Chicago - The Loop

May 27, 2013

I booked my trip to Chicago back in November when I saw a sale on Porter Airlines. I didn't want to bother my bf with driving plus it's a long journey by car for only a couple of days so it wasn't worth it for us. So I booked the flight and forgot about it since I was too busy planning our Euro trip instead.
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When I got back from Europe, I finally started researching for hotels and found out that a big convention was happening on the same weekend. I panicked when I saw the hotels  being completely booked or charging a ridiculous amount of money per night. We debated re-booking the trip for another time but then we decided to look for accommodations on Air BnB instead. 
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After contacting a couple of hosts, we finally booked our apartment and couldn't be more excited to explore Chicago for the first time. Thanks to Chantelle, we had a general idea on what we wanted to visit while there.
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It was also my first time flying Porter Airlines which is conveniently located in our city centre. I didn't have to show up 3 hours before my flight or line up for hours to pass through security. Plus the Porter lounge is amazing!! it's stocked with coffee, tea, juice, water, etc. and light snacks. Everyone was relaxed and enjoying the amenities for free instead of paying so much money just to drink water.

The flight was approximately 1 hour and 20 minutes. Chicago is behind 1 hour in time zone with Toronto. It was a little bumpy flying to Chicago but the service was impeccable. Finally, real glassware instead of plastic cups for everyone not just for business/first class.
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We landed at Midway Airport and it was a nightmare at customs. Another flight was ahead of us in the line and everyone had to be finger printed and photographed on that flight. So we waited for 2 hours just to get a 2 second stamp on our passport. It was absolutely annoying.
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The airport was easy to access by public transportation. We took the Orange Line to our destination and the rest of the time we took the Pink line to the Loop. The CTA has all the information you need to explore the city by train or bus. I just love that the trains are elevated and not underground. I was so amazed to see the train get so close to some buildings when turning.

Once, you get to the loop, you can easily explore the sights on foot.


  1. where i'm from!!! well, near though so i just say that, haha :) and yah, i LOVE airbnb and always use it for traveling these days!! so handy.

  2. These photos are so beautiful :)

  3. These shots are fantastic. I love that photo of you!

  4. Eeeeek! I'm so glad you guys enjoyed Chicago - and NO PROBLEM! I love love love helping people out when traveling to places I know, because so many friends and family help me make trips as well.
    P.S. Bummer for the customs at Midway - the longest I've waited was 20 mins (usually I wait no more than 10 mins to clear it), and no fingerprint screening. I hope I don't have to deal with that on my way back to school in August. That would suck!

    1. The delay was caused by the another flight ahead of us in line :( We had to just wait until they got processed.


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