- $39.99and upMLB Chicago Cubs Wordmark HD Apple Watch Band - 38/40/41mm ShortTarget & 1 more
- SAVE $17.50$52.49$69.99Chicago Fire Leather Apple Watch BandFanatics
- SAVE $10.00$29.99$39.99Chicago Bears Silicone Apple Watch BandFanatics
- SAVE $10.00$29.99$39.99Chicago Cubs Silicone Apple Watch BandFanatics
- SAVE $10.00$29.99$39.99Chicago White Sox Silicone Apple Watch BandFanatics
- $39.99and upMLB Chicago White Sox Wordmark Engraved Apple Watch Band - 42/44/45/49mmTarget & 1 more
- SAVE $10.00$29.99$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
- SAVE $10.00$29.99$39.99Chicago White Sox 42/44/45mm Apple Watch Sports BandFanatics
- $19.99Chicago City Flag Printed Watch Strap Compatible with Replacement IWatch Band 38-40mm 42-44mmAmazon
- $38.49Original 1890's R. Chester Frost & Company Chicago Jeweler Pocket Watch Advertising EnvelopeEtsy
- $149.99'Illinois, Chicago, Millennium Park, Pritzker Pavilion, Spectators Watching the Show' Photographic Print on Canvas East Urban Home Size: 20" H x 60" WWayfair
- $111.99Gametime Chicago Bears Leather Band fits Apple Watch (38/40mm S/M Tan). Watch not included.JTV
- $111.99Gametime Chicago Bears Leather Band fits Apple Watch (42/44mm M/L Tan). Watch not included.JTV
- $58.99Gametime Chicago Bears Navy Silicone Band fits Apple Watch (38/40mm M/L). Watch not included.JTV
- SAVE $10.90$44.09$54.99Timex Chicago Cubs Rivalry WatchFanatics
- $119.00Timex Chicago Chrono Leather WatchBuckle
- $41.24and upTimex Chicago Bears Rivalry WatchFanatics & 1 more
- $31.95MLB Chicago Cubs Charm Watch, SilverAmazon
- $24.95NHL Chicago Blackhawks Spirit WatchAmazon
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 42/44/45/49mm - BrownTarget
- $59.99and upBrown Chicago Cubs Leather Apple Watch BandFanatics & 1 more
- $59.99and upTan Chicago Bears Leather Apple Watch BandFanatics & 2 more
- $59.99and upBlack Chicago Bears Leather Apple Watch BandOfficial NFL Shop & 2 more
- SAVE $7.64$37.31$44.95Timex TWZFBEAYA NFL Recruit Chicago Bears WatchAmazon
- $94.99Vintage International Harvester Dual Globe Watch Fob ChicagoEtsy
- SAVE $8.75$26.24$34.99Youth Timex Chicago Cubs Recruit WatchFanatics
- $39.99NFL Chicago Bears Apple Watch Compatible Silicone Band 38/40/41mm - BlueTarget
- $35.09and upSparo Chicago Bears Wood Watch and Phone Wallet Gift SetFanatics & 1 more
- $65.99Spectators Watching a Baseball Match in a Stadium, Wrigley Field, Chicago, Cook County, Illinois Photographic Print on CanvasWayfair
- $59.99and upTan Chicago White Sox Leather Apple Watch BandFanatics & 1 more
- SAVE $10.00$39.95$49.95Timex Men's NHL Pride 40mm Watch – Chicago Blackhawks with Black FastWrap StrapAmazon
- $39.95Timex Men's NFL Pride 40mm Watch – Chicago Bears with Black FastWrap StrapAmazon
- $54.95Timex Tribute Unisex NHL Rivalry 33mm Watch – Chicago Blackhawks with Black FastWrap StrapAmazon
- $44.95Timex Tribute TWZHBLAYA NHL Recruit Chicago Blackhawks WatchAmazon
- $56.24and upMen's Timex Chicago Bears Citation WatchOfficial NFL Shop & 2 more
- $59.99and upBlack Chicago Blackhawks Leather Apple Watch BandNational Hockey League & 1 more
- $59.99and upBrown Chicago Blackhawks Leather Apple Watch BandNational Hockey League & 1 more
- SAVE $20.00$59.99$79.99Tan Chicago Cubs Leather Apple Watch BandFanatics
- SAVE $5.50$16.49$21.99Black Chicago Maroons Samsung 22mm Watch BandFanatics
- $49.99and upGame Time Chicago Bears Leather Watch Band Compatible with Apple Watch (38/40/41mm Chesnut Brown Long)Amazon & 2 more
- $24.99and upNFL Chicago Bears Wordmark Apple Watch Band - 42/44/45/49mmTarget & 2 more