Title: Cheap Flights from Chicago to St. Thomas (MDW to STT) - Expedia.co.uk ![](https://images.trvl-media.com/place/6140138/57cc4b04-8c90-4cee-a0ef-1a113eaebf69.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6140138/57cc4b04-8c90-4cee-a0ef-1a113eaebf69.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights from Chicago (MDW) to St. Thomas (STT) - [Return](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only ## Popular airlines from Chicago Midway Airport (MDW) to Cyril E. King Airport (STT) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.co.uk/Flights-Search?leg1=from:mdw,to:stt,departure:30/09/2025TANYT&leg2=from:stt,to:mdw,departure:07/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:mdw,to:stt,departure:30/09/2025TANYT&leg2=from:stt,to:mdw,departure:07/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) ![notification illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 25% on select hotels after you book a flight\* ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.co.uk/login) ## Find the cheapest month to fly from Chicago (MDW) to St. Thomas (STT) ### September is typically the cheapest month to fly From £265 - £816 per traveller. ## Frequently asked questions ### How much is a flight from Midway Intl. Airport (MDW) to Cyril E. King Airport (STT)? > If you're planning on travelling from Midway Intl. Airport (MDW) to STT, round-trip flights start from . This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year, so don't let a good deal slip through your fingers. Book today and save yourself money and time. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Midway Airport to STT? > Most flights can be cancelled online, but whether or not you incur a fee differs between airlines. If you do have to cancel your escape, follow the easy instructions in the [Customer Service Portal](https://www.expedia.co.uk/service/?langid=1033). ### How do I find cheap flights from Chicago Airport to STT that have flexible change policies? > Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Chicago Airport to Cyril E. King Airport (STT) flights, you'll see a "no change fees" filter for you to select. ### How far is the flight from MDW to Cyril E. King Airport? > Expect to be cruising at altitude for a while, as the flight distance between Chicago Airport and Cyril E. King Airport is 3,400 kilometres. Set up a playlist of your favourite songs before leaving home to stay entertained during the flight. ### Which airlines fly direct from Midway Airport to Cyril E. King Airport? > Flying nonstop between Midway Intl. Airport (MDW) and STT isn't possible right now. However, you'll still be able to find a flight to St. Thomas with at least one stop. ### Are MDW to Cyril E. King Airport flight tickets cheaper when they're purchased at the last minute? > Last-minute planners can occasionally pick up a bargain, with some super cheap fares from Midway Airport to Cyril E. King Airport popping up a few weeks prior to the departure date. If you'd rather book ahead of time, Expedia compares and updates the best flight deals frequently — as early as a year in advance in some cases. It does depend on the carrier though, as not all airlines issue prices so far in advance. ## Travel information | Origin airport | Midway Intl. | | --- | --- | | Destination airport | Cyril E. King | | Distance | 3364 km | ## Book with confidence ### Compare flights from Chicago to St. Thomas easily and book with confidence For travelling on business or for pleasure, Expedia makes it easy to book your flights from Chicago to St. Thomas. Operating between them flights per day, airlines cover the route. And fly direct, getting you to Cyril E. King in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Midway Intl. to Cyril E. King.   To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights.  Grab a great deal on your flight from Midway Intl. (MDW) to Cyril E. King (STT) The easiest way to view the best deals on flights from Chicago to St. Thomas today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Midway Intl. to Cyril E. King start at just and range up to .   To find an even better deal, try   - being flexible on your dates – midweek flights can be cheaper - looking for other airports near Chicago and St. Thomas - booking your flight during , the cheapest month on this route - varying your flight times – early morning and late at night are sometimes cheaper  Why you should book your Chicago to St. Thomas flight with Expedia! We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Midway Intl. to Cyril E. King for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.   Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.   ## Explore a world of travel with Expedia - Trending Routes - Trending Flights - Top Flights Destinations - Related Airlines - Nearby Airports - Cheap Flights from Other Airports - Expedia's Latest Trends ### Top Routes from Chicago - [Chicago to Delhi (MDW - DEL)](https://expedia.co.uk/lp/flights/mdw/del/chicago-to-delhi) ### Top Routes to St. Thomas - [Newark Liberty Intl. Airport to St. Thomas (EWR - STT)](https://expedia.co.uk/lp/flights/ewr/stt/newark-liberty-intl-airport-to-st-thomas) - [Washington to St. Thomas (DCA - STT)](https://expedia.co.uk/lp/flights/dca/stt/washington-to-st-thomas) - [Fort Lauderdale to St. Thomas (FLL - STT)](https://expedia.co.uk/lp/flights/fll/stt/fort-lauderdale-to-st-thomas) - [Boston to St. Thomas (BOS - STT)](https://expedia.co.uk/lp/flights/bos/stt/boston-to-st-thomas) - [Hartford to St. Thomas (BDL - STT)](https://expedia.co.uk/lp/flights/bdl/stt/hartford-to-st-thomas) - [Edinburgh to St. Thomas (EDI - STT)](https://expedia.co.uk/lp/flights/edi/stt/edinburgh-to-st-thomas) - [Denver to St. Thomas (DEN - STT)](https://expedia.co.uk/lp/flights/den/stt/denver-to-st-thomas) - [Oranjestad to St. Thomas (AUA - STT)](https://expedia.co.uk/lp/flights/aua/stt/oranjestad-to-st-thomas) - [New York to St. Thomas (JFK - STT)](https://expedia.co.uk/lp/flights/jfk/stt/new-york-to-st-thomas) - [Dublin to St. Thomas (DUB - STT)](https://expedia.co.uk/lp/flights/dub/stt/dublin-to-st-thomas) - [Birmingham to St. Thomas (BHX - STT)](https://expedia.co.uk/lp/flights/bhx/stt/birmingham-to-st-thomas) - [London to St. Thomas (LHR - STT)](https://expedia.co.uk/lp/flights/lhr/stt/london-to-st-thomas) ### Top Routes to St. Thomas - [JetBlue Airways Hartford to St. Thomas](https://expedia.co.uk/lp/flight-routes/jetblue-airways-from-bradley-intl-to-cyril-e-king/b6/bdl/stt) - [JetBlue Airways New York to St. Thomas](https://expedia.co.uk/lp/flight-routes/jetblue-airways-from-john-f-kennedy-intl-to-cyril-e-king/b6/jfk/stt) - [Delta Birmingham to St. Thomas](https://expedia.co.uk/lp/flight-routes/delta-from-birmingham-to-cyril-e-king/dl/bhx/stt) ### Top Flight Destinations - [Flights to St. Thomas](https://expedia.co.uk/Cheap-Flights-To-St-Thomas.d6140138.Travel-Guide-Flights) - [Flights to St. John](https://expedia.co.uk/Cheap-Flights-To-St-John.d601376.Travel-Guide-Flights) ### Related Airlines - [KLM](https://expedia.co.uk/KLM-Flights.cKL.Travel-Guide-Airlines) - [Air France](https://expedia.co.uk/Air-France-Flights.cAF.Travel-Guide-Airlines) - [Virgin Atlantic](https://expedia.co.uk/Virgin-Atlantic-Flights.cVS.Travel-Guide-Airlines) - [Delta](https://expedia.co.uk/Delta-Flights.cDL.Travel-Guide-Airlines) - [Porter Airlines](https://expedia.co.uk/Porter-Airlines-Flights.cPD.Travel-Guide-Airlines) - [Air Transat](https://expedia.co.uk/Air-Transat-Flights.cTS.Travel-Guide-Airlines) - [WestJet](https://expedia.co.uk/WestJet-Flights.cWS.Travel-Guide-Airlines) - [Aeromexico](https://expedia.co.uk/Aeromexico-Flights.cAM.Travel-Guide-Airlines) - [LATAM Airlines Group](https://expedia.co.uk/LATAM-Airlines-Group-Flights.cLA.Travel-Guide-Airlines) - [Volaris](https://expedia.co.uk/Volaris-Flights.cY4.Travel-Guide-Airlines) - [Korean Air](https://expedia.co.uk/Korean-Air-Flights.cKE.Travel-Guide-Airlines) Chicago Airports #### Chicago [O'Hare Intl. to St. Thomas](https://expedia.co.uk/lp/flights/ord/stt/chicago-to-st-thomas) £666.90 ### Nearby Airports - [O'Hare Intl. Airport (ORD)](https://expedia.co.uk/lp/airports/ord/flights-from-ohare-intl-airport) - [Dupage Airport (DPA)](https://expedia.co.uk/lp/airports/dpa/flights-from-dupage-airport) - [Kenosha Regional Airport (ENW)](https://expedia.co.uk/lp/airports/enw/flights-from-kenosha-regional-airport) - [Greater Rockford Airport (RFD)](https://expedia.co.uk/lp/airports/rfd/flights-from-greater-rockford-airport) - [General Mitchell Intl. Airport (MKE)](https://expedia.co.uk/lp/airports/mke/flights-from-general-mitchell-intl-airport) - [Purdue University Airport (LAF)](https://expedia.co.uk/lp/airports/laf/flights-from-purdue-university-airport) - [Central Illinois Regional Airport (BMI)](https://expedia.co.uk/lp/airports/bmi/flights-from-central-illinois-regional-airport) - [Kalamazoo-Battle Creek Intl. Airport (AZO)](https://expedia.co.uk/lp/airports/azo/flights-from-kalamazoo-battle-creek-intl-airport) - [Dane County Regional Airport (MSN)](https://expedia.co.uk/lp/airports/msn/flights-from-dane-county-regional-airport) - [University Of Illinois Urbana-Champaign Williard Airport (CMI)](https://expedia.co.uk/lp/airports/cmi/flights-from-university-of-illinois-urbana-champaign-williard-airport) ### Expedia's Latest Trends Hotels - [Amaronda Resort & Spa](https://expedia.co.uk/Eretria-Hotels-Amaronda-Resort-Spa.h1498062.Hotel-Information) - [The Ritz-Carlton, St. Thomas](https://expedia.co.uk/St-Thomas-Hotels-The-Ritz-Carlton.h329494.Hotel-Information) - [Hotel Apartamentos Bajondillo](https://expedia.co.uk/Torremolinos-Hotels-Hotel-Apartamentos-Bajondillo.h1475566.Hotel-Information) - [Hodson Bay Hotel](https://expedia.co.uk/Athlone-Hotels-Hodson-Bay-Hotel.h2197837.Hotel-Information) - [Hotel Rosamar Benidorm](https://expedia.co.uk/Benidorm-Hotels-Hotel-Rosamar.h1411824.Hotel-Information) - [Hotels with smoking rooms in Bournemouth](https://expedia.co.uk/Bournemouth-Hotels-Hotels-With-Smoking-Rooms.0-0-d654-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Hotels in Peterborg](https://expedia.co.uk/Peterborg-Hotels.d6051405.Travel-Guide-Hotels) - [Sunset Jamaica Grande Resort Sp](https://expedia.co.uk/Ocho-Rios-Hotels-Sunset-Jamaica-Grande-Resort-Sp.h11562480.Hotel-Information) - [All-Inclusive Hotels in South Coast](https://expedia.co.uk/South-Coast-Hotels-All-Inclusive-Hotel.0-0-d3000383018-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [B&B Hebden Bridge](https://expedia.co.uk/Hebden-Bridge-Bed-And-Breakfasts.d10470-aaBedAndBreakfasts.Travel-Guide-Accommodation) - [NINE TREE BY PARNAS SEOUL MYEONDONG 2](https://expedia.co.uk/Seoul-Hotels-Nine-Tree-Premier-Hotel-Myeongdong-2.h17447885.Hotel-Information) - [Hotels near Loch Tay](https://expedia.co.uk/Loch-Tay-Hotels.0-l553248634855452142-0.Travel-Guide-Filter-Hotels) - [Bonavista Apartments - Passeig de Gracia](https://expedia.co.uk/Barcelona-Hotels-Bonavista-Apartments-Passeig-De-Gracia.h10245491.Hotel-Information) - [The Harp Inn](https://expedia.co.uk/Hereford-Hotels-The-Harp-Inn.h40069903.Hotel-Information) - [Grand Uysal Beach&Spa Hotel - All inclusive](https://expedia.co.uk/Alanya-Hotels-Grand-Uysal-Beach-Hotel-All-Inclusive.h15737224.Hotel-Information) - [Chatsworth Hotel - Worthing](https://expedia.co.uk/Worthing-Hotels-Chatsworth-Hotel-Worthing.h1820805.Hotel-Information) Flights - [Tsaradia](https://expedia.co.uk/Tsaradia-Flights.cTZ.Travel-Guide-Airlines) - [Cheap Flights from Lahore (LHE) to Karachi (KHI)](https://expedia.co.uk/lp/flights/lhe/khi/lahore-to-karachi) - [Cheap Flights from Edinburgh (EDI) to Seville (SVQ)](https://expedia.co.uk/lp/flights/edi/svq/edinburgh-to-seville) - [Flights from Estate Little Saint James Island](https://expedia.co.uk/lp/flights/553248635975876432/flights-from-estate-little-saint-james-island) - [Cheap Flights from London (LHR) to Prague (PRG)](https://expedia.co.uk/lp/flights/lhr/prg/london-to-prague) - [Cheap Flights to Milos](https://expedia.co.uk/Cheap-Flights-To-Milos.d2349.Travel-Guide-Flights) - [Cheap Flights from Chambery (CMF) to London (LHR)](https://expedia.co.uk/lp/flights/cmf/lhr/chambery-to-london) - [Cheap Flights to Montecatini Terme](https://expedia.co.uk/Cheap-Flights-To-Montecatini-Terme.d4956.Travel-Guide-Flights) - [Cheap Flights from New York (JFK) to Austin (AUS)](https://expedia.co.uk/lp/flights/jfk/aus/new-york-to-austin) Activities - [Things to do in Pezenas](https://expedia.co.uk/Things-To-Do-In-Pezenas.d6023388.Travel-Guide-Activities) - [Things to do in Charlotte Amalie](https://expedia.co.uk/Things-To-Do-In-Charlotte-Amalie.d3289.Travel-Guide-Activities) Packages - [Hadrian's Gate](https://expedia.co.uk/Hadrians-Gate-Antalya-City-Centre.d6068021.Attraction) General - [Visit Estate Little Saint James Island](https://expedia.co.uk/Estate-Little-Saint-James-Island.dx553248635975876432) - [Visit Llanes](https://expedia.co.uk/Llanes.dx603040) \*Available to Expedia members. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](https://a.travel-assets.com/mad-service/qr-code/footer_qr/3_QR_FOOTER.png)