This Chicago thoroughfare is one of Time Out’s coolest streets in the world

It’s official—Chicago is home to one of the coolest streets in the world (again!).

Roscoe Street is No. 28 on Time Out’s annual rankings of the coolest streets in the world. Barely a mile west of Wrigley Field lies “the village within the city”: Roscoe Village, a quaint, family-oriented neighborhood lined with three-story walk-ups, local watering holes and quirky boutiques. There’s an almost cinematic friendliness to Roscoe Street, the Village’s main thoroughfare: parents swapping weekend plans while kids pop wheelies on the sidewalk, bartenders regaling patrons with vivid stories and free shots, bakeries remembering regulars’ orders by heart. 

In the summer, you’ll find Chicagoans flocking to Roscoe Street to celebrate Retro on Roscoe, an annual festival where antique vendors and classic cars pack a six-block stretch of Roscoe Street. No matter the season, you won’t be hard-pressed to fill an entire day here: Spend an afternoon searching for your next thrift score at Shangri-La Vintage, fuel up on mole enchiladas at the family-owned Cafe El Tapatio and round out the day by throwing back limoncello “fizz” shots and dollar oysters at Volo.

What makes a street cool, exactly? Well, for one, there’s much more to do than just walking. You could spend entire days exploring the avenues on the list, which boast bold, creative new ventures in the food and beverage scene, plus tons of nightlife and culture. Topping this year’s rankings is Rua do Senado in Rio de Janeiro, Brazil, followed by Orange Street in Osaka and Porto’s Rua do Bonjardim.

Here’s the full list of Time Out’s 31 Coolest Streets in the World:

1. Rua do Senado, Rio de Janeiro
2. Orange Street, Osaka
3. Rua do Bonjardim, Porto
4. Fanghua Street, Chengdu
5. Sherbrooke Street West, Montreal
6. Montague Road, Brisbane
7. Maybachufer, Berlin
8. Olympou Street, Thessaloniki
9. Orchard Street, New York City
10. Vinh Khanh Street (District 4, HCMC), Ho Chi Minh
11. Rue de Flandre, Brussels
12. Nishihara Shotengai, Tokyo
13. Rue des Gravilliers, Paris
14. Joo Chiat, Singapore
15. Avendia Alvaro Obregon, Mexico City
16. Jalan Kemang Raya, Jakarta
17. Via Panisperna, Rome
18. Nakpil St, Malate, Manila
19. Alserkal Avenue, Dubai
20. Cambie Street, Vancouver
21. Calle del Barquillo, Madrid
22. Kloof Street, Cape Town
23. Blackstock Road, London
24. Defensa, San Telmo, Buenos Aires
25. Pacific Coast Highway, Central Malibu, Los Angeles
26. Charoen Nakhon Road, Bangkok
27. Jalan Pudu, Kuala Lumpur
28. Roscoe Street, Chicago
29. Swan Street, Richmond, Melbourne
30. Boulevard Pasteur, Tangier
31. Northdown Road, Margate