Find Cheap Flights from Chicago to Saint Thomas (CHI - STT)

Flights overview

Useful information for finding cheap flights from Chicago to Saint Thomas and booking your next trip

Cheapest round-trip flights	$335	Spirit 1 stop 7 hr Mon, May 4 — Wed, May 13	The cheapest round-trip flight from Chicago to Saint Thomas is currently $335
Cheapest one-way flight	$155	Spirit 1 stop 7 hr Mon, May 4	The cheapest one-way flight from Chicago to Saint Thomas is currently $155
Cheapest nonstop flights	$621	United Nonstop 6 hr Sat, May 16 — Sat, May 23	The cheapest nonstop round-trip flight from Chicago to Saint Thomas is currently $621
Last-minute weekend getaway	$672	Southwest 1 stop 7 hr Fri, Apr 17 — Mon, Apr 20	The cheapest last-minute weekend getaway from Chicago to Saint Thomas is currently $672
Cheapest business class flights	$1,083	American 2 stops 16 hr Sat, May 9 — Fri, May 15	The cheapest business class round-trip flight from Chicago to Saint Thomas is currently $1,083

Fastest flight	5 hr 1 min	The fastest nonstop flight from Chicago to Saint Thomas takes 5 hr 1 min
Nonstop flights	Every day	There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Chicago to Saint Thomas is typically October. The most expensive month to fly is typically March.

October Cheapest	Typical prices: $275–445
March Most expensive	Typical prices: $335–710

Popular airlines from Chicago to Saint Thomas

Southwest

from $547

Typical price: $590–1,200

924 weekly connecting flights

MDW, ORD - STT Every day
United

Nonstop

from $388

Typical price: $460–1,150

7 weekly nonstop flights

ORD - STT Every day

167 weekly connecting flights

ORD - STT Every day
American

from $580

Typical price: $510–870

489 weekly connecting flights

ORD - STT Every day
Delta

from $580

Typical price: $650–1,350

373 weekly connecting flights

MDW, ORD - STT Every day
Spirit

from $337

Typical price: $300–600

22 weekly connecting flights

ORD - STT Every day
JetBlue

10 weekly connecting flights

ORD - STT Every Mon, Tue, Wed, Thu, Fri, Sun

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 25 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 24 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Popular airports near Saint Thomas

Cyril E. King Airport (STT)

Saint Thomas U.S. Virgin Islands 22 min 5 mi
St Thomas Island Charlotte Amalie SPB (SPB)

Saint Thomas United States 16 min 2 mi

Frequently asked questions about flying from Chicago to Saint Thomas

The cheapest flights from Chicago to Saint Thomas are usually in October. Typical ticket prices in October range from $275 to $445.

The cheapest round-trip flight from Chicago to Saint Thomas recently found on Google Flights was with Spirit from $335. The cheapest one-way flight was with Spirit from $155.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Chicago to Saint Thomas is $547, flying from Jul 12 to Jul 20.
The cheapest United flight from Chicago to Saint Thomas is $388, flying from May 4 to May 12.
The cheapest American flight from Chicago to Saint Thomas is $580, flying from Jul 2 to Jul 8.
The cheapest Delta flight from Chicago to Saint Thomas is $580, flying from Jul 12 to Jul 21.
The cheapest Spirit flight from Chicago to Saint Thomas is $337, flying from May 4 to May 11.

The cheapest round-trip flight from Chicago to Saint Thomas starts at $335 from Mon, May 4 to Wed, May 13. The cheapest one-way flight starts at $155 and departs on Mon, May 4.

5 hr 1 min is the shortest flight time from Chicago to Saint Thomas.

Peak travel season runs Dec–Mar, with hot daytime temperatures and breezy evenings. Apr–Aug is balmy and generally dry, while Aug–Nov is rainy/hurricane season. The island’s biggest yearly event is its colourful Carnival celebration in Apr/May.

It's easy to use Google Flights to find the cheapest days to fly from Chicago to Saint Thomas.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Chicago to Saint Thomas really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Chicago to Saint Thomas.

In terms of nonstop flights, United is the most popular. United offers 7 nonstop flights and 167 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Cyril E. King Airport (STT) .

In terms of flights, Southwest is the most popular. Southwest offers 924 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Cyril E. King Airport (STT) .

Other popular airlines flying from Chicago to Saint Thomas are:

American offers 489 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Cyril E. King Airport (STT) .
Delta offers 373 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Cyril E. King Airport (STT) .
Spirit offers 22 connecting flights per week. Spirit flies from Chicago O'Hare International Airport (ORD) to Cyril E. King Airport (STT) .
JetBlue offers 10 connecting flights per week. JetBlue flies from Chicago O'Hare International Airport (ORD) to Cyril E. King Airport (STT) .

The number of connecting flights refers to distinct flights with at least one stop between Chicago and Saint Thomas.

The cheapest round-trip flight from Chicago to Saint Thomas recently found on Google Flights was with Spirit from $335. The cheapest one-way flight was with Spirit from $155.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Chicago to Saint Thomas is $547, flying from Jul 12 to Jul 20.
The cheapest United flight from Chicago to Saint Thomas is $388, flying from May 4 to May 12.
The cheapest American flight from Chicago to Saint Thomas is $580, flying from Jul 2 to Jul 8.
The cheapest Delta flight from Chicago to Saint Thomas is $580, flying from Jul 12 to Jul 21.
The cheapest Spirit flight from Chicago to Saint Thomas is $337, flying from May 4 to May 11.

United flies direct from Chicago to Saint Thomas.

There are 7 United direct flights from Chicago to Saint Thomas per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Chicago and Saint Thomas at price $672 is offered by Southwest from Fri, Apr 17 to Mon, Apr 20.

United flies direct from Chicago to Saint Thomas.

There are 7 United direct flights from Chicago to Saint Thomas per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

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

The cheapest direct (nonstop) round-trip flights between Chicago and Saint Thomas start at $621 from Sat, May 16 to Sat, May 23 with United.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to Saint Thomas, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Chicago and Saint Thomas start at $1,083 from Sat, May 9 to Fri, May 15 with American.

The cheapest economy class round-trip flights between Chicago and Saint Thomas start at $335 from Mon, May 4 to Wed, May 13.

To book business class trips from Chicago to Saint Thomas, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Chicago and Saint Thomas starts at $672 from Fri, Apr 17 to Mon, Apr 20 with Southwest.

The cheapest last-minute deal between Chicago and Saint Thomas at price $672 is offered by Southwest from Fri, Apr 17 to Mon, Apr 20.

To find last-minute flight deals from Chicago to Saint Thomas, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.