STT - ORD

$217 Find Cheap Flights from Saint Thomas Island to Chicago - 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 Saint Thomas Island to O'Hare Intl departing on 9/29. 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.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$493
JetBlue
Wed 9/16Sun 9/20
STT - ORD • 2 stops
Cheapest non-stop
$771
American Airlines
Tue 12/22Tue 12/29
STT - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Economy Plus adds up to six inches more legroom than standard economy.
American Main Cabin Extra includes early boarding and complimentary drinks.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
Sat
You can fly direct with United Airlines. Average duration is 0
Direct flights
Direct flights
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+1
Direct flights
Direct flights
+1
Top airlines
Cheapest • from $493 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
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Airline reviews
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Flight Deals

Cheap Flights from Saint Thomas Island to O'Hare Intl (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 O'Hare Intl 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

Wed, Sep 16 - Sun, Sep 20
JetBlue Logo
3:00 pm - 11:08 pm
STT
-
ORD
9h 08m
2 stops
JetBlue Logo
3:00 pm - 2:01 pm
ORD
-
STT
22h 01m
2 stops
$493JetBlue
Thu, Sep 10 - Tue, Sep 15
JetBlue Logo
3:00 pm - 11:08 pm
STT
-
ORD
9h 08m
2 stops
JetBlue Logo
8:24 pm - 2:01 pm
ORD
-
STT
16h 37m
2 stops
$524JetBlue
Thu, Sep 17 - Sun, Sep 20
JetBlue Logo
3:00 pm - 11:08 pm
STT
-
ORD
9h 08m
2 stops
JetBlue Logo
8:24 pm - 2:01 pm
ORD
-
STT
16h 37m
2 stops
$588JetBlue
Wed, Sep 16 - Sun, Sep 20
JetBlue Logo
3:00 pm - 11:08 pm
STT
-
ORD
9h 08m
2 stops
JetBlue Logo
8:24 pm - 2:01 pm
ORD
-
STT
16h 37m
2 stops
$589JetBlue
Sat, Sep 19 - Sat, Oct 10
United Airlines Logo
2:10 pm - 10:15 pm
STT
-
ORD
9h 05m
1 stop
United Airlines Logo
5:30 am - 3:43 pm
ORD
-
STT
9h 13m
1 stop
$590United Airlines
Thu, Sep 10 - Tue, Sep 15
JetBlue Logo
3:00 pm - 1:45 pm
STT
-
ORD
23h 45m
2 stops
JetBlue Logo
7:05 am - 2:01 pm
ORD
-
STT
29h 56m
2 stops
$594JetBlue
Thu, Sep 17 - Mon, Sep 21
JetBlue Logo
3:00 pm - 11:08 pm
STT
-
ORD
9h 08m
2 stops
JetBlue Logo
8:24 pm - 2:01 pm
ORD
-
STT
16h 37m
2 stops
$619JetBlue
Wed, Sep 16 - Mon, Sep 21
JetBlue Logo
3:00 pm - 11:08 pm
STT
-
ORD
9h 08m
2 stops
JetBlue Logo
8:24 pm - 2:01 pm
ORD
-
STT
16h 37m
2 stops
$619JetBlue
Sat, Sep 19 - Sat, Oct 10
American Airlines Logo
1:41 pm - 11:50 pm
STT
-
ORD
11h 09m
2 stops
American Airlines Logo
6:40 pm - 12:39 pm
ORD
-
STT
16h 59m
1 stop
$685American Airlines
Wed, Sep 16 - Thu, Oct 8
American Airlines Logo
1:41 pm - 8:38 am
STT
-
ORD
19h 57m
2 stops
American Airlines Logo
5:18 am - 12:39 pm
ORD
-
STT
6h 21m
1 stop
$700American Airlines
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 Sundays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Chicago, Thursday is the cheapest day to fly and Saturday is the most expensive.

Can I save money by flying with a layover from Saint Thomas Island to Chicago O'Hare Intl Airport?

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

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $1,120 on average.

Expert advice

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

 
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
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.

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.

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

Cheapest flight

$217
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 5 days, the lowest price for a flight from Saint Thomas Island to Chicago O'Hare Intl Airport was $217 for a one-way ticket and $493 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 is the only airline alliance operating flights between Saint Thomas Island and Chicago.

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

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

  • 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 $330 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

United Airlines

See more direct flights

Direct returns

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

Saturday

United Airlines

United Airlines

See more direct flights

Reviews of the top airline flying 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.
7.1
American AirlinesOverall score based on 11845 reviews
6.8Entertainment
7.2Comfort
7.9Crew
6.4Food
7.5Boarding
Airline reviews

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

10.0 ExcellentAnonymous, Jul 2026
LAX - ORD
Read more American Airlines reviews

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

This may have been the hottest cabin temperatures I have experienced on any flight prior to take off lasting for approximately 30 minutes. I am not typically one to complain but I was genuinely worried about the health of several passengers on the flight due to the extreme temperatures including a small toddler.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

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

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