CHI - STT

$233 Find Cheap Flights from Chicago to Saint Thomas Island - Compare and Save

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 9/7. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$460
Typical prices: $771-$319
JetBlue
Mon 8/3Tue 8/11
ORD - STT • 1 stop
Cheapest non-stop
$791
Typical prices: $3,562-$537
United Airlines
Sat 6/27Sat 7/4
ORD - STT • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Main Cabin Extra adds early boarding; United Economy Plus boosts legroom.
Use the American app for entertainment; check United Wi-Fi coverage before buying.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
Sat
You can fly direct with United Airlines. Average duration is 5h 01m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top airlines
Cheapest • from $460 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $590 (round-trip)
Shortest trip • 6h 35m (one-way)
Insights
Insights
Insights
Insights
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 76% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 7% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 61% price drop
Most popular
Good to know
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Flight 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

Mon, Aug 3 - Tue, Aug 11
JetBlue Logo
8:10 pm - 2:03 pm
ORD
-
STT
16h 53m
1 stop
JetBlue Logo
2:58 pm - 10:06 am
STT
-
ORD
20h 08m
2 stops
$460JetBlue
Thu, Jul 30 - Tue, Aug 4
JetBlue Logo
8:10 pm - 1:59 pm
ORD
-
STT
16h 49m
1 stop
JetBlue Logo
2:58 pm - 7:30 pm
STT
-
ORD
29h 32m
2 stops
$469JetBlue
Mon, Aug 24 - Fri, Aug 28
JetBlue Logo
8:20 pm - 2:03 pm
ORD
-
STT
16h 43m
1 stop
JetBlue Logo
2:58 pm - 12:59 pm
STT
-
ORD
23h 01m
2 stops
$491JetBlue
Mon, Sep 21 - Sat, Sep 26
Southwest Logo
5:00 am - 1:50 pm
MDW
-
STT
7h 50m
1 stop
Southwest Logo
2:05 pm - 8:55 pm
STT
-
MDW
7h 50m
1 stop
$543Southwest
Sat, Aug 29 - Sun, Sep 6
Southwest Logo
6:00 pm - 1:25 pm
MDW
-
STT
18h 25m
2 stops
Southwest Logo
2:10 pm - 9:50 pm
STT
-
MDW
8h 40m
1 stop
$572Southwest
Tue, Sep 22 - Tue, Sep 29
Delta Logo
6:05 am - 1:44 pm
MDW
-
STT
6h 39m
1 stop
Delta Logo
2:54 pm - 10:25 pm
STT
-
MDW
8h 31m
1 stop
$580Delta
Sun, Aug 16 - Sat, Aug 29
Delta Logo
6:05 am - 1:34 pm
MDW
-
STT
6h 29m
1 stop
Delta Logo
4:13 pm - 10:36 pm
STT
-
MDW
7h 23m
1 stop
$585Delta
Tue, Sep 22 - Tue, Sep 29
Delta Logo
6:05 am - 1:44 pm
MDW
-
STT
6h 39m
1 stop
Delta Logo
2:54 pm - 10:25 pm
STT
-
MDW
8h 31m
1 stop
$590Delta
Sun, Aug 16 - Sat, Aug 29
Delta Logo
6:05 am - 1:34 pm
MDW
-
STT
6h 29m
1 stop
Delta Logo
4:13 pm - 10:36 pm
STT
-
MDW
7h 23m
1 stop
$595Delta
Mon, Sep 21 - Sat, Sep 26
Southwest Logo
5:00 am - 1:50 pm
MDW
-
STT
7h 50m
1 stop
Southwest Logo
2:05 pm - 8:55 pm
STT
-
MDW
7h 50m
1 stop
$636Southwest
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Saint Thomas Island departing in August.

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 $580 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 Thursdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Saint Thomas Island, Sunday 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 April, where tickets cost $80 (return) on average. On the other hand, the most expensive months are June and September, where the average cost of round-trip tickets is $287 and $261 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.

No, with an average price for the route of $634, prices are generally cheapest when you fly direct.

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 3 weeks before departure, which saves you about 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Saint Thomas Island

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

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.

Marisa Garcia

Marisa Garcia

Expert on STT

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.

Good to know

Low seasonAugust
Cheapest flight$233
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Chicago Midway 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 5 days, the lowest price for a flight from Chicago to Saint Thomas Island was $233 for a one-way ticket and $460 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?

    American Airlines, and JetBlue offer 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?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Saint Thomas Island, with SkyTeam being the most commonly used for this route.

  • 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 Southwest?

    The two airlines most popular with KAYAK users for flights from Chicago to Saint Thomas Island are Delta and Southwest. With an average price for the route of $684 and an overall rating of 7.9, Delta is the most popular choice. Southwest is also a great choice for the route, with an average price of $760 and an overall rating of 7.9.

  • 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 $671 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.
7.9
SouthwestOverall score based on 4235 reviews
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

10.0 ExcellentAnonymous, Jun 2026
DEN - ORF
Read more Southwest reviews

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

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

Information on your arrival and departure airports