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Need help planning weekend in Chicago!

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I have a friend coming in from New York to visit Chicago for the first time this weekend. I want to make the most of his trip here because we're celebrating his birthday, but I'm horribly indecisive and of course, want him to try EVERYTHING. Impossible. So I beseech all you fantastic folk out there to help narrow things down. He gets in at 3 on Friday and we'll be staying at the Hotel Monaco (Wabash and Wacker) but I don't mind driving around. Here's kind of a vague idea I have for the weekend.

FRIDAY:
- Early cocktails at C-View or Cityscape (something with a good view I thought would be a nice first glimpse of the city....any other good places for that at that time?)
- Dinner at Spring (he wants to spend 100-150 a head, but he doesn't want to wear a dinner jacket. Something "modern" but not necessarily haute, which I have no idea what that translates to for him, but he likes fusion foods -nothing like Alinea :(- but alternative ideas are welcome
-late show at 2nd city
-Thinking drinks at The Drawing Room to finish off the night

So Saturday is really what's tearing me apart. If we were to go everywhere I want, we would be comatose by 3.

SATURDAY
-Breakfast/brunch at Big Jones or M. Henry (Between is closed for brunch til March!)
- I know this isn't food, but he's an Architecture buff and I'm an ignoramus in that department so any tour ideas? was thinking to take that hop on/off trolley bit, and that way I can hit up the Art Institute and other areas easily without being restricted.
- Thinking Hot Dougs for lunch or saving that for a mid afternoon snack and trying Custom House or Cafe Spaggia
- What are good bars/pubs to visit during the day/afternoon in Chicago? I am thinking something lowkey, warm and friendly. Hopleaf is high on my list, but should I save that for after dinner?
-Publican or Avec for dinner.
-Where to go for post dinner drinks. Figure we'll jump to two or three places. And here are some ideas I've culled.

Nacional 27, Weegee's, The Hideout, Duke of Perth, The matchbox, The Chipp Inn, The California Clipper, Red Lion Pub, Bungalow, and potentially Hopleaf if not earlier in the day.

Opinions?

This whole itinerary is highly open for change and suggestion. Thanks everyone!

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  1. Friday sounds okay. Spring is very good but is not likely to blow anyone away. Personally, I think North Pond is the perfect choice for what you're looking for, with its location hidden away in Lincoln Park, the skyline over the opposite shore of the pond, Bruce Sherman's wonderful contemporary cuisine, etc.

    For your Saturday daytime itinerary, if you happen to be in Andersonville, I like Big Jones, but I love M. Henry, so M. Henry would be my pick. If he loves sweeter items, he'll like it too. Check out their websites to get a better idea of what they offer. However, if you're NOT going to be in Andersonville, then instead I would recommend either location of Bongo Room, especially if he loves sweeter items. For a non-sweet Saturday brunch option, a bit more offbeat - what about Mexican? Frontera Grill in River North, and Mundial Cocina Mestiza in Pilsen, both serve brunch on Saturdays.

    Also, I'm not sure why you need a mid-afternoon meal between brunch and dinner. But if you MUST have that mid-afternoon snack, I'd probably pick TAC Quick for Thai food. Hot Doug's? Not unless he's really into exotic hot dogs or duck fat fries; otherwise be aware that you'll kill a couple of hours going there and back, so think twice if you think he'll be asking, "Huh? Why did we spend all that time..." You also mention Hopleaf and Custom House for mid-afternoon on Saturday. However, Hopleaf doesn't open till 3 pm and the kitchen (for mussels and fries) doesn't open till 5 pm, and Custom House isn't open for lunch on Saturdays, either. So both of those are out. And I love Cafe Spiaggia, but I wouldn't take a visitor from New York to an Italian restaurant!

    I absolutely would NOT take a visitor to Avec for dinner on Saturday, when waits for seating are typically 90 minutes and more. (Again, his reaction is likely to be "Huh? Why???") I'm not particularly fond of Avec, either, with its NOISE, its uncomfortable hard bench communal seating, etc. Go some place where you can make a reservation in advance. Again, North Pond is an excellent choice; so is Aigre Doux.

    For the ultimate for after-dinner drinks, the Violet Hour is THE place to go. Caution - if you haven't been there, the entrance is almost invisible from the street (so as to resemble a Prohibition speakeasy). Hopleaf is another possibility, especially if you happen to be on the north side.

    For your architecture tours, the ArchiCenter of the Chicago Architecture Foundation on South Michigan Avenue is the place to start. They conduct tours by foot as well as by bus. (The warmer part of the year, they offer architectural river cruises which are delightful!) You'll find more info at www.architecture.org/cac.html

    2 Replies
    1. re: nsxtasy

      Thanks for the advice! Like I said, I tend to go overkill. Always need help reigning it in.

      1. re: gumibear

        As I usually do, I totally agree with nsxtasy on Aigre Doux and North Pond. North Pond is much more romantic.

        Two other new options in the casual fine dining--had dinner at both in the last month--are Province and Mexique. Province is an organic-themed place with varying "plate size" so you can share a bunch of things. Mexique is french-influenced mexican and was really very inventive. Chef's whole family works there (his brother in medical school was our waiter and his wife is the hostess). Both have informative websites.

    2. An alternative dinner selection for someone who likes "modern" food but not molecular gastronomy, and does not want to wear a jacket would be Perennial. We ate there 2 weeks ago and had an excellent meal. Dinner for 2, including 2 bottles of wine, before tip was about $200 -- right in your price range.

      Also, if your friend is an architecture buff, you might want to try to work in breakfast or lunch at the Atwood Cafe in the Burnham Hotel. The restoration of that property is fabulous and the food quite good. You'll be in the vicinity if you do the Architecture Foundation tour, go to the Art Institute (a must for an architecture buff to see the old Board of Trade floor), or Millennium Park.

      1 Reply
      1. re: masha

        Perennial is on my short list. I cannot tell you how difficult this has been with how obsessively I've been scouring

        Thank you so much for reminding me of Atwood. Before I moved, I loved doing high tea there- although I probably seemed like a child playing dress up. Now that I'm back, I'm looking forward to revisiting.

      2. I would strongly recommend M. Henry as the brunch/breakfast choice. I just ate there over the weekend and I'm still thinking about their winter brunch plate...bacon and squash crepe...yummy...

        But I digress. A trip out to Oak Park for some Frank Lloyd Wright action might be fun for an architecture buff! As for food, I've always been a big fan of Avec, but I tend to take people there later in the night (after 10) esp if we've been eating most of the day already. I probably wouldn't go there during the dinner hour since the wait would be annoying.