Title: Cheap flights from Singapore to Chicago from $588 (SIN to ORD) - Expedia.com ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $588 Cheap Flights from Singapore (SIN) to Chicago (ORD) [View $588 flight on Wed, Sep 23, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:SIN,to:ORD,departure:9/23/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:587.13&airProductToken=AQpnCjIIy4oBEgM2NDYYkmogyGgo9b6YAzD2wZgDOFVAAFgBagdFWVNBVkVScghVTEUwMEFFSwoxCMuKARICMzcYyGggrhwo5MKYAzDmyJgDOFVAAVgBagdFWVNBVkVScghVTEUwMEFFSxIKCAEQARgBKgJLRRgBIgQIARABKAIoBCgGMAE) ## Popular airlines from Singapore Changi Airport (SIN) to Chicago O'Hare Intl. Airport (ORD) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.com/Flights-Search?leg1=from:SIN,to:ORD,departure:4/3/2026TANYT&leg2=from:ORD,to:SIN,departure:4/10/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_KE.svg) Korean Air [](https://www.expedia.com/Flights-Search?leg1=from:SIN,to:ORD,departure:4/3/2026TANYT&leg2=from:ORD,to:SIN,departure:4/10/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"KE"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NH.svg) All Nippon Airways [](https://www.expedia.com/Flights-Search?leg1=from:SIN,to:ORD,departure:4/3/2026TANYT&leg2=from:ORD,to:SIN,departure:4/10/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NH"}}]) - ![](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:SIN,to:ORD,departure:4/3/2026TANYT&leg2=from:ORD,to:SIN,departure:4/10/2026TANYT&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_QR.svg) Qatar Airways [](https://www.expedia.com/Flights-Search?leg1=from:SIN,to:ORD,departure:4/3/2026TANYT&leg2=from:ORD,to:SIN,departure:4/10/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"QR"}}]) - ![](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:SIN,to:ORD,departure:4/3/2026TANYT&leg2=from:ORD,to:SIN,departure:4/10/2026TANYT&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_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:SIN,to:ORD,departure:4/3/2026TANYT&leg2=from:ORD,to:SIN,departure:4/10/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](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 Singapore to Chicago (SIN-ORD) Prices were available within the past 7 days and start at $588 for one-way flights and $814 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Jun 23 - Tue, Jul 14 SIN Singapore ORD Chicago $814 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:SIN,to:ORD,departure:6/23/2026TANYT&leg2=from:ORD,to:SIN,departure:7/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:813.73&airProductToken=AQppCjEI1YIBEgEyGJJqILJxKK23kAMw3r6QAzhLQABYAWoIRUNPQkFTSUNyCEtMQThSU0I5CjQI1YIBEgQxNzYzGLJxIK4cKP7CkAMwh8WQAzhLQAFYAWoIRUNPQkFTSUNyCEtMQThSU0I5CmkKMwjVggESAzI0NhiuHCCycSi-qJIDMNOqkgM4S0AAWAFqCEVDT0JBU0lDcghLTEE4UlNCOQoyCNWCARICMjkYsnEgkmoo4quSAzC7s5IDOEtAAVgBaghFQ09CQVNJQ3IIS0xBOFJTQjkSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAB) ![All Nippon Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/NH.gif) Tue, Oct 20 - Tue, Nov 10 SIN Singapore ORD Chicago $850 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:SIN,to:ORD,departure:10/20/2026TANYT&leg2=from:ORD,to:SIN,departure:11/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:849.53&airProductToken=AQpnCjIIzpABEgM4MDIYkmogrZwBKPfwmgMwqvSaAzhLQABYAWoGRUNPVkFMcghLTEE3UlM0SwoxCM6QARICMTIYrZwBIK4cKMD1mgMwi_uaAzhLQAFYAWoGRUNPVkFMcghLTEE3UlM0SwpyCj0IzpABEgQ3MDA5GK4cIKcbKP7mnAMwre2cAzhLQABYAWoGRUNPVkFMcghLTEE3UlM0S3oJCNWCARIDODgxCjEIzpABEgM4NDMYpxsgkmoovfCcAzD_85wDOEtAAVgBagZFQ09WQUxyCEtMQTdSUzRLEgoIARABGAEqAk5IGAEiBAgBEAEoAigDKAQwAQ) ![Korean Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/ke.gif) Fri, Sep 11 - Fri, Oct 2 SIN Singapore ORD Chicago $956 Roundtrip found 15 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:SIN,to:ORD,departure:9/11/2026TANYT&leg2=from:ORD,to:SIN,departure:10/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:955.13&airProductToken=AQpnCjIIy4oBEgM2NDYYkmogyGgo9beXAzD2upcDOFFAAFgBagdFWVNBVkVScghRTEUwWkFFSwoxCMuKARICMzcYyGggrhwo5LuXAzDmwZcDOFFAAVgBagdFWVNBVkVScghRTEUwWkFFSwpnCjEIy4oBEgIzOBiuHCDIaCimr5kDMJa2mQM4UUAAWAFqB0VZU0FWRVJyCFFMRTBaQUVLCjIIy4oBEgM2NDMYyGggkmoogsCZAzCDw5kDOFFAAVgBagdFWVNBVkVScghRTEUwWkFFSxIKCAEQARgBKgJLRRgBIgQIARABKAIoBCgGMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Sep 23 - Wed, Oct 14 SIN Singapore ORD Chicago $966 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:SIN,to:ORD,departure:9/23/2026TANYT&leg2=from:ORD,to:SIN,departure:10/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:965.13&airProductToken=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) ![Japan Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/JL.gif) Wed, Apr 15 - Wed, Sep 30 SIN Singapore ORD Chicago $981 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:SIN,to:ORD,departure:4/15/2026TANYT&leg2=from:ORD,to:SIN,departure:9/30/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:980.13&airProductToken=AQprCjQIypgBEgM3MTIYkmogrZwBKOWuigMwjrKKAzhPQABYAWoIRUNPU1BTVkNyCE9ORTA4UloxCjMIypgBEgI1NhitnAEgrhworbqKAzDkv4oDOE9AAVgBaghFQ09TUFNWQ3IIT05FMDhSWjEKZwoxCMqYARIBORiuHCCnGyjemZkDMP6fmQM4T0AAWAFqCEVDT1NQU1ZDcghPTkUwOFJaMQoyCMqYARICMzUYpxsgkmooiaOZAzCyppkDOE9AAVgBaghFQ09TUFNWQ3IIT05FMDhSWjESCggBEAEYASoCSkwYASIECAEQASgCKAMoBDAB) ![Turkish Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TK.gif) Mon, Jul 6 - Mon, Jul 27 SIN Singapore ORD Chicago $1,135 Roundtrip found 19 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:SIN,to:ORD,departure:7/6/2026TANYT&leg2=from:ORD,to:SIN,departure:7/27/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1134.43&airProductToken=AQpcCiwI1JYBEgMyMDkYkmogyJwBKN7KkQMwgdCRAzhXQABYAWoCUFNyBldGM1hQQwosCNSWARIDMTg1GMicASCuHCiS1pEDMLDbkQM4V0ABWAFqAlBTcgZXRjNYUEMKWgoqCNSWARIBNhiuHCDInAEopsGTAzCmxpMDOFdAAFgBagJQU3IGV0YzWFBDCiwI1JYBEgMyMDgYyJwBIJJqKNXHkwMw2syTAzhXQAFYAWoCUFNyBldGM1hQQxIKCAEQARgBKgJUSxgBIgQIARABKAIoAygEMAE) ![EVA Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/BR.gif) Sat, Sep 5 - Sat, Sep 26 SIN Singapore ORD Chicago $1,140 Roundtrip found 7 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:SIN,to:ORD,departure:9/5/2026TANYT&leg2=from:ORD,to:SIN,departure:9/26/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1139.33&airProductToken=AQpNCiUIwqQBEgMyMjYYkmog8yMo9vmWAzCJ_JYDOFZAAFgBcgRWTFNHCiQIwqQBEgI1NhjzIyCuHCiQ_ZYDMMmDlwM4VkABWAFyBFZMU0cKTQokCMKkARICNTUYrhwg8yMoquaYAzDH7ZgDOFZAAFgBcgRWTFNHCiUIwqQBEgMyMjUY8yMgkmoo4u6YAzDr8JgDOFZAAVgBcgRWTFNHEgoIARABGAEqAkJSGAEiBAgBEAEoAigEKAYwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, Sep 7 - Mon, Sep 28 SIN Singapore ORD Chicago $1,156 Roundtrip found 15 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:SIN,to:ORD,departure:9/7/2026TANYT&leg2=from:ORD,to:SIN,departure:9/28/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1155.43&airProductToken=AQp-Cj0IwYIBEgQ4Mzk5GJJqIKcbKL6UlwMw3ZeXAzhRQABYAWoHTUFJTlNGTHIIUUxFMDhZTjN6CAjKmAESAjM2Cj0IwYIBEgQ4NDA1GKcbIK4cKJCblwMw0aCXAzhRQAFYAWoHTUFJTlNGTHIIUUxFMDhZTjN6CAjKmAESAjEwCoEBCj4IwYIBEgQ4NDU5GK4cIK2cASizgZkDMMmHmQM4T0AAWAFqB01BSU5TRkxyCE9ORTA4Uk4zeggIypgBEgI1NQo_CMGCARIEODQ4MhitnAEgkmoo4YmZAzCUjZkDOE9AAVgBagdNQUlOU0ZMcghPTkUwOFJOM3oJCMqYARIDNzExEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwAQ) ![Cathay Pacific](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/CX.gif) Mon, Sep 14 - Mon, Oct 5 SIN Singapore ORD Chicago $1,260 Roundtrip found 14 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:SIN,to:ORD,departure:9/14/2026TANYT&leg2=from:ORD,to:SIN,departure:10/5/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1259.83&airProductToken=AQpsCjQIw7ABEgM3MTQYkmogxzIo6dmXAzDe25cDOFFAAFgBaglFQ09OTElHSFRyCFFSMjFTR0FSCjQIw7ABEgM4MDYYxzIgrhwo2t6XAzDo5ZcDOFFAAVgBaglFQ09OTElHSFRyCFFSMjFTR0FSCmwKNAjDsAESAzgwMRiuHCDHMij70pkDMKzamQM4UUAAWAFqCUVDT05MSUdIVHIIUVIyMVNHQVIKNAjDsAESAzY1ORjHMiCSaijJ3JkDMKremQM4UUABWAFqCUVDT05MSUdIVHIIUVIyMVNHQVISCggBEAEYASoCQ1gYASIECAEQASgCKAQoBjAB) ![Lufthansa](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/LH.gif) Mon, Jan 18 - Mon, Feb 8 SIN Singapore ORD Chicago $1,348 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:SIN,to:ORD,departure:1/18/2027TANYT&leg2=from:ORD,to:SIN,departure:2/8/2027TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1347.13&airProductToken=AQp2CjMIzJABEgM3NjkYkmogjBUo0e2iAzDd86IDOEtAAFgBaghFQ09TQVZFUnIIS1g1WERZTkMKPwjMkAESBDkyNjgYjBUgrhwosfaiAzD6-qIDOEtAAVgBaghFQ09TQVZFUnIIS1g1WERZTkN6CQjVggESAzk1MgqEAQpACMyQARIENzk0ORiuHCChpAEo292kAzC74aQDOEtAAFgBaghFQ09TQVZFUnIIS1g1WERZTkN6CQjVggESAzk3MgpACMyQARIENzI0NhihpAEgkmoozOKkAzC_6KQDOEtAAVgBaghFQ09TQVZFUnIIS1g1WERZTkN6CQjTogESAzMwMxIKCAIQARgCKgJMSBgBIgQIARABKAIoAygEMAs) ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:SIN,to:MDW,departure:4/3/2026TANYT&leg2=from:MDW,to:SIN,departure:4/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. Closest 16 min [Flights from $2,637 ](https://www.expedia.com/Flights-Search?leg1=from:SIN,to:MDW,departure:4/3/2026TANYT&leg2=from:MDW,to:SIN,departure:4/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Find the cheapest month to fly from Singapore (SIN) to Chicago (ORD) ### September is typically the cheapest month to fly From $686 - $1,022 per traveler. ## Frequently asked questions ### How much does a flight from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) cost? ### What is the cheapest month to fly from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)? ### Which airlines fly direct from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)? ### What is the cheapest airline that flies from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)? ### How do I find cheap flights from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)? ### What is the best time to fly from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)? ### What is the earliest flight from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)? ### What are the most popular departure times for flights from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)? ### How long does it take to fly from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)? ### Can you fly business or first class from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)? ### How do I earn miles on a Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia? ### What airports do you fly into for Chicago from Changi (SIN)? ### Is it cheaper to buy a plane ticket from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) at the last minute? ### Is it cheaper to book a Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package? ### Can I cancel or change the date of my flight from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)? ## Travel information | Origin airport | Changi | | ------------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Destination airport | O'Hare Intl. | | Airlines serving | Air Canada, Alaska Airlines, All Nippon Airways, American Airlines, British Airways, Cathay Pacific, Delta, EVA Airways, Emirates, Etihad Airways, Japan Airlines, JetBlue Airways, KLM, Korean Air, Lufthansa, Qatar Airways, Singapore Airlines, Swiss International Air Lines, Turkish Airlines, United | | Roundtrip price | $814 | | Distance | 9351 mi | ## Book with confidence # Singapore to Chicago Flights The cheapest times to fly from Singapore to Chicago 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 Singapore to Chicago are during the month of June. You can find some of the cheapest flights from Singapore to Chicago with Expedia's search tool and vast selection of airlines. The best time to book a flight from Singapore to Chicago Sunday is one of the best days to book for cheap flights from Singapore to Chicago: 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 Singapore to Chicago 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 Singapore to Chicago in 2026\. You can also book with separate airlines for your outbound and return journeys, from $588 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 Singapore to Chicago 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 Singapore to Chicago 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 - Flights - Packages - Cars - Vacation Rentals - Other - [Chicago Hotels ](https://www.expedia.com/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Hotels near O'Hare Station ](https://www.expedia.com/OHare-Station-Hotels.d6210225.Travel-Guide-Hotels) - [Rosemont Hotels ](https://www.expedia.com/Rosemont-Hotels.d7581.Travel-Guide-Hotels) - [Hotels near Donald E. 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