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One Day Foodie Tour of Chicago

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The Cloud Gate and the Chicago Skyline

Chicago is a great city filled with lots of great food (as well as plenty of landmarks, like Millennium Park’s Cloud Gate!). It isn’t possible to stop into every great restaurant in town on a one day or weekend trip (unless you have a truly limitless appetite and plan your schedule very well), but it is possible to get a sampling of some of the foods that the city is best known for. This is exactly what my game plan was on a recent trip. My only plan was to hit at least one Rick Bayless restaurant, have some deep dish pizza and eat at least one Chicago-style hot dog, and I figured that the rest would come on its own.

XOCO churros

This foodie day starts off with a breakfast trip to Rick Bayless’s XOCO restaurant. This quick service Mexican restaurant is famous for its beans-to-cup hot chocolate that is made fresh every day. I’ve devoted a whole post to this place if you want the full details, but the churros and hot chocolate are well worth stopping in for no matter what your other dining plans are. And, fortunately, the they are both served all day.

Next on my list was a Chicago style hot dog, and after a little bit of sightseeing, I took a recommendation from a friend and went to Portillo’s to get a fix.


Portillo's Interior

Portillo’s is a well known chain of restaurants that has been serving Chicago-style hot dogs since 1963. A Chicago-style hot dog is a steamed (or simmered) all-beef hot dog topped with yellow mustard, chopped white onions, sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sweet peppers, and a dash of celery salt. No ketchup. It is like hot dog turned into a sandwich, and the combination of flavors is fantastic. I am a big fan of ketchup on hot dogs, but with the toppings here it is clear that ketchup would just overwhelm the other flavors. The dog was well-spiced, the toppings were fresh, the pickle was crunchy and I loved the sweet peppers on top.


Making Chicago Dogs

I also have to say that this particular Portillo’s was absolutely packed with people and it was fun to watch the hot dogs being prepped through the kitchen window, three or more at a time. It put me in the mood to eat my own dog!

Chicago Dog

Rock n' Roll McDonalds

I didn’t eat at the Rock n’ Roll McDonald’s, but this McDonald’s location happens to be right across the street from Portillo’s and is one of the most famous McDonald’s locations in the country. In addition to looking very chic, upstairs there is a little museum that walks you though the history of the company through the decades and it’s actually quite fun to walk through.

Grahamwich sign

My next stop was at Grahamwich. Grahamwich is a fast casual concept by chef Graham Elliot. Elliot owns a fine dining restaurant (called Graham Elliot) in Chicago, has appeared on Top Chef Masters and is a judge on the US version of the show Master Chef. The restaurant is hard to find as it doesn’t exactly have a prominent sign. In fact, I saw more than a few people – myself included – walk right past the front door two or three times before realizing that they were in the right spot!


Grahamwich specializes in sandwiches and snacks, all served with a gourmet twist. For instance, the sandwiches include a BBQ pork belly and waygu beef – not your typical deli fare. All of the ingredients are high quality and most are made in-house. The menu also includes pastries, gourmet sodas, snacks (like popcorn with truffle oil and chips with bacon bits) and soft serve. Still a bit full from my Chicago dog, I kept things light here with a waygu beef sandwich on a pretzel roll and a soft serve.


The restaurant was packed and it was a little difficult to find enough elbow room to use my camera, so I wil fully admit that this shot doesn’t do justice to the tender beef, spicy whole-grain mustard and the surprisingly soft pretzel roll that made up this sandwich. I guess I’ll have to try it again one of these days for an excuse to get a better photo – but I might have to opt for the grilled cheese next time, which I hear is excellent.


As much as I enjoyed my sandwich, I think that I enjoyed my soft serve even more. It was incredibly creamy with a tremendous vanilla flavor. The soft serve wasn’t that impressive to look at, but it hit a home run in the flavor department. The vanilla bean soft serve was topped with warm nutella, caramelized bananas and marshmallow creme. The sundae wasn’t huge – which made me feel justified in eating the whole thing. The other flavor on the menu was “cinnamon stick,” topped with roasted apples, salted caramel and bits of pie crust.


I went to Topolobampo for dinner one night, but the other night I had classic Chicago deep dish pizza. Like the Chicago dogs, there are many great places to have an authentic Chicago pizza experience. I hear that die-hard fans get pretty competitive about which has the best pizza and that many places claim that the style was invented at their restaurant. I’m not going to get into which is the best or which was the first. I got my deep-dish at Giordano’s, which seems to be one of the most consistently recommended pizza places in town (and, predictably, has founders that claim that their family invented the style).


Chicago-style deep dish pizza is almost like the pizza version of a bread bowl. The pizza has a very rich and buttery crust that is filled with layers of cheese, meat, cheese, veggies, cheese and sauce. There is a lot of cheese on a Chicago-style pizza. At Giordano’s, I ordered the “special,” which included sausage, mushrooms, green peppers and onion, in addition to all that cheese. The pizza is gorgeous to look at when it is first sliced and you can see all the layers. I didn’t try to pick it up and simply ate it with a knife and fork, savorying every bite. I have to admit that I am a thin-crust pizza gal at heart and don’t think I’ll be switching to deep dish on a regular basis, but I have to admit that the buttery crust was a delicious way to contain all those toppings!

Chicago Style Pizza

Giordano's Pizza

Deep dish pizza takes a while to cook, so be patient when you order it in a restaurant and don’t be tempted to order an appetizers while you wait 30 or 40 minutes for your pizza to come out. Chicago-style is very filling and with a salad or bruschetta beforehand, you might not be able to manage more than one slice of the pizza when it arrives!

This isn’t by any means the only way a food lover can eat in Chicago. I have to say that if I had to do it all over again, I’d do exactly the same thing! For any Chicago food fans, feel free to leave some recommendations of your favorite places in the comments so that I and the rest of the readers will know what your favorite spots are, too!

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  • cupcake packaging
    June 16, 2011

    I love Rick Bayless and Topolobampo. I just love Mexcian food period. Those Churros look so tasty I feel like flying back to Chicago to try some. Next time you are in Chicago please try the Portillos double cheeseburger. It is to die for. If you want some great tasting pizza you must go Unos as their deep dish pizza is magical. Please dont forget to visit Carmines on Rush street, the pasta there is unbelievable. Thanks looked the pics!

  • Collette
    June 16, 2011

    I’m so glad you had a great time in Chicago and ate so many lovely things! My favorite restaurant is actually Frontera Grill and I’ve been going there for *cough* 22 *cough* years. 😉 The Thursday special torta at Xoco is wonderful–mole poblano. Yum.

    I do have to make a slight correction. Giordano’s is stuffed pizza, not deep dish. Deep dish doesn’t have a top crust like Giordano’s. Pizzeria Uno and Due as well as Gino’s are deep dish and Giordano’s and Edwardo’s are stuffed. People in Chicago can be really freaky about pizza! That said, one of my favorite pizzas in Chicago is from Coalfire which is neither stuffed nor deep dish!

    If you ever get back, try and get to The Girl and The Goat which is Stephanie Izard’s (of Top Chef fame) place. I fully admit that I was a little afraid to go because of all the hype. Both my husband and I were happy to find that the hype was completely justified. Completely. Reserve way ahead of time on Opentable and expect to go early or just go and take your chances. You’ll eat eventually. 😉

    I am always happy to tell people where to go (!) so give a shout out if you make it back.

  • Karen
    June 16, 2011

    My brother lives in Chicago and every time I visit him I HAVE to eat at Giordano’s at least once. It’s the perfect chicago style pizza. It has my heart.

  • SeeNikkiCook
    June 17, 2011

    Other must eat at places:

    More cupcakes
    Garrett popcorn (we take the train to Chicago–from central IL– and devour the popcorn on the ride home)

  • Thanks for the tour Nicole! My husband is absolutely busting to visit Chicago (we’re Aussies), and now at least I know where to go to get a great feed when we finally visit!

  • Lauren at Keep It Sweet
    June 17, 2011

    I’ve actually never been to Chicago, but I want to go and eat every single thing that you had!

  • Shilpa
    June 17, 2011

    Brilliant post and made a great read…McDonald’s has a museum? Learn new things / facts / information every day… Thanks for sharing…

    Never been to Chicago but need to plan a visit to this historic museum now….

    Love you style of writing..


  • Angela
    June 17, 2011

    Nicole, you read my mind!! I’ve been planning to visit Chicago for a while- a megabus ticket is cheap and convenient where I live- but I’ve never gone. This summer I finally decided that my other half and I ARE going! I’m a foodie and excited to try these places; he’ll find something more traditional at these eateries to satisfy him too, I’m sure.

    Thanks again, and thank you Collette for your suggestions as well!

  • sarah
    June 17, 2011

    Definitely have to go to Garret’s for carmel corn. Reza’s on Ontario and Nuevo Leon are my two must go stop at places when I return to Chicago.

  • Yatee
    June 17, 2011

    I have always wanted to try a pretzel bun or roll! I can only imagine trying it at a place like Grahamwich. And that soft serve looks so good … I would definitely get the cinnamon stick sundae.

  • Angel Johnson
    June 17, 2011

    Next time you go to Portillo’s, get a beef and cheddar croissant. Actually, just make sure you try one of their Italian beef offerings. Their hot dogs are fine, but the Italian beef is where it’s at.

    Portillo’s and Giordano’s may be the two things I miss most about living in the Chicago area… :3

  • M
    June 20, 2011

    I lived in Chicago for 2 years (and grew up near the city) and in my opinion no culinary tour of Chicago is complete without visits to Hot Doug’s (gourmet hot dogs, they also apparently have a great vegetarian dog, according to my brother-in-law. I recommend anything off the specials menu, especially the Game of the Day) and Kuma’s Corner (heavy metal burgers with inventive toppings).


  • Louise Tomschin
    June 20, 2011

    I live in Chicago, have my whole life, and I can tell you the best Chicago dog is at Jimmy’s on Grand and Pulaski. The fries are so “greasy” that the bag where your hot dog is in, looks wet!! Also not a fan of deep dish pizza, the best for me is at Al’s in Cicero, it’s a neighborhood Italian restaurant and their pizza is the best, in my opinion. The Ricotta, Spinach, garlic is unbelievable. Also if you like Gelato the best in town is also in Cicero, at a place called Freddie’s at 16st and 61st Ave. The line into the place can stretch around the block at lunch time. Also great Italian sandwiches. Eating is outside or in their small dinning area. It’s really an Italian Deli. Love the place.


  • Susan Osborne
    June 21, 2011

    Good suggestions for Chicago food! I am a foodies and am anxious to make my first trip to Chicago to try some of it out first-hand.
    I have a list of Chicago pizza places on my site (http://www.completelypizza.com) but somehow completely (sorry for the pun!) left out Giordano’s. Not sure how I let that happen – but I will be including it in my recommendations tonight! thanks!

  • Raquel
    June 27, 2011

    I must say you went to the best places Chicago has to offer. My personal favorites are Portillo’s and Giordano’s! I’m glad you enjoyed the food!

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