Food Truck Challenge: 30 Must-Try Chicago Area Food Trucks

Following the Pizza Challenge list (which is still ongoing) that I released at the end of spring, I was ready for a new foodie adventure. I wanted to focus on something that represented both the city and summer perfectly…What better than food trucks?

Food trucks have variety, they have personality, and they are all unique in their own way which makes it almost impossible to rank them. So here’s your first HEADS UP:

THESE ARE NOT RANKED!

With a little help from my friends and the Chicago Food Truck Finder, I made stops from Libertyville…to Palwaukee Airport…to Rosemont…to the middle of Daley Plaza, to try something new and delicious each week. I found trucks on street corners, outside suburban office buildings, on the perimeter at concerts and festivals, on an airstrip, and in front of the (Bruce) Willis Tower.

I’ll include the Facebook profile and Twitter handle for each truck, along with any available menus for you to peruse before diving into your own Food Truck Challenge. I’ll also keep adding trucks to this list to serve as a database, so any recommendations are more than welcome.

1. The Slide Ride

#1 Slide Ride

“The Bacon Baby Trio”

Angus beef, brown sugar bacon, melted cheddar and mustard onions on a sesame bun

Finding “The Pink Lady” truck was a priority for me to kickoff this challenge. Who doesn’t love sliders? Each slider is $3.50 or you can snag 3 for $9. Not just burgers either; pork, chicken and even tilapia make the rotation. 

Facebook / Twitter / Menu

2. Gino’s Steaks Truck Chicago

#2 Gino's Steak Truck

“Steak and Cheese”

steak, onions, peppers, melted swiss, pickle, herbs and mayo

While “The Fatty” sounds amazing, which you’ll find on the menu, I had to go with a classic. What also struck me about this truck was how cool the guys were running it. Very personable and conversational, which is nice while you wait on your sandwich.

Facebook / Twitter / Menu

3. Toasty Cheese Mobile Eatery

#3 Toasty Cheese

“The Chef’s Choice”

Duck bacon, provolone, fresh spinach, baby arugula, Sicilian cherry tomatoes and aioli

Very prevalent in the northwest suburbs, you can find this awesome grilled cheese truck outside offices, town festivals, and even breweries. Don’t fear the Duck Bacon either. It’s so thick and the flavor is fantastic….and goes great on the cheese fries.

Facebook / Twitter / Menu

4. Beaver’s Donuts

#4 Beavers Donuts

“Reese’s Minis”

chocolate and peanut butter…what else? 

An underrated food item in Chicago has to be THE DOUGHNUTS we have here. So many fantastic shops (some that run out before you even make it down from the burbs…looking at you, Doughnut Vault), and the trucks are no different…Beavers is by far the most unique though with their mini servings and fun toppings. 4 minis is just $2, 9 is just $4.

Facebook / Twitter / Menu

5. Haute Sausage

#5 Haute Sausage

“Bacon Guacamole”

bacon sausage, roast poblano & corn guacamole, Merkt’s cheddar, and chipotle mayo

The Haute Sausage truck certainly makes it’s way around town. I’ve had it outside of my old work studio, at local beer festivals, and in the middle of the Daley Plaza food truck wagon circle. What’s very clutch with these sausages are the Texas toast style buns and homemade chips.

Facebook / Twitter / Menu

6. DönerMen

#6 DonerMen

“The Döner Box”

fries and greens topped with roasted chicken, tomato/cucumber shirazi, onion, spicy harissa, and tzatziki yogurt sauce

Fittingly, I got to try this masterpiece for a concert at Montrose Beach. Forking threw each layer to the sounds of Mumford and Sons was a treat, as was the curry wurst.

Facebook / Twitter / Menu

7. Tamale Spaceship

#7 The Tamale Spaceship

“Complicate de Carne”

flank steak tamale with traditional Oaxacan black mole and sesame seeds

The best part of this food challenge for me was trying new things. Confession: I had never had a tamale before boarding the “spaceship”…and now I love them. Thank you for that, Spaceship.

Facebook / Twitter / Menu

8. Best Truckin’ BBQ

#8 Best Truck'n BBQ

“The Interstate”

hand seasoned pork shoulder, smoked for twelve hours, chopped and sauced on a pretzel bun

Another truck that you’ll find in the suburbs and the sauce is to die for…I’m not even kidding. Some of the best sauce I’ve had in the Chicagoland area.

Facebook / Twitter / Menu

9. Cheesie’s

#9 Cheesie's

“The Melt”

American cheese, Chihuahua cheese, bacon, marinated chicken breast, 1,000 Island dressing, and tomato on Texas toast w/ pesto mayo dip

With pub locations on Belmont and in Evanston, this truck sparked my fascination with food trucks years ago at Riot Fest. Since then, I’ve found it outside of the Merch Mart, the Willis Tower, and regularly in line at Clark and Monroe. ALL THE SANDWICHES ARE PERFECT (All Caps necessary)

Facebook / Twitter / Menu

10. Jerk Grill

#10 Jerk

“Jerk Chicken”

with Rude Girl sauce on toast

The hype is real on the Jerk truck, and I am dying to pickup a hat or t-shirt from them that just says “Jerk.” The food actually may be magical…Why? Sharing it got me on-stage to see Spoon at The Taste of Chicago.

Proof:

Spoon

Facebook / Twitter / Menu

11. The Happy Lobster Truck

#11 The Happy Lobster Truck

“The Holy Guaca-Rolly”

Maine lobster, guac, and pickled onions

This made me a believer in lobster rolls, even after having it for the first time at Fenway Park.

Facebook / Twitter / Menu

12. The Model Chef

#12 The Model Chef

“Jerk Chicken Tacos”

Burgers, tacos, and crepes…? Oh my. Really nice lunch portions and I’m in need of a second visit to try the peach cobbler.

Facebook / Twitter / Menu

13. Ms. Tittle’s Cupcakes

#13 Ms. Tittle's Cupcakes

“Turtle and German Chocolate”

Ms. Tittle’s was the first of 3 cupcake trucks I tried, each one different from the other. You can find her in both the city and out in the suburbs.

Facebook / Twitter

14. Pierogi Wagon

#14 Pierogi Wagon

“Braised Beef Pierogis”

w/ bacon and sour cream

As I mentioned before, THIS IS NOT A RANKING…however…

If I were to rank the trucks, the Pierogi Wagon is in my Top 3. I introduced it to some friends from California (half of which were Polish) and they loved it.

(They seem to be going through some rebranding with their online presence, but I have found the truck at Millennium Park, Clark & Monroe, and Wacker & Adams)

15. Yum Dum

#15 Yum Dum

“Pork Belly Baowiches”

slow braised with Taiwanese spices, topped with pickled mustard greens, crushed peanuts and cilantro

Another first for me…Baos. Delicious beyond description and the “Baowiches” were very original to me. Like a pancake tortilla shell, that I couldn’t get enough of.

Facebook / Twitter / Menu

16. Windy City Patty Wagon

#16 Windy City Patty Wagon

“Gouda Burger”

smoked gouda, bacon, chipotle aioli, red onions and fries

Awesome truck name. Very unique taste with the hand-pressed burgers which I enjoyed with their seasoning. Would love to try the “stuffed patty” too.

Facebook / Twitter / Menu

17. La Cocinita

#17 La Cocinita

“Burri-Tacos”

with lechon, spiced cream and jalepeno salsa 

One of the best Latin American trucks I’ve tried. Greatly appreciated the “build-your-own” style and more importantly…Mexican Coke.

Facebook / Twitter / Menu

18. Chicago Pizza Boss

#18 Chicago Pizza Boss

“Sausage Pizza Puff”

You may recall that Pizza Boss ranked fairly high on the Pizza Challenge list, and deservedly so. I had to go back and try the pizza puff..and it was TOP NOTCH!

Facebook / Twitter / Menu

19. The Jibarito Stop

#19 The Jibarito Stop

“Beef & Cheese Empanadas”

Amazing Puerto Rican food and another first for me…empanadas. Yes, I feel weak admitting that, but I’ve had quite a few since trying them over a month ago.

Facebook / Twitter / Menu

20. More Cupcakes

#20 More Cupcakes

“Salted Caramel”

Yes please…Great surprisingly whipped frosting (given it’s appearance). And who says no to cupcakes when offered?

Facebook / Twitter / Menu

21. Blue Street Market

#21 Blue Street Market

“Mushroom Braised Beef Sandwich”

with caramelized shallot and shroom sauce

Very nice variety of lunch selections and sandwiches with excellent sides. You can’t tell me that “bacon wrapped chorizo stuffed pork” doesn’t involuntarily make you make Homer Simpson drool noises…

Facebook / Twitter / Menu

22. 5411 Empanadas

#22 5411 Empanadas

“Empanadas”

with dates & goat cheese and ham & cheese

Nothing does this truck justice like the webpage for the menu, so I’ll let you carry on to that immediately…You’re welcome.

Facebook / Twitter / Menu

23. Bruges Brothers

#23 Bruges Brothers

“Oxtail Poutine”

oxtail braised in red wine and thyme, gravy, cheddar cheese curds and crispy leeks

Not only is it remarkable poutine and a beautiful mess, these may be some of the best french fries I’ve ever had. I’ve had a lot of fries in my day (*Grandpa Simpson voice*), and those fries truly stuck out to me. Hurray, superlatives!

Facebook / Twitter / Menu

24. Fat Shallot

#24 The Fat Shallot

“Jumbo Polish”

with giardiniera, coarse grain mustard on a pretzel bun

Another truck I would place in my “Top 3” with incredibly cool folks working it, I’d love to go back and try everything. I got to enjoy this bad boy to the sweet rocking sounds of Motorhead at Riot Fest.

Facebook / Twitter / Menu

25. Grill Chasers

#25 Grill Chasers

“Skewer Taster & Bacon Beer Cheese Fries”

A pretty extensive menu of grilled chicken options like wings, sandwiches and skewers. The cheese fries make it well worth the feast, and I can imagine they pair great with any of the breweries they park out front of.

Facebook / Twitter / Menu

26 The Cajun Connoisseur

 #26 The Cajun Connoisseur

“Lobster Po-Boy”

….cajun style.

I’m no expert on cajun food, but this truck did make me want to explore it more. Very cool folks running the truck as well.

Facebook / Twitter / Menu

27. Chicago Cupcake

#27 Chicago Cupcake

“Turtle and Peanut Butter Cupcakes”

These are my favorite cupcakes around Chicago. They taste like cheesecake in cupcake form, and they are perfect because of it. They are actually served at the Coalfire pizza place in West Town as well.

Facebook / Twitter / Menu

28. Kate & Jan Hot Dogs

#28 Kate & Jan Hot Dogs

“German Oktoberfest Sausage”

There’s a sweet variety of selections beyond your typical hot dogs, like polish and even french sausages. It’s also sweet having the option to put on your own toppings outside of the truck as well.

Facebook / Twitter

29. Aztec Dave’s

#29 Aztec Dave's

“Al Pastor and Skirt Steak Quesadillas”

Amazing design on the truck, super outgoing people serving, and delicious Mexican food. I think that sums it up nicely.

Facebook / Twitter 

30. Jack’s Fork in the Road

#30 Jack's Fork in the Road

“Corned Beef Grilled Cheese”

with Guinness onions, aged english cheddar and whole grain mustard on dark rye

Capping the summer-long adventure was another favorite that I looked forward to trying the entire time. I could probably have these gourmet sandwiches for lunch everyday…and there are plenty to choose from.

Facebook / Twitter / Menu

Send anymore Food Truck recommendations or just follow along as The Adventure Continues on Facebook and Twitter

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