The Essential Sips and Bites in Chicago


Explore Chicago   Travel and Eats  


Chicago is a cultural hub for several reasons, however, I think we can agree that one of its major contributions is the food! No trip to Chicago would be complete without sampling all the bites and sips it has to offer such as classics like deep dish pizza and Chicago-style hot dogs to new twists like the beach-side Mediterranean, reinvented Mexican, and home-town American fares as well. Take a look at some of my absolute top picks eating and drinking your way through the Windy City.


Tastebud Tours

Tastebud Tours Picture Credits: Tastebud Tours


If there is anyone who knows the Chicago food scene, it’s Lynn & Karon Jaynes. The couple has lived in Chicago for more than 30 years, surrounded by so many incredible restaurants that, in 2009, they were inspired to turn their passion into their career and Tastebud Tours was born. If you are visiting Chicago, their Taste of Chicago Food Tour is an absolute must. You’ll be able to taste the best food in Chicago’s Downtown Loop neighborhood including delicious cuisine from famous eateries like Pizano’s Pizza, the Goddess and the Baker, the Berghoff, Al’s Beef, Chicago Kernel, and Fannie May Chocolates. Be sure to wear comfy clothes and come hungry so you won’t skip a single bite.



Spiaggia Picture Credits: Spiaggia


Spiaggia is an experience to modern Italy for the senses thanks to Chef-Partner Tony Mantuano and Executive Chef Joe Flamm (Top Chef Season 15 winner!) carefully curating your meal with exquisite detail and care. This restaurant has stirred up their fair share of recognition as well since being awarded the “Best of Award of Excellence” from Wine Spectator and is also being named one of “America’s 100 Best Wine Restaurants” year after year by Wine Enthusiast. Wine lovers will thrive with their 700-bottle wine list and careful notes from the award-winning Sommelier, Rachael Lowe as well. Whether you’re there for the food or the drink, experience this unique is meant to be shared with friends and family whenever possible. And don’t forget to save room for their stunning (and mouth-watering) desserts!



Secret Food Tours

Picture Credits: Secret Food Tours


The guides over at Secret Food Tours are Chi-Town foodies of the first order and are so excited to share with you all the culinary delights the historic Midwestern city has to offer. You’ll be able to discover each facet of the unique city, including historic enclaves, stunning architecture, an extensive collection of publicly displayed civic artwork, and a culinary style steeped in history, while you walk and eat your way through Chicago’s Loop District.

Book the Classic Chicago Food Tour and experience all the city’s biggest food hits, many dishes with roots the city’s 150-year history of Italians settlements. This moving feast incorporates a walk through some of the city’s world-renowned architecture and public art as well as tastes from the city’s very best restaurants.



Chicago Detours

Picture Credits: Chicago Detours


Since 2010, Chicago Detours has brought thousands of guests on public walking tours of downtown Chicago’s interiors, historic drinking establishments, underground tunnels, and other famous and unexpected locations. These fun and educational summer tours include the “Best Architecture Walking Tour for Design Lovers” with its chronological walk through Chicago’s architectural history downtown and the “Old Polonia and Wicker Park Food Tour” of changing communities in northwest neighborhoods. This summer marks the return of their popular “Factories to Calories Fulton Market Food Tour,” which explores the dramatic transformation of Chicago’s most rapidly booming neighborhood.


Duke of Perth

Picture Credits: Duke of Perth


Established in 1989, the Duke of Perth brings the true essence of Scottish pub culture to Chicago. The cozy pub offers the city’s largest selection of single malt Scotch whiskey as well as some of the finest beers in the world and good old fashioned comfort food. Be sure to try the Duke’s Fish and Chips, (all you can eat on Wednesdays and Fridays), known as the best on this side of the Atlantic.



Delilah’s Chicago

Delilah's Chicago Picture Credits: Delilah’s Chicago


Delilah’s opened in 1993 and has been spinning Rock & Roll, Punk Rock, Metal, Ska & Reggae, Soul, Maximum R&B, Hard Country, Garage & Rockabilly every day since.  This bourbon bar is one of the best of the best and has been featured in Icons of Whisky, Eater, Timeout Chicago, and Men’s Journal. In addition to the drinks and music, Delilah’s also offers a regular line up of special events including art openings, film screenings & beer tastings. Whether you go for the whiskey, art, beer, or company, Delilah’s is a Chicago favorite that you can’t miss.


Sheffield’s Chicago

Picture Credits: Sheffields Chicago


For over 25 years Sheffield’s Beer and Wine Garden has been known for pioneering the Chicago craft beer movement and more recently for its authentic in-house smoked BBQ. A local favorite during Chicago’s beautiful summers, Sheffield’s is a great spot to enjoy the Chicago sun. After ordering a drink from the large antique bar, grab an elevated booth seat and settle in for a good conversation with friends while sipping on one of the delicious brews and indulging in some decadent BBQ with options ranging from baby back ribs to beef brisket.


Caffe Oliva

Caffe Oliva Picture Credits: Caffe Oliva


Looking for an island getaway without leaving Chicago? Look no further than Caffe Oliva located at the Ohio Street Beach. Caffe Oliva is the local oasis where you and your friends can relax in one of the private lakefront cabanas and enjoy weekly live music! And don’t forget the Mediterranean fare like grilled calamari, hummus and pita, and greek salads – all served up by a courteous and welcoming staff. There’s nothing quite like feeling the sand between your toes while sipping a handcrafted cocktail with your favorite people. They even offer group “fishbowl” cocktails that are always sure to please (the “Sunny Paloma” is my favorite). They offer plenty of space and facilities to host your next private event here too, just check their website and they will make sure you can enjoy a stress-free and elegant event on the sand!


The Coffee Studio

The Coffee Studio Picture Credits: The Coffee Studio


The Coffee Studio has been a java-lovers’ fixture in Chicago since it opened in 2007 by husband-wife duo Miguel and Lee Corrina Cano. Born out of their passion for the craft of coffee this warm, minimalist space is beloved by many local creative and influencers. They make sure that their single-origin coffee is all sourced via direct trade with the growers to ensure the highest quality that coffee aficionados crave. In addition to their beloved brews, they also make all sauces and syrups in-house in addition to their mouth-watering ice creams and coffee and tea-inspired cocktails. Bon Appétit magazine has even praised them as one of the “Top 10 Boutique Coffee Shops in the country! The only thing missing at this happening locale is you.



Picture Credits: Fountainhead


Established in 2009, Fountainhead has been dedicated to providing locals and visitors alike with delicious, yet approachable food in a friendly pub-type atmosphere. Owner and Operator Aaron Zacharias have been in the food industry since he was 15 years old, and has established a name for himself as a highly trained and respected fixture in the Chicago service industry. I highly recommend travelers go check out the food and drink he and his team have come up with.

Come savor home-cooked comfort foods given new life such as mac & cheese, meat pie, mussels, chicken, and steak! All offers pair excellently with their impressive and well-curated drink list of beer, wine, bourbons, whiskeys, creative cocktails, and much more. Ask your bartender or wait staff for the monthly specials and featured drafts if you’re looking for something different and unexpected!


Mi Tocaya

Mi Tocaya Picture Credits: Mi Tocaya


Opening in March of 2017 the hip locale that is Mi Tocaya is the place for bold and inventive fare all inspired from owner Diana Dávila’s Mexican heritage. Not only is space itself bright and fresh but these elements are also reflected in the food that Diana crafts with experience and care.

Both the restaurant and the chef have a long list of well-deserved accolades they have accumulated by offering visitors a chance to experience Mexico through the eyes (and taste buds) of the creative forces in the kitchen. Come see what’s cooking from who Food & Wine magazine has named one of the “Best New Chefs” in 2018 in a space that will perhaps make you reminisce of a place you’ve never been before!


Carnitas Uruapan Chicago

Carnitas Uruapan Chicago Picture Credits: Carnitas Uruapan


A true celebration of all things pork, Carnitas Uruapan serves up authentic carnitas (and more) as they do in the owner’s hometown of Uruapan. Making carnitas daily since 1975, owner “El Guero” Carbajal has become nationally recognized as a master of the craft. Whether ordered by the taco or by the pound, the carnitas here is something to travel to Chicago for. On the menu, you’ll also find a host of classic dishes that compliment this dish such as refried beans, chicharrones, and menudo. After a trip here you’ll start to understand why this restaurant believes that “people think better with a full belly.” Do yourself a favor and order a pound of chicharrones to take with you when you leave too!

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About the Author: Keith Perrotta

Keith is a freelance writer, English teacher, baker, and travel junkie currently based in Madrid, Spain. When not creating content or teaching ESL he enjoys going to the beach, researching bread recipes, looking through bookstores, and relaxing with a glass of wine. Having lived in the USA, France, Ghana, Kenya, and now Spain, his main goal in life is to visit every continent once (including Antarctica). You can usually catch him eating ice cream in the park or stopping someone in the street to ask to pet their dog.

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