Cheap flights from the U.S. Virgin Islands to Chicago from $280
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the U.S. Virgin Islands to Chicago departing on 11/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
Saint Thomas IslandChicago
STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl
STTORD
Saint Thomas Island Cyril E King
Tue 11/3
1:07 pm-9:36 pm
1 stop10h 29m
Chicago O'Hare Intl
Mon 11/9
9:06 pm-3:38 pm
1 stop16h 32m
Saint Thomas IslandChicago
STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl
STTORD
Saint Thomas Island Cyril E King
Tue 11/3
3:15 pm-11:30 pm
2 stops10h 15m
Chicago O'Hare Intl
Mon 11/9
9:06 pm-3:38 pm
1 stop16h 32m
Saint Thomas IslandChicago
STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl
STTORD
Saint Thomas Island Cyril E King
Tue 11/3
3:15 pm-12:01 am
2 stops10h 46m
Chicago O'Hare Intl
Mon 11/9
6:49 pm-1:13 pm
1 stop16h 24m
Saint Thomas IslandChicago
STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl
STTORD
Saint Thomas Island Cyril E King
Tue 11/3
4:53 pm-8:00 am
1 stop17h 07m
Chicago O'Hare Intl
Mon 11/9
6:49 pm-1:13 pm
1 stop16h 24m
Saint Thomas IslandChicago
STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl
STTORD
Saint Thomas Island Cyril E King
Tue 11/3
1:07 pm-10:30 pm
2 stops11h 23m
Chicago O'Hare Intl
Mon 11/9
9:06 pm-1:13 pm
1 stop14h 07m
Saint Thomas IslandChicago
STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl
STTORD
Saint Thomas Island Cyril E King
Tue 11/3
3:15 pm-11:56 pm
1 stop10h 41m
Chicago O'Hare Intl
Mon 11/9
9:06 pm-1:13 pm
1 stop14h 07m
Saint Thomas IslandChicago
STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl
STTORD
Saint Thomas Island Cyril E King
Tue 11/3
4:33 pm-12:01 am
1 stop9h 28m
Chicago O'Hare Intl
Mon 11/9
8:57 pm-12:16 pm
2 stops13h 19m
Saint Thomas IslandChicago
STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl
STTORD
Saint Thomas Island Cyril E King
Tue 11/3
2:01 pm-11:09 pm
2 stops11h 08m
Chicago O'Hare Intl
Mon 11/9
8:57 pm-12:16 pm
2 stops13h 19m
Saint Thomas IslandChicago
STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl
STTORD
Saint Thomas Island Cyril E King
Tue 11/3
5:59 pm-1:44 pm
2 stops21h 45m
Chicago O'Hare Intl
Mon 11/9
7:00 am-5:08 pm
2 stops32h 08m
Saint Thomas IslandChicago
STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl
STTORD
Saint Thomas Island Cyril E King
Tue 11/3
5:59 pm-11:57 pm
2 stops31h 58m
Chicago O'Hare Intl
Mon 11/9
2:59 pm-4:15 pm
2 stops23h 16m
See travel insights to Chicago from
How to get the cheapest flight ticket from U.S. Virgin Islands to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $486. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from U.S. Virgin Islands to Chicago for around $684.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from U.S. Virgin Islands to Chicago during this time can be as low as $486. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $541.
What is the cheapest U.S. Virgin Islands to Chicago flight route?
Fly from Saint Thomas Island Cyril E King to Chicago O'Hare Intl for the best U.S. Virgin Islands - Chicago flight prices
What cabin class options are available on U.S. Virgin Islands to Chicago flights?
There are 2 cabin classes available to choose from on U.S. Virgin Islands to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Cheap U.S. Virgin Islands to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from U.S. Virgin Islands to Chicago
Frequently asked questions about flying from the U.S. Virgin Islands to Chicago
When did momondo last update prices for flights from U.S. Virgin Islands to Chicago?
Prices for flights from U.S. Virgin Islands to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from U.S. Virgin Islands to Chicago?
As of October 2026, there is 1 operator available to choose from for flights from U.S. Virgin Islands to Chicago.
How old do you have to be to fly from U.S. Virgin Islands to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from U.S. Virgin Islands to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from U.S. Virgin Islands to Chicago?
momondo data reveals that the most frequently booked plane model on the route from U.S. Virgin Islands to Chicago is Boeing 737-800, representing 50.00% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 25.00% and Airbus A319 at 25.00%.
Best airlines flying from U.S. Virgin Islands to Chicago
Compare and see reviews for airlines that fly from U.S. Virgin Islands to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $306 | Free Cancellation | Rating 7.0 12,130 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from U.S. Virgin Islands to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from U.S. Virgin Islands to Chicago. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from U.S. Virgin Islands to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from U.S. Virgin Islands which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from U.S. Virgin Islands to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from U.S. Virgin Islands.
I’m not ready to book a flight from U.S. Virgin Islands to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for U.S. Virgin Islands to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.