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Progressive Dinner in Chicago

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I am heading to Chicago in two weeks and wanted to do a progressive dinner of some sorts. Ideally looking in one night to hit up the first restaurant that has some great shareable appetizers, the second restaurant for an entree and the third restaurant known for desserts. We want to be able to walk our way through this so any ideas would be great. Looking at medium to high price ranges. Looking to walk no more than 10 blocks to hit all the locations. Thanks in advance for your time

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  1. Sounds like fun!

    Here are two different itineraries, one featuring places that are between Superior Street and the river, the other featuring places that go from Superior Street north.

    Itinerary 1 - South of Superior Street

    For appetizers, I would start with a "small plates" restaurant, either Sable or Quartino. Or, Bin 36 (a wine bar), or Pops for Champagne (ditto).

    For entrees, maybe David Burke's Primehouse if you like steak, or Shaw's Crab House if you like seafood, or whichever of the small plates places you don't start at, or Bandera (I've heard they have great burgers), or Uno/Due for deep-dish pizza (although it can be pretty darn filling, unless you can limit your intake), or Shanghai Terrace for high-end Chinese.

    For desserts, I'd then go to TRU for their dessert tasting menu. Note that TRU is formal (jackets required) in the main dining room, but you can sit in the bar if you're dressed more casually (figure business casual). Another option for a Friday or Saturday night is the Chocolate Bar in the Lobby (that's the name of the restaurant in the Peninsula Hotel - same hotel as Shanghai Terrace); they have an all-you-can-eat buffet of around 40 different chocolate-based desserts, all in small portion sizes so you can try a lot of them.

    All of these are quite close to each other, as you can see on the map to your right.

    Itinerary 2 - North of Superior Street

    For appetizers, you could start at Cafe Iberico, which serves tapas. Note - This is the only place I'm mentioning, other than the pizza places, that does not accept reservations. It's a few blocks west of the others.

    For mains, you could then go to Spiaggia (high-end Italian), Cafe Spiaggia (mid-priced Italian), Pane Caldo (ditto), Bistronomic (French bistro), Cafe des Architectes (contemporary American), Gibson's (steakhouse), Hugo's (seafood), or Shanghai Terrace (high-end Chinese).

    For dessert, go to the Chocolate Bar in the Peninsula, as described above.

    These too are all close together and shown on the map.

    Let each place you're going know what your plans are when making your reservations.

    Enjoy!

    -----
    Pizzeria Due
    619 N Wabash Ave, Chicago, IL 60611

    Pizzeria Uno
    29 E Ohio St, Chicago, IL 60611

    Cafe Iberico
    737 N Lasalle Drive, Chicago, IL 60654

    David Burke's Primehouse
    616 N Rush Street, Chicago, IL 60611

    Tru Restaurant
    676 North Saint Clair, Chicago, IL 60611

    Quartino
    626 N. State Street, Chicago, IL 60654

    Cafe Spiaggia
    980 North Michigan Ave, Chicago, IL 60611

    Shanghai Terrace
    108 E Superior, Chicago, IL 60611

    Bin 36
    339 N. Dearborn, Chicago, IL 60610

    Hugo's Frog Bar & Fish House
    1024 North Rush, Chicago, IL 60611

    Cafe des Architectes
    20 East Chestnut Street, Chicago, IL 60611

    Shaw's Crab House
    21 East Hubbard St., Chicago, IL 60611

    Spiaggia
    980 North Michigan Ave, Chicago, IL 60611

    Bandera Restaurant
    535 N Michigan Ave Ste 208, Chicago, IL 60611

    Gibsons Bar & Steakhouse
    1028 North Rush, Chicago, IL 60611

    Pane Caldo
    72 E Walton, Chicago, IL 60611

    The Lobby
    108 E Superior, Chicago, IL 60611

    Sable Kitchen & Bar
    505 North State Street, Chicago, IL 60654

    Pops for Champagne
    601 N State St, Chicago, IL 60654

    Bistronomic
    840 N Wabash Ave, Chicago, IL 60611

    2 Replies
    1. re: nsxtasy

      AWESOME!! Thank you so much for the recommendations!! Going to run it by the group. Looking forward to some great eats in Chicago.

      1. re: readytonosh

        My vote would be for nsxtasy's first option: Sable -> Primehouse -> TRU

    2. Bear in mind that Chicago weather in mid-late November can be wildly unpredictable.