Title: Chicago to Singapore cheap flights from $342 (ORD to SIN) - Expedia.com ![Gardens by the Bay which includes night scenes, a garden and modern architecture](https://images.trvl-media.com/place/6193104/16f05d8e-e7b7-4d2d-b3c7-df61dae96d31.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6193104/16f05d8e-e7b7-4d2d-b3c7-df61dae96d31.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $342 Cheap Flights from Chicago (ORD) to Singapore (SIN) [View $342 flight on Tue, Aug 11, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:ORD,to:SIN,departure:8/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:341.10&airProductToken=AQp-CigIwaYBEgMzMzcYrhwgkgEo7-iUAzCJ65QDOFFAAFgBcgdPTE9YQlVTCigI0KQBEgMxMjUYkgEgrFsosuyUAzDw8pQDOE9AAVgBcgdPTE9YQlVTCigI0KQBEgM1MTEYrFsgkmoou_OUAzCh9ZQDOE9AAVgBcgdPTE9YQlVTEgoIARABGAEqAlBSGAEiBAgBEAEoAigDKAQwAQ) ## Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Singapore Changi Airport (SIN) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_EY.svg) Etihad Airways [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SIN,departure:3/27/2026TANYT&leg2=from:SIN,to:ORD,departure:4/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"EY"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_EK.svg) Emirates [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SIN,departure:3/27/2026TANYT&leg2=from:SIN,to:ORD,departure:4/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"EK"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SIN,departure:3/27/2026TANYT&leg2=from:SIN,to:ORD,departure:4/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_BR.svg) EVA Airways [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SIN,departure:3/27/2026TANYT&leg2=from:SIN,to:ORD,departure:4/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"BR"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_TK.svg) Turkish Airlines [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SIN,departure:3/27/2026TANYT&leg2=from:SIN,to:ORD,departure:4/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"TK"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_CX.svg) Cathay Pacific [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SIN,departure:3/27/2026TANYT&leg2=from:SIN,to:ORD,departure:4/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"CX"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SIN,departure:3/27/2026TANYT&leg2=from:SIN,to:ORD,departure:4/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![](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\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## Cheap Flights from Chicago to Singapore (ORD-SIN) Prices were available within the past 7 days and start at $342 for one-way flights and $703 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, Oct 8 - Thu, Oct 15 ORD Chicago SIN Singapore $703 Roundtrip found 5 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIN,departure:10/8/2026TANYT&leg2=from:SIN,to:ORD,departure:10/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:702.23&airProductToken=AQqBAQopCMGmARIDMzM3GK4cIJIBKL_1mQMw2feZAzhRQABYAXIITzlMQlVTODUKKQjQpAESAzEyNRiSASCsWyjy-JkDMLD_mQM4T0ABWAFyCE85TEJVUzg1CikI0KQBEgM1MTEYrFsgkmoo-_-ZAzDhgZoDOE9AAVgBcghPOUxCVVM4NQqBAQopCNCkARIDNTA4GJJqIKxbKMa8mgMwtr6aAzhPQABYAXIITzlMQlVTODUKKQjQpAESAzEyNBisWyCSASirwJoDMJnGmgM4T0ABWAFyCE85TEJVUzg1CikIwaYBEgMzMjgYkgEgrhwovsiaAzCwypoDOFFAAVgBcghPOUxCVVM4NRIKCAEQARgBKgJQUhgBIgQIARABKAIoAygEMAE) ![Korean Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/ke.gif) Wed, Oct 28 - Tue, Nov 17 ORD Chicago SIN Singapore $793 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIN,departure:10/28/2026TANYT&leg2=from:SIN,to:ORD,departure:11/17/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:792.63&airProductToken=AQpnCjEIy4oBEgIzOBiuHCDIaCjr05sDMO_amwM4VEAAWAFqB0VZU0FWRVJyCFRKWDBaUEJaCjIIy4oBEgM2NDUYyGggkmooutubAzDK3psDOFRAAVgBagdFWVNBVkVScghUSlgwWlBCWgpnCjIIy4oBEgM2NDQYkmogyGgoxrOdAzC9tp0DOFRAAFgBagdFWVNBVkVScghUSlgwWlBCWgoxCMuKARICMzcYyGggrhwo5LidAzDmvp0DOFRAAVgBagdFWVNBVkVScghUSlgwWlBCWhIMCAEQARgBKgJLRTIAGAEiBAgBEAEoAigEKAYwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Aug 26 - Mon, Sep 7 ORD Chicago SIN Singapore $804 Roundtrip found 12 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIN,departure:8/26/2026TANYT&leg2=from:SIN,to:ORD,departure:9/7/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:803.63&airProductToken=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) ![Cathay Pacific](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/CX.gif) Tue, Sep 1 - Tue, Sep 8 ORD Chicago SIN Singapore $822 Roundtrip found 13 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIN,departure:9/1/2026TANYT&leg2=from:SIN,to:ORD,departure:9/8/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:821.63&airProductToken=AQpsCjQIw7ABEgM4MDEYrhwgxzIorNSWAzDs25YDOFFAAFgBaglFQ09OTElHSFRyCFFLMjFVU0lSCjQIw7ABEgM2NTkYxzIgkmooid6WAzDq35YDOFFAAVgBaglFQ09OTElHSFRyCFFLMjFVU0lSCmwKNAjDsAESAzYzNhiSaiDHMij1npcDMOqglwM4UUAAWAFqCUVDT05MSUdIVHIIUUsyMVVTSVIKNAjDsAESAzgwNhjHMiCuHCi6ppcDMMitlwM4UUABWAFqCUVDT05MSUdIVHIIUUsyMVVTSVISCggBEAEYASoCQ1gYASIECAEQASgCKAQoBjAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Apr 20 - Mon, Apr 27 ORD Chicago SIN Singapore $845 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIN,departure:4/20/2026TANYT&leg2=from:SIN,to:ORD,departure:4/27/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:844.53&airProductToken=AQqCAQo_CNWCARIENzkxMRiuHCCnGyjV8YoDMP_3igM4S0AAWAFqCEVDT0JBU0lDcghLSlgwMEVCUnoJCM6QARIDMTExCj8I1YIBEgQ3OTkxGKcbIJJqKML5igMw8PyKAzhLQAFYAWoIRUNPQkFTSUNyCEtKWDAwRUJSegkIzpABEgM4NDMKaQoxCNWCARIBMhiSaiCycSictosDMKq9iwM4S0AAWAFqCEVDT0JBU0lDcghLSlgwMEVCUgo0CNWCARIEMTk1OBiycSCuHCj4wYsDMITEiwM4S0ABWAFqCEVDT0JBU0lDcghLSlgwMEVCUhIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAE) ![Turkish Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TK.gif) Sun, Sep 20 - Thu, Oct 1 ORD Chicago SIN Singapore $914 Roundtrip found 5 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIN,departure:9/20/2026TANYT&leg2=from:SIN,to:ORD,departure:10/1/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:913.63&airProductToken=AQpaCioI1JYBEgE2GK4cIMicASiGrJgDMIaxmAM4V0AAWAFqAlBTcgZXVjNYUEMKLAjUlgESAzIwOBjInAEgkmooiLKYAzCNt5gDOFdAAVgBagJQU3IGV1YzWFBDClsKKwjUlgESAjU1GJJqIMicASiJo5kDMKeomQM4V0AAWAFqAlBTcgZXVjNYUEMKLAjUlgESAzE4NRjInAEgrhwo8qiZAzCQrpkDOFdAAVgBagJQU3IGV1YzWFBDEhQIAhABGAIqAlRLMghBSVJNT0RUSxgBIgQIARABKAIoAygEMAE) ![All Nippon Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/NH.gif) Wed, Oct 28 - Tue, Nov 17 ORD Chicago SIN Singapore $927 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIN,departure:10/28/2026TANYT&leg2=from:SIN,to:ORD,departure:11/17/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:926.03&airProductToken=AQprCjQIzpABEgQ3MDA5GK4cIKcbKN7UmwMwjdubAzhLQABYAWoIRUNPQkFTSUNyCEtKWDAwRUJSCjMIzpABEgM4NDMYpxsgkmoond6bAzDf4ZsDOEtAAVgBaghFQ09CQVNJQ3IIS0pYMDBFQlIKagozCM6QARIDODQyGJJqIKcbKIWunQMwlbGdAzhLQABYAWoIRUNPQkFTSUNyCEtKWDAwRUJSCjMIzpABEgMxMTIYpxsgrhwo1bidAzCgvp0DOEtAAVgBaghFQ09CQVNJQ3IIS0pYMDBFQlISDAgBEAEYASoCTkgyABgBIgQIARABKAIoAygEMAE) ![Etihad Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/EY.GIF) Mon, Mar 23 - Tue, Apr 7 ORD Chicago SIN Singapore $1,001 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIN,departure:3/23/2026TANYT&leg2=from:SIN,to:ORD,departure:4/7/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1000.43&airProductToken=AQplCjAIxbIBEgIxMBiuHCCAPSj-tIgDMJ67iAM4VUAAWAFqBllCQVNJQ3IIVUxOMUVIMTkKMQjFsgESAzQ5OBiAPSCSaijdv4gDMJ_DiAM4VUABWAFqBllCQVNJQ3IIVUxOMUVIMTkKZAoxCMWyARIDNDk5GJJqIIA9KOzaiQMwpN6JAzhVQABYAWoGWUJBU0lDcghVTE4xRUgxOQovCMWyARIBORiAPSCuHCi_34kDMK_miQM4VUABWAFqBllCQVNJQ3IIVUxOMUVIMTkSCggBEAEYASoCRVkYASIECAEQASgCKAMoBDAB) ![Qatar Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/QR.gif) Thu, Apr 16 - Thu, Apr 30 ORD Chicago SIN Singapore $1,051 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIN,departure:4/16/2026TANYT&leg2=from:SIN,to:ORD,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:1050.53&airProductToken=AQpqCjMI0aQBEgM3MjYYrhwgwzsotMWKAzDPy4oDOFRAAFgBaghFQ0xBU1NJQ3IIVExVU1AxUkUKMwjRpAESAzk0OBjDOyCSaijF0IoDMJHUigM4VEABWAFqCEVDTEFTU0lDcghUTFVTUDFSRQpqCjMI0aQBEgM5NDcYkmogwzso_NyLAzDc4IsDOFRAAFgBaghFQ0xBU1NJQ3IIVExVU1AxUkUKMwjRpAESAzcyNRjDOyCuHCiW5YsDMJXsiwM4VEABWAFqCEVDTEFTU0lDcghUTFVTUDFSRRIKCAEQARgBKgJRUhgBIgQIARABKAIoBCgGMAE) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Fri, Jan 22 - Sun, Jan 31 ORD Chicago SIN Singapore $1,051 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIN,departure:1/22/2027TANYT&leg2=from:SIN,to:ORD,departure:1/31/2027TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1050.53&airProductToken=AQpWCikIwmwSBDU1NjIYrhwgwzso8p6jAzCIpaMDOE9AAFgBcghPTFVTUDFSRQopCMJsEgQ1NTgzGMM7IJJqKLemowMwjaqjAzhPQAFYAXIIT0xVU1AxUkUKVgopCMJsEgQ1NTg0GJJqIMM7KKP2owMwg_qjAzhPQABYAXIIT0xVU1AxUkUKKQjCbBIENTU2MRjDOyCuHCjs-qMDMI6CpAM4T0ABWAFyCE9MVVNQMVJFEgwIARABGAEqAkI2MgAYASIECAEQASgCKAMoBDAB) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=FTG_SPRING_PROMO_) ## Alternative airports near Singapore Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SIN,departure:3/27/2026TANYT&leg2=from:SIN,to:ORD,departure:4/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) SIN Changi Cheapest 18 min [Flights from $1,041 ](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SIN,departure:3/27/2026TANYT&leg2=from:SIN,to:ORD,departure:4/3/2026TANYT&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 (ORD) to Singapore (SIN) ### September is typically the cheapest month to fly From $663 - $1,061 per traveler. ## Frequently asked questions ### How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi) cost? ### What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi)? ### Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi)? ### What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi)? ### How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi)? ### What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi)? ### What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi)? ### What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi)? ### How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi)? ### Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi)? > - Japan Airlines > - Korean Air > - United Airlines > - Qatar Airways > - All Nippon Airways > - Lufthansa > - Swiss International Air Lines > - Emirates > - Cathay Pacific > - Turkish Airlines > > > First class cabins are available on: > > > - Swiss International Air Lines > - Lufthansa > - Emirates > - British Airways > - Japan Airlines ### How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi) flight with Expedia? ### What airports do you fly into for Singapore from O'Hare Intl. (ORD)? ### Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi) at the last minute? ### Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi) flight and hotel package? ### Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Singapore (SIN-Changi)? ## Travel information | Origin airport | O'Hare Intl. | | ------------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Destination airport | Changi | | Airlines serving | Air Canada, Alaska Airlines, All Nippon Airways, American Airlines, British Airways, Cathay Pacific, Delta, EVA Airways, Emirates, Etihad Airways, Finnair, Japan Airlines, JetBlue Airways, Korean Air, Lufthansa, Malaysia Airlines, Qatar Airways, Swiss International Air Lines, Turkish Airlines, United | | Roundtrip price | $702 | | Distance | 9351 mi | ## Book with confidence # Chicago to Singapore Flights The cheapest times to fly from Chicago to Singapore 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 Singapore are during the month of October. You can find some of the cheapest flights from Chicago to Singapore with Expedia's search tool and vast selection of airlines. The best time to book a flight from Chicago to Singapore Sunday is one of the best days to book for cheap flights from Chicago to Singapore: 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 Singapore 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 Singapore in 2026\. You can also book with separate airlines for your outbound and return journeys, from $342 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 Singapore 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 Singapore 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\. The percentages you see are averages. \*Flight schedules are subject to change. ## Explore a world of travel with Expedia - Lodging - Packages - Cars - [Hotels near Changi Airport Station ](https://www.expedia.com/Changi-Airport-Station-Hotels.d6163642.Travel-Guide-Hotels) - [Hostels in Changi Airport Station ](https://www.expedia.com/Changi-Airport-Station-Hostels.d6163642-aaHostels.Travel-Guide-Accommodation) - [Cheap Hotels in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Cheap-Hotels.0-n6359514-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Family-Hotel.0-n6359514-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Hotels-With-Free-Airport-Shuttle.0-n6359514-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Hotels near Changi ](https://www.expedia.com/Changi-Singapore-Hotels.0-n6359514-0.Travel-Guide-Filter-Hotels) - [Hotels with Laundry Facilities in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Hotels-With-Laundry-Facilities.0-n6359514-0-tHotelswithLaundryFacilities.Travel-Guide-Filter-Hotels) - [Resorts & Hotels with Spas in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Spa-Hotel.0-n6359514-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Hotels-With-Hot-Tubs.0-n6359514-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Historic Hotels in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Historic-Hotel.0-n6359514-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Golf-Hotel.0-n6359514-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Luxury-Hotel.0-n6359514-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Beach Hotels in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Beach-Hotel.0-n6359514-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Hotels-With-Complimentary-Breakfast.0-n6359514-0-tHotelswithComplimentaryBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Bars in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Bar-Hotel.0-n6359514-0-tBarHotel.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Hotels-With-Balconies.0-n6359514-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels near Changi Swimming Pool ](https://www.expedia.com/Changi-Swimming-Pool-Hotels.0-l553248621532741616-0.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Hotels-With-Smoking-Rooms.0-n6359514-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Hotel-With-Early-Check-In.0-n6359514-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Aparthotels in Changi Airport Station ](https://www.expedia.com/Changi-Airport-Station-Apart-Hotels.d6163642-aaApartHotels.Travel-Guide-Accommodation) - [Hotel with a Concierge Hotels in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Hotel-With-A-Concierge.0-n6359514-0-tHotelwithaConcierge.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Changi ](https://www.expedia.com/5Star-Changi-Singapore-Hotels.s50-n6359514-0.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-Couples-Resorts-Hotels.0-n6359514-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Gay friendly Hotels in Changi ](https://www.expedia.com/Changi-Singapore-Hotels-LGBT-Welcoming-Hotel.0-n6359514-0-tLGBTWelcomingHotel.Travel-Guide-Filter-Hotels) - [Visit Changi ](https://www.expedia.com/Singapore-Changi.dx6359514) - [Changi Vacations ](https://www.expedia.com/Changi.d6359514.Destination-Travel-Guides) - [Car rentals near Slide @ T3 ](https://www.expedia.com/Car-Rentals-In-Slide-T3.d553248621532741614.Car-Rental-Guide) \*Available to One Key members.