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long weekend in Chicago

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I need the ultimate 3day+ plan for a long weekend in Chicago
I am taking my partner for his 60th in mid-August (a surprise) We lived there throughout the 1980's and have returned from time to time since. We have also lived in various parts of the US and the UK and now live in FL so fish/seafood is not a priority.
We will be going to Cubs v. Cardinals so will definitely have some Chicago Dogs (Sports Corner?)
Some of his favorites in the past were -
cheeseburgers at the Billy Goat; Giordano's stuffed spinach pizza; martinis at the Pump Room; ribs at Twin Anchors; steak at Gene and Georgettis; breakfast at Lou Mitchells or the Oak Tree (when it was on Oak Street); Spiaggia; Cafe Babareeba; I need a Greek Town recommendation (Courtyards of Plaka was our old favorite): ;Michael Foley's Printers Row (ooh, the duck); The Garden at the Art Institute; Hatsuahana; Bistro 110; so many choices...
We will have dinner on THUR after we arrive and dinner alone on Fri; dinner with friends for the birthday celebration on Sat night (venue recommendation for around 10 guests?); we are meeting two good friends for what we have termed a "casual evening" on Sunday; of course there are breakfast and lunch oppotunities throughout the visit and maybe even tea in kace of lunch on one afternoon
I want this to be fun and memorable but we don't need to gain 10 pounds nor do we need to do three big meal "events"every day.
Anyone feel up to suggestind a complete weekend itinerary???

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  1. Two quick suggestions:
    1. The ferris wheel at navy pier followed by lunch at Riva
    2. NoMi- amazing view if you get a window table overlooking the water tower and great food.

    Have fun,
    Pam

    1. For one of your breakfast/brunch/lunch options, hit the Bongo Room in Wicker Park for a wonderfully decadent brunch. I would recommend splitting an order of one of their amazing pancake options and ordering something savory to balance it (they'll let you order a half order of pancakes, too). Warning, if you go on a Saturday or Sunday, go early or be prepared to wait for a table. You're best off making this a Friday morning excursion.

      For your Thursday or Friday dinner, try Quartino (at State and Ontario). It's an Italian wine bar and the menu is all small plates for sharing. The food and wine are wonderful and an incredible value (heck, even the valet parking is only $5) and it's a fun way to share a dinner with a partner. I do NOT recommend it for your big dinner, because it gets waaaay too loud in there and you'll never be able to talk to someone at the other end of the table. They do take reservations