CHI - STT

$116 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 10/20. 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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Flights Deals

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

Tue, Aug 19 - Tue, Aug 26
Spirit Airlines Logo
8:12 pm - 1:48 pmORD-STT
16h 36m2 stops
Spirit Airlines Logo
2:43 pm - 10:22 pmSTT-ORD
8h 39m1 stop
$220Spirit Airlines
Find Deal
Sat, Nov 8 - Wed, Nov 12
Spirit Airlines Logo
6:05 am - 3:11 pmORD-STT
7h 06m1 stop
Spirit Airlines Logo
4:06 pm - 9:23 pmSTT-ORD
7h 17m1 stop
$223Spirit Airlines
Find Deal
Wed, Nov 5 - Tue, Nov 11
Spirit Airlines Logo
6:05 am - 3:11 pmORD-STT
7h 06m1 stop
Spirit Airlines Logo
4:06 pm - 9:23 pmSTT-ORD
7h 17m1 stop
$224Spirit Airlines
Find Deal
Sat, Oct 25 - Sat, Nov 1
Spirit Airlines Logo
11:48 am - 12:56 pmORD-STT
24h 08m2 stops
Spirit Airlines Logo
2:01 pm - 9:58 pmSTT-ORD
8h 57m1 stop
$231Spirit Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
Spirit Airlines Logo
8:56 pm - 1:56 pmORD-STT
16h 00m2 stops
Spirit Airlines Logo
4:06 pm - 9:23 pmSTT-ORD
7h 17m1 stop
$232Spirit Airlines
Find Deal
Mon, Aug 18 - Fri, Aug 22
Spirit Airlines Logo
8:12 pm - 1:48 pmORD-STT
16h 36m2 stops
Spirit Airlines Logo
2:43 pm - 10:22 pmSTT-ORD
8h 39m1 stop
$233Spirit Airlines
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
$584Delta
Find Deal
Mon, Dec 1 - Wed, Dec 17
Delta Logo
6:00 am - 2:22 pmMDW-STT
6h 22m1 stop
Delta Logo
3:32 pm - 9:44 pmSTT-MDW
8h 12m1 stop
$609Delta
Find Deal
Sat, Aug 23 - Sat, Aug 30
Delta Logo
6:04 am - 3:10 pmMDW-STT
8h 06m1 stop
Delta Logo
3:23 pm - 9:12 pmSTT-MDW
6h 49m1 stop
$614Delta
Find Deal
Sun, Aug 10 - Sun, Aug 17
 Logo
8:35 am - 9:48 amMDW-STT
24h 13m2 stops
 Logo
2:43 pm - 11:41 amSTT-MDW
21h 58m2 stops
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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Saint Thomas Island.

Our data shows that the cheapest route for a return flight from Chicago to Saint Thomas Island cost $500 and was between Chicago O'Hare Intl Airport (ORD) and Saint Thomas Island (STT). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $500.

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 $467 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $782 and $766 respectively.

Can I save money by flying with a layover from Chicago to Saint Thomas Island?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $1,250 on average.

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 2 weeks before departure, which saves you about 17% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$116
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 27% 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 $116 for a one-way ticket and $220 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.

  • Which airline alliances offer flights from Chicago to Saint Thomas Island?

    Star Alliance is the only airline alliance operating flights between Chicago and Saint Thomas Island.

  • On which days can I fly direct from Chicago to Saint Thomas Island?

    You can catch a nonstop flight from Chicago to Saint Thomas Island on on Saturday.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Saint Thomas Island are Delta and American Airlines. With an average price for the route of $647 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $659 and an overall rating of 7.2.

  • 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 $328 or less one-way and $574 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

United Airlines

See more direct flights

Direct returns

Saint Thomas Island Cyril E King to Chicago

Saturday

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.
8.0
DeltaOverall score based on 7980 reviews
8.2Boarding
7.9Comfort
8.5Crew
7.9Entertainment
7.3Food
Airline reviews

Delayed and took off even later than the scheduled delay time

8.0 ExcellentAnonymous, Jul 2025DTW - SEA
Read more Delta reviews

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

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!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

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.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Had a issue with catching flight due to airline, was unable to board flight

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Not great. Seats uncomfortable. Crew a little rude. Amenities like wifi and drinks way too expensive.

Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

We sat on the tarmac for an hour waiting for a gate to deplane.

Friendly employees, good seat, on time, Great flight. Pilot and attendants greeted passengers as we deplaned. However, I could not ever understand what the flight attendant was saying on the mic. It was too fast, and too loud.

Everything was fine, but there was no food or entertainment, so I didn’t know how to rate that.

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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