https://dawindycity.com/bears-get-encouraging-update-on-ozzy-trapilo-s-accelerated-recoveryDa Windy CityenBears get encouraging update on Ozzy Trapilo’s accelerated recoveryDan Roushar,Ozzy Trapilo,Chicago Bears2026-09-11T17:00:01Z2026-09-11T17:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3676,h_2067,x_1457,y_224/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m28cyfkjg0ygsg6bg2.jpghttps://dawindycity.com/white-sox-are-running-out-of-breathing-room-atop-the-al-centralDa Windy CityenWhite Sox are running out of breathing room atop the AL CentralSox,White Sox,White,Cardinals,Cleveland,Pirates,Chicago,comments,al central,South Siders2026-09-11T16:00:29Z2026-09-11T16:00:29Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3664,h_2061,x_930,y_95/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m28j22cwxyy5kfr79g.jpgAug 17, 2026; Chicago, Illinois, USA; Chicago White Sox manager Will Venable (1) before the game against the Chicago Cubs at Wrigley Field. Mandatory Credit: David Banks-Imagn Imageshttps://dawindycity.com/jon-gruden-drops-massive-caleb-williams-prediction-before-bears-season-beginsDa Windy CityenJon Gruden drops massive Caleb Williams prediction before Bears season beginsGruden,Chicago,Bears,nfl,Caleb Williams,Luther Burden,Jon Gruden,Chicago Bears2026-09-11T15:00:01Z2026-09-11T15:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_6000,h_3375,x_0,y_169/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m27d0sb1knedf3ardk.jpgJon Gruden watches practice during training camp at Meijer Performance Center in Allen Park on Monday, July 28, 2025.https://dawindycity.com/bears-leave-door-open-for-theo-benedet-despite-naming-braxton-jones-the-starterDa Windy CityenBears leave door open for Theo Benedet despite naming Braxton Jones the starterChicago Bears,Ozzy Trapilo,Ben Johnson2026-09-11T14:00:03Z2026-09-11T14:00:03Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_2423,h_1362,x_917,y_195/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m26jgfy49ewqjpkajs.jpghttps://dawindycity.com/brewers-sweep-leaves-cubs-with-no-room-for-error-in-wild-card-raceDa Windy CityenBrewers sweep leaves Cubs with no room for error in Wild Card raceCubs,Brewers,Reds,Chicago Cubs,Pirates,mlb,Chicago,Padres,philadelphia phillies,Atlanta Braves2026-09-11T13:01:13Z2026-09-11T13:01:13Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4163,h_2341,x_1241,y_162/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m288sgazvw5pc01daw.jpgSep 7, 2026; Milwaukee, Wisconsin, USA; Chicago Cubs manager Craig Counsell gets some snacks before game against the Milwaukee Brewers at American Family Field. Mandatory Credit: Benny Sieu-Imagn Imageshttps://dawindycity.com/bears-have-3-intriguing-backup-plans-if-josh-sweat-trade-goes-nowhereDa Windy CityenBears have 3 intriguing backup plans if Josh Sweat trade goes nowhereBears,Chicago,Montez Sweat,Ryan Poles,Josh Sweat,Kayvon Thibodeaux,New York Giants,Maxx Crosby,Raiders,Las Vegas Raiders,Chicago Bears,Alex Highsmith,Pittsburgh Steelers,Arizona Cardinals2026-09-11T12:00:21Z2026-09-11T12:00:21Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4000,h_2250,x_0,y_126/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m285dca4tgykc1xbtr.jpgNov 23, 2025; Glendale, Arizona, USA; Arizona Cardinals linebacker Josh Sweat (10) against the Jacksonville Jaguars at State Farm Stadium. Mandatory Credit: Mark J. Rebilas-Imagn Imageshttps://dawindycity.com/5-matchup-advantages-the-panthers-have-over-the-bears-in-week-1Da Windy Cityen5 matchup advantages the Panthers have over the Bears in Week 1Carolina Panthers,Jaylon Johnson,Chicago Bears2026-09-10T23:00:01Z2026-09-10T23:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_1535,h_863,x_0,y_103/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m26a7t64smscdawgcj.jpgAug 22, 2026; Cincinnati, Ohio, USA; Chicago Bears head coach Ben Johnson stands on the sidelines during the second half in the game against the Cincinnati Bengals at Paycor Stadium. Mandatory Credit: Katie Stratman-Imagn Imageshttps://dawindycity.com/sam-antonacci-s-latest-controversy-is-not-as-dirty-as-it-looksDa Windy CityenSam Antonacci’s latest controversy is not as dirty as it looksSox,White Sox,White,Thursday,Pirates,Wednesday,Chicago,Contreras,Wilson,Ball2026-09-10T22:00:00Z2026-09-10T22:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3035,h_1707,x_831,y_112/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m26fcqq7y1ac07a27v.jpghttps://dawindycity.com/adam-schefter-predicts-caleb-williams-will-become-bears-first-4-000-yard-passerDa Windy CityenAdam Schefter predicts Caleb Williams will become Bears' first 4,000-yard passerBears,nfl,Williams,Caleb Williams,Chicago Bears,Chicago,Ben Johnson,Schefter,Caleb,Adam Schefter2026-09-10T21:00:01Z2026-09-10T21:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_8001,h_4500,x_0,y_284/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m269qd2dxxrz61seed.jpghttps://dawindycity.com/luther-burden-iii-just-made-the-colston-loveland-hype-explode-ahead-of-week-1Da Windy CityenLuther Burden III just made the Colston Loveland hype explode ahead of Week 1Luther Burden III,Colston Loveland,Bears2026-09-10T19:00:01Z2026-09-10T19:00:01Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_6000,h_3375,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m264r19cyaxjqayhds.jpgChicago Bears tight end Colston Loveland (84) on the field.https://dawindycity.com/5-matchup-advantages-the-chicago-bears-can-exploit-against-the-panthersDa Windy Cityen5 matchup advantages the Chicago Bears can exploit against the PanthersChicago Bears,Bryce Young,Ben Johnson2026-09-10T17:00:02Z2026-09-10T17:00:02Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_2135,h_1200,x_1434,y_79/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m24babfa8se2qtk651.jpghttps://dawindycity.com/caleb-williams-an-overlooked-winner-of-drake-maye-s-week-1-collapseDa Windy CityenCaleb Williams an overlooked winner of Drake Maye's Week 1 collapse Caleb Williams ,NFL ,Thursday ,Chicago Bears 2026-09-10T15:00:00Z2026-09-10T15:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_2596,h_1460,x_1227,y_36/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m24pxwpg9kas3c3c3v.jpgAug 5, 2026; Lake Forest, IL, USA; Chicago Bears quarterback Caleb Williams (18) stands on the field during training camp at Halas Hall. Mandatory Credit: Kamil Krzaczynski-Imagn Imageshttps://dawindycity.com/connor-bedard-takes-encouraging-step-toward-long-awaited-blackhawks-returnDa Windy CityenConnor Bedard takes encouraging step toward long-awaited Blackhawks returnBlackhawks,Chicago,Connor Bedard,Chicago Blackhawks,nhl2026-09-10T13:00:00Z2026-09-10T13:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3809,h_2142,x_0,y_90/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m23yc3t7sz177wzthj.jpgFeb 28, 2026; Denver, Colorado, USA; Chicago Blackhawks center Connor Bedard (98) during the third period against the Colorado Avalanche at Ball Arena. Mandatory Credit: Ron Chenoy-Imagn Imageshttps://dawindycity.com/packers-laughable-offseason-approach-is-a-double-win-for-the-bearsDa Windy CityenPackers' laughable offseason approach is a double win for the BearsBears,Packers,Green Bay Packers2026-09-10T11:00:03Z2026-09-10T11:00:03Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_1453,h_817,x_216,y_118/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m23nvbcfcej0ame2mp.jpgGreen Bay Packers head coach Matt LaFleur during Green Bay Packers Family Night.https://dawindycity.com/white-sox-suddenly-have-a-problem-nobody-expected-to-see-in-septemberDa Windy CityenWhite Sox suddenly have a problem nobody expected to see in SeptemberPittsburgh,Cleveland,chicago white sox,White Sox,Pittsburgh Pirates,Cleveland Guardians,Sean Burke2026-09-09T23:00:00Z2026-09-09T23:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_2911,h_1637,x_0,y_147/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m23zpk0ew75efntkc4.jpgSep 8, 2026; Chicago, Illinois, USA; Chicago White Sox pitcher Sean Burke (59) throws the ball against the Pittsburgh Pirates during the first inning at Rate Field. Mandatory Credit: David Banks-Imagn Imageshttps://dawindycity.com/kyler-gordon-update-raises-more-questions-for-bearsDa Windy CityenKyler Gordon Update Raises More Questions for BearsKyler Gordon,Chicago Bears,Ryan Poles2026-09-09T22:00:00Z2026-09-09T22:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4829,h_2716,x_839,y_247/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m23xty7sqshpns0dtc.jpghttps://dawindycity.com/cubs-are-watching-their-worst-trade-deadline-decision-come-back-to-haunt-themDa Windy CityenCubs are watching their worst trade deadline decision come back to haunt themCubs,Chicago,Jed Hoyer,Chicago Cubs,Counsell,trade deadline,Craig Counsell,Hoyer,Milwaukee Brewers,Carson Kelly,Jacob Webb,Christian Yelich,Jackson Chourio,Kevin Gausman,Clay Holmes,Ryan Zeferjahn2026-09-09T21:30:00Z2026-09-09T21:30:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_6000,h_3375,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m23z3feq1zw7gp66tg.jpgSep 23, 2025; Chicago, Illinois, USA; Chicago Cubs president Jed Hoyer talks to the press before a game against the New York Mets at Wrigley Field. Mandatory Credit: David Banks-Imagn Imageshttps://dawindycity.com/bears-braxton-jones-decision-comes-with-an-obvious-asteriskDa Windy CityenBears' Braxton Jones decision comes with an obvious asteriskBraxton Jones,Bears,Ozzy Trapilo2026-09-09T20:30:00Z2026-09-09T20:30:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_2823,h_1587,x_0,y_215/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ReutersImages/mmsport/258/01m23nhas22b5rrn08rc.jpgChicago Bears offensive tackle Braxton Jones (70) on the sidelines