Title: Chicago to St. Thomas cheap flights from $166 (MDW to STT) - Expedia.com ![](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) # $166 Cheap Flights from Chicago (MDW) to St. Thomas (STT) [View $166 flight on Tue, May 5, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:MDW,to:STT,departure:5/5/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:166.00&airProductToken=AQpiCi8I15wBEgQzODM4GOywASDMcCj0lIwDMI-WjAM4VkAAWAFqA1dHQXIHVkxBVlcyRgovCNecARIEMzIxMxjMcCDynAEowZaMAzDwl4wDOFZAAVgBagNXR0FyB1ZMQVZXMkYSDAgBEAEYASoCV04yABgBIgQIARABKAIoAygEMAE) ## Popular airlines from Chicago Midway Airport (MDW) to Cyril E. King Airport (STT) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:STT,departure:4/15/2026TANYT&leg2=from:STT,to:MDW,departure:4/22/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:STT,departure:4/15/2026TANYT&leg2=from:STT,to:MDW,departure:4/22/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) ## Cheap Flights from Chicago to St. Thomas (MDW-STT) Prices were available within the past 7 days and start at $166 for one-way flights and $388 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, May 5 - Tue, May 12 MDW Chicago STT St. Thomas $388 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:STT,departure:5/5/2026TANYT&leg2=from:STT,to:MDW,departure:5/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:387.84&airProductToken=AQpiCi8I15wBEgQzODM4GOywASDMcCj0lIwDMI-WjAM4VkAAWAFqA1dHQXIHVkxBVlcyRgovCNecARIEMzIxMxjMcCDynAEowZaMAzDwl4wDOFZAAVgBagNXR0FyB1ZMQVZXMkYKYgovCNecARIENDUyNhjynAEgzHAogueMAzDP6IwDOEFAAFgBagNXR0FyB0FMQVVXMkYKLwjXnAESBDEyNTAYzHAg7LABKMfpjAMw8eqMAzhBQAFYAWoDV0dBcgdBTEFVVzJGEgwIARABGAEqAldOMgAYASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, May 5 - Tue, May 12 MDW Chicago STT St. Thomas $428 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:STT,departure:5/5/2026TANYT&leg2=from:STT,to:MDW,departure:5/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:427.84&airProductToken=AQpiCi8I15wBEgQzODM4GOywASDMcCj0lIwDMI-WjAM4VkAAWAFqA1BMVXIHVkxBVlc0RgovCNecARIEMzIxMxjMcCDynAEowZaMAzDwl4wDOFZAAVgBagNQTFVyB1ZMQVZXNEYSDAgBEAEYASoCV04yABgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Sun, May 3 - Tue, May 12 MDW Chicago STT St. Thomas $440 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:STT,departure:5/3/2026TANYT&leg2=from:STT,to:MDW,departure:5/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:439.84&airProductToken=AQpiCi8I15wBEgQzODM4GOywASDMcCj9_YsDMJP_iwM4QUAAWAFqA1dHQXIHQUxBVVcyRgovCNecARIEMzIxMxjMcCDynAEo9_-LAzCmgYwDOEFAAVgBagNXR0FyB0FMQVVXMkYKYgovCNecARIENDUyNhjynAEgzHAogueMAzDP6IwDOEFAAFgBagNXR0FyB0FMQVVXMkYKLwjXnAESBDEyNTAYzHAg7LABKMfpjAMw8eqMAzhBQAFYAWoDV0dBcgdBTEFVVzJGEgwIARABGAEqAldOMgAYASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, May 5 - Thu, May 7 MDW Chicago STT St. Thomas $458 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:STT,departure:5/5/2026TANYT&leg2=from:STT,to:MDW,departure:5/7/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:457.84&airProductToken=AQpiCi8I15wBEgQzODM4GOywASDMcCj0lIwDMI-WjAM4VkAAWAFqA1dHQXIHVkxBVlcyRgovCNecARIEMzIxMxjMcCDynAEowZaMAzDwl4wDOFZAAVgBagNXR0FyB1ZMQVZXMkYKkgEKLwjXnAESBDQ1MjYY8pwBIMxwKPaujAMww7CMAzhHQABYAWoDV0dBcgdHTEFWVjJGCi4I15wBEgQzMTA5GMxwIINYKI6xjAMwuLKMAzhHQAFYAWoDV0dBcgdHTEFWVjJGCi8I15wBEgQxNTk0GINYIOywASjlsowDMOezjAM4R0ABWAFqA1dHQXIHR0xBVlYyRhIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Mon, Apr 27 - Thu, Apr 30 MDW Chicago STT St. Thomas $464 Roundtrip found 10 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:STT,departure:4/27/2026TANYT&leg2=from:STT,to:MDW,departure:4/30/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:463.84&airProductToken=AQpiCi8I15wBEgQzODM4GOywASDMcCjbuosDMPG7iwM4QUAAWAFqA1dHQXIHQUxBVVcyRgovCNecARIEMzIxMxjMcCDynAEo1byLAzD_vYsDOEFAAVgBagNXR0FyB0FMQVVXMkYKYQovCNecARIENDUyNhjynAEgzHAoluCLAzDj4YsDOEZAAFgBagNXR0FyB0ZMQVZLMkYKLgjXnAESAzEzOBjMcCDssAEo4uOLAzCR5YsDOEZAAVgBagNXR0FyB0ZMQVZLMkYSDAgBEAEYASoCV04yABgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, May 5 - Tue, May 12 MDW Chicago STT St. Thomas $468 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:STT,departure:5/5/2026TANYT&leg2=from:STT,to:MDW,departure:5/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:467.84&airProductToken=AQpiCi8I15wBEgQzODM4GOywASDMcCj0lIwDMI-WjAM4VkAAWAFqA1BMVXIHVkxBVlc0RgovCNecARIEMzIxMxjMcCDynAEowZaMAzDwl4wDOFZAAVgBagNQTFVyB1ZMQVZXNEYKYgovCNecARIENDUyNhjynAEgzHAogueMAzDP6IwDOEFAAFgBagNQTFVyB0FMQVVXNEYKLwjXnAESBDEyNTAYzHAg7LABKMfpjAMw8eqMAzhBQAFYAWoDUExVcgdBTEFVVzRGEgwIARABGAEqAldOMgAYASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Sun, Apr 19 - Thu, Apr 23 MDW Chicago STT St. Thomas $478 Roundtrip found 5 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:STT,departure:4/19/2026TANYT&leg2=from:STT,to:MDW,departure:4/23/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:477.84&airProductToken=AQpiCi8I15wBEgQzODM4GOywASDMcCi94IoDMNPhigM4VkAAWAFqA1dHQXIHVkxBVlcyRgovCNecARIEMzIxMxjMcCDynAEot-KKAzDm44oDOFZAAVgBagNXR0FyB1ZMQVZXMkYKYQovCNecARIENDUyNhjynAEgzHAotpGLAzCDk4sDOFVAAFgBagNXR0FyB1VMQVZQMkYKLgjXnAESAzEzOBjMcCDssAEogpWLAzCxlosDOFVAAVgBagNXR0FyB1VMQVZQMkYSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Sun, May 3 - Wed, May 13 MDW Chicago STT St. Thomas $480 Roundtrip found 12 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:STT,departure:5/3/2026TANYT&leg2=from:STT,to:MDW,departure:5/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:479.84&airProductToken=AQpiCi8I15wBEgQzODM4GOywASDMcCj9_YsDMJP_iwM4QUAAWAFqA1dHQXIHQUxBVVcyRgovCNecARIEMzIxMxjMcCDynAEo9_-LAzCmgYwDOEFAAVgBagNXR0FyB0FMQVVXMkYKYgovCNecARIENDUyNhjynAEgzHAoovKMAzDv84wDOFpAAFgBagNXR0FyB1pMQVZLMkYKLwjXnAESBDEyNTAYzHAg7LABKOf0jAMwkfaMAzhaQAFYAWoDV0dBcgdaTEFWSzJGEgwIARABGAEqAldOMgAYASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Mon, Apr 13 - Thu, Apr 30 MDW Chicago STT St. Thomas $491 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:STT,departure:4/13/2026TANYT&leg2=from:STT,to:MDW,departure:4/30/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:490.84&airProductToken=AQpiCi8I15wBEgQzODM4GOywASDMcCibnYoDMLGeigM4RkAAWAFqA1dHQXIHRkxBN1cyRgovCNecARIEMzIxMxjMcCDynAEolZ-KAzC_oIoDOEZAAVgBagNXR0FyB0ZMQTdXMkYKYQovCNecARIENDUyNhjynAEgzHAoluCLAzDj4YsDOEZAAFgBagNXR0FyB0ZMQVZLMkYKLgjXnAESAzEzOBjMcCDssAEo4uOLAzCR5YsDOEZAAVgBagNXR0FyB0ZMQVZLMkYSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, May 9 - Tue, May 12 MDW Chicago STT St. Thomas $555 Roundtrip found 6 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:STT,departure:5/9/2026TANYT&leg2=from:STT,to:MDW,departure:5/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:554.84&airProductToken=AQpwCjYIxJgBEgQxMjg1GOywASDgXCiLwowDMIbDjAM4RUAAWAFqCU1BSU5CQVNJQ3IIVk5OTjBOQloKNgjEmAESBDE4ODkY4Fwg8pwBKIzEjAMw5cWMAzhFQAFYAWoJTUFJTkJBU0lDcghWTk5OME5CWhIMCAEQARgBKgJETDIAGAEiBAgBEAEoAigDKAQwAQ) ## Alternative airports near St. Thomas Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:STT,departure:4/15/2026TANYT&leg2=from:STT,to:MDW,departure:4/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) STT Cyril E. King Cheapest [Flights from $614 ](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:STT,departure:4/15/2026TANYT&leg2=from:STT,to:MDW,departure:4/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Find the cheapest month to fly from Chicago (MDW) to St. Thomas (STT) ### September is typically the cheapest month to fly From $359 - $1,084 per traveler. ## Frequently asked questions ### How much does a flight from Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King) cost? ### What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King)? ### Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King)? ### What is the cheapest airline that flies from Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King)? ### How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King)? ### What is the best time to fly from Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King)? ### What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King)? ### What are the most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King)? ### How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King)? ### Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King)? ### How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King) flight with Expedia? ### What airports do you fly into for St. Thomas from Midway Intl. (MDW)? ### Is it cheaper to buy a plane ticket from Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King) at the last minute? ### Is it cheaper to book a Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King) flight and hotel package? ### Can I cancel or change the date of my flight from Chicago, IL (MDW-Midway Intl.) to St. Thomas (STT-Cyril E. King)? ## Travel information | Origin airport | Midway Intl. | | ------------------- | ------------------------- | | Destination airport | Cyril E. King | | Airlines serving | Delta, Southwest Airlines | | Roundtrip price | $388 | | Distance | 2102 mi | ## Book with confidence # Chicago to St. Thomas Flights The cheapest times to fly from Chicago to St. Thomas On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to St. Thomas are during the month of May. You can find some of the cheapest flights from Chicago to St. Thomas with Expedia's search tool and vast selection of airlines. The best time to book a flight from Chicago to St. Thomas Sunday is one of the best days to book for cheap flights from Chicago to St. Thomas: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance. How to find cheap round-trip tickets from Chicago to St. Thomas Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to St. Thomas in 2026\. You can also book with separate airlines for your outbound and return journeys, from $166 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference\*. This is available for a small fee, and is free to One Key Gold and Platinum tier members. Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to St. Thomas flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps. You could also save big by booking one of Expedia's [vacation packages](https://www.expedia.com/package-deals). Bundling together your Chicago to St. Thomas airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures. \*Terms apply. Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. 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