A Winter Get-Away to Chicago for People Who Like to Eat and Drink

This past weekend, Steve and I went to Chicago! Since Jax was born 17 1/2 months ago, we have not been away from home for longer than 24 hours. This time we took an airplane!

I was excited to explore one of my favorite cities with my hubbie! It’s no secret we like to eat and drink – this vacation was a glutton’s paradise!

For all you “foodies” out there – here’s our eating and drinking itinerary for our winter trip to Chicago.

Dinner at Frontera

This restaurant is supposedly one of the “best in the world.” Rick Bayless is famous, that’s for sure, but the dishes we tried were mediocre. Don’t get me wrong, it was good food, but it didn’t give us the wow-factor we were looking for, especially with all the hype. (The exception was the guacamole – it was the best I’ve ever had.) We chose a variety of “Street Food” small plates. The enchiladas potosinas were spicy little corn turnovers with an arugla salad on top. The sopes rancheros were filled with tender and delicious shredded beef. (These were my favorite dish.) The smoked chicken taquitos were Steve’s favorite and reminded me of the taquitos I could get in San Diego. We also tried the fresh corn tamale which was smooth and creamy. Our least favorite dish was the mole poblano enchiladas – the meat was dry and they were slightly bland. Since the restaurant is famous for mole, I had high expectations – oh well. The restaurant is cool – it has a good vibe and the service was great. I don’t think it deserves all the hype, though. Overall, we’d recommend it, but instead of the Street Food, we’d check out the entrees. 

Drinks on the 96th floor of the Hancock Building

Don’t pay to go to the observatory, instead pay the same amount of money for a drink in the Signature Lounge. Same great views, plus alcohol. Wow! On clear days, you can see for 35 miles. It was hazy and cloudy when we went, but we still had a fantastic view of the city.

Hancock Building

Lunch at Little Goat Diner

Everyone told us to go to The Girl and the Goat for dinner, but I totally slacked off and couldn’t get a reservation. Luckily right across the street, there’s the Little Goat Diner – which is sort of more our speed anyway. If you’re looking for excellent diner food, unique Bloody Mary’s (they got voted best Bloodies in Chicago), local beers on tap, cool staff, and a fun, bright atmosphere, then this is your place.

We ordered the Ruben which comes with spicy kimchi on top of the sauerkraut – wow! Steve said it was the best Ruben he’s ever had and that’s saying a lot! I got a sandwich called Los Drowned and that was a fitting name because I thought I had died and gone to heaven. It was a tender steak sandwich with a slight Mexican flare served with au jus. The sides are humongous – we didn’t need to get the smoked fries and the hashbrowns, but they were both fresh and crispy.

I didn’t care for the Bloody Mary because it tasted too much like meat. Bummer. I found out later that they are make with smoky BBQ sauce and kimchi, so that makes sense now! Poor Steve had to drink both of them… 🙂 I switched to beer. We would absolutely recommend this place – GO HERE – you will not be disappointed (especially if you’re a little hung-over and need some good diner food)!

Andy’s Jazz Club

Of course, we had to see some live music in Chicago! Andy’s Jazz Club is a cool, small bar and music starts early – like 5:00 early! This place fills up fast, so the sooner you get there, the better chance you have of getting a seat. There are window ledges that people sit on while waiting for a table. But you can see the stage from anywhere, so it’s no big deal. We scored seats at the bar and listened to the trumpet wail, the bass boom, and the keys dance. I missed the feel of music in my bones!

Dinner at Sunda

OK – you want to talk about an unexpected jackpot?! After and evening of live music, we decided we were ready for dinner. We are slightly out of touch and thought we’d get a table on a Saturday night at 9:30 no problem. Well, this is the big city, folks – make a reservation! After trying 3 places with 2-hour wait times, we stumbled upon Sunda. It looks tiny and unassuming from the front, but once you walk in, you instantly realize you’re in for a treat. Somehow, they combined a hip, chick dance club and a calm, peaceful Asian garden into one incredibly beautiful restaurant.

We ordered the pork belly steamed buns and loved the crispy pork belly combined with the warm, soft bun. The Kalbi Wraps were the best thing I.have.ever.eaten. Seriously. Spare ribs marinated in sesame soy wrapped in roti prata (a type of Asian flatbread). The key ingredient for me was the gochujang,. Once I took a bite of the fermented condiment made from chilies, rice, and soy, I was hooked. Anyone know where I can get some of this?! We topped off our meal with the Flaked Pork Adobo Fried Rice. Sounds boring? It wasn’t. I think the vinegar soy sauce was the kicker for me. Absolutely delicious.

Sunda also has a huge sushi bar that looked wonderful. (We’re just not sushi people.)

Both Steve and I walked out of there in love with Sunda (and each other, of course!). Sunda gets my my top recommendation for food in Chicago.

Lunch at Giordano’s

I’m fully aware that people from Chicago don’t actually eat much deep dish pizza, but we had to go for it. We chose Giordano’s because it’s right next to Millennium Park and it was on our way back to the hotel. Meh. Our server was awkward and the pizza was bland.  I’ve been here before and it was better so maybe we got an off day. If you must have deep dish pizza in Chicago, I think  Gino’s is much better. Nothing special here, folks, move along.

I think I gained 18 pounds over the weekend. We had a blast – we really needed a break! By Sunday, though, we were both ready to get home to our little rug-rat. We missed our sweet boy! I thought I might be over-the-top worried about leaving Jax for the whole weekend, but I was surprisingly calm about it. He was in good hands with his Grandma and aunts and uncles and we know he had a blast, too! But he probably didn’t eat as much as we did…


Author: Andrea M

Oh man, what an adventure! I went into labor unexpectedly when I was 23w3d pregnant. Jaxson was born weighing 1 lb 8 oz. A tiny little peanut, but boy was he feisty. He still is! We love it now, but we probably won't when he is a teenager. I write about our journey and all other things that come with it, including a brain tumor. We look forward to "meeting" you - come hang out with us...we're pretty cool.

7 thoughts on “A Winter Get-Away to Chicago for People Who Like to Eat and Drink”

  1. What an awesome trip you two had. It is vital that you get away and be with one another. It’s so easy to lose yourself in your children espeically those with extra needs like micropreemies! Jax is a product of your love and you honored that connection with a trip full of food, drink, and fun! Craig and I will have to go on a date soon. ; )


  2. I am so happy for the both of you. You deserved that weekend and I am glad you enjoyed every minute. Do it again when time allows!!!


  3. Sounds like a delicious weekend. My hubby would love you for your adventures in food. Mexican here is “tacos in a bowl” on a good day Taco Bell, Chipotle i’ve learned to like. As a pizza expert I can see the dissapointment in not getting a good slice. Im glad you found a few off the beaten path places. Sometimes the big hype is just that, hype. Glad to hear you both relaxed, and knowing Jax was happy and in loving,caring hands definately had to help 🙂


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