03/26/2026
14 years today how our fearless band leader Richie left us,
Rest in Power.
We honor him tonight,
Cafe Bolero Crew and
Juan Antonio
Cafe Bolero Chicago
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Cafe Bolero Chicago is a restaurant that specializes in Cuban and Caribbean cuisine while also serving coffee. With a motto of "Love is the excuse of life," the restaurant offers an ambiance that encourages guests to revel in the moment. Cafe Bolero hosts weekly live Latin jazz performances at nearby El Cid, where patrons can enjoy margaritas and cocktails by the fireplace while dancing to upbeat rhythms.
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Chicago, IL
For the Caribbean restaurant and cafe, take the bus or train to the Red Line Argyle stop. From there, walk a few blocks east until you reach the intersection of Argyle Street and Sheridan Road. The restaurant is located on Sheridan Road.
For the Cuban restaurant, take the bus or train to the Blue Line Division stop. From there, walk a few blocks south until you reach Division Street. The restaurant is located on Division Street.
If driving, for both restaurants, take Lake Shore Drive to its end and exit onto Hollywood Avenue. Turn left at Sheridan Road and continue straight until you see the restaurant on your left. For parking options, check nearby streets for metered parking or use available parking garages in the area.
Opening Hours
| Monday | 10am - 11pm |
| Tuesday | 10am - 11pm |
| Wednesday | 10am - 11pm |
| Thursday | 10am - 11pm |
| Friday | 10am - 11pm |
| Saturday | 10am - 11pm |
| Sunday | 10am - 11pm |
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What people say
Cuban restaurants are known for their vibrant atmosphere, lively music, and delicious cuisine. Cafe Bolero Chicago is no exception to this rule. Located in the heart of Chicago, this Cuban restaurant offers a unique dining experience that transports you straight to Havana.
One of the highlights of Cafe Bolero Chicago is their Latin Jazz band that performs regularly at El Cid, the restaurant's partner venue. Guests can enjoy live music while sipping on delicious Mezcal Margaritas by the cozy fireplace. The ambiance is perfect for a romantic date or a night out with friends.
The menu at Cafe Bolero Chicago features classic Cuban dishes such as Ropa Vieja, Lechon Asado, and Arroz con Pollo. The food is flavorful and authentic, made with fresh ingredients that transport your taste buds to Cuba.
The staff at Cafe Bolero Chicago is friendly and welcoming, making sure that every guest has an enjoyable dining experience. They are knowledgeable about the menu and happy to recommend dishes based on your preferences.
Overall, Cafe Bolero Chicago is a must-visit destination for anyone looking for an authentic Cuban dining experience in Chicago. From the lively atmosphere to the delicious food and drinks, this restaurant has it all.