the great chicago food tour

the messiest of buns hair tutorial

My friend Allyson and I briefly talked about taking a trip to Chicago last year. It was one of those “we should definitely do that!” things that are sometimes hard to get on the calendar.

But we finally booked the flights and made our way up there. I know what you are thinking–Chicago in March? Are you out of your mind?

Besides the relentless wind, we were lucky enough to experience sun both days which made it quite pleasant!

My parents live roughly 30 minutes west of the city, so we stayed with them. It worked perfectly to eat a quick and delicious home cooked breakfast before we went into the city both days. 

Allyson did all of the food-related research before we left. She’s a fantastic cook and loves trying new things and discovering places to eat off the beaten path.

I’m picky and like to go to the same place over and over, so it was really nice to have her choose all the places.

We arrived friday evening and stopped at Portillo’s on the way home. That was one of my non-negotiable spots that I required we eat at. It’s delicious. And not having access to it regularly means I eat there as often as I can, when I can.

On Saturday we took the train in and went directly to the Art Institute. We walked through a Picasso exhibit that was much more extensive than I could have imagined. We were both surprised to learn how diverse he was. I only think of the abstract/angular paintings, but he’s done some pretty detailed and realisitic drawings as well.

After the museum, we made the trek out to Little Goat Diner. The decor alone is worth checking out. It’s a neat mixture of retro, modern, and restoration hardware. The wait was about 45 minutes, so we wandered back to the coffee and bread section of the diner. 

It was plenty entertaining just to people watch and stare at the bread while we waited to be seated. 

Once we sat down, I ordered the Patty Melt and Allyson ordered the Chicken and French Toast. She’s a lot more adventerous than I am!

We both loved our meals. I tried a bite of Allyson’s dish, and while I could understand the appeal (it was full of deliciuos flavors), I preferred my piping hot Patty Melt. 

Before we left, I used the bathroom–which happen to be some of the neatest bathrooms I’ve ever been in. I also met a lovely blog reader while I was waiting!

We walked back into the city a few blocks and stopped in Zara. We killed about an hour or so shopping on State Street, and met my mom on the side of the road in her car. We hopped in and made our way over to Michigan Avenue.

The plan was to eat at Frontera Grill, one of Rick Bayless’ restaurants, but despite arriving 5 minutes after it opened for dinner, the wait was 2 hours! So, we walked over to Maggianos to grab a quick bite before the Bulls game.

Sunday morning we drove into the city and went directly to Ann Sather for breakFEAST. Holy cow the cinnamon rolls were incredible. We were trying to figure out how to split an entree but to also get a side of cinnamon rolls, and  we managed to order enough food to feed a small family.

As it turns out, each breakfast entree comes with a side option. One of those side options is two heaping cinnamon rolls. I ordered two cinnamon rolls for myself, so we had four monster cinnamon rolls on the table. It was a good thing–they were absolutely delicious.

Stuffed, we walked over to Bucktown to do a little resale shopping. A little bit later we drove to Inteligencia Coffee, however the iPhone map directed us to the manufacturing plant of Inteligencia! We finally figured it out and located an actual coffee shop just off of Michigan Ave. 

The coffee was delicious. I ordered an Americano, and while it was very bold, it had a really smooth flavor. Allyson got the coffee of the day and enjoyed it as well.

There was a lot of men in skinny jeans, beards, prescription-less glasses, and alternative hair. It was perfectly fitting for a cool coffee shop. 

We walked up Michigan a bit, and then drove over to Floriole, a cute cute cute little spot on the Lincoln Park neighborhood. 

The front of the restaurant is made up of glass panels that they open up in the summer. It was definitely the most charming place we ate. 

Finally, we headed back home and ordered in Giordano’s. Allyson had her first taste of authentic chicago style deep dish pizza, and she loved it!

We headed home yesterday, and both discussed the need for much exercise and clean eating to compensate for such a scrumptious food-heavy weekend. 

If you are visiting Chicago, or even if you live there, be sure to check out the places I mentioned. Allyson knows how to pick the great ones! 


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caschelldorf says · 03.05.13

I just went to the Little Goat Diner a few weeks ago. Had the apple stuffed pancakes-to die for!!! Chicago is my favorite city–I love to visit 🙂

Amy says · 03.05.13

wow, yum. That grill cheese looks like it was to die for1
Coffee Beans and Bobby Pins

Mary Nichol Handbag Giveaway!

LoloMyDear says · 03.05.13

Awesome post! Hubby and I are going to Chicago for a long weekend in early June. These food tips are great!

kimberleyek says · 03.05.13

There is nothing better than hunting out the local cuisine and just pigging out!! Totally my favorite thing to do 🙂
It looks like you had a great time, ate a lot of great food, and took some great pictures too!!

Nana T says · 03.05.13

Sounds like a yummy trip! With a side of visit with parents to top it off.
My family is in Chicago, always fun to visit.

Michelle Yocum says · 03.05.13

You hit all the great spots in the city. My hubby & I moved to the burbs almost 2 years ago and I miss the city so much. Love Ann Sathers cinnamon rolls!!!

chicagobears says · 03.05.13

I live in Chicago now and am about a 2 minute walk from an Ann Sather–it is deadly for my wallet and my jean size. It is seriously the best breakfast place I’ve ever been to.

Adrienne says · 03.05.13

You’ve opened my eyes to give my city a chance! 😉 I may save some shopping money and head down one afternoon. I’m such a suburban girl but I’ve always wanted to check out Zara’s. 🙂

So glad you had a great time and explored new places! And inspired ME! 😀

Kristin Brown says · 03.05.13

Ah man, too bad you didn’t make it in Frontera…it’s AMAZING! Had I been lucky enough to be there with you, I would have advised waiting because a lot of people leave due to the “long wait time”, so the wait time ends up being not that bad. Plus, a few margaritas make the time go by quickly : ) I’m sure you’ll give it another shot. And Portillos is always a must. I’m baffled as to why they don’t open one in Northern IL by the border. I wish it was a franchise, I’d put the money down to open one by me!!

Kacie Jackson says · 03.05.13

I have only been to Chicago a few times in my life, most recently in 2009 for a Twins/Cubs baseball game. I missed going to a couple eateries that was in the plans, but hopefully I can get back there soon to check them out. I think it may be my second favotie big city (after Minnepaolis, I live 3.5 hours away from there)! I enjoyed reading yout trip summary, as well as the pics you posted here and on Instagram!

Daisy Tails says · 03.05.13

Thanks so much for this post. My husband and I are going to Chicago in May so hopefully we will be able to make it to a couple of the places that you talked about.

Emily H says · 03.05.13

Haha I love Ann Sather. Definitely adding that to my list of places to visit before I move away from Chicago.

dxeechick says · 03.05.13

sounds fun! i love chicago – definitely need to spend more time there

Valeska Mengert says · 03.05.13

Sounds like you had a great trip!

Mags Pomichowski says · 03.05.13

mmmm This post made me hungry. I am now craving cinnamon rolls. And I love intelligensia we have one in downtown Pasadena, walking distance from where I live and I love going there for coffee and tea.


kitty crafter says · 03.05.13

The Portillo’s factory is less than a mile from my house (I live in Naperville, about 30 miles west of Chicago), and you can smell their Italian beefs cooking in the early morning. Not always what I want to smell before I’ve had my first cup of coffee, but I’m not complaning! 😉

Nicole G says · 03.05.13

This is a great post! I love food tours! Living in NYC – I’m always documenting our food journeys. I’ve only been to Chicago once forever ago, but thinking I may need to make another trip out there! Maybe when Spring comes!


Reply says · 03.05.13

Hi Kate. So glad you mentioned Intelligentsia–our local coffee grind with worldwide appeal! Just brewed a cup this morning for our snow day here in Wheaton. Also, recommend XOCO, Rick Bayless’ “fast-food” restaurant with the best Mexican hot chocolate and churros.

Keep up the awesome work.

Burdine Family says · 03.05.13

This post couldn’t have come at a better time! I literally just booked our hotels for a trip to Chicago in about two weeks. It is my first time visiting the city and I LOVE trying all the new restaurants! Thanks so much!

Ava says · 03.05.13

I was at Frontera Grill Saturday night!!! We arrived at 4:30 and got sat at the bar at 5:15. Even arriving that early we had a 2 hour wait for the dining room. It was my first time there, but we were with family who knew to arrive early. A tip for your next trip. It was amazing, so you’ll have to try to get back there!

Kate says · 03.05.13

how was it?

Dott says · 03.07.13

Try Xoco next door to Frontera next time. Its not as time consuming when you’re only in the city for a short time and its totally delish!

SBGirl says · 03.05.13

Great post and I LOVE the fact that the iPhone sent you to the intelligencia plant instead of the the coffee shop (although I’m sure you didn’t LOVE that). Those kinds of things are what make trips memorable 🙂 Oh, and I want one of those cinnamon rolls…NOW!

Madison Collins says · 03.05.13

I really like that you said you met your mom on the side of the road…that is so funny! 🙂 It sounds like you and Allyson had a wonderful trip.

::Sara in Texas:: says · 03.05.13

Now I miss Chicago even more than usual! Sounds perfect!


Emily says · 03.05.13

I was also in Chicago last weekend and am planning a Chicago post! Crazy! We even almost went to the art institute but ended up doing the field museum instead. Isn’t the Chicago food amazing? We had the most amazing Chicago pizza from a place called Pequods. So glad you had as much fun as we did!

Shasta says · 03.05.13

Sounds like you had a great time in Chicago! Love the food photos, now I want food….

Ericka says · 03.05.13

I was in Chicago this weekend too! And we went to Giordano’s for dinner on Saturday night…best pizza ever!

Kayla Gilbert says · 03.05.13

Funn! We live just about 4 hours south of Chicago! : )


Karen says · 03.05.13

My husband, me and some friends of ours are planning a trip to Chicago in late May. I’ve been looking for good places to eat and now I have a great list! Thank you!

Jen @ Bungalov says · 03.05.13

OK LOVe this one. I am biased though cause I am a born and raised Chi-town girl. And from the city not the burbs. That is a big deal when you really do come from the city. Ask my sister’s bfriend. We argue over this nonstop cause he a burbs guys. Anyways. I must not take advantage of our city enough cause you did more in a weekend than I have done in years. I will agree Portillo’s is my #1 fav and I tried Intelligentsia coffee at Lollapalooza a couple years ago and man oh man was it yummo! If you have never been and come back you have to have Super Dawg. I live right by there and it is a summer fav. Grab a dog and there super delic malts.

R2P2 says · 03.05.13

Ohmygosh, I want one of those cinnamon rolls. NOW.

thehedbergs says · 03.05.13

Such a great post! My husband and I just moved to the west coast from Chicago – this makes me miss it so much (not the bone-chilling wind though)! You and Allyson picked some fantastic Chicago restaurants too. And Portillo’s…charbroiled burgers, crinkle fries, and a thick chocolate shake…yum, yum, yummy! Can’t not stop at Portillo’s if you’re going to be in Chitown!

Kristin says · 03.05.13

My parents live in Chicago too. Portillos and Giardonos are a must eat when I visit too! It seems like all I do is eat when I visit. So much good food.

Hannah @ Just Call Me HaHa says · 03.05.13

I live in the city and haven’t been to Little Goat yet or Floriole (although that’s not far from me), but both look amazing! Ann Sathers, Gio’s and Portillos are musts! Sounds like a great weekend!

Jenn says · 03.05.13

Bummer that you didn’t get into Frontera! Ya, always a wait, but usually when we go there we are with a group so some get there earlier than others, get on the list, and we cocktail it up in the bar until we’re all there and seated. I agreed that his walk-in place next door with the tortas is great though. They even have a version of it in O’hare so when in the airport, I think it was Terminal B? Anyway, for ppl looking for a great brunch place, try Feast in Wicker Park. You may need to make a reservation because it can get busy, but it’s really tasty and eclectic. Glad you had a great trip!

Ashley @ Coffee and Apple Juice says · 03.05.13

My dad and stepmom live in Bloomington and frequent Chicago. I am going to refer her to this blog post to see if she has visited these places…they look amazing. I love Chicago and have not been there in a very long time!!

Veronica and Daniel says · 03.05.13

I live about 30 min west of downtown chicago as well…but don’t make it into the city much – you have inspired me to make a trip in to try these restaurants! Intelligentsia is my favorite coffee and a shop in my town sells their beans, so I don’t have to go far to get them. And we live less than a mile from a Portillos….which is not always a good thing! 🙂 Glad you enjoyed your visit!

Chelzz says · 03.05.13

Those cinnamon rolls look amazing!

Rachel Krizz says · 03.05.13

You have to go to Lou Malnati’s next time you’re in town! Waaaay better than Giordano’s! 🙂

Kristi Fischer says · 03.05.13

We just ate for the second time at Girl and the Goat which is amazing. There are so many places you need to try next time like Tank, Pequods (I will take over Lou’s or Giordano’s any day)and even Chicago Cut! Ack… I am hungry!

Andrea Kaplan says · 03.05.13

You picked some great spots! I’m a Chicago native and moved to California 3 years ago…and it doesn’t even compare. Chicago has EVERYTHING. If you ever go again and need some more ideas, let me know! I’d love to help.

XO Andrea

Amy @ Polka Dots and Stripes says · 03.05.13

I live 40 minutes SW of Chicago and I have an amazing suggestion…have you ever been to Chicago Pizza and Ovengrinders? AMAZING PIZZA! Seriously, the BEST! You have to be prepared to wait and they only take cash but it’s so worth it! They are these amazing, mushroom shaped individual pizzas they flip onto your plate. And…you have to try the Mediterranian Bread for an appetizer…YUM! Another Italian suggestion is La Sorella on Taylor St. Everything there is amazing but the half roasted chicken is unbelievable!!! Glad you had a great time…I will have to try some of your suggestions! (We live 5 minutes away from a Portillos…yum, right?!)

Rachel [at] floral and fudge says · 03.05.13

love Portillo’s. love Ann Sather’s. love Maggiano’s. and LOVE Giordano’s! Miss my city.
Soungs like such a fun trip!

Kristina says · 03.05.13

Ann Sather is amaaaaaazing for breakfast. Last time I was there I somehow managed to leave my leftover cinnamon rolls behind, sad I’ve been meaning to try Little Goat, it sounds really interesting.

I went to the Picasso exhibit last week, I was really surprised about how diverse he was too! I posted about it here.


Kristina does the Internets

Paula White says · 03.05.13

Our fav place for pizza is Lou Malnati’s , but maybe next time we will try something different! And my hubby and I spent the weekend in Michigan, snowed the entire time,but was great to get away sans kids!

....... says · 03.05.13

what a fun trip! xx. gigi. food and beauty blogger @

Suzie Home-Maker says · 03.06.13

I would love to see how you control hair in crazy wind!!

Ashton says · 03.06.13

Living in the NW burbs, I don’t make it into the city that often, however; we ALWAYS make time for a stop at Molly’s Cupcakes on Clark. They have the BEST cupcakes. You should stop by the next time you are in town.

Gold kelchen says · 03.06.13

very nice blog!

greetz from germany (

Beth says · 03.06.13

I’m headed to Chicago for the first time ever in April. I’m jotting down some of these names for my trip. Hoping it will be a little warmer by the time I arrive. 🙂

HLane says · 03.06.13

Great post! I used to live near Lisle about 10 years ago, and your mentions of Portillo’s and Chicago style pizza make me crave it! You are right, there is absolutely nothing better than getting a Chicago dog in your hand. 🙂
Glad it was a good trip!

Emily Sumpter says · 03.06.13

Thanks for the kind words about Floriole! We’re glad you were able to stop in and that you enjoyed yourself.
-Emily Sumpter

General Manager
Floriole Cafe & Bakery

Unknown says · 03.06.13

I lived in the NW suburbs for 3 years and ate at Portillo’s EVERY Wednesday. It was our regular “Mom thing” before Gymboree Class. Oh how I miss living there! As always, I love reading your blog. Your hair tutorials are just my speed!

moolalaba says · 03.06.13

This is great timing. Hubby and I are heading up there tomorrow morning (brrr!) for our son’s graduation. We will check out the spots you mentioned. Thanks!

Rebecca Vajda says · 03.07.13

Wow! I live less than an hour away from Chicago and go there often, but I’ve never heard of these places! I’ll have to try them next time, thanks for your “reviews” on them 😛 (except for Portillo’s we have one by us, my dad knows the owner)

Brianne Bracco says · 03.07.13

My husband and I loved Giordano’s so much when we went to Chicago.. that a few months after our trip.. we had it FedEx’d overnight to us in California cause we were craving it! 🙂

Such a fun trip and now I want to go back to try more yummy places!

RompinAround says · 03.07.13

I work downtown in the Loop so you were right by me for some of your stops! You picked some great places. This city has the best food!

Sam says · 03.08.13

Oh man. I miss Chicago. I lived about 45 minutes from the city growing up and we ate Gino’s East after every school dance. My family and I are relocating to NC at the end of this month and on our stop in Chicago to see family overnight, we are eating Portillo’s Italian Beef sandwiches and Gino’s East if I have to roll the rest of the way to NC.
Thanks for posting. I’d love to see any photos you took of the sights– I miss home!

Daniyal Ali says · 05.11.13

I found this really cool interesting food tour of Indian Food and Culture check it out:

Daniyal Ali says · 05.11.13

I found this really cool interesting food tour of Indian Food and Culture check it out:

william willi says · 03.07.14

What a resourceful topic on Chicago delicious food and drinks.I should say! It’s a resourceful guidelinefor the visitors as well as the distinguished residents of Chicago who are planning for outing.

Mark Brown says · 03.19.14

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Kristy says · 06.30.15

Which Ann Sather’s did you go to? I’ve always wanted to go but don’t know about parking. Were you able to park close-by; you said you drove there?

Jillian says · 04.30.22

We’re going to Chicago in June! I realize this post is from quite a few years ago and wondered if you have any other recommendations for places to eat or things to do?