for up to six inches more legroom than standard economy seats.


Check United's Wi-Fi coverage map before purchasing Wi-Fi for better connectivity.

Airports
ORD

For a quicker commute to downtown Chicago, take the CTA Blue Line train from ORD, which runs 24 hours and avoids traffic delays.

Read more about ORDby Stefanie Waldek
STT

At STT, USVI-licensed taxis are available with dome lights and 'TP' plates. Confirm rates before boarding to avoid surprises.

Read more about STTby Marisa Garcia
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Marisa Garcia

Marisa Garcia

Expert on STT

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Booking Insights

KAYAK's insights & trends for Chicago to Saint Thomas Island flights

Get data-powered insights and trends into flights from Chicago to Saint Thomas Island to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Saint Thomas Island?

What is the cheapest Chicago to Saint Thomas Island flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Saint Thomas Island costs $500 on the route between Chicago O'Hare Intl Airport (ORD) and Saint Thomas Island (STT). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Saint Thomas Island?

The average price of all round-trip flights from Chicago to Saint Thomas Island clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Saint Thomas Island, look for departures on Wednesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Saint Thomas Island, Wednesday is the cheapest day to fly and Friday is the most expensive.

What is the cheapest month to fly from Chicago to Saint Thomas Island?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Saint Thomas Island, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Saint Thomas Island is September, where tickets cost $539 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $851 and $766 respectively.

How far in advance should I book a flight from Chicago to Saint Thomas Island?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Saint Thomas Island, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Saint Thomas Island, you should book around 4 weeks before departure, which saves you about 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$114
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Chicago O'Hare Airport to Saint Thomas Island

When to book flights from Chicago to Saint Thomas Island

Are your dates flexible? Find out the best times to travel from Chicago to Saint Thomas Island based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Saint Thomas Island

  • Which concierge services are available at STT Airport?

    STT offers meet and greet, porter services, and VIP lounge access suitable for corporate travelers. Request the services before arriving at the airport and once you step out of the aircraft, a personal assistant with your name tag will meet you. Your airport assistant will escort you to the private VIP lounge or an executive limousine while a dedicated porter will take care of your luggage.

  • Can I rent a car at STT?

    Yes. Travelers who wish to tour Charlotte Amalie and the surrounding driving can rent a car at STT upon arrival. In the arrivals hall, you will find car rental counters operated by Avis, Budget, and Hertz. They offer various types of cars, including SUVs, sedans, and vans.

  • Which airport in Chicago is suitable for traveling animals?

    Greater Rockford Airport (RFD) in Chicago is an ideal option for travelers accompanied by their pets or service animals. The airport allows service animals into the terminal building and provides pet-friendly facilities such as a doggie bag station and pet waste station. The airport has pet lodge services with pet relief and wash areas.

  • Are there public artworks at RFD?

    Yes. There are about 200 art pieces exhibited in the RFD terminal which passengers can walk around enjoying viewing during their downtime at the airport. You can also pass by the art gallery near the baggage claim to learn more about the airport's art collection.

  • What is the cheapest flight from Chicago to Saint Thomas Island?

    In the last 3 days, the lowest price for a flight from Chicago to Saint Thomas Island was $114 for a one-way ticket and $224 for a round-trip.

  • Do I need a passport to fly between Chicago and Saint Thomas Island?

    Yes, you’ll need a passport to travel to Saint Thomas Island from Chicago.

  • Which airports will I be using when flying from Chicago to Saint Thomas Island?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. Saint Thomas Island Cyril E King is the only airport in Saint Thomas Island. You’ll usually find the cheapest deals if you fly from Chicago O'Hare Airport.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Saint Thomas Island?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Saint Thomas Island flight route.

  • Which aircraft models fly most regularly from Chicago to Saint Thomas Island?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago to Saint Thomas Island flight route.

  • What is the most popular layover when flying to Saint Thomas Island from Chicago?

    Orlando is the most popular layover city among KAYAK users traveling from Chicago to Saint Thomas Island.

  • Which is the best airline for flights from Chicago to Saint Thomas Island, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Saint Thomas Island are Delta and United Airlines. With an average price for the route of $645 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $761 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Saint Thomas Island?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Saint Thomas Island.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Saint Thomas Island?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Saint Thomas Island from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Saint Thomas Island?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Saint Thomas Island with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Saint Thomas Island?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Saint Thomas Island from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Saint Thomas Island

  • Looking for a cheap flight? 25% of our users found flights on this route for $283 or less one-way and $595 or less round-trip.
  • Corporate travelers can consider Chicago O’Hare International Airport (ORD) to Cyril E King Airport (STT) route since ORD airport provides business facilities necessary to travelers on a business or work trip. Hilton O'Hare Airport Hotel near Terminals 1, 2, and 3 has a business center featuring meeting facilities such as ballrooms, workstations, and conference rooms where you can update your work or hold a short briefing before boarding.
  • Family travelers will gladly book their flights from Midway Airport (MDW) as it provides convenient family facilities. There is a baby care room on Concourse C near the yoga room which is private and comfortable for breastfeeding. Baby change rooms are available in all the washrooms throughout the airport. The airport’s restaurants provide kid-friendly menus and children’s high chairs.
  • If you are planning to drive to their departure airport, consider booking your flight from ORD Airport. The airport offers ample and safe parking facilities to its travelers. The main parking lots A, B, and C provide short-term and daily parking services. You can opt for extended stay services at the economy parking lots E and G. Travelers with international flights should consider parking at the International Lot D.
  • STT Airport is a suitable landing airport for disabled passengers. The airport provides special facilities to accommodate travelers with physical disabilities. Wheelchair-accessible public telephones, elevators, ramps, and automatic doors are available throughout the airport. Passengers on wheelchairs can also access toilets with grab rails in the terminals. The airport also provides ambulift to disembark from the aircraft.
  • STT Airport relieves its passengers from the hustle of looking for transportation services to get to their desired destinations after arriving as it offers various efficient ground transportation services to its arriving travelers. Group travelers can consider bus services provided by VITRAN, line 102 connecting the airport with multiple destinations in the city. Taxis run from the airport to the city center and are found outside the terminal.

Prefer to fly direct from Chicago to Saint Thomas Island?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Saint Thomas Island Cyril E King.
Find which airlines fly direct from Chicago to Saint Thomas Island Cyril E King Airport, which days they fly and book direct flights.

Direct departures

Chicago to Saint Thomas Island Cyril E King

Saturday

United Airlines, American Airlines

United Airlines, American Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Saint Thomas Island Cyril E King to Chicago

Saturday

United Airlines, American Airlines

United Airlines, American Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top 4 airlines serving from Chicago to Saint Thomas Island

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Saint Thomas Island. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Saint Thomas Island? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 7957 reviews
7.9Comfort
8.2Boarding
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

8.0 ExcellentTarun, Sep 2025MCO - LHR
Read more Delta reviews

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

Spirit rescheduled a 4:30 PM flight to 8:52 AM. That's ridiculous and borderline fraud.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The terminal crew is so rude cabin crew is extremely rude flight is very good

Spirit is low fare air line. Food also cost you. No free food.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

Everything you need to know for your flight from Chicago to Saint Thomas Island

Information on your arrival and departure airports

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