Last Updated On: October 21, 2018

I love being able to take my friends or my hubby to cute little places that I have found. I’m always looking for hidden gems all over the city. Some of these spots are so special to me that they are even included in my novel, A Girl’s Guide to Chicago.

So, I thought that I would share some of my favorite hidden gems, bars and restaurants with all of you. These hidden gems are perfect for a great cocktail or glass of wine and to share an appetizer or two.

This girls guide to hidden gems in Chicago is perfect for both Chicagoans and visitors alike, so take a look below and read about some of my favorite hidden little spots.

Broken Shaker at the Freehand Chicago

The Broken Shaker is hidden at the back of the Freehand Chicago. Opening at 4 pm each day this little bar is so cozy, very quaint and has a really laid back vibe. You can find a cozy seat in the bar or feel free to sit on a roomy couch in the lobby and a server will still come and take care of you. Make sure you stop by for happy hour, weekdays from 4 pm to 6 pm to enjoy $7 cocktails and $5 wine and draft beer.

Celeste Rooftop

Celeste is located in River North on Hubbard Street. Head right to the rooftop to enjoy a delicious cocktail in what feels like an English garden. Seating for the rooftop is first come, first served basis so go early to grab a table. They also have a happy hour weekdays from 5 pm to 8 pm.

The Hampton Social

The Hampton Social is one of my favorite places to go to in the summer. I love the east coast feel and especially on warm days when all the windows are wide open. I always try to get a seat right next to the window. Go early (4 pm) for a great happy hour with 1/2 glasses of rose and 1/2 pizza. Perfect for a Friday afternoon!

photo credit: The Hampton Social

The Berkshire Room

The Berkshire Room is another hidden gem at the ACME Hotel located right next to The Broken Shaker. So, try to stop by both spots. The Berkshire Room is more intimate and known for their crafty cocktails (ask for the dealer’s choice). This bar would be a perfect place to stop by any day of the week.

The Z Bar at the Peninsula Hotel

The Z Bar is a perfect spot on a chillier night in Chicago. This is one of Chicago’s coolest new rooftops bars. The view of Michigan Avenue is amazing and it’s the perfect spot during the summer or during the fall and winter months. It has a cozy, 1950’s vibe, with comfy couches inside and chic tables and fire pits outside.


Drumbar is pretty popular to those who know of it of course. It can be quite the hot spot on the weekends. But, what makes this a hidden gem is that Drumbar is on the rooftop of an adorable boutique hotel, the Raffaello Hotel. (Which years ago, I used to live right next door too.) It just has a cozy feeling like you are on someone’s private penthouse rooftop. They also do have a happy hour from 8 pm to 10 pm. Perfect for a weeknight nightcap!

Three Dots and a Dash

Three Dots and a Dash is perfect if you want to feel like you are on a tropical vacation. You will love how these cocktails are served to you! They are very fun and really good! What’s also fun about this place is that the entrance is through an alley so if you bring some newbies, they might wonder… where are you taking us!?

Coq d’Or at the Drake Hotel

Coq d’Or at the Drake Hotel is really old-school and has some cool history. It was the second bar in the city to get a license after the Prohibition. This bar definitely had a great vibe and it’s another perfect spot on a chilly night in Chicago. They also have a happy hour daily from 5 pm to 7 pm.

RM Champagne Salon

RM Champagne Salon is great during the summer and winter months. You can sip champagne outside in their adorable outdoor garden on warm summer nights or cozy up indoors by the fire during the winter.

The Dawson

The Dawson has a large and really pretty patio which is perfect on summer evenings. I love the twinkly lights that hang above you that make you feel like you are in someone’s back garden. Great food, great drinks, and great company make for the perfect night out.

The Violet Hour

The Violet Hour is one of the coolest bars in Chicago. First, there is a hidden door so it’s really tricky to find this place. But, once you step through the big velvet curtains you find yourself in a place that I can only describe as like being in Alice in Wonderland. The cocktails are mysterious and wonderful and very very strong.

La Creperie

La Creperie is one of my favorite spots to go to and it’s located right in my neighborhood, Lakeview. I love to sit up front by the cozy fire on cold nights. But, many people don’t know that La Creperie has an adorable back garden patio. It’s not too busy back there and I’ve always managed to get a table outside. I love sitting in the back garden especially on Tuesday nights when they have 1/2 price bottles of wine.


Pastoral in Lakeview is a must if you LOVE wine and cheese. Inside this cozy little restaurant, you can enjoy amazing cheeses and wines from all over the World. They will also pack you a picnic that you can bring over and enjoy in the park or over by the lakefront.

Band of Bohemia

I was recently introduced to Band of Bohemia when my friend had a brewery bar crawl for her birthday over in Ravenwood. Which, by the way, I never knew existed and I will definitely do a guide to planning a brewery bar crawl soon! Band of Bohemia is a great brunch spot with the girls and once you walk inside you will love the decor of this place. It reminds me of the 1920’s with amazing cocktails to match. Make a reservation and head there asap!

Bistro Campagne

Bistro Campagne is located in adorable Lincoln Square. I love French food and this restaurant has great food and an adorable patio in the summer. If you find yourself exploring this area this is the place you want to go to.

Waterfront Cafe

I discovered Waterfront Cafe last summer and I LOVE it. You don’t feel like you are in the city at all. This cafe is literally right on the lake and it’s really quirky and cute with the palm trees,  pretty lights, and live music at night. You really feel like you are on a tropical vacation! I suggest going during the day to see how beautiful the scenery is and then plan on going again at night for the live music.

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Hidden gem bars and restaurants in Chicago

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A Girl's Guide to Chicago

Based on the true story of a girl in her twenties who packs her bags and follows her lifelong dream of moving to Chicago. Take a journey with Kelly and discover the hidden gems you never knew about – as she starts a new career, makes new friendships, and even falls into an unexpected romance. Learn more...

  • • Perfect for the girl who loves exploring and living in Chicago.
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Girl's Guide Chicago