https://dawindycity.com/bears-fans-have-every-reason-to-worry-about-the-nfl-s-latest-international-pushDa Windy CityenBears fans have every reason to worry about the NFL’s latest international pushCaleb Williams ,MLB ,Chicago Bears ,Wednesday 2026-05-20T19:00:57Z2026-05-20T19:00:57Zhttps://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/258/01ks0z6k2990rarw2n3d.jpgMay 8, 2026; Lake Forest, IL, USA; Chicago Bears defensive back Dillon Thieneman (31) speaks during Rookie Minicamp at Halas Hall. Mandatory Credit: Kamil Krzaczynski-Imagn Imageshttps://dawindycity.com/bears-insider-may-be-overlooking-what-chicago-actually-needs-at-edge-rusherDa Windy CityenBears insider may be overlooking what Chicago actually needs at edge rusherChicago Bears,Von Miller,Dayo Odeyingbo2026-05-20T15:00:00Z2026-05-20T15:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_2965,h_1667,x_0,y_183/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ks0y3px3s5qt1c9sq3.jpghttps://dawindycity.com/cubs-have-little-to-lose-by-taking-a-flyer-on-aaron-bummerDa Windy CityenCubs have little to lose by taking a flyer on Aaron BummerChicago Cubs ,MLB ,Wednesday ,Aaron Bummer 2026-05-20T13:00:00Z2026-05-20T13:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3770,h_2120,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ks0zazbyq1zqbsgjz7.jpgMay 3, 2026; Denver, Colorado, USA; Atlanta Braves pitcher Aaron Bummer (49) on the bench in the fifth inning against the Colorado Rockies at Coors Field. Mandatory Credit: Ron Chenoy-Imagn Imageshttps://dawindycity.com/bears-may-have-quietly-accomplished-exactly-what-they-wanted-this-offseasonDa Windy CityenBears may have quietly accomplished exactly what they wanted this offseasonRome Odunze,Caleb Williams,Chicago Bears,Darnell Wright2026-05-20T11:00:06Z2026-05-20T11:00:06Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_8120,h_4567,x_0,y_60/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ks0xgnk683engmrr3t.jpghttps://dawindycity.com/kyle-monangai-could-force-bears-into-difficult-d-andre-swift-decisionDa Windy CityenKyle Monangai could force Bears into difficult D'Andre Swift decisionBears,D'Andre Swift,Kyle Monangai2026-05-19T23:00:00Z2026-05-19T23:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_6579,h_3700,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ks0shmc43wadbdm41b.jpgDec 16, 2024; Minneapolis, Minnesota, USA; Chicago Bears running back D'Andre Swift (4) runs the ball against the Minnesota Vikings during the third quarter at U.S. Bank Stadium. Mandatory Credit: Jeffrey Becker-Imagn Imageshttps://dawindycity.com/biggest-question-facing-every-bears-position-group-before-training-campDa Windy CityenBiggest question facing every Bears position group before training campCaleb Williams,Chicago Bears,Tyrique Stevenson,Ben Johnson2026-05-19T21:00:00Z2026-05-19T21:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_6671,h_3752,x_0,y_127/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ks09yprb1r0jr6gem1.jpghttps://dawindycity.com/colston-loveland-skepticism-ignores-one-major-bears-realityDa Windy CityenColston Loveland skepticism ignores one major Bears realityColston Loveland,Chicago Bears,Bears roster2026-05-19T19:01:18Z2026-05-19T19:01:18Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_7406,h_4165,x_0,y_231/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01ks090geqw8d5448q7t.jpgJan 18, 2026; Chicago, IL, USA; Chicago Bears tight end Colston Loveland (84) runs nto the field during player introductions before an NFC Divisional game against the Los Angeles Rams at Soldier Field. Mandatory Credit: David Banks-Imagn Imageshttps://dawindycity.com/bulls-may-have-found-their-michael-jordan-blueprint-in-caleb-wilsonDa Windy CityenBulls may have found their Michael Jordan blueprint in Caleb WilsonMichael Jordan,Bulls,Caleb Wilson2026-05-19T17:00:00Z2026-05-19T17:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3669,h_2063,x_0,y_261/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01kry4ksbcsrvcq90c6f.jpgJan 3, 2026; Dallas, Texas, USA; North Carolina Tar Heels forward Caleb Wilson (8) looks on during the game between the Mustangs and the Tar Heels at Moody Coliseum. Mandatory Credit: Jerome Miron-Imagn Imageshttps://dawindycity.com/bears-quarterback-room-may-have-already-answered-tyson-bagent-s-long-term-questionDa Windy CityenBears quarterback room may have already answered Tyson Bagent's long term questionChicago Bears,Tyson Bagent,Bears roster2026-05-19T14:00:02Z2026-05-19T14:00:02Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3570,h_2008,x_22,y_384/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01kryxayzq5gy6bjhgfy.jpghttps://dawindycity.com/bears-may-have-stumbled-into-a-fantasy-football-breakout-candidateDa Windy CityenBears may have stumbled into a fantasy football breakout candidateChicago Bears,Kyle Monangai,bears depth chart2026-05-19T11:00:04Z2026-05-19T11:00:04Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3000,h_1687,x_0,y_41/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01kryn5pmd25yfjnz5y7.jpgWm. Glasheen /USA TODAY NETWORK-Wisconsin.https://dawindycity.com/bears-quietly-revealed-their-long-term-plan-with-surprising-roster-rankingDa Windy CityenBears quietly revealed their long-term plan with surprising roster rankingbears roster,Caleb Williams,Chicago Bears2026-05-18T23:00:00Z2026-05-18T23:00:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3399,h_1911,x_0,y_77/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01kry34k3h52arp37xrw.jpghttps://dawindycity.com/bears-quietly-found-hidden-value-in-overlooked-quarterback-roleDa Windy CityenBears quietly found hidden value in overlooked quarterback roleChicago Bears,Caleb Williams,Case Keenum2026-05-18T21:40:49Z2026-05-18T21:40:49Zhttps://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/258/01kry3vnm165grzz3sh0.jpghttps://dawindycity.com/cubs-vs-brewers-series-could-decide-early-control-of-the-nl-centralDa Windy CityenCubs vs. Brewers series could decide early control of the NL CentralBrewers,Chicago,nl central,Crosstown Classic,Nico Hoerner,Ian Happ,cubs news2026-05-18T21:02:41Z2026-05-18T21:02:41Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_3896,h_2191,x_0,y_0/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01krydpw2h14ze2y8g2a.jpgMay 14, 2026; Atlanta, Georgia, USA; Chicago Cubs pitcher Daniel Palencia (48) and shortstop Dansby Swanson (7) celebrate after a victory over the Atlanta Braves at Truist Park. Mandatory Credit: Brett Davis-Imagn Imageshttps://dawindycity.com/bears-finally-have-the-perfect-breakout-setup-for-luther-burdenDa Windy CityenBears finally have the perfect breakout setup for Luther Burden IIIBears,Luther Burden III,Chicago Bears2026-05-18T20:00:02Z2026-05-18T20:00:02Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_2114,h_1189,x_1315,y_99/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01kry3m4v993b0qz1mt6.jpgChicago Bears wide receiver Luther Burden III (10) celebrateshttps://dawindycity.com/bears-finally-have-the-stability-fans-have-been-waiting-decades-to-seeDa Windy CityenBears finally have the stability fans have been waiting decades to seeChicago Bears,Ben Johnson,Caleb Williams2026-05-18T19:30:00Z2026-05-18T19:30:00Zhttps://images2.minutemediacdn.com/image/upload/c_crop,w_4500,h_2531,x_0,y_236/c_fill,w_2880,ar_16:9,f_auto,q_auto,g_auto/images/ImagnImages/mmsport/258/01kry227brqjd004arvt.jpg