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

Flights overview

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

Cheapest round-trip flights	$366	Spirit 1 stop 11 hr Thu, May 21 — Thu, May 28	The cheapest round-trip flight from Saint Thomas to Chicago is currently $366
Cheapest one-way flight	$208	Spirit 1 stop 11 hr Thu, Jul 23	The cheapest one-way flight from Saint Thomas to Chicago is currently $208
Cheapest nonstop flights	$581	United Nonstop 6 hr Sat, Jul 11 — Sat, Jul 18	The cheapest nonstop round-trip flight from Saint Thomas to Chicago is currently $581
Last-minute weekend getaway	$562	Southwest 1 stop 9 hr Thu, Apr 30 — Sun, May 3	The cheapest last-minute weekend getaway from Saint Thomas to Chicago is currently $562
Cheapest business class flights	$1,055	United 1 stop 8 hr Sun, Jul 26 — Sun, Aug 2	The cheapest business class round-trip flight from Saint Thomas to Chicago is currently $1,055

Fastest flight	5 hr 34 min	The fastest nonstop flight from Saint Thomas to Chicago takes 5 hr 34 min
Nonstop flights	Some days	There are direct flights on this route 4 days a week: Mon, Tue, Wed, Sat.

When is the cheapest time to fly?

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

October Cheapest	Typical prices: $275–500
December Most expensive	Typical prices: $370–610

Popular airlines from Saint Thomas to Chicago

Southwest

from $637

Typical price: $630–1,200

794 weekly connecting flights

STT - MDW, ORD Every day
Delta

from $580

Typical price: $660–1,350

331 weekly connecting flights

STT - MDW, ORD Every day
United

Nonstop

from $430

Typical price: $475–1,200

4 weekly nonstop flights

STT - ORD Every Mon, Tue, Wed, Sat, Sun

81 weekly connecting flights

STT - ORD Every day
American

from $580

Typical price: $520–870

245 weekly connecting flights

STT - ORD Every day
Spirit

from $366

Typical price: $310–590

32 weekly connecting flights

STT - ORD Every day
JetBlue

1 weekly connecting flight

STT - ORD Every Sat

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

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 26 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 25 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

Frequently asked questions about flying from Saint Thomas to Chicago

The cheapest flights from Saint Thomas to Chicago are usually in October. Typical ticket prices in October range from $275 to $500.

The cheapest round-trip flight from Saint Thomas to Chicago recently found on Google Flights was with Spirit from $366. The cheapest one-way flight was with Spirit from $208.

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

The cheapest Southwest flight from Saint Thomas to Chicago is $637, flying from Apr 27 to May 4.
The cheapest Delta flight from Saint Thomas to Chicago is $580, flying from Jul 23 to Jul 29.
The cheapest United flight from Saint Thomas to Chicago is $430, flying from May 9 to May 18.
The cheapest American flight from Saint Thomas to Chicago is $580, flying from Jul 9 to Jul 16.
The cheapest Spirit flight from Saint Thomas to Chicago is $366, flying from May 21 to May 28.

The cheapest round-trip flight from Saint Thomas to Chicago starts at $366 from Thu, May 21 to Thu, May 28. The cheapest one-way flight starts at $208 and departs on Thu, Jul 23.

5 hr 34 min is the shortest flight time from Saint Thomas to Chicago.

Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.

It's easy to use Google Flights to find the cheapest days to fly from Saint Thomas to Chicago.
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 Saint Thomas to Chicago 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 Saint Thomas to Chicago.

In terms of nonstop flights, United is the most popular. United offers 4 nonstop flights and 81 connecting flights per week. United flies from Cyril E. King Airport (STT) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 794 connecting flights per week. Southwest flies from Cyril E. King Airport (STT) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Saint Thomas to Chicago are:

Delta offers 331 connecting flights per week. Delta flies from Cyril E. King Airport (STT) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
American offers 245 connecting flights per week. American flies from Cyril E. King Airport (STT) to Chicago O'Hare International Airport (ORD) .
Spirit offers 32 connecting flights per week. Spirit flies from Cyril E. King Airport (STT) to Chicago O'Hare International Airport (ORD) .
JetBlue offers 1 connecting flights per week. JetBlue flies from Cyril E. King Airport (STT) to Chicago O'Hare International Airport (ORD) .

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

The cheapest round-trip flight from Saint Thomas to Chicago recently found on Google Flights was with Spirit from $366. The cheapest one-way flight was with Spirit from $208.

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

The cheapest Southwest flight from Saint Thomas to Chicago is $637, flying from Apr 27 to May 4.
The cheapest Delta flight from Saint Thomas to Chicago is $580, flying from Jul 23 to Jul 29.
The cheapest United flight from Saint Thomas to Chicago is $430, flying from May 9 to May 18.
The cheapest American flight from Saint Thomas to Chicago is $580, flying from Jul 9 to Jul 16.
The cheapest Spirit flight from Saint Thomas to Chicago is $366, flying from May 21 to May 28.

United flies direct from Saint Thomas to Chicago.

There are 4 United direct flights from Saint Thomas to Chicago per week. Flights are available on Monday, Tuesday, Wednesday, Saturday and Sunday.

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

The cheapest last-minute deal between Saint Thomas and Chicago at price $562 is offered by Southwest from Thu, Apr 30 to Sun, May 3.

United flies direct from Saint Thomas to Chicago.

There are 4 United direct flights from Saint Thomas to Chicago per week. Flights are available on Monday, Tuesday, Wednesday, Saturday and Sunday.

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

Direct flights from Saint Thomas to Chicago are only available on Monday, Tuesday, Wednesday and Saturday.

The cheapest direct (nonstop) round-trip flights between Saint Thomas and Chicago start at $581 from Sat, Jul 11 to Sat, Jul 18 with United.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Saint Thomas to Chicago, 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 Saint Thomas and Chicago start at $1,055 from Sun, Jul 26 to Sun, Aug 2 with United.

The cheapest economy class round-trip flights between Saint Thomas and Chicago start at $366 from Thu, May 21 to Thu, May 28.

To book business class trips from Saint Thomas to Chicago, 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 Saint Thomas and Chicago starts at $562 from Thu, Apr 30 to Sun, May 3 with Southwest.

The cheapest last-minute deal between Saint Thomas and Chicago at price $562 is offered by Southwest from Thu, Apr 30 to Sun, May 3.

To find last-minute flight deals from Saint Thomas to Chicago, 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.