Title: $2,395 Cheap flights from Chicago to Tobago (CHI to TAB) - Expedia.com ![Panorama Paria bay in colour](https://images.trvl-media.com/place/602308/66b63438-495b-4c81-8640-2076b367424c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/602308/66b63438-495b-4c81-8640-2076b367424c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $2,395 Cheap Flights from Chicago (CHI) to Tobago (TAB) [View $2,395 flight on Sun, Feb 15, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:ORD,to:TAB,departure:2/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:2394.80&airProductToken=AQqCAQo0CMGGARIDNTA4GK4cIJjOASijoYUDMIaihQM4QkAAWAFqCExBVElUVURFcghCTkEwQTFMVAokCMKuARIDNjAxGJjOASDPkwEokKSFAzDkpoUDOFlAAVgBcgFZCiQIwq4BEgQxNTA2GM-TASCTCCj1p4UDMI6ohQM4WUABWAFyAVkSCggBEAEYASoCQlcYASIECAEQASgCKAMoBDAB) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travelers 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 to Tobago (TAB-A.N.R. Robinson Intl.) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:TAB,departure:2/24/2026TANYT&leg2=from:TAB,to:CHI,departure:3/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](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:CHI,to:TAB,departure:2/24/2026TANYT&leg2=from:TAB,to:CHI,departure:3/3/2026TANYT&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_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:TAB,departure:2/24/2026TANYT&leg2=from:TAB,to:CHI,departure:3/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](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:CHI,to:TAB,departure:2/24/2026TANYT&leg2=from:TAB,to:CHI,departure:3/3/2026TANYT&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_F9.svg) Frontier Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:TAB,departure:2/24/2026TANYT&leg2=from:TAB,to:CHI,departure:3/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](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:CHI,to:TAB,departure:2/24/2026TANYT&leg2=from:TAB,to:CHI,departure:3/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![](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:CHI,to:TAB,departure:2/24/2026TANYT&leg2=from:TAB,to:CHI,departure:3/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](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 Tobago (CHI-TAB) Prices were available within the past 7 days and start at $2,395 for one-way flights and $1,451 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) Sat, Apr 4 - Thu, Apr 9 ORD Chicago TAB Tobago $1,451 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/4/2026TANYT&leg2=from:TAB,to:ORD,departure:4/9/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1450.33&airProductToken=AQpmCh8I1YIBEgM3NjUYrhwgjAIovrmJAzCEu4kDOFFAAFgBCiAIwq4BEgM0ODMYjAIgz5MBKP67iQMw372JAzhRQAFYAQohCMKuARIEMTU0MBjPkwEgkwgo676JAzCEv4kDOFdAAVgBCmYKIQjCrgESBDE1MDMYkwggz5MBKNfwiQMw8PCJAzhXQABYAQogCMKuARIDNDgwGM-TASDlWijy8YkDMOfziQM4VEABWAEKHwjVggESAzY1MRjlWiCuHCjK9YkDMJ_3iQM4UUABWAESCggBEAEYASoCQlcYASIECAEQASgIKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, Apr 4 - Mon, Apr 13 ORD Chicago TAB Tobago $1,475 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/4/2026TANYT&leg2=from:TAB,to:ORD,departure:4/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1474.33&airProductToken=AQpmCh8I1YIBEgM3NjUYrhwgjAIovrmJAzCEu4kDOFFAAFgBCiAIwq4BEgM0ODMYjAIgz5MBKP67iQMw372JAzhRQAFYAQohCMKuARIEMTU0MBjPkwEgkwgo676JAzCEv4kDOFdAAVgBCmcKIQjCrgESBDE1NDMYkwggz5MBKK6aigMwx5qKAzhXQABYAQogCMKuARIDNDgyGM-TASDMcCiOnooDMJygigM4R0ABWAEKIAjVggESBDIyMDYYzHAgrhwo3KGKAzCao4oDOFFAAVgBEgoIARABGAEqAkJXGAEiBAgBEAEoCCgEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Fri, Apr 10 - Mon, Apr 13 ORD Chicago TAB Tobago $1,515 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/10/2026TANYT&leg2=from:TAB,to:ORD,departure:4/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1514.33&airProductToken=AQpnCiAI1YIBEgQxNjQzGK4cIMxwKJf9iQMwyv6JAzhRQABYAQogCMKuARIDNDg1GMxwIM-TASjN_4kDMMKBigM4SEABWAEKIQjCrgESBDE1MzYYz5MBIJMIKM6CigMw54KKAzhXQAFYAQpnCiEIwq4BEgQxNTAxGJMIIM-TASivnYoDMMidigM4V0AAWAEKIAjCrgESAzQ4NBjPkwEgjAIotp6KAzCroIoDOEdAAVgBCiAI1YIBEgQyMTA2GIwCIK4cKN2higMwuaOKAzhRQAFYARIKCAEQARgBKgJCVxgBIgQIARABKAgoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, Apr 4 - Wed, Apr 15 ORD Chicago TAB Tobago $1,525 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/4/2026TANYT&leg2=from:TAB,to:ORD,departure:4/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1524.53&airProductToken=AQpmCh8I1YIBEgM3NjUYrhwgjAIovrmJAzCEu4kDOFFAAFgBCiAIwq4BEgM0ODMYjAIgz5MBKP67iQMw372JAzhRQAFYAQohCMKuARIEMTU0MBjPkwEgkwgo676JAzCEv4kDOFdAAVgBCmkKIQjCrgESBDE1NDEYkwggz5MBKIy7igMwpbuKAzhXQABYAQohCMKuARIDNjAyGM-TASCYzgEo1LyKAzDBv4oDOFFAAVgBCiEI1YIBEgQzNDczGJjOASCuHCjXwIoDMNLBigM4WUABWAESCggBEAEYASoCVUEYASIECAEQASgIKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Apr 6 - Mon, Apr 13 ORD Chicago TAB Tobago $1,545 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/6/2026TANYT&leg2=from:TAB,to:ORD,departure:4/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1544.33&airProductToken=AQpnCiAI1YIBEgQxNjQzGK4cIMxwKJfQiQMwytGJAzhRQABYAQogCMKuARIDNDg1GMxwIM-TASjN0okDMMLUiQM4TEABWAEKIQjCrgESBDE1NDIYz5MBIJMIKLLWiQMwy9aJAzhXQAFYAQpnCiEIwq4BEgQxNTAxGJMIIM-TASivnYoDMMidigM4V0AAWAEKIAjCrgESAzQ4NBjPkwEgjAIotp6KAzCroIoDOEdAAVgBCiAI1YIBEgQyMTA2GIwCIK4cKN2higMwuaOKAzhRQAFYARIKCAEQARgBKgJCVxgBIgQIARABKAgoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, Apr 4 - Sat, Apr 11 ORD Chicago TAB Tobago $1,547 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/4/2026TANYT&leg2=from:TAB,to:ORD,departure:4/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1546.53&airProductToken=AQpmCh8I1YIBEgM3NjUYrhwgjAIovrmJAzCEu4kDOFFAAFgBCiAIwq4BEgM0ODMYjAIgz5MBKP67iQMw372JAzhRQAFYAQohCMKuARIEMTU0MBjPkwEgkwgo676JAzCEv4kDOFdAAVgBCmkKIQjCrgESBDE1NDEYkwggz5MBKIyOigMwpY6KAzhXQABYAQohCMKuARIDNjAyGM-TASCYzgEo1I-KAzDBkooDOE5AAVgBCiEI1YIBEgQzNDczGJjOASCuHCjXk4oDMNKUigM4WUABWAESCggBEAEYASoCVUEYASIECAEQASgIKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Apr 6 - Thu, Apr 9 ORD Chicago TAB Tobago $1,550 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/6/2026TANYT&leg2=from:TAB,to:ORD,departure:4/9/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1549.33&airProductToken=AQpmCh8I1YIBEgM0NzAYrhwgjAIokM-JAzDa0IkDOFFAAFgBCiAIwq4BEgM0ODMYjAIgz5MBKL7SiQMwn9SJAzhMQAFYAQohCMKuARIEMTU0MBjPkwEgkwgoq9WJAzDE1YkDOFdAAVgBCmYKIQjCrgESBDE1MDMYkwggz5MBKNfwiQMw8PCJAzhXQABYAQogCMKuARIDNDgwGM-TASDlWijy8YkDMOfziQM4VEABWAEKHwjVggESAzY1MRjlWiCuHCjK9YkDMJ_3iQM4UUABWAESCggBEAEYASoCQlcYASIECAEQASgIKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, Apr 4 - Tue, Apr 14 ORD Chicago TAB Tobago $1,569 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/4/2026TANYT&leg2=from:TAB,to:ORD,departure:4/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1568.53&airProductToken=AQpmCh8I1YIBEgM3NjUYrhwgjAIovrmJAzCEu4kDOFFAAFgBCiAIwq4BEgM0ODMYjAIgz5MBKP67iQMw372JAzhRQAFYAQohCMKuARIEMTU0MBjPkwEgkwgo676JAzCEv4kDOFdAAVgBCmkKIQjCrgESBDE1MTUYkwggz5MBKJmrigMwsquKAzhXQABYAQohCMKuARIDNjAwGM-TASCYzgEor6yKAzCcr4oDOEhAAVgBCiEI1YIBEgQyMTA5GJjOASCuHCj0s4oDMO-0igM4WUABWAESCggBEAEYASoCVUEYASIECAEQASgIKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Apr 8 - Mon, Apr 13 ORD Chicago TAB Tobago $1,575 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/8/2026TANYT&leg2=from:TAB,to:ORD,departure:4/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1574.33&airProductToken=AQpmCiAI1YIBEgQxNjQzGK4cIMxwKNfmiQMwiuiJAzhRQABYAQogCMKuARIDNDg1GMxwIM-TASiN6YkDMILriQM4QkABWAEKIAjCrgESAzQyMhjPkwEgkwgou-yJAzDe7IkDOFdAAVgBCmcKIQjCrgESBDE1MDEYkwggz5MBKK-digMwyJ2KAzhXQABYAQogCMKuARIDNDg0GM-TASCMAii2nooDMKugigM4R0ABWAEKIAjVggESBDIxMDYYjAIgrhwo3aGKAzC5o4oDOFFAAVgBEgoIARABGAEqAkJXGAEiBAgBEAEoCCgEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Fri, Apr 10 - Sat, Apr 11 ORD Chicago TAB Tobago $1,599 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/10/2026TANYT&leg2=from:TAB,to:ORD,departure:4/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1598.33&airProductToken=AQpnCiAI1YIBEgQxNjQzGK4cIMxwKJf9iQMwyv6JAzhRQABYAQogCMKuARIDNDg1GMxwIM-TASjN_4kDMMKBigM4SEABWAEKIQjCrgESBDE1MzYYz5MBIJMIKM6CigMw54KKAzhXQAFYAQpnCiEIwq4BEgQxNTAxGJMIIM-TASjvhooDMIiHigM4V0AAWAEKIAjCrgESAzQ4NBjPkwEgjAIo9oeKAzDriYoDOFRAAVgBCiAI1YIBEgQyMTA2GIwCIK4cKJ2LigMw-YyKAzhIQAFYARIKCAEQARgBKgJCVxgBIgQIARABKAgoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Apr 8 - Thu, Apr 9 ORD Chicago TAB Tobago $1,613 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/8/2026TANYT&leg2=from:TAB,to:ORD,departure:4/9/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1612.33&airProductToken=AQpmCiAI1YIBEgQxNjQzGK4cIMxwKNfmiQMwiuiJAzhRQABYAQogCMKuARIDNDg1GMxwIM-TASiN6YkDMILriQM4QkABWAEKIAjCrgESAzQyMhjPkwEgkwgou-yJAzDe7IkDOFdAAVgBCmcKIQjCrgESBDE1MDEYkwggz5MBKK_wiQMwyPCJAzhXQABYAQogCMKuARIDNDg0GM-TASCMAii28YkDMKvziQM4VEABWAEKIAjVggESBDIxMDYYjAIgrhwo3fSJAzC59okDOFFAAVgBEgoIARABGAEqAkJXGAEiBAgBEAEoCCgEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Apr 6 - Sat, Apr 11 ORD Chicago TAB Tobago $1,629 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/6/2026TANYT&leg2=from:TAB,to:ORD,departure:4/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1628.33&airProductToken=AQpnCiAI1YIBEgQxNjQzGK4cIMxwKJfQiQMwytGJAzhRQABYAQogCMKuARIDNDg1GMxwIM-TASjN0okDMMLUiQM4TEABWAEKIQjCrgESBDE1NDIYz5MBIJMIKLLWiQMwy9aJAzhXQAFYAQpnCiEIwq4BEgQxNTAxGJMIIM-TASjvhooDMIiHigM4V0AAWAEKIAjCrgESAzQ4NBjPkwEgjAIo9oeKAzDriYoDOFRAAVgBCiAI1YIBEgQyMTA2GIwCIK4cKJ2LigMw-YyKAzhIQAFYARIKCAEQARgBKgJCVxgBIgQIARABKAgoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Apr 6 - Sun, Apr 12 ORD Chicago TAB Tobago $1,646 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/6/2026TANYT&leg2=from:TAB,to:ORD,departure:4/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1645.53&airProductToken=AQpmCh8I1YIBEgM0NzAYrhwgjAIokM-JAzDa0IkDOFFAAFgBCiAIwq4BEgM0ODMYjAIgz5MBKL7SiQMwn9SJAzhMQAFYAQohCMKuARIEMTU0MBjPkwEgkwgoq9WJAzDE1YkDOFdAAVgBCmkKIQjCrgESBDE1NDMYkwggz5MBKI6PigMwp4-KAzhXQABYAQohCMKuARIDNjEwGM-TASCYzgEo35KKAzDMlYoDOE5AAVgBCiEI1YIBEgQ1NDE4GJjOASCuHCj7looDMPaXigM4WUABWAESCggBEAEYASoCVUEYASIECAEQASgIKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Fri, Apr 10 - Sun, Apr 12 ORD Chicago TAB Tobago $1,654 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/10/2026TANYT&leg2=from:TAB,to:ORD,departure:4/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1653.53&airProductToken=AQpnCiAI1YIBEgQxNjQzGK4cIMxwKJf9iQMwyv6JAzhRQABYAQogCMKuARIDNDg1GMxwIM-TASjN_4kDMMKBigM4SEABWAEKIQjCrgESBDE1MzYYz5MBIJMIKM6CigMw54KKAzhXQAFYAQppCiEIwq4BEgQxNTQzGJMIIM-TASiOj4oDMKePigM4V0AAWAEKIQjCrgESAzYxMBjPkwEgmM4BKN-SigMwzJWKAzhOQAFYAQohCNWCARIENTQxOBiYzgEgrhwo-5aKAzD2l4oDOFlAAVgBEgoIARABGAEqAlVBGAEiBAgBEAEoCCgEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Apr 8 - Sat, Apr 11 ORD Chicago TAB Tobago $1,659 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/8/2026TANYT&leg2=from:TAB,to:ORD,departure:4/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1658.33&airProductToken=AQpmCiAI1YIBEgQxNjQzGK4cIMxwKNfmiQMwiuiJAzhRQABYAQogCMKuARIDNDg1GMxwIM-TASiN6YkDMILriQM4QkABWAEKIAjCrgESAzQyMhjPkwEgkwgou-yJAzDe7IkDOFdAAVgBCmcKIQjCrgESBDE1MDEYkwggz5MBKO-GigMwiIeKAzhXQABYAQogCMKuARIDNDg0GM-TASCMAij2h4oDMOuJigM4VEABWAEKIAjVggESBDIxMDYYjAIgrhwonYuKAzD5jIoDOEhAAVgBEgoIARABGAEqAkJXGAEiBAgBEAEoCCgEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sun, Apr 5 - Mon, Apr 13 ORD Chicago TAB Tobago $1,694 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:4/5/2026TANYT&leg2=from:TAB,to:ORD,departure:4/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1693.13&airProductToken=AQppCiEI1YIBEgQyNDk2GK4cIJjOASiByYkDMOzJiQM4WUAAWAEKIQjCrgESAzYwMRiYzgEgz5MBKPTKiQMwyM2JAzhOQAFYAQohCMKuARIEMTUwNBjPkwEgkwgo2c6JAzDyzokDOFdAAVgBCmcKIQjCrgESBDE1MDEYkwggz5MBKK-digMwyJ2KAzhXQABYAQogCMKuARIDNDg0GM-TASCMAii2nooDMKugigM4R0ABWAEKIAjVggESBDIxMDYYjAIgrhwo3aGKAzC5o4oDOFFAAVgBEgoIARABGAEqAlVBGAEiBAgBEAEoCCgEMAE) ![Iberia](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/IB.gif) Wed, Feb 11 - Tue, Feb 17 ORD Chicago TAB Tobago $3,152 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:2/11/2026TANYT&leg2=from:TAB,to:ORD,departure:2/17/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:3151.43&airProductToken=AQpGCiEIyYQBEgQzNjM1GK4cIOuJASiB94QDMNf6hAM4TUAAWAEKIQjCggESBDIxNTkYy7EBIJMIKJiFhQMwtoqFAzhNQAFYAQpGCiEIwoIBEgQyMTU4GJMIIMuxASifuIUDMIG9hQM4QkAAWAEKIQjJhAESBDQyMDkY64kBIK4cKNO-hQMw5cKFAzhPQAFYARIKCAEQARgBKgJJQhgBIgQIARABKAgoBDAB) ![Iberia](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/IB.gif) Thu, Feb 12 - Tue, Feb 17 ORD Chicago TAB Tobago $3,202 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TAB,departure:2/12/2026TANYT&leg2=from:TAB,to:ORD,departure:2/17/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:3201.43&airProductToken=AQpGCiEIyYQBEgQzNjMzGK4cIOuJASiOgIUDMN-DhQM4TUAAWAEKIQjCggESBDIxNTkYy7EBIJMIKJiFhQMwtoqFAzhNQAFYAQpGCiEIwoIBEgQyMTU4GJMIIMuxASifuIUDMIG9hQM4QkAAWAEKIQjJhAESBDQyMDkY64kBIK4cKNO-hQMw5cKFAzhPQAFYARIKCAEQARgBKgJJQhgBIgQIARABKAgoBDAB) __Flights from Chicago (ORD) to Tobago (TAB)__ | Origin airport | O'Hare Intl. | | ------------------- | --------------------- | | Destination airport | A.N.R. Robinson Intl. | | Roundtrip price | $1,450 | | Distance | 2683 mi | ## Chicago to Tobago Flights The cheapest times to fly from Chicago to Tobago 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 Tobago are during the month of April. You can find some of the cheapest flights from Chicago to Tobago with Expedia's search tool and vast selection of airlines. The best time to book a flight from Chicago to Tobago Sunday is one of the best days to book for cheap flights from Chicago to Tobago: 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 Tobago 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 Tobago in 2026\. You can also book with separate airlines for your outbound and return journeys, from $2,395 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 Tobago 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 Tobago 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 - [Hotels near Store Bay ](https://www.expedia.com/Store-Bay-Hotels.0-l553248621533157525-0.Travel-Guide-Filter-Hotels) - [Crown Point Hotels ](https://www.expedia.com/Crown-Point-Hotels.d11941.Travel-Guide-Hotels) - [All-inclusive Resorts in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-All-Inclusive-Hotel.0-0-d11941-tAllinclusiveHotel.Travel-Guide-Filter-Hotels) - [Guest Houses in Crown Point ](https://www.expedia.com/Crown-Point-Guest-Houses.d11941-aaGuestHouses.Travel-Guide-Accommodation) - [Beach Hotels in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Beach-Hotel.0-0-d11941-tBeachHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Romantic-Hotel.0-0-d11941-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Apartments in Crown Point ](https://www.expedia.com/Crown-Point-Apartments.d11941-aaApartments.Travel-Guide-Accommodation) - [Hotels with a Pool in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Hotel-With-Pool.0-0-d11941-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts & in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Honeymoon-Hotels.0-0-d11941-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Hotels-With-Hot-Tubs.0-0-d11941-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Cheap-Hotels.0-0-d11941-tCheapHotels.Travel-Guide-Filter-Hotels) - [Resorts & Hotels with Spas in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Spa-Hotel.0-0-d11941-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Hotels-With-Kitchens.0-0-d11941-tHotelswithKitchens.Travel-Guide-Filter-Hotels) - [Resorts in Crown Point ](https://www.expedia.com/Crown-Point-Resorts.d11941-aaResorts.Travel-Guide-Accommodation) - [Hotel Wedding Venues Hotels in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Wedding-Hotels.0-0-d11941-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Hotels with Bars in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Bar-Hotel.0-0-d11941-tBarHotel.Travel-Guide-Filter-Hotels) - [Villas in Crown Point ](https://www.expedia.com/Crown-Point-Villas.d11941-aaVillas.Travel-Guide-Accommodation) - [Boutique Hotels in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Boutique-Hotel.0-0-d11941-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cottages in Crown Point ](https://www.expedia.com/Crown-Point-Cottages.d11941-aaCottages.Travel-Guide-Accommodation) - [Luxury Hotels in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Luxury-Hotel.0-0-d11941-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d11941-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Historic Hotels in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Historic-Hotel.0-0-d11941-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Hotels-With-Complimentary-Breakfast.0-0-d11941-tHotelswithComplimentaryBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with an Outdoor Pool in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Hotels-With-Outdoor-Pool.0-0-d11941-tHotelswithOutdoorPool.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Crown Point ](https://www.expedia.com/4Star-Crown-Point-Hotels.s40-0-d11941.Travel-Guide-Filter-Hotels) - [B&B in Crown Point ](https://www.expedia.com/Crown-Point-Bed-And-Breakfast.d11941-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels with Free Parking in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Hotels-With-Free-Parking.0-0-d11941-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Condo Rentals in Crown Point ](https://www.expedia.com/Crown-Point-Condos.d11941-aaCondos.Travel-Guide-Accommodation) - [Hotels with a Gym in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Hotels-With-Fitness-Center.0-0-d11941-tHotelswithFitnessCenter.Travel-Guide-Filter-Hotels) - [Bon Accord Village Hotels ](https://www.expedia.com/Bon-Accord-Village-Hotels.d6337888.Travel-Guide-Hotels) - [Beach Hotels in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Hotels-Beach-Hotel.0-0-d6337888-tBeachHotel.Travel-Guide-Filter-Hotels) - [Guest Houses in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Guest-Houses.d6337888-aaGuestHouses.Travel-Guide-Accommodation) - [Hotel Wedding Venues Hotels in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Hotels-Wedding-Hotels.0-0-d6337888-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Resorts & Hotels with Spas in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Hotels-Spa-Hotel.0-0-d6337888-tSpaHotel.Travel-Guide-Filter-Hotels) - [All-inclusive Resorts in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Hotels-All-Inclusive-Hotel.0-0-d6337888-tAllinclusiveHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Hotels-Boutique-Hotel.0-0-d6337888-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Hotels-Romantic-Hotel.0-0-d6337888-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Hotels with an Outdoor Pool in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Hotels-Hotels-With-Outdoor-Pool.0-0-d6337888-tHotelswithOutdoorPool.Travel-Guide-Filter-Hotels) - [Hotels near Pigeon Point Beach ](https://www.expedia.com/Pigeon-Point-Beach-Hotels.0-l6119416-0.Travel-Guide-Filter-Hotels) - [Canaan Hotels ](https://www.expedia.com/Canaan-Hotels.d6343440.Travel-Guide-Hotels) - [Villas in Canaan ](https://www.expedia.com/Canaan-Villas.d6343440-aaVillas.Travel-Guide-Accommodation) - [Guest Houses in Canaan ](https://www.expedia.com/Canaan-Guest-Houses.d6343440-aaGuestHouses.Travel-Guide-Accommodation) - [Apartments in Canaan ](https://www.expedia.com/Canaan-Apartments.d6343440-aaApartments.Travel-Guide-Accommodation) - [Cottages in Canaan ](https://www.expedia.com/Canaan-Cottages.d6343440-aaCottages.Travel-Guide-Accommodation) - [Hotels near Nylon Pool ](https://www.expedia.com/Nylon-Pool-Hotels.0-l553248621558078509-0.Travel-Guide-Filter-Hotels) - [Hotels near Buccoo Reef ](https://www.expedia.com/Buccoo-Reef-Hotels.0-l6337824-0.Travel-Guide-Filter-Hotels) - [Hotels with Free Wifi in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Hotel-With-Wifi.0-0-d11941-tHotelwithwifi.Travel-Guide-Filter-Hotels) - [Beach Hotels in Canaan ](https://www.expedia.com/Canaan-Hotels-Beach-Hotel.0-0-d6343440-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels with Connecting Rooms in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Hotels-With-Adjoining-Rooms.0-0-d11941-tHotelswithAdjoiningRooms.Travel-Guide-Filter-Hotels) - [Villas in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Villas.d6337888-aaVillas.Travel-Guide-Accommodation) - [Hotels with Bars in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Hotels-Bar-Hotel.0-0-d6337888-tBarHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Golf-Hotel.0-0-d11941-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Hotels-With-Tennis-Courts.0-0-d11941-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Hotels-Couples-Resorts-Hotels.0-0-d6337888-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Wifi in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Hotels-Hotel-With-Wifi.0-0-d6337888-tHotelwithwifi.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Crown Point ](https://www.expedia.com/2Star-Crown-Point-Hotels.s20-0-d11941.Travel-Guide-Filter-Hotels) - [Hotels near Swallows Beach ](https://www.expedia.com/Swallows-Beach-Hotels.0-l791074088716632064-0.Travel-Guide-Filter-Hotels) - [Hotels near Fort Millford ](https://www.expedia.com/Fort-Millford-Hotels.0-l6119426-0.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Crown Point ](https://www.expedia.com/Crown-Point-Hotels-Hotels-With-Balconies.0-0-d11941-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Non-Smoking Hotels in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Hotels-Smoke-Free-Hotels.0-0-d6337888-tSmokeFreeHotels.Travel-Guide-Filter-Hotels) - [Hotels with Air Conditioning in Bon Accord Village ](https://www.expedia.com/Bon-Accord-Village-Hotels-Hotels-With-Air-Conditioning.0-0-d6337888-tHotelswithAirConditioning.Travel-Guide-Filter-Hotels) - [Flights to Crown Point ](https://www.expedia.com/Cheap-Flights-To-Crown-Point.d11941.Travel-Guide-Flights) - [Flights from Crown Point ](https://www.expedia.com/lp/flights/11941/flights-from-crown-point) - [Flights to Canaan ](https://www.expedia.com/Cheap-Flights-To-Canaan.d6343440.Travel-Guide-Flights) - [Visit Crown Point ](https://www.expedia.com/Crown-Point.dx11941) - [Crown Point Vacations ](https://www.expedia.com/Crown-Point.d11941.Destination-Travel-Guides) - [Bon Accord Village Vacations ](https://www.expedia.com/Bon-Accord-Village.d6337888.Destination-Travel-Guides) - [Pigeon Point Beach ](https://www.expedia.com/Pigeon-Point-Beach-Crown-Point.d6119416.Vacation-Attraction) - [Kilgwyn Bay ](https://www.expedia.com/Kilgwyn-Bay-Crown-Point.d553248634328712169.Vacation-Attraction) - [Visit Canaan ](https://www.expedia.com/Canaan.dx6343440) - [Canaan Vacations ](https://www.expedia.com/Canaan.d6343440.Destination-Travel-Guides) - [Nylon Pool ](https://www.expedia.com/Nylon-Pool-Crown-Point.d553248621558078509.Vacation-Attraction) - [Buccoo Reef ](https://www.expedia.com/Buccoo-Reef-Tobago.d6337824.Vacation-Attraction) - [Car rentals near Crown Point ](https://www.expedia.com/Car-Rentals-In-Crown-Point.d11941.Car-Rental-Guide) - [Alamo Rent A Car Rental Cars in Crown Point ](https://www.expedia.com/Alamo-Rent-A-Car-Car-Rentals-In-Crown-Point.d11941-c6.Car-Rental-Guide-Suppliers) - [Car rentals near Canaan ](https://www.expedia.com/Car-Rentals-In-Canaan.d6343440.Car-Rental-Guide) - [Car rentals near Swallows Beach ](https://www.expedia.com/Car-Rentals-In-Swallows-Beach.d791074088716632064.Car-Rental-Guide) - [Dollar Rent A Car Rental Cars in Crown Point ](https://www.expedia.com/Dollar-Rent-A-Car-Car-Rentals-In-Crown-Point.d11941-c43.Car-Rental-Guide-Suppliers) - [ADA Rental Cars in Crown Point ](https://www.expedia.com/ADA-Car-Rentals-In-Crown-Point.d11941-c1109.Car-Rental-Guide-Suppliers) - [Europcar Rental Cars in Crown Point ](https://www.expedia.com/Europcar-Car-Rentals-In-Crown-Point.d11941-c14.Car-Rental-Guide-Suppliers) - [Discount Car Rentals Rental Cars in Crown Point ](https://www.expedia.com/Discount-Car-Rentals-Car-Rentals-In-Crown-Point.d11941-c11.Car-Rental-Guide-Suppliers) - [Crown Point Vacation Rentals ](https://www.expedia.com/Crown-Point-Vacation-Rentals.d11941.Travel-Guide-VacationRentals) - [Bon Accord Village Vacation Rentals ](https://www.expedia.com/Bon-Accord-Village-Vacation-Rentals.d6337888.Travel-Guide-VacationRentals) - [Things to do in Crown Point ](https://www.expedia.com/Things-To-Do-In-Crown-Point.d11941.Travel-Guide-Activities) - [Things to do in Bon Accord Village ](https://www.expedia.com/Things-To-Do-In-Bon-Accord-Village.d6337888.Travel-Guide-Activities) - [Things to do in Canaan ](https://www.expedia.com/Things-To-Do-In-Canaan.d6343440.Travel-Guide-Activities) \*Available to One Key members.