Chicago for Anniversary - restaurant help

[sterl724]

H and I are going to Chicago in about a month. I've got things to do covered - I'm from central Illinois, so I've been to Chicago numerous times. H has only been there with me for a Cubs game (up and back in a day) and for a wedding. He's never done the touristy stuff, but I already have several days planned out of stuff to do.

Here is where I need help. H and I's 5 year anniversary is the end of July. We are going to Chicago for about 4 days in early August. (Because of some schedule issues with work/other commitments, we couldn't make it work on our actual anniversary.)
We plan to do a nice night out one evening to celebrate our anniversary. I have no idea where to go! I need some idea/suggestions.

Some things to keep in mind: 
1. H doesn't really do super dressy. He works in Agriculture and wears jeans and boots everyday, so his "dress clothes" wardrobe consists of one pair of dress kakhi slacks and a dressy polos, and two suits. (But being August and a short trip, I'm not packing a suit.) I'd like somewhere nice enough to dress up some, but not so much he has to be in a jacket and tie.
2. We are taking the train (Amtrak) to Chicago and not renting a car. Most of what we have planned is walkable and/or short cab rides. Where ever we go needs to be in the general downtown area. (We are still finalizing the hotel. Taking a cab is fine, just not forever and a day away.)
3. I know it's Chicago, and will be more expensive then central Illinois, but we'd like to keep it under $100. (Or in that general range.)

Suggestions/Recommendations?

[snipsnsnails]

Frontera Grill has greaat food. Limited take-ahead reservations, but it's a nice spot to go down and wait. His more casual restaurant is next door and also delicious.

[sterl724]

Jul 6, 2015 15:24:42 GMT -5 @stpete said:

Do you two drink? Is the $100 going to include cocktails/wine or just food?

H is a bigger drinker than I am, but only drinks beer. 

I am a super occasional drinker - it usually triggers my chronic migraines, and we're TTC. 

Likely, it would include one drink/person. (If that is what puts us over 100, not a big deal. Ideally, under 100 for food.)

[wavepool]

We had fun and had great food at Nacional 27! Stays open for dancing later if you're in to that.
The walking food tours are fun!

[sterl724]

Jul 6, 2015 15:36:20 GMT -5 turdferguson said:

What type of food are we talking about? Steak? Italian? Sushi?

Neither of us eats seafood/fish/sushi. 

Both love Italian. 

I love steak - H prefers pork, but will eat steak. (However, I'm guessing a good quality steakhouse will be more expensive than what we want to spend. We are on a somewhat budget for the trip.)

No allergies or dietary restrictions.

[MixedBerryJam]

Posting here so I can see your recs, too. I'm in Chicago next week! Happy anniversary, @sterl724!

[cabbagecabbage]

Quartino is really delicious and reasonable for Italian. The ambiance can be loud but it's pretty.

[sterl724]

Jul 6, 2015 15:41:08 GMT -5 MixedBerryJam said:

Posting here so I can see your recs, too. I'm in Chicago next week! Happy anniversary, @sterl724!

Aww, thanks!

[mbcdefg]

The Purple Pig

[moreace01]

Chicago is not dressy - no worries there. We just...don't get dressed up here.

Some thoughts:
Bavette's (steak - this might go over budget though)
Siena Tavern - Italian
Piccolo Sogno - also Italian (supposed to have a very romantic patio - sadly, I have still not been here)


Girl and the Goat is always good - but it is small plates and most guys...don't really like small plates. If you call, you should be able to get a reservation if you are flexible on time.

[Deleted]

How about deep dish pizza? It's not fancy, but it's delicious. Lou Malnati's? Giordano's? Chicago folks will have the best recs obviously.

I liked Purple Pig and Publican, but I don't know if they will fit the budget for dinner.

[mbcdefg]

Jul 6, 2015 15:50:26 GMT -5 @misoangry said:

How about deep dish pizza? It's not fancy, but it's delicious. Lou Malnati's? Giordano's? Chicago folks will have the best recs obviously.

I liked Purple Pig and Publican, but I don't know if they will fit the budget for dinner.

I went to Purple Pig on a business trip (twice, actually) because I read your blog. I made sure to get that milk-braised pork, YUM. 

I had a $50 per diem from work. I was able to get a cocktail, two plates, and a dessert for $47 the first night. For lunch the next day I spent $47 on a cocktail and two plates. I tipped out of pocket. 

[sterl724]

Jul 6, 2015 15:50:26 GMT -5 @misoangry said:

How about deep dish pizza? It's not fancy, but it's delicious. Lou Malnati's? Giordano's? Chicago folks will have the best recs obviously.

I liked Purple Pig and Publican, but I don't know if they will fit the budget for dinner.

I already planned on doing Giodano's at some point. I love their pizza! 

[Deleted]

Jul 6, 2015 15:54:06 GMT -5 mbcdefg said:

Jul 6, 2015 15:50:26 GMT -5 @misoangry said:

How about deep dish pizza? It's not fancy, but it's delicious. Lou Malnati's? Giordano's? Chicago folks will have the best recs obviously.

I liked Purple Pig and Publican, but I don't know if they will fit the budget for dinner.

I went to Purple Pig on a business trip (twice, actually) because I read your blog. I made sure to get that milk-braised pork, YUM. 

I had a $50 per diem from work. I was able to get a cocktail, two plates, and a dessert for $47 the first night. For lunch the next day I spent $47 on a cocktail and two plates. I tipped out of pocket. 

Sweeeeet! I really enjoyed that place! I'm so happy you did, too!

[shell24]

Jul 6, 2015 15:54:14 GMT -5 sterl724 said:

Jul 6, 2015 15:50:26 GMT -5 @misoangry said:

How about deep dish pizza? It's not fancy, but it's delicious. Lou Malnati's? Giordano's? Chicago folks will have the best recs obviously.

I liked Purple Pig and Publican, but I don't know if they will fit the budget for dinner.

I already planned on doing Giodano's at some point. I love their pizza! 

Go to Pequods instead. You can thank me later!

You could try RPM Italian, although it may not be easy getting a reservation.

[whiskeyandwine]

Club Lago is my #1 recommendation right now. Small, family owned, great food, good prices, all around great.

[beefcheeks]

I heartily second Bavette's, and Sienna Tavern is really good too. Xoco was also mentioned I believe, and it's casual and very good. Noon O Kabab off the Brown line is awesome (Persian). Reza's is good (also Med/Persian).

[RoxMonster]

For Italian: Rosebud Cafe or RPM Italian

I second the previous rec for Frontera Grill

I would not eat dinner there but would also recommend getting a drink at the Signature Lounge at John Hancock if you haven't been there.

[cbwm1]

Jul 6, 2015 15:54:14 GMT -5 sterl724 said:

Jul 6, 2015 15:50:26 GMT -5 @misoangry said:

How about deep dish pizza? It's not fancy, but it's delicious. Lou Malnati's? Giordano's? Chicago folks will have the best recs obviously.

I liked Purple Pig and Publican, but I don't know if they will fit the budget for dinner.

I already planned on doing Giodano's at some point. I love their pizza! 

Lou Malnati's is leaps and bounds better than Giordano's!!

[cinderbella]

Rosebud or RPM Italian!

[boiler717]

Bavettes!

[annieh22]

Cafe Ba Ba Reeba. Tapas and sangria. Yummy and fun.

[sterl724]

All these places look so good! I'm going to have to spend some time looking at menus!

Thanks ladies!

[lissaholly]

Chicago has many amazing italian restaurants;)

It has turned into a chain, but Mia Francesca's is always amazing. I think it would hit your price point,too. Definitely do a drink at the signature lounge, cheaper than the observation deck.

Nacional 27 has the best mocktails, if you prefer not to drink. Bavette's Is really on trend and delicious.

[maddiepaddy]

I second the recs for Quartino and RPM Italian. Between the two, I'd definitely do RPM. I've been two or three times now and have not been disappointed by anything.

[rachelgreen]

Jul 6, 2015 16:09:06 GMT -5 whiskeyandwine said:

Club Lago is my #1 recommendation right now. Small, family owned, great food, good prices, all around great.

We know what my Mexican (and your DH's) would be...cheap and delish, hahaha. Taco Burrito King

You seem to be more of my type of people. We aren't fancy eaters but enjoy a tasty or fun meal.

Art of Pizza
Pizza Parlor
Au Cheval
Mr. Beef (not Portillos)

[christy082]

Quartino, La Madia, Sable.

[appleaday]

Jul 6, 2015 17:11:28 GMT -5 annieh22 said:

Cafe Ba Ba Reeba. Tapas and sangria. Yummy and fun.

Agreed. Also, we just randomly tried Bella Bacino's on the whim last week and it was pretty good. Had their bruschetta and pizze:

[ndgrl]

Chicago's q is good too. Upscale bbq. Hush puppies are amazing.