Chicago Hidden Gem: Mid-Century Cocktail Bars Walking Tour

Chicago, USA

1 hour 30 minutes (approx.)
Mobile ticket
Offered in: English

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Overview

Step into Chicago’s coolest hidden bars on a mid-century cocktail adventure! Join a local guide to discover vintage lounges, secret speakeasies, and retro bars most tourists miss. Savor expertly crafted cocktails (own expense), hear untold stories of the city’s nightlife boom, and soak in stylish decor straight from the 1950s and 60s. This small-group tour is perfect for cocktail lovers, architecture buffs, and anyone seeking an off-the-beaten-path night out in the Windy City.

What's Included

Water - Important to Hydrate
Storytelling - Get to know a bit from the locations and surroundings
Guidance - Visit a few hidden bars hard to find
Cover charge - Cover charge entrance is included at the last bar.

Private transportation
Gratuities
Alcoholic Beverages

Meeting and Pickup

Meeting point

921 N Western Ave, Chicago, IL 60622, USA
We will meet at the first Speakeasy, EZ Inn.

End point

This activity ends back at the meeting point.

Operating hours
.8:00 pm

What To Expect

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Near public transportation

Most travelers can participate
This tour/activity will have a maximum of 16 travelers

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Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Reviews

5.0

based on 4 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Unique Bars and Vibes

Ashley_N, Mar 2026

Really fun!! Ronaldo was very kind, knowledgeable, and curated a fun mix of bars with unique elements to them.

Great tour

Julia_H, Mar 2026

Great tour guide and full of information. Great bars visited. It was a cheap uber ride from downtown and worth it.

This is a great way to...

Shalini_S, Jan 2026

This is a great way to experience a less touristy Chicago neighborhood. Real bars with history and hanging out with the locals! We went to 3 bars in two neighborhoods - lots of different drinks is to try and options to dance if you want to stay later. Ronaldo is a great guide and fun to hang out with as well!

Really cool bars and a...

Stacey_B, Apr 2025

Really cool bars and a really great host. He really knows the neighborhood super friendly and very accommodating. He did the most to make us comfortable and happy with our experience. Would definitely recommend.