- $39.99and upNFL Chicago Bears Wordmark HD Apple Watch Band - 38/40/41mm ShortTarget & 2 more
- $29.99and upChicago Bears Silicone Apple Watch BandFanatics & 1 more
- $69.99Chicago Fire Leather Apple Watch BandFanatics
- $29.99and upChicago Bears Silicone Apple Watch BandFanatics & 2 more
- $39.99and upMLB Chicago Cubs Wordmark HD Apple Watch Band - 38/40/41mm ShortTarget & 1 more
- $29.99and upChicago White Sox Silicone Apple Watch BandFanatics & 1 more
- $39.99and upMLB Chicago Cubs Wordmark Engraved Apple Watch Band - 38/40/41mmTarget & 1 more
- $29.99and upChicago White Sox Debossed Silicone Apple Watch BandFanatics & 1 more
- $39.99Chicago Cubs 42/44/45mm Apple Watch Sports BandFanatics
- SAVE $50.00$149.99$199.99Chicago Maroons Gold-Tone Stainless Steel Watch with Black LeatherFanatics
- $39.99Chicago White Sox 38/40/41mm Apple Watch Sports BandFanatics
- $49.50and upChicago Bears 38/40/41mm Personalized Silicone Apple Watch BandOfficial NFL Shop & 1 more
- $37.12and upChicago Bears 38/40/41mm Personalized Silicone Apple Watch BandOfficial NFL Shop & 1 more
- SAVE $10.00$29.99$39.99Chicago Cubs 42/44/45mm Logo Silicone Apple Watch BandFanatics
- SAVE $10.00$29.99$39.99Chicago White Sox 38/40/41mm Logo Silicone Apple Watch BandFanatics
- $111.99Gametime Chicago Bears Leather Band fits Apple Watch (38/40mm M/L Black). Watch not included.JTV
- $41.24and upTimex Chicago Bears Rivalry WatchFanatics & 1 more
- $31.95MLB Chicago Cubs Charm Watch, SilverAmazon
- $79.99and upTan Chicago Bears Leather Apple Watch BandOfficial NFL Shop & 2 more
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 42/44/45/49mm - TanTarget
- $79.99and upNFL Chicago Bears Apple Watch Compatible Leather Band 42/44/45/49mm - BrownTarget & 2 more
- $59.99and upTan Chicago Cubs Leather Apple Watch BandFanatics & 1 more
- $79.99and upMLB Chicago Cubs Apple Watch Compatible Leather Band 42/44/45/49mm - BrownTarget & 1 more
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 42/44/45/49mm - BrownTarget
- $79.99and upMLB Chicago Cubs Apple Watch Compatible Leather Band 42/44/45/49mm - BlackTarget & 1 more
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 42/44/45/49mm - BlackTarget
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 38/40/41mm - BrownTarget
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 38/40/41mm - TanTarget
- $39.99NFL Chicago Bears Apple Watch Compatible Silicone Band 38/40/41mm - BlueTarget
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 38/40/41mm - BlackTarget
- $94.99Vintage International Harvester Dual Globe Watch Fob ChicagoEtsy
- $59.99and upBrown Chicago Blackhawks Leather Apple Watch BandFanatics & 1 more
- $79.99and upBlack Chicago Bears Leather Apple Watch BandOfficial NFL Shop & 1 more
- $79.99and upBlack Chicago Blackhawks Leather Apple Watch BandNHL Shop & 1 more
- $59.99and upBrown Chicago Blackhawks Leather Apple Watch BandFanatics & 1 more
- $79.99and upTan Chicago Blackhawks Leather Apple Watch BandFanatics & 1 more
- $59.99and upTan Chicago Bears Leather Apple Watch BandFanatics & 1 more
- SAVE $18.75$56.24$74.99Men's Timex Chicago Bears Citation WatchOfficial NFL Shop
- SAVE $5.50$16.49$21.99Blue Chicago Maroons Samsung 22mm Watch BandFanatics
- $59.99and upBlack Chicago Blackhawks Leather Apple Watch BandNHL Shop & 1 more
- $24.99and upNFL Chicago Bears Wordmark Apple Watch Band - 42/44/45/49mmTarget & 2 more
- SAVE $5.50$16.49$21.99Gray Chicago Maroons Samsung 22mm Watch BandFanatics
- $79.99Black Chicago Cubs Leather Apple Watch BandFanatics
- SAVE $5.50$16.49$21.99Teal Chicago Maroons Samsung 22mm Watch BandFanatics
- SAVE $11.25$33.74$44.99Men's Timex Chicago Cubs Clutch WatchFanatics
- SAVE $18.75$56.24$74.99Men's Timex Chicago Blackhawks Citation WatchFanatics
- $56.24and upMen's Timex Chicago Cubs Citation WatchFanatics & 1 more
- $84.99and upMen's Timex Chicago Cubs Acclaim WatchFanatics & 1 more
- $84.99and upMen's Timex Chicago Blackhawks Acclaim WatchNHL Shop & 4 more
- $39.99and upNavy Chicago Bears Debossed Silicone Apple Watch BandOfficial NFL Shop & 2 more
- $49.50Royal Chicago Cubs Personalized Silicone Apple Watch BandFanatics
- SAVE $20.00$59.99$79.99Black Chicago White Sox Leather Apple Watch BandFanatics
- SAVE $10.00$29.99$39.99Blue Chicago Cubs Logo Silicone Apple Watch BandFanatics
- SAVE $12.38$37.12$49.50Royal Chicago Cubs Personalized Silicone Apple Watch BandFanatics
- $29.99and upNavy Chicago Bears Logo Silicone Apple Watch BandFanatics & 1 more
- $39.99and upNavy Chicago Bears 22mm Samsung Compatible Watch BandOfficial NFL Shop & 1 more
- $29.99and upNavy Chicago Bears Logo Silicone Apple Watch BandFanatics & 1 more
- $29.99and upNavy Chicago Bears 20mm Samsung Compatible Watch BandFanatics & 1 more
- SAVE $10.00$29.99$39.99Blue Chicago Cubs Logo Silicone Apple Watch BandFanatics
- $29.99and upWhite Chicago Blackhawks Debossed Silicone Apple Watch BandFanatics & 1 more