5 Restaurants to Try Before Leaving Chicago

Like A Local Guide • 24 Oct, 2016

Being a Chicago local who hosts guests from around the world, Jaclyn is often asked for recommendations. Truth be told, most of her tips are food-related. When you come to Chicago, you must eat! What you may not know is that there are many alternatives to deep dish.

With 77 neighbourhoods and a transit system that can get you anywhere you need to go, the options are endless. This can seem overwhelming for visitors, so Jaclyn has taken the challenge of suggesting five must-try spots.

1. 90 Miles Cuban Cafe

Logan Square and Roscoe Village

This tends to be my first recommendation for anyone wanting to spend time in Chicago’s Near North Side or Northwest Side. The food is delicious (the Cubano Sandwich is a must) and it’s BYOB. Bring your own wine and try their sangria mix! Best of all, there’s live entertainment on certain nights.

Pro tip: it tends to get crowded around dinnertime, so be sure to make a reservation.

14237705_10154506379387241_5425293614849104498_nPhoto credit: 90 Miles Cuban Cafe

2. Little Goat

West Loop

So, you waited a bit too long to make a reservation at Girl & The Goat, Stephanie Izard’s award-winning restaurant. Don’t panic. Little Goat is an equally delicious and more affordable alternate where you can still try some of her creative diner-style dishes, the quesadilla and patty melt being two of my personal favourites.

I’d advise against skipping an appetiser here – all options are great!

little_goat_corn_dogPhoto credit: Little Goat

3. Waterfront Cafe


We’ve been talking about tasty food, but let’s be honest, the restaurant experience is almost just as important. Waterfront Cafe is a hidden gem in Berger Park offering one of the best dinner views at a reasonable price.

Serving wraps, sandwiches and beachside eats, this restaurant sits adjacent to the lake, providing beautiful views from every angle. Additionally, its crab cakes were featured on Chicago’s Best. It also has live entertainment a few nights a week during the summer.

13465934_1020922171296948_227575202128720311_n-1Photo credit: The Waterfront Cafe

4. The Winchester

Ukrainian Village

I’m a huge fan of breakfast food. Naturally I had to add a brunch spot to this list, which is a tough choice because there are almost too many places to get a great morning meal in Chicago.

The Winchester always tops my list when people ask for recommendations. Tucked away in the Ukrainian Village neighbourhood, it offers food made with locally sourced ingredients, which means the menu is always changing.

The bright, minimalist décor is just what’s needed first thing in the morning. Your taste buds will thank you.

1620979_213574818831297_1864418469_nPhoto credit: The Winchester

5. 5411 Empanadas

Various locations

Whether you’re looking for a small snack or a full meal, 5411 Empanadas is a choice you won’t regret. With many locations and a food truck, it’s easy to stop by and try their famous bacon, date and goat cheese empanada. Don’t forget the chimichurri!

1505577_10152273500715660_6019515414633505181_nPhoto credit: 5411 Empanadas

Admittedly, I could go on. Creating a top five was hard because Chicago is a place where foodies can rejoice. With so many delicious things to try, it’s a guarantee you won’t leave hungry!

DSC_0108Jaclyn Crawford is a freelance writer and blogger based in Chicago, Illinois. She loves playing badminton, hosting Airbnb guests, spending time with her dog, Sundae, and going thrift shopping with her husband.

Opening photo credit: The Winchester

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Like A Local Guide is about stepping off the tourist trail and finding cool and cosy spots where locals like to spend their time. We built a website and mobile app to bring insider recommendations from around the world to your fingertips.

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