| ★ |  Chicago Vlog with a Trip to Wool & Co. | | 225 | Estados Unidos | |
| 1 |  What I spend in a week as a 28-year-old in Chicago (who tries to spend mindfully) | Morgan Evelyn Cook @morganevelyncook | — | — | 77 |
| 6 |  Chicago USA: Why It's a Must-Visit | CoolVision @realcoolvision | — | Estados Unidos | 76 |
| 11 |  Wild Viral Video Shows Daylight Robbery In Chicago | TheDC Shorts @dailycallervideo | — | — | 74 |
| 9 |  Shockingly, They've Been Lying to Me About Chicago | Ray Delahanty | CityNerd @citynerd | 219.8K | Estados Unidos | 74 |
| 2 |  A day of Street photography with Flash in Chicago (Walkie Talkie with Amado De Leon) | | 36.6K | Estados Unidos | 77 |
| 13 |  Relaxing Night Walk in CHICAGO 🏙️ Downtown The Loop Walking Tour 4K | WALKS and the CITY @walks_and_the_city | 26.8K | Estados Unidos | 74 |
| 7 |  Chicago: Story of an American Giant | | 22.9K | Estados Unidos | 75 |
| 18 |  CHICAGO - Night Walking Tour Downtown, Illinois, USA, 4K UHD | WALKS and the CITY @walks_and_the_city | 13.6K | Estados Unidos | 72 |
| 4 |  CHICAGO VLOG Travel Vlog 🌇 | A Weekend Exploring The City, Cubs Game, Sky Deck & More! 🌭🐻🎇 | Ashlynne Eaton @ashlynneeaton | 5.3K | Estados Unidos | 76 |
| 20 |  Is There An Amen Clinics Near You? | | 2.1K | Estados Unidos | 72 |
| 17 |  2 DÍAS PERFECTOS en Chicago (¿La joya CULTURAL de EE.UU.?) 😍 Qué hacer + Dónde comer | Bitácora de viajero @bitacoradeviajero | 1.9K | Estados Unidos | 73 |
| 8 |  mi ciudad natal | primera semana en Chicago | Diego Montes @diego.montes | 1.4K | Chile | 75 |
| 10 |  De CHICAGO a Detroit. Viaje por los Estados Unidos🌆🏖️✈️ | el VLOG de una MOCHILA @backpackvlogsinspanish | 566 | Estados Unidos | 74 |
| 19 |  ARQUITECTA EXPLORA CHICAGO | Artquitectura by Adriana Haro @adrianaharo | 332 | — | 72 |
| 15 |  Chicago Weekend Trip: Shawnee National Forest (Illinois’ Most Scenic Escape) | Erin Parro – The Scenic Route Traveler @scenicroutetraveler | 179 | Estados Unidos | 73 |
| 3 |  CHICAGO VLOG | 48 hours in chicago | visiting my childhood bestie | could I MOVE here?! | | 88 | Reino Unido | 76 |
| 5 |  Vlog Chicago P.I | Curiosidad por el SCRAPBOOK @curiosidadporelscrapbook3131 | 24 | España | 76 |
| 12 |  What's the BEST Way to Explore Chicago | Things To Do In Chicago | Travel Tapestry @traveltapestry-y1y | 11 | Emiratos Árabes Unidos | 74 |
| 14 |  CHICAGO FINAL | Educational Travel Adventures @educationaltravels | 4 | Estados Unidos | 73 |
| 16 |  Moving to chicago: 10 Things to Know About Living in Chicago illinois | | 1 | Estados Unidos | 73 |