Canada, Greece, Turkey, and Italy: Intro and Greensboro to Chicago

Intro and Greensboro to Chicago
Air Canada Maple Leaf Lounge Toronto and Exploring Toronto
Air Canada Executive First Suite Toronto to Istanbul
14 Hours in Istanbul
Aegean Airlines Business Class Istanbul to Athens
Hotel Amalia Athens and Exploring Athens (Part 1)
Exploring Athens (Part 2)
Athens Airport Lounges and Aegean Airlines Athens to Santorini
Anamnesis Luxury Spa Hotel and Exploring Santorini (Part 1)
Exploring Santorini (Part 2)
Exploring Santorini (Part 3) and Aegean Airlines Santorini to Athens
Holiday Inn Athens Airport and Aegean Airlines Athens to Milan
UNA Hotel Cusani and Exploring Milan
United Business Class Milan to Newark to Greensboro


As you probably have read, a few weeks ago, the Mrs. Guru and I took an incredible trip to Greece, with quick stops in Istanbul (on the outbound) and Milan (on the return).  I’ve posted a few times with some details on how this trip came together, so I’ll summarize some of those points here, with links to more detail if you missed any of those discussions or want to refer back to them.

I started planning this trip last December, when United announced that they would be raising the cost of awards starting in February.  Any trips booked before February 1, 2014 (even for travel after February) would be bookable at the old/lower prices, but after February 1, the prices would go up – for Business Class to Europe, United raised the price from 100,000 miles roundtrip to 140,000 miles roundtrip, so I definitely wanted to book before the 40% increase!  I had only been to Greece once (for just a few days), and the Mrs. Guru had never been to Greece, so we decided that it would be a great destination.

Santorini, Greece
Santorini, Greece

After much research into available flights, I was able to book our flights as a roundtrip between Greensboro and Athens, with no stopovers (longer than 24 hours).  Both the stops in Istanbul and Milan were scheduled to be less than 24 hours, so they were simply long layovers.  As a result, we are currently still en route on this trip – we’re back home in North Carolina, on a 3 month stopover before we continue on down to the Cayman Islands.  You can read more about this stopover trick in this post here.

I specifically booked our outbound flights on Air Canada for 2 reasons:

  1. Air Canada’s Executive First Class offers fully flat seats, which is an excellent way to spend 10 hours overnight.
  2. Air Canada flies from Toronto to Istanbul, and Istanbul has one of the newest, most luxurious lounges anywhere in the world.

Although there were a number of schedule changes between when we booked the trip and when we actually left, our itinerary ended up looking like this:

  • 8/1 United 5867: Depart Greensboro 6:00 am, Arrive Chicago 6:58 am
  • 8/1 United 3656: Depart Chicago 9:00 am, Arrive Toronto 11:29 am
  • 8/1 Air Canada 810: Depart Toronto 4:25 pm, Arrive Istanbul 9:25 am (+1 day)
  • 8/2 Aegean 995: Depart Istanbul 11:20 pm, Arrive Athens 11:59 pm
  • 8/4 Aegean 362: Depart Athens 9:35 pm, Arrive Santorini 10:20 pm
  • 8/7 Aegean 361: Depart Santorini 8:25 pm, Arrive Athens 9:10 pm
  • 8/8 Aegean 660: Depart Athens 8:30 am, Arrive Milan 10:10 am
  • 8/9 United 18: Depart Milan 10:20 am, Arrive Newark 1:30 pm
  • 8/9 United 4702: Depart Newark 4:59 pm, Arrive Greensboro 6:38 pm

So overall, we had a full day in Istanbul, 2 full days in Athens, 4 full days in Santorini, and a full day in Milan.

Our trip started early in the morning on Friday, August 1.  We had actually taken Uber on Thursday night to the Hampton Inn Greensboro Airport, which has a complimentary airport shuttle and is only a few miles away from the airport.  We took the 5:00 am shuttle, getting to the airport before 5:10.  We checked in at the United counter, with a plan to check our bags all the way through to Athens so that we would go out and explore Istanbul without having to worry about our luggage.  Unfortunately, the check in agent was only able to check our bags to Istanbul.  I thought that wouldn’t be a big deal, and in hindsight, should have pressed harder to get them checked all the way through…unfortunately, it ended up causing us some more-than-minor-but-not-catastrophic headaches in Istanbul.  More on that when I write about Istanbul.

With our luggage checked, we went through security.  Having signed up for TSA PreCheck about 6 months ago, I was able to speed through the PreCheck line (we signed up the Mrs. Guru a few months ago, but hadn’t been able to schedule an interview for her until our layover in Newark on the way home from this trip…so she now happily has PreCheck as well).  I was through security in about 60 seconds, but the Mrs. Guru was stuck behind a man who appeared to be flying for the first time, so it took her a few extra minutes…but we were through and at the gate before 5:25:

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Waiting to board United 5837 to Chicago in Greensboro
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Waiting to board United 5837 to Chicago in Greensboro

A few minutes later, boarding began for our flight.  Unfortunately, most United flights in and out of Greensboro are on single cabin (only Coach, no Business or First Class) planes, so even though our award ticket was all in Business in First Class, we’d be in Coach for this first flight.  We made our way to seats 6C and 6D, sleepy but excited to finally get the trip underway.

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United Express Embraer 145 GSO to ORD

We pushed back just a few minutes late, but taxied quickly and were on our way in no time.  It was fun to think back to last September, when we set off on our Honeymoon, on this exact same 6:00 am flight from Greensboro to Chicago, en route to Bali and the Seychelles.

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En Route from Greensboro to Chicago

The flight was smooth, though not anything special (not like a 1.5 hour flight on a 50-seat regional jet really is ever very special)….but there would be plenty of special flights to come on this trip!

We landed in Chicago a few minutes early, arriving into the F concourse.

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F Concourse – Chicago O’Hare

Our connecting flight to Toronto would be leaving from the C concourse, which is a 15 or so minute walk…there is a shuttle running between the F and C concourses, but we figured it couldn’t hurt to stretch our legs a bit, so we took the walk, including the famous underground walkway between the B and C concourses:

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Underground Walkway – Chicago O’Hare

We had about 45 minutes before our flight to Toronto would be departing, so we stopped in the United Club near gate C18…which was also where we waited for our Chicago to Tokyo flight at the beginning of our Honeymoon trip.  The lounge was quiet and relaxing, although the food options are pretty limited (as with most domestic lounges):

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United Club Chicago O’Hare
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United Club Chicago O’Hare
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United Club Chicago O’Hare

Next, we’d be off to Toronto…even though I’ve been to a lot of places around the world, this would be my very first time to Canada, so I was bursting with excitement to see our neighbors to the North!

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