CHI - STT

$61 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 3/9. 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
$375
Overall average: $665
Spirit Airlines
Sun 2/15Sun 2/22
ORD - STT • 2 stops
Cheapest non-stop
$521
Typical prices: $560-$1,547
American Airlines
Wed 3/4Wed 3/11
ORD - STT • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
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 airlines
Spirit Airlines
Cheapest • from $375 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD
-
STT
Cheapest
ORD
-
STT
Most popular
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 7% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 15% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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We hope you love your trip to Saint Thomas Island!
Flight Deals
Booking Insights
Expert advice
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

Sun, Feb 15 - Sun, Feb 22
Spirit Airlines Logo
4:43 pm - 2:31 pm
ORD
-
STT
19h 48m
2 stops
Spirit Airlines Logo
3:36 pm - 7:54 am
STT
-
ORD
18h 18m
2 stops
$375Spirit Airlines
Thu, Mar 19 - Thu, Mar 26
Spirit Airlines Logo
7:17 am - 1:26 pm
ORD
-
STT
29h 09m
2 stops
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
$376Spirit Airlines
Mon, Mar 23 - Sun, Mar 29
Spirit Airlines Logo
8:41 pm - 1:26 pm
ORD
-
STT
15h 45m
2 stops
Spirit Airlines Logo
4:35 pm - 8:00 pm
STT
-
ORD
28h 25m
2 stops
$377Spirit Airlines
Thu, Mar 19 - Wed, Mar 25
Spirit Airlines Logo
10:55 am - 3:28 pm
ORD
-
STT
27h 33m
3 stops
Spirit Airlines Logo
4:35 pm - 2:16 pm
STT
-
ORD
22h 41m
2 stops
$378Spirit Airlines
Wed, Feb 11 - Sat, Feb 21
Spirit Airlines Logo
5:15 am - 4:37 pm
ORD
-
STT
9h 22m
1 stop
Spirit Airlines Logo
3:36 pm - 7:54 am
STT
-
ORD
18h 18m
2 stops
$379Spirit Airlines
Tue, Jul 14 - Tue, Jul 21
Spirit Airlines Logo
5:32 pm - 9:33 am
ORD
-
STT
15h 01m
1 stop
Spirit Airlines Logo
3:12 pm - 10:08 pm
STT
-
ORD
7h 56m
1 stop
$380Spirit Airlines
Mon, Apr 13 - Sun, Apr 19
Multiple Airlines Logo
9:04 pm - 1:26 pm
MDW
-
STT
15h 22m
1 stop
Multiple Airlines Logo
2:36 pm - 8:04 am
STT
-
MDW
18h 28m
1 stop
$384Multiple Airlines
Wed, Apr 8 - Tue, Apr 14
Southwest Logo
8:50 pm - 1:35 pm
MDW
-
STT
15h 45m
2 stops
Southwest Logo
2:10 pm - 11:05 pm
STT
-
MDW
9h 55m
2 stops
$468Southwest
Sat, Feb 28 - Fri, Mar 6
Southwest Logo
5:20 am - 2:55 pm
MDW
-
STT
7h 35m
1 stop
Southwest Logo
2:50 pm - 7:40 am
STT
-
MDW
18h 50m
2 stops
$484Southwest
Mon, Mar 2 - Thu, Mar 5
Southwest Logo
3:25 pm - 2:55 pm
MDW
-
STT
21h 30m
2 stops
Southwest Logo
2:50 pm - 11:00 pm
STT
-
MDW
10h 10m
2 stops
$514Southwest
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 February.

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 Thursdays and avoid leaving on a Saturday, 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 May, where tickets cost $546 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $980 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.

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 2 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 seasonSeptember
Cheapest flight$61
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 8% 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 $61 for a one-way ticket and $375 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?

    There are nonstop flights from Chicago to Saint Thomas Island on a daily basis.

  • 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 $669 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 $748 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 $352 or less one-way and $606 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

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Saint Thomas Island Cyril E King to Chicago

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American 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 8130 reviews
8.5Crew
8.1Boarding
7.9Comfort
7.2Food
7.8Entertainment
Airline reviews

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

2.0 MediocreTodd, Jan 2026
IAH - ATL
Read more Delta reviews

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

It was smooth sailing snags we had a really smooth landing and a great flight!

I know it's a low-cost airline. However, the seats are very basic, so after two hours of travel, they feel very uncomfortable and cannot be reclined. The two flights from Bogota to Orlando and the return flight were very punctual. The check-in process on the app works very well. I really liked the self-check-in process for luggage at the Orlando airport; it was quick, easy, and very convenient.

The entire experience was so surprisingly pleasant. And the blocked extra seat between us was such an amazing and nice bonus. Great experience all around and I can’t wait to fly with spirit again!

Everything was OK, the deicing took a long time, our connections were almost missed.

All very good except they didn’t load our walker so haven’t gotten it yet

Flight was cancelled. But kayak thought it was still on time.

For the cost you can't e too critical, but the inablitiy to recline the seat and minimal cushioning in the seats made for a less than comfortable flight. Other than that we had an ealry departure and arrival, boarding was smooth.

The flight was delayed by 2 hours and we had no food or water or chargers

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

Nothing everything cost money a bottle of water is 5 dollars and there wasn't even an outlet to plug 🔌 in my 📱 phone

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

Information on your arrival and departure airports