A weekend in the Windy City with Mile High and Hungry


I’ve been traveling a bit this holiday season and found myself in Chicago last weekend. Chicago is a wonderful food city with tons of tasty food and fun restaurants. There are a few places I need to go to every time I am in Chicago, but you should always try some new spots when traveling. So I did what any good food blogger does and reached out to a few Chicago food instagrammers for recommendations of new places.

Yes, we are Mile High and Hungry, but there are so many Chicago transplants here in Denver and it’s a city all of you should visit sometime- so here’s a recap of some of my favorite meals from the weekend~


Siena Tavern

Siena Tavern is one of Top Chef Fabio Viviani’s Chicago restaurants, a modern take on a rustic Italian restaurant with a bit of a Chicago flair.

Their website describes the atmosphere best;

“The 10,000 square foot space’s décor reflects a hybrid of a rustic Italian market, fine dining restaurants, and a modern, industrial tavern, bridging old world comfort and hospitality with a contemporary menu and design.”

It’s a great spot for mimosas and bloodys and a fun place to share a few dishes among a group. I’m a HUGE of their brunch and make sure to go there every time I am in the city. The breakfast Pizza and the monkey bread are so so so good. Breakfast potatoes can be boring, but theirs are so perfect they are really worth the trip on their own, so that’s really just the capper.



Every year from mid November until Christmas eve, the Christkindlmarket pops up in Chicago. Basically a big bavarian style christmas market to get you into the holiday spirit with some great food and gifts. There’s tons of unique handmade gifts from Germany and, of course, lots of food.

If you like hot drinks they have cider, hot chocolate and Glühwein, a type of spiced german wine served hot. Traditional german food options like sausages and potato pancakes are available too. Potato pancakes might be my favorite holiday food and if you haven’t tried them you should really make that happen.



If you aren’t familiar with Eataly, read closely.

aIt’s basically a huge italian grocery store with a bunch of booths and spots to eat. This is another spot I am always sure to make it to when I am in Chicago, they have an insane wine list and absurdly good burrata and charcuterie. If you like really good italian, or want to get gifts for a food lover in your life, add this to your list.

They have charcuterie sections, a huge collection of italian meats, cheeses, wines, desserts and more. I am yet to eat anything there I wouldn’t want to eat again and again.

Eataly of course is a fantastic place for an afternoon drink. Not only do they have an extensive wine selection at any price point, but they can do some super yummy cocktails. Finishing some apps off with a negrini is something I think everyone needs to do more, and Eatally does it beautifully.

They also have locations in NYC, LA, Vegas and Boston (and a ton internationally… Istanbul, Moscow, Stockholm and yes, Italy)


Mad Social

Mad Social is a little more on the west side of the city but still very much within walking distance of everything and in a really cool neighborhood. It has a cute, young atmosphere with some great soft lighting and long booths. It felt like a bar but still a comfortable brunch spot, which I liked a lot.

The chicken and waffles and the pancakes were the biggest recommendations we got there, and I went with the chicken and waffles. The waffles are churro pressed so they’re super fluffy but crispy on the outside so they didn’t get soggy with the syrup. Our server recommended we try the house made hot sauce with it, and this was seriously some of the best chicken and waffles we have ever had. If you’re a comfort food fan, this is a great stop if you’re in Chicago. We also went with the mac n cheese (of course) which was covered with brussel sprouts and filled with mushrooms.


Lou Malnati’s

Everyone I knew from Chicago told me this is where I needed to go for Chicago deep dish. As I was planning this trip I knew I was going to need a real good Chicago style deep dish pizza and the feedback from everyone included some mention of Lou Malnati’s.

They have a bunch of locations and if you want Chicago pizza, I absolutely give this my stamp of approval, I left there with my pizza itch satisfied.


Fig and Olive

Its Mediterranean food… kinda

Fig and Olive was the nice dinner of the trip and I would even recommend it for some apps. They had a super cool lounge area and an awesome location in the Gold Coast neighborhood. If you like Mediterranean food, they cook with a lot of olive oil and have some awesome crostinis.

Fig and Olive was delicious but it’s definitely a bit pricey. If you want a decent bottle of wine and an entree, you will be payng a lot. The apps are pretty big though and they have some awesome bread with olive oil and balsamic. If you’re feeling some small bites and a glass of wine, it’s a great spot.  

Chicago Athletic AssociationCindysInterior2Thomas Shelby CRPD1600x900.jpg
Image via ChicagoAthleticAssociation.com

Cindy’s Rooftop

Cindys was my favorite bar of the trip because its just so chicago. Located on the rooftop of the Chicago Athletic Association, it feels like you’re back in the 50’s with a great deck overlooking Michigan avenue and the lake. If you want a great cocktail and a fun spot to socialize, this is the place.  

They also have a shake shack on the bottom floor of the Chicago Athletic Association, so thats an extra Cindy’s bonus.

Chicago influencer Recs

While I didn’t get to hit every spot, there were a ton of other places that were highly recommended. I didn’t want to leave them out so here are some of the culinary  hotspots I need to get to next time:

  • Girl and the Goat: The chef was on Top Chef and it was nominated for a James Beard award. Menu has lots of shareable dishes and a wine list focused on small producers.
  • Pequod’s: Another Chicago deep dish option that was highly recommended. They advertise that they specialize in caramelized crusts
  • Little Bad Wolf: looks like sort of an upscale/creative bar food type place
  • Sun Wah: Authentic chinese BBQ with a James Beard award to show for it.

Have questions about Chicago? Travelling and want recommendations for places to eat? Have a travel photo you want us to share?

DM us or email us at milehighandhungry@gmail.com

One thought on “A weekend in the Windy City with Mile High and Hungry”

Leave a Reply

Your email address will not be published. Required fields are marked *