Chicago – Amtrak train & Willis Tower

After 4 wonderful days in New Orleans, it was time to kiss the city and the heat goodbye and make our way north to Chicago.

Back when we were still in Australia, we booked the Amtrak train to Chicago as we thought it would be a cool experience to cross the country from south to north by land.

We also booked a roomette to ensure we could sleep properly on this 19 hours journey – it’s a long one.

The roomette was a lot smaller than what we thought it would be, but was still big enough for us both to be comfortable. Larger than business class on a plane, but not by much.

All up I think our tickets were over $600AUD for the both of us, more expensive than if we’d flown. However, it was an amazing experience to ride past American cities along the way and watch the sunset over the fields. We started in Louisiana, before cutting through Mississippi, Tennessee, and heading up in to Illinois along the Indiana border.

We saw quite a few remote towns that certainly wouldn’t be on the beaten touristy track, and more trailer parks than you can shake a stick at!

As the price of the roomette included meals, we enjoyed an ok meal at the restaurant wagon with mains, drinks and deserts. This would have cost over $80 if we had to pay, which would have been ridiculous for what was basically microwave food. We were happy it was included, but had packed enough snacks to last a week as back up anyway!

Before getting to bed, I took a shower in the shower area of the sleeping cabins before it got trashed by other passengers. It is hard staying still showering on a moving train, but I survived to tell the tale.

We then transformed our seats to make our beds for the night. As I got top bunk, Nick forced me to put the safety harness up to avoid any accident whilst sleeping in these very narrow beds.

The night wasn’t fabulous as the train’s horns were on every 2 minutes, and a moving train is not as soothing as we thought it would be.

We woke up at 6.30am to ensure we’d be able to get breakfast, as it was finishing at 7.15am. Getting up this early also allowed us to enjoy a beautiful sunrise over the corn fields. After a while, we realised the stop we were at was still hours away from Chicago! Overnight, we had stopped because a car was parked on the rails delaying our trip by nearly 3 hours!

We finally arrived in the iconic Chicago railway station after nearly 22 hours of travels.

We made our way to our home for the next 4 days in the Division suburb of Chicago, just a couple of stops away from the famous ‘loop’ (city center).

It seems to be a very hipster neighborhood, and this weekend was the home of a huge craft market that we enjoyed browsing.

Our accommodation is really good! It’s a hostel with private rooms and shared bathrooms, and well equipt kitchen and common areas. It’s clean and spacious and in an awesome neighbourhood. Highly recommend!

In the afternoon we decided to go check out the Willis Tower to enjoy the view over the city.

It is the second highest building in the US, 14th in the world (it was the tallest for over 20 years), from which you have a brilliant unobstructed 360 degree view over the city.

It was pretty busy when we arrived (about 1 hour wait to get to the lift), but the views from up there were really beautiful over the city, other states and Lake Michigan.

We then queued again to get our spot on ‘The Ledge’, a bit of glass sticking out of the tower with a glass bottom that gives you a view down over the street below. Pretty cool.

After these 2 hours of basically queuing we’d worked up an appetite, so we visited Giordanos. This is one of the most well known pizza restaurants in Chicago, and known for their ‘deep-dish Pizza’. They call it pizza, but it’s essentially pizza ingredients mixed and stuffed within a quiche pastry crust. It’s huge (we ordered the small one; it was still too big for 1 meal for both of us!) but very good (and very fat!).

All in all, a great start to our journey in Chicago!


  • Go early to Giordanos, they’ll be queues at the door at peak times.
  • If you can, visit the Willis Tower observation deck mid-week. We went Saturday as the weather was good, but paid the price queueing.

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