Chicago Best Restaurants
- Wow Bao - Water Tower Place
- Writers' Theatre
- Wynwood Chicago
- Xippo
- Xoco
- XOCO Bistro
- XO Marshmallow
- Yak-Zies Bar & Grill
- Yard House
- Yasotorn
- Yassa African Restaurant
- Y Bar
- Yim Siam
- Yolk (South Loop)
- Yolk - Streeterville
- Yolo Mexican Eatery
- Yoshi's Cafe
- Yummy Bowl Restaurant
- Yu's Mandarin Restaurant
- Yuzu Sushi & Robata Grill
- Zanies Comedy Night Club - Chicago
- Zanies Comedy Night Club - St. Charles
- Zanies Comedy Night Club - Vernon Hills
- Zaytune Mediterranean Grill
- ZaZa's Trattoria
- Zebra Lounge
- Zelda's Sweet Shoppe
- Zia's Trattoria
- Zoku Sushi