Weekend with the GF
Going to Chicago on Friday for the first time in about a year. We are doing Avec for dinner on Saturday, and we are looking for some advice for Friday night.
Not picky at all, love sushi, italian, french, etc. Would prefer something with entrees less than $25 and an excellent draft beer list and great wine. We are each 22 years old, so something fun and hip is preferred.
Thanks in advance.
I'm not sure where you're staying or whether you lean more toward trendy or more hipster when you say hip, but I can offer a couple of suggestions.
Over by Avec, you could try the Publican or Au Cheval (good for food and beer selection), Nellcote (behind it is RM Champagne Salon where you can grab cocktails or wine after, but not sure about the beer list), Girl and the Goat (we had cocktails but remember good beer/wine lists). Further north in the Bucktown area you could try the Bristol. Revolution Brewery is more pub style and is one of the few breweries in the city. These are all the lower key kind of hip.
Closer to the River North / Near North areas you could try one of the Rick Bayless restaurants for Mexican, Slurping Turtle is fun for Ramen, Gilt Bar is trendy with a lot of beer on tap, Sable has great cocktails and food, Purple Pig for Mediterranean style small plates and wine list. That whole area around Hubbard is swarming with restaurants and then bars and clubs for after if that's your thing. Good Italian at Coco Pazzo and Piccolo Sogno but less on the fun / hip vibe.
Certainly not a comprehensive list, but these are places I've been in my early-mid 20s for date nights and had an all around good time.
That's a really great overview and summary recommendations by velvet. So good that I only have a few comments to add.
One is to beware of long waits at a few of these places that don't take reservations - specifically, Avec and Purple Pig. Granted, some people don't mind waiting 90-120 minutes or more to be seated - if you don't, that's fine - but it's worth the warning, in case you do. If you want to do Purple Pig, you have the option of going at lunchtime, when they have the same menu and waits aren't nearly as long. Avec and Purple Pig are also quite similar to each other, both small places specializing in Mediterranean small plates, so that may be a bit much for the same weekend.
Also, I'll second his/her recommendation of our contemporary Mexican restaurants. Many people don't mention those when listing the kinds of places they like, because they don't exist in most other cities this side of the border with Mexico. The Rick Bayless places - Frontera Grill and Topolobampo - are excellent, but may be tough to reserve for dinner, not so bad for lunch. (Of those two, Topolobampo will also exceed your price target at dinner, not at lunch.) Other excellent ones are Mexique, Mundial Cocina Mestiza, Mixteco Grill, and Salpicon. Mexique is on a trendy stretch of Chicago Avenue in West Town, not far from downtown, and atmosphere is hip festive bistro.
I'll also second the comments about geography; if we know where in town you're staying and/or spending time, we can give you an idea of distances and maybe additional recommendations of places that are particularly convenient.
As you do your research, feel free to ask additional questions and maybe post a tentative itinerary for comments.
Be aware that reservations at Girl and the Goat fill up three months in advance. After that they still take some walk-in traffic, but not a lot. If you arrive before 5:00 (they open the doors at 4:30), you can generally walk right in, but later than that, you're looking at typical waits to be seated of 90-120 minutes or more. Maybe this is okay with you, but maybe not - especially since this is a significant chunk of your brief time here - and either way, it's at least worth being aware of.
This is for this coming weekend? If I were you, I'd see if you could snag a reservation at Sable, which is not as hard to reserve, has food that IMHO is better than G&TG, has great craft cocktails, and is only a couple of blocks from where you're staying. Another choice not mentioned above is GT Fish & Oyster, which is a few blocks further west, has excellent food (also small plates, but seafood-oriented, as the name implies), and also great craft cocktails. Quartino is another small plates place near your hotel, which specializes in Italian; IMHO the food is good but not as good as Sable and GT Fish. Another good choice nearby that isn't small plates is Piccolo Sogno Due, which has great Italian food. All of these accept reservations on Opentable.com as well as over the phone, and don't book up three months in advance.
Note that you're staying right near Purple Pig, another small plates choice. As mentioned above, they don't take reservations and waits are horrendous at dinnertime; however, given its convenience, you could try to go, either for lunch when waits aren't as bad, or stop by to leave your name at dinnertime, go back to your hotel or go for a drink nearby (maybe at Pops for Champagne or Gilt Bar or Bin 36), then swing back there after 60-90 minutes for a shorter wait to be seated.