https://dawindycity.com/bears-analyst-identifies-one-glaring-weakness-still-threatening-chicago-s-2026-hopesDa Windy CityenBears analyst identifies one glaring weakness still threatening Chicago's 2026 hopesChicago Bears ,NFL ,Wednesday ,Austin Booker 2026-06-10T21:00:01Z2026-06-10T21:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_7853,h_4417,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktpm9h7j90ay665qxb.jpgMay 18, 2026; Chicago, Illinois, USA; Chicago Bears player Austin Booker throws out a ceremonial first pitch before a game between the Chicago Cubs and the Milwaukee Brewers at Wrigley Field. Mandatory Credit: David Banks-Imagn Imageshttps://dawindycity.com/bears-insider-names-3-surprising-trade-destinations-for-cole-kmetDa Windy CityenBears insider names 3 surprising trade destinations for Cole KmetCole Kmet ,NFL ,Chicago Bears ,Wednesday 2026-06-10T20:00:00Z2026-06-10T20:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_8205,h_4615,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktpkyx6b00xfp1cpjt.jpgJan 18, 2026; Chicago, IL, USA; Chicago Bears tight end Cole Kmet (85) catches a fourteen-yard touchdown pass thrown by quarterback Caleb Williams (not pictured) against Los Angeles Rams cornerback Cobie Durant (14) with eighteen seconds remaining in the fourth quarter of an NFC Divisional Round game at Soldier Field. Mandatory Credit: David Banks-Imagn Imageshttps://dawindycity.com/adam-schefter-s-latest-bears-report-should-have-chicago-fans-concernedDa Windy CityenAdam Schefter's latest Bears report should have Chicago fans concernedBears,Chicago,Schefter,Adam Schefter,nfl,comments,Illinois2026-06-10T19:00:00Z2026-06-10T19:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_8001,h_4500,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01kts96mpsrv6eej4q8m.jpgJan 17, 2022; Inglewood, California, USA; Adam Schefter on the ESPN Monday Night Countdown set before a NFC Wild Card playoff football game between the Los Angeles Rams and the Arizona Cardinals at SoFi Stadium. Mandatory Credit: Kirby Lee-Imagn Imageshttps://dawindycity.com/white-sox-top-prospect-braden-montgomery-makes-mlb-history-in-unforgettable-debutDa Windy CityenWhite Sox top prospect Braden Montgomery makes MLB history in unforgettable debutMontgomery,White Sox,Sox,mlb,Chicago2026-06-10T18:00:02Z2026-06-10T18:00:02Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_6723,h_3781,x_0,y_696/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01kts7v10dcq61yq2q9a.jpgJun 9, 2026; Chicago, Illinois, USA; Chicago White Sox right fielder Braden Montgomery (24) talks with the media before the team’s game against the Atlanta Braves at Rate Field. Mandatory Credit: Matt Marton-Imagn Imageshttps://dawindycity.com/bears-have-one-massive-edge-over-packers-heading-into-2026-seasonDa Windy CityenBears Have One Massive Edge Over Packers Heading Into 2026 SeasonChicago Bears ,Luther Burden ,NFL ,Wednesday 2026-06-10T17:00:01Z2026-06-10T17:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4960,h_2790,x_0,y_11/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktpkvceej1a8ezy6p8.jpgDec 14, 2025; Chicago, Illinois, USA; Chicago Bears wide receiver Luther Burden III (10) walks off the field during halftime of the game against the Cleveland Browns at Soldier Field. Mandatory Credit: David Banks-Imagn Imageshttps://dawindycity.com/bulls-may-have-already-found-their-josh-giddey-contingency-plan-in-the-2026-nba-draftDa Windy CityenBulls may have already found their Josh Giddey contingency plan in the 2026 NBA DraftBulls,Josh Giddey,Ebuka Okorie2026-06-10T16:00:02Z2026-06-10T16:00:02Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_2371,h_1333,x_1318,y_180/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktpsrn49dqtgkbpag1.jpgChicago Bulls guard Josh Giddey (3)https://dawindycity.com/bears-need-caleb-williams-to-win-earlier-in-2026Da Windy CityenBears Need Caleb Williams to Win Earlier in 2026Caleb Williams ,NFL ,Chicago Bears ,Wednesday 2026-06-10T15:00:01Z2026-06-10T15:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_6671,h_3752,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktpkmqxq345nkhv0cw.jpgJan 18, 2026; Chicago, IL, USA; Chicago Bears quarterback Caleb Williams (18) throws a pass against the Los Angeles Rams during the third quarter of an NFC Divisional Round game at Soldier Field. Mandatory Credit: Matt Marton-Imagn Imageshttps://dawindycity.com/bears-fans-can-only-hope-this-wild-justin-jefferson-trade-prediction-comes-trueDa Windy CityenBears fans can only hope this wild Justin Jefferson trade prediction comes trueBears,Justin Jefferson,Vikings2026-06-10T14:00:00Z2026-06-10T14:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_7517,h_4228,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktprhreby8nmj2hdax.jpgMinnesota Vikings wide receiver Justin Jefferson (18) warms up https://dawindycity.com/ben-johnson-s-comments-reveal-surprising-role-for-kalif-raymond-in-bears-offenseDa Windy CityenBen Johnson's comments reveal surprising role for Kalif Raymond in Bears offenseBen Johnson,Chicago Bears,Kalif Raymond2026-06-10T13:00:06Z2026-06-10T13:00:06Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_5392,h_3033,x_0,y_102/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktprz3y8bk5rgwyx3g.jpghttps://dawindycity.com/bears-coach-all-but-confirms-massive-darrell-wright-payday-is-comingDa Windy CityenBears coach all but confirms massive Darrell Wright payday is comingChicago Bears,Darnell Wright,Ben Johnson2026-06-10T12:00:05Z2026-06-10T12:00:05Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4488,h_2524,x_0,y_109/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktpqzp86rhr05wh06n.jpghttps://dawindycity.com/cubs-should-consider-calling-braves-to-solve-dansby-swanson-woesDa Windy CityenCubs should consider calling Braves to solve Dansby Swanson woes Dansby Swanson ,MLB ,Tuesday ,Chicago Cubs 2026-06-10T11:00:01Z2026-06-10T11:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3991,h_2244,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktmazx2h0pep6cq7x3.jpgMay 23, 2026; Chicago, Illinois, USA; Chicago Cubs shortstop Dansby Swanson (7) tags out Houston Astros center fielder Brice Matthews (0) at second base on a steal attempt during the ninth inning at Wrigley Field. Mandatory Credit: David Banks-Imagn Imageshttps://dawindycity.com/bears-fans-have-every-reason-to-believe-colston-loveland-is-ready-for-a-breakoutDa Windy CityenBears Fans Have Every Reason to Believe Colston Loveland Is Ready for a BreakoutColston Loveland ,NFL ,Chicago Bears ,Tuesday 2026-06-10T10:00:00Z2026-06-10T10:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3545,h_1994,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktmawcm3ckrd0738c7.jpgJan 18, 2026; Chicago, IL, USA; Chicago Bears tight end Colston Loveland (84) extends but cannot catch a pass thrown by quarterback Caleb Williams (not pictured) against the Los Angeles Rams during the third quarter of an NFC Divisional Round game at Soldier Field. Mandatory Credit: David Banks-Imagn Imageshttps://dawindycity.com/bears-legend-matt-forte-voices-concern-over-team-s-indiana-stadium-pursuitDa Windy CityenBears Legend Matt Forte Voices Concern Over Team's Indiana Stadium PursuitBears,Forte,Matt Forte,Chicago,Chicago Bears,bears news2026-06-09T23:30:00Z2026-06-09T23:30:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3500,h_1968,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktq932bb9necswasaq.jpghttps://dawindycity.com/bears-have-a-real-chance-to-end-embarrassing-16-year-defensive-droughtDa Windy CityenBears Have a Real Chance to End Embarrassing 16-Year Defensive DroughtChicago Bears ,Dennis Allen ,NFL ,Tuesday 2026-06-09T22:34:36Z2026-06-09T22:34:36Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4500,h_2531,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktma49k1nk4fc1jae3.jpgJul 23, 2025; Lake Forest, IL, USA; Chicago Bears defensive coordinator Dennis Allen speaks during training camp at Halas Hall. Mandatory Credit: Kamil Krzaczynski-Imagn Imageshttps://dawindycity.com/bears-tyson-bagent-trade-buzz-faces-one-major-obstacle-before-training-campDa Windy CityenBears' Tyson Bagent trade buzz faces one major obstacle before training campPittsburgh Steelers,Tyson Bagent,Chicago Bears2026-06-09T21:00:00Z2026-06-09T21:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4894,h_2752,x_0,y_78/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktmcbx7ft67ea8p69w.jpghttps://dawindycity.com/bears-must-keep-close-eye-on-caleb-williams-as-expectations-reach-new-heightsDa Windy CityenBears Must Keep Close Eye on Caleb Williams as Expectations Reach New HeightsCaleb Williams ,NFL ,Chicago Bears ,Monday 2026-06-09T20:00:15Z2026-06-09T20:00:15Zhttps://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/258/01ktjq9amh9evnppyfe5.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/4-bears-players-with-the-most-to-lose-during-the-2026-seasonDa Windy Cityen4 Bears players with the most to lose during the 2026 seasonCole Kmet ,NFL ,Chicago Bears ,Monday 2026-06-09T19:00:03Z2026-06-09T19:00:03Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3600,h_2025,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktjqfng9znqebqw54p.jpgDec 20, 2025; Chicago, Illinois, USA; Chicago Bears tight end Cole Kmet (85) takes the field before the game against the Green Bay Packers at Soldier Field. Mandatory Credit: Mike Dinovo-Imagn Imageshttps://dawindycity.com/bulls-draft-failures-under-former-front-office-make-bryson-graham-s-job-look-easyDa Windy CityenBulls draft failures under former front office make Bryson Graham's job look easyArturas Karnisovas,Bulls,Marc Eversley,Ayo Dosunmu,Chicago Bulls,NBA draft,Milwaukee Bucks,Phoenix Suns,Stacey King,Bryson Graham2026-06-09T17:00:02Z2026-06-09T17:00:02Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4200,h_2362,x_0,y_117/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktn3axms5xvk2v8z0c.jpghttps://dawindycity.com/luther-burden-iii-s-latest-comments-should-excite-bears-fans-about-2026Da Windy CityenLuther Burden III's latest comments should excite Bears fans about 2026Caleb Williams,Luther Burden,Bears2026-06-09T15:00:01Z2026-06-09T15:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3657,h_2057,x_3509,y_1098/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktm8dw9qf5rczwhy6h.jpgChicago Bears wide receiver Luther Burden III (10)https://dawindycity.com/cubs-latest-injury-setback-puts-even-more-pressure-on-front-office-ahead-of-trade-deadlineDa Windy CityenCubs' latest injury setback puts even more pressure on front office ahead of trade deadlineCubs,Taillon,injuries,Chicago,trade deadline,Craig Counsell2026-06-09T14:00:00Z2026-06-09T14:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_7290,h_4100,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktp6ph6t4gxfgpfjky.jpgApr 29, 2026; San Diego, California, USA; Chicago Cubs starting pitcher Jameson Taillon (50) stands on the mound as San Diego Padres left fielder Miguel Andujar (41) rounds the bases after Andujar hit a two-run home run during the fifth inning at Petco Park. Mandatory Credit: Denis Poroy-Imagn Imageshttps://dawindycity.com/micah-parsons-caleb-williams-prediction-should-worry-packers-fansDa Windy CityenMicah Parsons' Caleb Williams prediction should worry Packers fansCaleb Williams,Micah Parsons,Green Bay Packers2026-06-09T13:00:04Z2026-06-09T13:00:04Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_6413,h_3607,x_0,y_316/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktmbev9mbm1e5gqjwe.jpghttps://dawindycity.com/cubs-star-pete-crow-armstrong-earns-nl-player-of-the-week-honorsDa Windy CityenCubs star Pete Crow-Armstrong earns NL Player of the Week honorsCubs,Armstrong,Nico Hoerner,Hoerner,Seiya Suzuki,Craig Counsell,Counsell,PCA2026-06-09T11:00:03Z2026-06-09T11:00:03Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4200,h_2362,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktn27xz6n8zj3d0wyz.jpgJun 3, 2026; Chicago, Illinois, USA; Chicago Cubs center fielder Pete Crow-Armstrong (4) hits a two-run home run against the Athletics during the third inning at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Imageshttps://dawindycity.com/latest-prediction-shows-caleb-williams-finally-flipped-the-narrativeDa Windy CityenLatest prediction shows Caleb Williams finally flipped the narrative Caleb Williams,Bears,Chicago Bears2026-06-08T23:00:01Z2026-06-08T23:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_2755,h_1549,x_0,y_381/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktm7anpc5xygdk9dgm.jpgChicago Bears quarterback Caleb Williams (18) celebrateshttps://dawindycity.com/bears-are-positioned-to-do-something-they-haven-t-done-in-over-a-decadeDa Windy CityenBears are positioned to do something they haven't done in over a decadeChicago Bears ,NFL ,Monday ,Ben Johnson2026-06-08T22:00:02Z2026-06-08T22:00:02Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4500,h_2531,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ktjqcc6pq1zza8ww0v.jpgMay 8, 2026; Lake Forest, IL, USA; Chicago Bears head coach Ben Johnson addresses the media at Halas Hall before Rookie Minicamp. Mandatory Credit: Kamil Krzaczynski-Imagn Images