CHI - STT

$145 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 5/29. 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.
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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 Flight Deals 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.

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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Saint Thomas Island.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
12:41 pm - 9:57 amORD-STT
20h 16m1 stop
Spirit Airlines Logo
10:52 am - 12:05 amSTT-ORD
14h 13m1 stop
$297Spirit Airlines
Find Deal
Tue, Jun 3 - Sat, Jun 7
Spirit Airlines Logo
7:47 am - 3:30 pmORD-STT
6h 43m1 stop
Spirit Airlines Logo
4:35 pm - 11:29 pmSTT-ORD
7h 54m1 stop
$300Spirit Airlines
Find Deal
Thu, May 29 - Thu, Jun 5
 Logo
7:47 am - 3:30 pmORD-STT
6h 43m1 stop
 Logo
2:41 pm - 12:20 amSTT-ORD
10h 39m1 stop
Thu, May 22 - Mon, May 26
American Airlines Logo
5:15 am - 3:55 pmORD-STT
9h 40m2 stops
American Airlines Logo
5:05 pm - 9:02 amSTT-ORD
16h 57m1 stop
$499American Airlines
Find Deal
Thu, Jul 24 - Thu, Jul 31
 Logo
7:35 pm - 9:57 amORD-STT
13h 22m1 stop
 Logo
6:05 pm - 6:29 pmSTT-ORD
25h 24m2 stops
Thu, May 15 - Sun, May 18
American Airlines Logo
6:55 pm - 12:50 pmORD-STT
16h 55m1 stop
American Airlines Logo
5:15 pm - 9:02 amSTT-ORD
16h 47m1 stop
$529American Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 13
Delta Logo
6:00 am - 3:00 pmMDW-STT
8h 00m1 stop
Delta Logo
3:02 pm - 9:41 pmSTT-MDW
7h 39m1 stop
$539Delta
Find Deal
Mon, Jul 28 - Fri, Aug 1
Delta Logo
6:00 am - 3:10 pmMDW-STT
8h 10m1 stop
Delta Logo
2:51 pm - 9:27 pmSTT-MDW
7h 36m1 stop
$579Delta
Find Deal
Mon, Jun 2 - Thu, Jun 5
United Airlines Logo
7:25 am - 1:15 pmORD-STT
4h 50mnonstop
United Airlines Logo
3:17 pm - 6:52 pmSTT-ORD
5h 35mnonstop
$580United Airlines
Find Deal
Sun, Oct 26 - Sun, Nov 2
United Airlines Logo
8:48 am - 2:54 pmORD-STT
5h 06mnonstop
United Airlines Logo
4:00 pm - 12:15 amSTT-ORD
9h 15m1 stop
$585United Airlines
Find Deal
Sat, Aug 9 - Sat, Aug 16
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. Confirm rates before boarding to avoid surprises. Renting a car is recommended for flexibility.

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
Useful Info

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.

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 $470 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 $470.

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, Thursday is the cheapest day to fly and Saturday 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 $447 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $867 and $753 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$145
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 42% 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 $145 for a one-way ticket and $297 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 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 $679 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $763 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 $328 or less one-way and $620 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?

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

Sunday

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
See more direct flights

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 7934 reviews
8.2Boarding
7.9Entertainment
8.5Crew
7.9Comfort
7.3Food
Airline reviews

Our bag was lost so that made unnecessary chaos On our trip

6.0 GoodBarbara, Apr 2025JFK - FCO
Read more Delta reviews

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

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.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

Flight was 2hours late they had no crew or the pilot.

I paid for streaming wifi and the connection was poor.

We had an 8 hr delay so it was not good

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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