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The Chicago Culinary Bucket List

Written By: Jessie White

If you have ever traveled to Chicago you surely didn’t leave hungry. The Windy City is one of the U.S’s foodie hot spots for a reason. With so many cultures blended together in one city, the culinary options are likely never going to leave room for want. All areas of Chicago will boast amazing international and local options and through the years the city has certainly developed its own signature tastes that at this point you’ll only be able to find in Chicago.

With a culinary history that’s hard to combat (Did you know that brownies were invented in Chicago? Twinkies, too!) it would make sense that upon entering the city you may feel a little overwhelmed by all of the options.  That’s why in the spirit of Chicago Restaurant Week later this month, the team at the Willows Hotel has taken our staff favorites and collected a list of the must-haves of Chicago’s tastiest options. Make sure you check out these top 5 Chicago must-haves before you have to head back to the airport.

The Chicago Dog

This wouldn’t be an accurate Chicago culinary bucket list without first mentioning Chicago’s #1 staple, the Chicago Dog. While many hotdogs will leave you satisfied, the Chicago dog is sure to take your taste buds to the next level. With an incredibly particular recipe to guarantee the Chicago style, you can chow down on one of these bad boys featuring an all-beef frankfurter in a steamed poppy seed bun topped with relish, celery salt, chopped onions, sliced tomatoes, sport peppers, and a pickle. In that order, of course. If you’re one that’s a fan of ketchup, we’re sorry, but you should probably keep that to yourself.

 Concierge Recommendation: Portillo’s

100 W Ontario St

Portillo’s is a Chicago staple for a reason and you won’t just find amazing hotdogs and burgers. This Chicagoan favorite is also made famous by the “Cake Shake”, a chocolate shake with an entire slice of cake inside. Sign us up!

Runner up: Devil Dawgs

937 W Belmont Ave

A close second to Portillo’s is Devil Dawgs in Lincoln Park, Lakeview, and Wicker Park. This delicious grease trap was the late Anthony Bourdain’s personal choice of Chicago-style hotdog.

Deep Dish Pizza

An incredibly close second to the Chicago Dog is none other than deep dish pizza. In the words of Nick Miller from New Girl, “I’m from Chicago. Thin crust pizza? No thanks. I’m from Chicago.” Nick Miller was certainly correct as the Thin Crust vs. Deep Dish debate has been a decades-long controversy. But do Chicagoans care? No way! We’ll take our layers of cheesy goodness and hold up our forks with pride anytime as we know which pizza is the actual reigning champion.

Concierge Recommendation: Pequod’s Pizza

 2207 N Clybourn Ave

We know what you’re thinking… not Lou Malnati’s? Yeah, we said it, and we meant it. This Lincoln Park hidden gem has some of the best pies in town and features caramelized crust. We know that was enough to get your taste buds excited for a Midwestern trip soon.

Runner up: Giordano’s

1040 W Belmont Ave

If you’re opting for a chain deep dish location, we’ve got to go with Giordano’s. Mainly because the crust is superior to Lou Malnati’s and it’s the official deep dish of the Chicago Cubs.

 Chicago Italian Beef Sandwich

If you’re a carnivore by nature you will find yourself surrounded by many foodie friends while in Chicago. One Chicago staple that’s your soon-to-be favorite is the Italian beef sandwich. This Chicago-style sandwich flaunts roasted sirloin strips cooked in beef broth stuffed inside of an Italian-style roll to gather all of those sweet sweet juices. They’re typically served with gravy and customizable toppings and will never leave you thinking, “You know, I’m still kinda hungry…”

Concierge Recommendation: Al’s Beef

3420 N Clark Street (Numerous locations)

In terms of the best Italian beef sandwich, Al’s Beef takes the crown by a landslide. At Al’s Beef you can order your sandwich “dry”, “wet”, or “dipped” in gravy. With options like those, Al’s Beef will be sure to please with the perfect bread-to-beef ratio

Runner up: Mr. Beef

666 N Orleans Street

Don’t tell Al, but we also recommend checking out Mr. Beef in the downtown Chicago area for a delectable bite. This bare-bones joint (don’t even bother to order a side salad) was once featured on David Letterman when Jay Leno brought an entire bag of Mr. Beef sandwiches on stage for his appearance, which is just about as Chicago as you can get.

Chicago Mix

Traveling and exploring cities isn’t all about meal time. You’ve got to make sure to leave space for snacking options while in the city, as Chicago will have many options to choose from. One choice that will rule them all is grabbing a bag (or bucket) of mixed popcorn from one of the many artisanal popcorn shops around the city. This popcorn isn’t like your typical AMC special or bag of jiffy pop. Chicago-style popcorn is flavored popcorn that comes in buttered, cheddar, caramel options, as well as a “mixed” option, which includes all 3 flavors in one. This quirky snack is a Chicago year-round indulgence that will unfortunately dampen all future popcorn experiences to come.

Concierge Recommendation: Garrett’s Popcorn

835 Michigan Ave

In all honesty, in writing this it was hard to not call this city fave “Garrett Mix”. Garrett Popcorn Shops can be located all around the city and will have the most popular recipe of the Chicago tradition. The moment you step inside a Garrett’s you’ll understand just by the smell why this is Chicago’s choice of popcorn.

Runner up: Nuts on Clark

3830 N Clark St

If you’re not able to head into a Garrett’s store while in town we recommend Nuts on Clark, located in the Lakeview and Wrigleyville area. Perfect for grabbing right before a Cubs game, you’ll have to taste this hype to believe it.


Hold up, did we say tamales? Yeah, we did! A more-recent Chicagoan craze has been the arrival of a particular individual who has made late-night Mexican possible for locals in bars all over the Westside. “The Tamale Guy” is a local legend, to some simply a rumor or myth. If you’re traveling to the city to taste some amazing late-night options, you’ll always be recommended to a tamale from the Tamale Guy. With no set schedule of locations, he often appears at bars that don’t have food options with a massive bag of deliciousness and a quick, “Tamales!” A late-night tradition for many locals, if you see the Tamale Guy, you’ll know what you need to taste next.

Concierge Recommendation: The Tamale Guy

Various bars in Logan Square, Wicker Park, and the Ukrainian Village

I mean, you’ve got to try this guy’s tamales. Fresh and filled with either chicken or beef, these authentic tamales are the perfect quick bite before (or after, or during) a drink with friends. The only downside of the Tamale Guy is that he bounces around the city every night and goes where the tamales are selling. So if you see him, make sure you have cash handy and grab one before he vanishes into the Chicago night and it’s too late.

Runner up: Las Fuentes Restaurant

2558 N Halsted Street

Listen, we understand that sometimes the night doesn’t end with the Tamales Guy’s entrance like you wanted. That’s why we recommend Las Fuentes in Lincoln Park for any Mexican-based cravings, as this spot with tamales will also have just about anything else you may be wanting to taste before leaving the city.

Need Hotel Accommodations?

The Willows Hotel

Located at the edge of Lakeview and Lincoln Park, accessible via Brown Line train

 The City Suites Hotel

In the heart of Boystown, accessible by the Red Line train

 The Majestic Hotel

Located in the heart of Wrigleyville, accessible via Red Line train

 The Ivy Hotel

Located near the Magnificent Mile in Chicago’s Loop

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