STT - ORD

$124 Find Cheap Flights from Saint Thomas Island to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Saint Thomas Island to O'Hare Intl departing on 10/11. 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 Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Saint Thomas Island to Chicago, 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 Saint Thomas Island to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Saint Thomas Island to Chicago (STT-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Saint Thomas Island to Chicago 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 Saint Thomas Island to O'Hare Intl

Mon, Oct 27 - Mon, Nov 3
Spirit Airlines Logo
11:01 am - 1:03 amSTT-ORD
15h 02m1 stop
Spirit Airlines Logo
2:14 pm - 10:51 amORD-STT
18h 37m1 stop
$293Spirit Airlines
Find Deal
Mon, Oct 27 - Mon, Nov 3
Spirit Airlines Logo
11:01 am - 1:03 amSTT-ORD
15h 02m1 stop
Spirit Airlines Logo
3:29 pm - 10:51 amORD-STT
17h 22m2 stops
$315Spirit Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Spirit Airlines Logo
10:49 am - 5:39 pmSTT-ORD
7h 50m1 stop
Spirit Airlines Logo
5:05 am - 9:56 amORD-STT
27h 51m1 stop
$324Spirit Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
Spirit Airlines Logo
10:49 am - 10:48 pmSTT-ORD
12h 59m1 stop
Spirit Airlines Logo
6:44 pm - 9:56 amORD-STT
14h 12m1 stop
$339Spirit Airlines
Find Deal
Mon, Oct 27 - Mon, Nov 3
Spirit Airlines Logo
11:01 am - 1:03 amSTT-ORD
15h 02m1 stop
Spirit Airlines Logo
7:25 am - 10:51 amORD-STT
25h 26m3 stops
$348Spirit Airlines
Find Deal
Wed, Nov 26 - Sun, Nov 30
American Airlines Logo
4:27 pm - 11:56 pmSTT-ORD
9h 29m1 stop
American Airlines Logo
5:00 am - 5:27 pmORD-STT
10h 27m1 stop
$584American Airlines
Find Deal
Wed, Nov 26 - Sun, Nov 30
American Airlines Logo
4:27 pm - 11:56 pmSTT-ORD
9h 29m1 stop
American Airlines Logo
6:07 am - 5:27 pmORD-STT
9h 20m2 stops
$634American Airlines
Find Deal
Wed, Nov 26 - Sun, Nov 30
United Airlines Logo
1:02 pm - 6:30 pmSTT-ORD
7h 28m1 stop
United Airlines Logo
9:30 am - 4:18 pmORD-STT
4h 48mnonstop
$649United Airlines
Find Deal
Tue, Mar 10 - Wed, Mar 11
United Airlines Logo
2:40 pm - 10:36 pmSTT-ORD
8h 56m1 stop
United Airlines Logo
9:30 am - 3:18 pmORD-STT
4h 48mnonstop
$659United Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Delta Logo
2:43 pm - 9:25 pmSTT-ORD
7h 42m1 stop
Delta Logo
5:30 am - 1:33 pmORD-STT
7h 03m1 stop
$759Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers extra legroom on this route.
Arrive at STT 3 hours early due to customs lines.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Spirit Airlines
Cheapest • from $293 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
2 days a week
There are direct flights from Saint Thomas Island to O'Hare Intl 2 days a week: Sat, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
Cheapest round-trip
$293
Spirit Airlines
Mon 10/27Mon 11/3
STT - ORD • 1 stop
Cheapest non-stop
$660
United Airlines
Tue 3/10Wed 3/11
STT - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to O'Hare Intl!
Expert advice

Expert advice for your flight from Saint Thomas Island to O'Hare Intl

 
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

American Airlines' Main Cabin Extra includes early boarding and complimentary alcoholic drinks.


American's Flagship Lounges offer upgraded seating, meals, and cocktail service for eligible passengers.

United Airlines

United's Economy Plus offers up to six inches more legroom than standard economy seats.


United's Premier Access provides priority check-in and boarding for eligible passengers.

Airports
STT

Arrive at STT at least three hours before departure due to customs lines, especially on busy days like Saturdays.

Read more about STTby Marisa Garcia
ORD

Take the CTA Blue Line train from ORD to downtown Chicago for a reliable 45-minute commute, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
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 Saint Thomas Island to O'Hare Intl flights

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

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

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

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

Good to know

Cheapest flight$124
Flight from Saint Thomas Island to Chicago

When to book flights from Saint Thomas Island to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Saint Thomas Island to O'Hare Intl 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 Saint Thomas Island to Chicago flights

  • What is the cheapest flight from Saint Thomas Island to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Saint Thomas Island to Chicago O'Hare Intl Airport was $124 for a one-way ticket and $293 for a round-trip.

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

    Yes

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

    When flying out of Saint Thomas Island you will be using Saint Thomas Island Cyril E King. You will be landing at Chicago, also known as Chicago O'Hare Intl.

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Saint Thomas Island to Chicago are United Airlines and American Airlines. With an average price for the route of $593 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $634 and an overall rating of 7.2.

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

    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 Saint Thomas Island to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Saint Thomas Island 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 Saint Thomas Island to Chicago?

    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 Chicago with an airline and back to Saint Thomas Island with another airline. Booking your flights between Saint Thomas Island and ORD can sometimes prove cheaper using this method.

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

    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 Chicago from Saint Thomas Island 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 Saint Thomas Island to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $382 or less one-way.

Prefer to fly direct from Saint Thomas Island to Chicago?

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

Direct departures

Saint Thomas Island Cyril E King to Chicago O'Hare Intl

Saturday

United Airlines, American Airlines

United Airlines, American Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago O'Hare Intl to Saint Thomas Island Cyril E King

Saturday

United Airlines, American Airlines

United Airlines, American Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top 3 airlines serving from Saint Thomas Island to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Saint Thomas Island to Chicago. 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 Saint Thomas Island to O'Hare Intl? 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.
7.4
United AirlinesOverall score based on 8924 reviews
7.3Comfort
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
Airline reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

8.0 ExcellentAnonymous, Aug 2025YOW - ORD
Read more United Airlines reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

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

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

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

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.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Everything you need to know for your flight from Saint Thomas Island to O'Hare Intl

Information on your arrival and departure airports

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