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Chicago’s West Randolph Street generally attracts foodies who are seeking out a hip, trendy, and eclectic experience. Since it has a wide variety of offerings, this guide will help you get started exploring this street.

Girl & The Goat

Diner, Restaurant, Beer, American

Girl and the Goat
© Edsel Little/Flickr
This farm-to-table restaurant has been the hottest restaurant on Randolph Street since it opened in the summer of 2010. Girl & The Goat is a culinary blast, and ensures an experience with each innovative small plate. While reservations are highly recommended, there’s also counter seating for those living life on the edge and attempting to snag a table last minute. While the crispy pig face is one of the most highly regarded items on the menu, their rotating list of craft beers from local Chicago breweries is a bonus. If Girl & The Goat is packed, then The Little Goat Diner is another Stephanie Izard wonder.

Kaiser Tiger

Bar, Belgian, Beer

20150226 17 Curling
@ Kaiser Tiger © David Wilson/Flickr
A night on Randolph Street is a marathon, but it helps when there is actually an Olympic game inside this bar. Kaiser Tiger has ice curling in the winter. Their back patio is one of its best features and anytime it’s 32 degrees and below, ice curling is a huge hit here. Conveniently seated at the west end of Randolph, it’s perfectly situated for a post-bar-crawl order of Belgian frites or a beer-and-sausage flight. We recommend, ‘The Kaiser Board’, which consists of sausage, potato salad, and a large soft pretzel accompanied by a variety of pickled vegetables, mustard, and cheese.

The Randolph Street Market Festival

Market, Street Food

The antiques at the monthly Randolph Street Market Festival draw a stylish crowd and it’s a fabulous way to spend a weekend afternoon. If you buy tickets online in advance, they generally run a few dollars cheaper. The entrance fee isn’t a scam either, because it helps the neighborhood with expenses and keeping the booth rentals down allowing them to charge you less for items. These items usually range from records, cameras, bikes, vintage typewriters, and more. The booths are staged both inside and outside which is convenient in case of bad weather. Finally, the food vendors and live band are a major plus.

Au Cheval

Bar, Diner, Restaurant, American

When seeking out the perfect burger, most of Chicago will respond with ‘Have you been to Au Cheval?’ This place is well known for good reason. As a late-night diner from Chicago’s restaurateur of the moment, Gilt Bar owner, Brendan Sodikoff has perfected the burger. It uses mornay sauce, garlic aioli, fried farmer eggs… are you drooling yet? Although, Au Cheval does not accept reservations, the accolades and long wait is well deserved. Besides the burger, it’s also recommended to order the bone marrow with beef cheek marmalade. If that doesn’t win you over, then the chopped chicken liver with salted butter and toast will.

City Winery

Bar, Restaurant, American, Beer, Wine

KT Tunstall 12
© GabboT/Flickr
With two impeccable locations, on the riverwalk and in the West Loop, the City Winery is guaranteed to be full of fun, radiant vibes. This West Loop location is a 30,000 square-foot venue that’s known for their concert hall, and garden courtyard for dining alfresco. Although there will be more wine choices than food choices, their Mediterranean bites are very enjoyable and come with a fantastic presentation. The must-haves include the savory, exquisite duck tacos as well as the crispy chicken thighs. Something to note is when the menu says ‘pickled peppers,’ they will be exceptionally hot and delicious.

The Aviary

Cocktail Bar, Cocktails, American

Once you go to The Aviary,you will never settle for an ordinary cocktail again. Sounds dramatic, but Grant Achatz sets up a really top-notch drink adventure with every sip. Technically this is two blocks north of Randolph, but it pairs very nicely as an apres dinner outing. Expect to see an army of mixologists behind a chain type wall creating alcoholic pieces of contemporary art. Because the quality of each drink is of the utmost importance and the timeliness is second to none, expect a larger price tag. However, have you ever tried a cocktail that involves CO2 and infusions to create drinks? The experience is worth it. Finally, if cocktails don’t tickle your fancy then there is also an incredible list of imported beers available.

Brew & Grow

This 7,500-square-foot warehouse has everything you need to brew and bottle your own beer, whether you’re a beginner or a pro brewer. It has the ingredients, offers the expertise, and even has classes available. Finally, it’s an option to grab some supplies for making cheese and growing microgreens as well. Nick is a growing guru and his staff at Brew & Grow is exceptionally well versed in the industry. Although this is also a few steps from Randolph, it’s tough to match this brewing expertise.

Big City Swing

Put your dancing shoes on. Big City Swing is THE place to go to learn how to swing dance. There’s always a moment at a wedding, fundraiser, or even a night out when you’re asked to dance and instead of sitting on the sidelines, take the reigns. The teachers are phenomenal, the prices are reasonable, you’ll meet dancers and make friends immediately; there are zero cons about attending. Even better, there are ‘First Fridays’ where the evening starts with a lesson for beginners, and they encourage you to swap partners every few minutes. Big City Swing will get you out on the floor with confidence and twirling to an infectious beat.

Haymarket Pub & Brewery

Pub, American, Belgian, Beer

If there’s a beer connoisseur among your friends, then this is where to take them. Haymarket Pub & Brewery specializes in classic Belgian and contemporary American beer styles. Beer isn’t the only thing to keep on your radar: Haymarket also takes pride in making their own sausages. There’s a variety to choose from including three which are made in-house. On Sundays, a tour and tasting is offered that allows all visitors into the fermentation room, distribution center, and back to the tables to taste some classics. It’s important to note that reservations are required. Finally, take note of the specials including Reuben Tuesdays and Pastrami Wednesdays!

Embeya

Restaurant, Asian

Although Embeya is known for their progressive Asian plates and craft cocktails, it also has some exotic dessert options. While the menus are subject to seasonal variation, you can always guarantee that the freshest fruit (rambutan, longan, dragon fruit and lychee) is being used as most of it is imported. Additionally, every quarter Embeya’s Chef, Mike Sheerin, invites one of Chicago’s best chefs to collaborate a five course dinner with wine pairings. Finally, it’s recommended to go with a special someone because it has recently been named as one of Chicago’s Sexiest Restaurants by Zagat!

About the author

Katie was born in Baltimore, Maryland, and attended Vanderbilt University as a Division I women's lacrosse player. She has been residing in Chicago since 2014. When she's not busy writing for Second City, Katie is most likely planning a trip or trying new restaurants around the city.

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