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Chicago: dining at the Trump!

Lol, this post I’m just revisiting to say that when we dined at Donald Trump’s restaurant (in 2014) he was no where near politics and in fact, whole woulda thunk it?!

But the reason I was keen to try it out was two-fold, including a New Zealand connection.

Do you remember the very first episode of Donald Trump’s ‘Apprentice’ which was won by Bill Rancic way back in 2004? Husband of E-TV’s Guiliana Rancic? The Posh and Becks of America, those two – but I digress…

Well, Bill’s prize was to choose which Trump property he would project manage, and he chose to oversee the construction of the Trump International Hotel and Tower in Chicago – and in 2014 I dined there.

Sit down and prepare to drool for I am about to walk you through our 2-hour lunch.

Chicago skyline
The Trump sits right on the river looking down to the lake

Terrace 16 (formerly Sixteen restaurant on the 16th floor, of course) is a two-Michelin star dining experience with floor to double-high ceiling windows opening onto a huge terrace that is thee place to be seen in summer hanging over the Chicago River with a cocktail in your hand.

As luck would have it, the food and beverage manager, Morgan Eagles, is a Kiwi lad! So I jumped at the chance to sit down with him and try the new fall menu from chef Thomas Lents, known for his amazing use of only high-end ingredients sourced locally and shipped from little nooks of the globe.

Here are some pics to entice you to at least go to Sixteen for lunch, but heck, you really should stay!

Trump Sixteen
We went for the three-course (+ dessert) option.
Amuse bouche at Sixteen Chicago
Chef sent out this amuse bouche of dungeness crab pannacotta which did a great job amusing my bouche before the main fare began.
Trump, sixteen dining
My starter of chestnut soup with bacon froth and foie gras, poured in front of me.
Trump Chicago
Husb had the smoked sea trout
Sixteen, Chicago
Morgan had Shigoku oyster with caviar on a watercress and navet cream (no I’ve never heard of that either)
Trump Chicago dining
I moved on to the whole Dover sole filleted at the table
Trump, Sixteen
Then the waiter spooned a cauliflower and pine nut grenobloise (nope, me neither) over it. Tasted ah-mazing!
Trump lobster
Husband went for the Maine lobster with potato gnocchi. So yum he didn’t even share!
Trump sixteen
Morgan had the roast sturgeon with a celeriac and chestnut ragout
Trump Chicago dining
My meaty course was this little roast squab – like a wee quail. I did have plate envy though – keep scrolling!
Trump Chicago
Husband had the venison with a huckleberry sauce spooned at the table
Sixteen dining, Chicago
Morgan had this exquisitely presented beef with horseradish crust
Sixteen Trump
As it happened there was still room in my pudding stomach so I managed at least half of this decadent chocolate mousse
Sixteen at Trump
Husb had the pumpkin spiced pannacotta (it’s nearly Thanksgiving)
Trump Chicago
Morgan went for apple streusel

And that, dear friends, was when I put my napkin down and headed outside for a long walk along the river!

As I write this post, they are waiting to hear whether Sixteen will win a third Michelin star. I shall update this post when I hear…

If you want to partake in the chef’s 6-course degustation dinner, come hungry and come with a fat wallet. Also have at least 3.5 hours free. The full tasting menu costs $185, match it with wine and you can add another $125 – or $750 if you’re after some special bottles that are kept hidden from the riff raff.

Click here for more info on the Trump Chicago >>>



I’m in Chicago via Fiji thanks to Fiji Airways who fly out of Auckland and twice a week from Christchurch Airport via Nadi to LA. A great way to get to America for South Islanders who don’t want to transit through Auckland


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Hi, I'm Megan Singleton and I'm the word slinger of this travel blog as well as on radio in NZ every Sunday. Former Travel Editor at Yahoo NZ and current freelance writer for a few newspapers and mags from time to time, I set off on this travel writing journey 20 years ago and I've pretty much always got a suitcase half packed (or half un-packed!) I'd love you to join me on Facebook or Twitter and sign up for my newsletters if you want loads of travel tips, advice and deals!