https://dawindycity.com/caleb-williams-2026-season-could-reshape-the-bears-financiallyDa Windy CityenCaleb Williams’ 2026 season could reshape the Bears financiallyCaleb Williams ,NFL ,Chicago Bears ,Monday2026-05-28T11:00:00Z2026-05-28T11:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_2663,h_1497,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ksejdsttb8pzt7pd8b.jpgJan 18, 2026; Chicago, IL, USA; Chicago Bears quarterback Caleb Williams (18) looks on during warmups before an NFC Divisional Round game against the Los Angeles Rams at Soldier Field. Mandatory Credit: David Banks-Imagn Imageshttps://dawindycity.com/cubs-finally-snap-brutal-losing-streak-with-offensive-eruption-against-piratesDa Windy CityenCubs finally snap brutal losing streak with offensive eruption against PiratesCubs,Ian Happ,Happ,Nico Hoerner,tuesday,Chicago2026-05-28T02:04:06Z2026-05-28T02:08:21Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_7131,h_4011,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01ksp533hrd9z8baw416.jpgMay 27, 2026; Pittsburgh, Pennsylvania, USA; Chicago Cubs left fielder Ian Happ (8) hits a three-run home run against the Pittsburgh Pirates during the seventh inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Imageshttps://dawindycity.com/bears-signing-joey-bosa-feels-like-an-obvious-move-ryan-poles-still-needs-to-make-Da Windy CityenBears signing Joey Bosa feels like an obvious move Ryan Poles still needs to makeBears,Bosa,Joey Bosa,Montez Sweat,Chicago Bears,Ben Johnson,Ryan Poles2026-05-28T01:00:29Z2026-05-28T01:00:29Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3936,h_2214,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01ksp0tjwxpmah047kp0.jpgBuffalo Bills defensive end Joey Bosa watches the offensive line on the field during second half action against the Tampa Bay Buccaneers on Nov 16, 2025 at Highmark Stadium in Orchard Park.https://dawindycity.com/cubs-fans-still-cannot-believe-javier-baez-pulled-this-off-five-years-agoDa Windy CityenCubs fans still cannot believe Javier Báez pulled this off five years agoCubs,Javy,baseball,Chicago,cubs news2026-05-27T22:02:23Z2026-05-27T22:02:23Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_2647,h_1488,x_0,y_182/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01ksnnqbvpta8bdgytww.jpgJul 26, 2021; Chicago, Illinois, USA; Chicago Cubs shortstop Javier Baez (9), reacts after hitting a walk off single against the Cincinnati Reds during the ninth inning at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Imageshttps://dawindycity.com/bears-veterans-already-facing-serious-pressure-entering-otasDa Windy CityenBears veterans already facing serious pressure entering OTAsKalif Raymond ,Chicago Bears ,NFL ,Monday 2026-05-27T21:00:00Z2026-05-27T21:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3610,h_2030,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ksej6ks0b7q0jwyahy.jpgDetroit Lions wide receiver Kalif Raymond (11) runs off the field after 34-10 win over Cleveland Browns at Ford Field in Detroit on Sunday, Sept. 28, 2025.https://dawindycity.com/bears-may-have-quietly-made-the-perfect-pitch-to-coby-bryantDa Windy CityenBears may have quietly made the perfect pitch to Coby BryantBears,Bryant,Chicago,Coby Bryant,Coby,Ben Johnson,nfl2026-05-27T20:02:29Z2026-05-27T20:02:29Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_5179,h_2913,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01ksnge1xk6b03q68sdt.jpgNov 9, 2025; Seattle, Washington, USA; Seattle Seahawks safety Coby Bryant (8) looks on before the game against the Arizona Cardinals at Lumen Field. Mandatory Credit: Kevin Ng-Imagn Imageshttps://dawindycity.com/bears-may-already-have-a-difficult-case-keenum-decision-loomingDa Windy CityenBears may already have a difficult Case Keenum decision loomingChicago Bears ,Case Keenum ,NFL ,Monday2026-05-27T19:14:40Z2026-05-27T19:14:40Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4971,h_2796,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ksejkzg0scrqdya1en.jpgOct 19, 2025; Chicago, Illinois, USA; Chicago Bears quarterback Case Keenum (11) during the second half against the New Orleans Saints at Soldier Field. Mandatory Credit: Mike Dinovo-Imagn Imageshttps://dawindycity.com/bears-writer-says-what-fans-already-know-about-glaring-roster-weaknessDa Windy CityenBears writer says what fans already know about glaring roster weaknessChicago Bears ,NFL ,Monday ,Montez Sweat2026-05-27T17:00:02Z2026-05-27T17:00:02Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4877,h_2743,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ksejqebhhyc52g953a.jpgOct 19, 2025; Chicago, Illinois, USA; Chicago Bears defensive end Montez Sweat (98) takes the field before the game against the New Orleans Saints at Soldier Field. Mandatory Credit: Mike Dinovo-Imagn Imageshttps://dawindycity.com/bears-rookie-skyler-thomas-already-has-a-realistic-path-to-chicago-s-rosterDa Windy CityenBears rookie Skyler Thomas already has a realistic path to Chicago's rosterChicago Bears,Skyler Thomas,Bears roster2026-05-27T15:00:01Z2026-05-27T15:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3114,h_1751,x_0,y_707/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01kskc73f3nrjen691mt.jpghttps://dawindycity.com/bears-coach-places-major-expectation-on-darnell-wright-entering-2026-seasonDa Windy CityenBears coach places major expectation on Darnell Wright entering 2026 seasonDarnell Wright,Chicago Bears,Ozzy Trapilo2026-05-27T13:09:54Z2026-05-27T13:09:54Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3449,h_1940,x_0,y_12/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01kskdhygqpw4sqvqjks.jpghttps://dawindycity.com/ryan-sweeney-perfectly-described-the-cubs-offensive-collapseDa Windy CityenRyan Sweeney perfectly described the Cubs' offensive collapseCubs,Ryan,Craig Counsell,Sweeney,Ryan Sweeney,baseball2026-05-27T11:00:03Z2026-05-27T11:00:03Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3471,h_1952,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01kskyhbeemc3dz4h7ak.jpgFebruary 25, 2015; Mesa, AZ, USA; Chicago Cubs center fielder Ryan Sweeney (6) waits outside the batting cage during a spring training workout at Sloan Park. Mandatory Credit: Kyle Terada-Imagn Imageshttps://dawindycity.com/bears-may-have-landed-the-biggest-defensive-steal-of-the-2026-nfl-draftDa Windy CityenBears may have landed the biggest defensive steal of the 2026 NFL DraftBears,nfl draft,Dillon Thieneman2026-05-26T23:00:01Z2026-05-26T23:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3163,h_1779,x_400,y_62/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01ksjrsm7ffh17eqh6pt.jpgOregon defensive back Dillon Thieneman speaks with reporters.https://dawindycity.com/bulls-have-to-take-a-clear-stance-on-jalen-duren-s-free-agencyDa Windy CityenBulls have to take a clear stance on Jalen Duren's free agencyBulls,Jalen Duren,Detroit Pistons2026-05-26T22:00:02Z2026-05-26T22:00:02Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3499,h_1968,x_178,y_37/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01ksjsrfh3njkvystzgv.jpgDetroit Pistons center Jalen Duren (0) reactshttps://dawindycity.com/bears-may-have-quietly-found-their-next-defensive-breakout-in-devin-bushDa Windy CityenBears may have quietly found their next defensive breakout in Devin BushChicago Bears,Dennis Allen,Devin Bush2026-05-26T20:00:00Z2026-05-26T20:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_6400,h_3600,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01ksjgc08p1wrtywvke2.jpghttps://dawindycity.com/latest-bears-rumor-feels-more-like-offseason-noise-than-realityDa Windy CityenLatest Bears rumor feels more like offseason noise than realityBears,Sweat,Chicago,Josh Sweat,Speculation,Tremaine Edmunds,Chicago Bears,bears news2026-05-26T19:00:01Z2026-05-26T19:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_5015,h_2820,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01ksjjaswe0w8sgw3gt6.jpgDec 21, 2025; Glendale, Arizona, USA; Arizona Cardinals linebacker Josh Sweat (10) against the Atlanta Falcons at State Farm Stadium. Mandatory Credit: Mark J. Rebilas-Imagn Imageshttps://dawindycity.com/bears-may-have-unlocked-luther-burden-s-true-role-in-ben-johnson-offenseDa Windy CityenBears may have unlocked Luther Burden's true role in Ben Johnson offenseBen Johnson,Luther Burden,Chicago Bears2026-05-26T17:00:02Z2026-05-26T17:00:02Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3688,h_2074,x_0,y_102/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01ksjfkzbfyj3kx69856.jpghttps://dawindycity.com/cubs-brutal-losing-streak-puts-craig-counsell-in-unfamiliar-territoryDa Windy CityenCubs' brutal losing streak puts Craig Counsell in unfamiliar territoryCubs,Craig Counsell,Chicago,Counsell,baseball,Brewers,cubs news2026-05-26T15:00:01Z2026-05-26T15:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_8322,h_4681,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01ksjakmkxsv2dtd6qxa.jpgMay 8, 2026; Arlington, Texas, USA; Chicago Cubs manager Craig Counsell (11) stands the dugout prior to a game against the Texas Rangers at Globe Life Field. Mandatory Credit: Raymond Carlin III-Imagn Imageshttps://dawindycity.com/bears-fans-will-crack-a-laugh-at-aaron-rodgers-position-in-qb-rankingsDa Windy CityenBears fans will crack a laugh at Aaron Rodgers' position in QB rankingsBears,Aaron Rodgers,Steelers2026-05-26T13:00:01Z2026-05-26T13:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_5171,h_2908,x_550,y_63/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/production/258/01ksg3df1nzbacm7rr7v.jpgPittsburgh Steelers quarterback Aaron Rodgers (8) warms up