| ★ |  Runner-up! Thank you! | Car Con Carne Podcast @carconcarnepodcast | 1.6K | — | |
| 3 |  Thanks to all who visited our Chicago Pop-Up! | Avenged Sevenfold @avengedsevenfold | — | — | 89 |
| 14 |  THANK YOU FOR VOTING!!! | | — | Australia | 87 |
| 15 |  I BROUGHT FIVE STARS TO PLAY THE BEST TEAM IN CHICAGO! 🫣💥 | | 607.0K | — | 87 |
| 4 |  I ❤️ CHICAGO! | | 242.4K | Reino Unido | 89 |
| 12 |  📍Kitchen & Kocktails - Chicago, IL #chicagorestaurants | | 58.8K | — | 87 |
| 9 |  I FOUND MY DREAM APARTMENT IN CHICAGO 🥹🏡 | Allison Baek @allison_baek | 55.0K | Estados Unidos | 87 |
| 2 |  Chicago is impressive! Food is great and tons to do #tastinghistory #chicago | Ketchup with Max and Jose @ketchupwithmaxandjose | 37.6K | Estados Unidos | 89 |
| 18 |  Who wants to be a Chicagoan? #shorts #chicago #comedy | | 34.9K | Estados Unidos | 87 |
| 10 |  I love you @LewisCapaldi. Thanks for coming out to Chicago! Hope to do this for real sometime soon | | 29.6K | Estados Unidos | 87 |
| 17 |  MY FAVORITE BURGER IN CHICAGO! 🍔 #chicagoburger #chicago #burger #foodreview | | 6.4K | Estados Unidos | 87 |
| 8 |  TOP 10 RESTAURANT IN CHICAGO? 🐷 #maxwellstrading #maxwellstradingchicago #chicagofood #chicago | | 3.9K | Estados Unidos | 88 |
| 13 |  Stationery favorites from #chicagostationeryfest ✨ | | 3.4K | Alemania | 87 |
| 11 |  POPULAR BAGEL POP UP IN CHICAGO! 🥯 #chicagobagels #chicagofood #chicago | | 3.0K | Estados Unidos | 87 |
| 20 |  Vlogmas | Viajando a Chicago 🎁⭐️ #vlog #vlogmas #viajes #chicago #girl #viaje #vlogger | | 2.5K | — | 87 |
| 1 |  Hey Chicago!! | BLISS JOY BULL @blissjoybull | 2.0K | — | 90 |
| 16 |  chicago invented your favorite music genre!! #chicagohousemusic #chicagomusic #chicagofootwork | Real Ones Show @realonesshow | 1.4K | Estados Unidos | 87 |
| 19 |  #chicago #chicagomustvisit #chicagosky | Paulene Nistal @paulenenistal | 706 | Canadá | 87 |
| 7 |  Best Effort: Chicago True Crime & Audience Insights #shorts | The Intersection by Oak Leyden @theintersectionoakleyden | 157 | Estados Unidos | 88 |
| 6 |  Invitation to #VoteWavestage2023 - BroadwayWorld Toronto Awards 2023 | Joey Colombo @joeycolombo2780 | 12 | — | 88 |
| 5 |  Chicago | Math Ninja @mathninja2014 | 2 | — | 88 |