Chicago Eats!

For Kevin’s birthday, we spent a long weekend in Chicago celebrating, walking, shopping, walking, seeing a game at Wrigley, walking, and eating in some seriously delicious restaurants. Here are just a few of the places we visited.. and the food I can’t stop thinking about! :)

Where to Eat in Chicago

Sunday Brunch @ Nightwood. The menu here changes daily and is handwritten every day. BTW, I had visions of turning this lovely handwriting into Pea Nightwood font. I tried to sneak out with a menu, but they tackled me at the door. Alas.

Where to Eat in Chicago

Oh you know we had to try that bacon butterscotch doughnut! Nightwood makes its own fresh doughnuts in the restaurant every morning.

And in the name of responsibility, we also went ahead and ordered the healthier variety, the Blueberry Cake Donut with créme fraiche. Heaven.

Where to Eat in Chicago

Friday Night Cupcakes @ Molly’s Cupcakes. After shopping, baseball, and deep dish pizza at Lou Malnati’s, we stopped in for some cupcakes at Molly’s Cupcakes. By the way, see the difference between taking photos during the day and night? The doughnut photo above was taken in the morning, near a window. The cupcake photo was taken at night.

I much prefer the former. The difference is like night and day.

Snarf. I crack myself up.

Where to Eat in Chicago

But let me assure you the lighting did not affect the taste of these delightful cupcakes one bit. Man, oh man, I really want to know how they did this! Did you see that? That’s cookie dough! Stuffed in the cupcake!

This is probably like my ultimate dessert, cupcakes & cookie dough.

Where to Eat in Chicago

Now this beauty, I totally couldn’t resist. This one was made with peanut butter, butterscotch, and chocolate, and topped with crushed Butterfingers.

I’m thinking I should’ve brought a couple of these home with me.

Where to Eat in Chicago

On our way back home, after spending a wonderful weekend in Chicago, we stopped halfway in Louisville, Kentucky at the Brown Hotel for their famous Kentucky Hot Brown. If you are ever in the area, I highly recommend it! The turkey was so incredible- it tasted just like Thanksgiving. And that tomato.. goodness, I’m still thinking about that tomato. And it was just on the side as a garnish!

But uh, dress like you’re going to the prom, man. I felt seriously under dressed in my comfy, 10 hour road trip clothes! *blush*

Where to Eat in Chicago
Photo via reallyboring

My favorite place we ate all weekend? Hands down, Old Fashioned Donuts in south Chicago. We stopped here on our way into town. My gracious these doughnuts were so unbelievably light and fluffy! It was like biting into a sweet, sugary cloud. Wishing I’d brought back a couple of these babies! :)

Did I say a couple? I meant a couple dozen!

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32 Responses
  1. Leigh

    I cant believe you came to Louisville and only ate at the Brown! Dont get me wrong, their hot brown is delish, but Lousiville is a dream city for a foodie, and we have so many lesser known places that will serve you some of the best food you have ever eaten, and cafes and delis that use all local meats, cheeses, and veggies and will serve you a sandwich as big as you head. If you ever stop in Louisville again, head to the Highlands (right around the corner from the Brown), park, and start walking. You will come across some of the most amazing places to eat, from candy shops to super fancy restaurants. There will be tons of people walking too, and since its the artsy part of town, people watching there is one of the best parts. The highlands isnt really that well known to people outside the city, most of our major events takes place in other parts of the city, and its a very old, historical part of the city, so theres no hotels there. Its a great place to walk around and really sample the local flair. (Some of the bars, like Molly Malones and Cahoots, have the best food!)

  2. Erin Wieland

    I live just up the street from Nightwood, I too just love that the menu changes daily. You never have the same dish twice!

  3. Jennifer White

    I am a student in Chicago and was so ecstatic to see you had stopped into a few of my favorite destinations!
    I LOVE Molly’s Cupcakes (specifically the Cookie Monster cookie dough filled cupcaked!!!!) AND Pitaya in Wicker Park.
    Next time you’re in town stop into Southport Grocery you will LOVE it!
    Great job on the blog!

  4. Paige

    Those cupcakes look soo good! I’ve tried the recipe for the cookie dough cupcakes, they are super easy! It really just requires a drop of cookie dough on top of the cupcake batter in a muffin tin. In the oven, it eventually drops to the bottom and bakes into the cake batter. Super easy, and so popular at events! (They’re best when shared, so they won’t tempt you around the house!)

  5. Yeisha Marie

    yummy! I live in Chicago and never heard of these spots. Thanx for putting it out there def. gonna be a tourist in my own city this weekend and check those spots out!!!

  6. Traci

    Now that’s what I call vacation – I could cry looking at the chocolate, peanut butter cupcake. Like all my dreams came true in a tiny beautiful package!

  7. Meechie

    OMG!!! I am so excited to see that familiar sign posted on your blog. Born and raised in Chicago, went to High School a few streets from the Old Fashioned Donuts shop they were and still are the best in town hands down…Krispy who?

  8. Ness at Drovers Run

    Ohmihat – those cupcakes! With the butterscotch, and the caramel, and the cookie dough and the crushed butterfingers! How is it that you don’t weight twice as much as you do!???

    Seriously, I may just need to bake today after having seen those!

  9. Denise aka Bear

    HI: Thank you for those pictures. I could feel my arteries clogging just looking at the photos. But I would love to indulge in that Chocolate/Peanut Butter Cupcake. Safe Home.

  10. Adrianne

    Loving these blogs about Chi town! My baby sister lives there, so I have been telling her to head over to your blog all week and get to book markin’ these fabulous finds so she can take us there next time we go for a visit! Yummo!

  11. Kerry


    I just read through this amazing Chicago trip… did cupcakes really outdo Lou Malnatti’s pizza?!?! Hehahahha… I am a PIZZA nut and a Chicago girl — long before they had such great cupcakes, makes me wish I was right back there right now! It was so fun seeing the pictures and vicariously living through you what I have missed the last 10 years! Amazing… you are the CUTEST and your energy and enthusiasm make it SO fun to follow along on EVERYTHING you do! Hhhehahahha… thank you!

    Totally random question… we just moved to a new city in Germany and after moving every year we have been married (7 moves and three were international continental moves), I think we might be staying here for “longer” than we have anywhere else. As we were discussing decoration he said we should get some pics of things that are inspiring to us or remind us of where we have been. Just last weekend I was looking for “Chicago” pics out here on German Ebay — nothing even came CLOSE to the pics that you took. Would you be willing to sell any of your prints?!?! Would you file attach them in an email?!? That would be SO cool to blow up in black and white even as all the prints in our hallway will be black and white and relatively large. We live in a high ceiling old style apartment right outside Stuttgart — home of Mercedes ;)

    Thanks Amanda!!!

  12. Allison

    So I totally was thinking the same thing about taking the font from the menu and added it to your Pea fonts! I love how you think. I thought it was hilarious that you tried to sneak out with it!

    And ohhhhh my goodnesssssss I wanted to eat both those cupcakes and the dinner. Looks soo soo good.

  13. beth

    It looks great! I went to Chi-town a few times recently and was amazed at the food! Went to a White Sox game and never saw so many people eating!

  14. Steph

    OMG – everything looks AMAZING. I’ll have to check out Nightwood & Molly’s cupcakes next time we are in Chicago. They look to DIE for!!

  15. TidyMom

    OK WOW…….you had some GOOOOOD eats!! we’re still raving about our meals at Carson’s Ribs and Bubba Gumps……I wish we had tried the cupcakes and donuts that you tried!!

    Seriously HOW do you eat like this when you travel and keep that weight off! lol…..Kudos to you Amanda!!

  16. JenM

    Mmmm, fooood! I asked this on a previous post, but you’ve done so well losing weight and keeping it off and you look fantastic – how on earth do you keep it off while eating all of the delicious food that you post about? Your gorgeous photos of the food make me drool and I almost put weight on just looking at the stuff!

  17. Maureen

    Amanda – thanks for sharing your visit of Chicago! Loved seeing what you did! Glad you had a good time. Hope you will be back. Happy Labor Day to you and Kevin.

  18. Janice Whiting

    Oh, girl, you must be taking itty bitty bites and then working out like a mad woman! So many pics of scrumptious looking food! I think your followers would love a realistic look at how you are eating all those lovely things and still looking FAB! ;)

    Much love!

  19. ava-j

    Hi Amanda, all the food looks just gorgeous! :) we have relatives in Louisville, i should send them a link to your blog so they can try out your recommended picks! Thanks for sharing!

  20. Glynis

    I can’t stop thinking about a bacon butterscotch donut, although those cupcakes looked like a little bit of heaven :) Thanks for sharing your food trip with us !

  21. Billie Parrott

    How do you do it? I got hooked up with your blog because of your
    weight loss story. I’m taking the vitamins and bought a bicycle
    and “try” to follow the 1200 calories a day. Then I read your
    blog post and wonder how quickly I can get to some cupcakes or
    donuts!!! You make them all sound so fabulous that I know you
    are at least tasting them. Do you eat the whole thing? When
    you bring some home, are they for your friends?
    Loved the tutorial on the SLR camera the other day. Very impressed
    at the model you’ve moved up to. I’m still saving for the model you
    used to use. Great photos. Thanks for sharing.

    1. Amanda

      Hi Billie! :)

      With all these sweet treats I’ve been posting lately, I’ve been getting a lot of “How do you eat like this and stay so thin??!” comments! :)

      Here’s what I do.

      1. I don’t eat like this every day!! :) Promise! :) When I’m at home, I still plan my meals and count calories every day and stay between 1200 – 1500 calories a day. Like I mentioned in my weight loss post, if you follow a simple 1200 calories a day diet, you’ll lose weight. After I lost my weight, I used this tool to determine how many calories a day I can eat to *maintain* my weight. (Tip: Always choose “sedentary” when it asks about your activity level.) The number it gave me was 1560, so I that’s how I determined to stay between 1200 and 1500. I don’t eat 1500 every day, even though I guess technically I could to maintain my weight. But I like to switch my calorie intake up every day to keep my metabolism guessing, and also allow me some wiggle room when we’re traveling! :)

      2. When we are traveling, we are normally walking a ton and getting more exercise than we normally would. We easily walked 4-6 miles a day in Chicago. Not that this necessarily made up for all the *eating* we did! lol! :) Since I am consistent with counting every day when I’m at home, I don’t normally count when I’m on vacation. (And I mean a big vacation.. not just a weekend trip to visit the folks! :)) And, especially with the sweets and desserts, I do try split as much as I can with Kevin or whoever I’m traveling with. :)

      3. Another thing that works for me is drinking water. Since I started counting calories in June 2009, I only drink water. No milk, juice, alcohol, coffee, or soda. Just water! And I always have a glass of water with me, it follows me around the house. I find that on the days I really flood myself with water, the next morning I wake up a little lighter than the day before. And for me personally, I would much rather eat my calories than drink them, but that might not be the case for everyone! :)

      So far, being consistent with counting calories every day, drinking water, and keeping a close eye on my weight (I weigh every day) has really helped me maintain my current weight and still allow myself a few “cheat” days every couple of months! :)

  22. Denise

    We are headed to Chicago this weekend for our 10th anniversary. I almost forgot about Chicago pizza! Definitely on our to-do list. Thanks for the trip reports ;)

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Meet Kevin & Amanda

Kevin and Amanda

We love to travel and to eat! Here we share our favorite quick and easy recipes, plus travel tips and guides for our favorite places around the world. If you have any questions about what camera I use or how I edit my photos, check out my photography tutorials.


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