The Chicago Highlights: An Epic Action Packed Trip To Chicago!

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Chicago was the last stop of our 3 week North American adventure and we couldn’t have picked a better place to end off the trip. Summer in the city was just perfect! There were festivals taking place, free movie nights at The Pavilion, outdoor concerts, and the weather was great for long days spent sightseeing. I also ate more pizza than I normally would in an entire year – yes, Chicago is considered the home of deep-dish pizza so I took it upon myself to try and find the best one.

Here’s a look at some of the highlights from the Windy City:

The Chicago Highlights: An Epic Action Packed Trip To Chicago! A Cubs game at Wrigley Field in Chicago.

Watching a baseball game at Wrigley Field

I know nothing about baseball. I grew up in Argentina where toddlers already know how to kick a ball in a little game we call fΓΊtbol! But since I was travelling with Sam who is a Cubs fan, we paid Wrigley Field a little visit to watch the Chicago Cubs play the Washington Nationals. I may not have understood the rules, but I got to witness some serious team spirit. The Cubs are said to have a bit of a curse (they haven’t won a World Series in 105 years!), but this doesn’t make Chicagoans love them any less. People came decked out in red and blue, they cheered for the team, and then sang “Take Me Out To The Ball Game” at the top of their lungs. It was a pretty cool experience, even for a non-sports lover.

Playing "Trapped in a Room with a Zombie" with Room Escape Adventures in Chicago.

Getting trapped in a room with a zombie

I love seeking out unique activities whenever I travel, and Trapped in a Room with a Zombie turned out to be exactly that. I first discovered the concept of room escape games when I was in Prague and I now try to do them in any city that offers them. The concept behind room escape games is that you’re locked in a room and you have 60 minutes to use the clues in front of you to figure a way out. It’s all about using your mind to problem solve and interpret the hidden messages in front of you. This particular game, however, had the added zombie factor. Yes, there was a pretty terrifying zombie chained to the wall and every 5 minutes its chain would grow longer. Try solving mind games with that kind of pressure! There were definitely a few screams along the way.

Finding the best deep-dish pizza in Chicago.

Going in search of the best deep-dish pizza

If there’s one food Chicago is known for, it’s deep-dish pizza! I wanted to see what all the fuss was about, so I decided to eat my way around Chicago’s pizzerias in 1 week. In the end, I made it to 5 different restaurants: Uno’s Pizzeria, Giordano’s, Gino’s East Side, Bacino’s, and Lou Malnati’s. More than 1 restaurant claimed to make the ‘best’ pizza in Chicago, but favourite was ultimately Uno’s. That being said, I don’t see myself eating another slice of pizza for a very very long time.

Watching a free movie at Millennium Park on a summer evening.

Catching some summer entertainment at Millennium Park

Summer in Chicago is a lot of fun and there seemed to be daily activities at Millennium Park. During my week there and I ended up stumbling onto a free movie night where they were screening Ghostbusters, and I also caught a free concert over in the lawn. It’s a very casual setting and people come with their blankets and picnic baskets.

Sue the T-rex at The Field Museum in Chicago.

Seeing a T-rex at the Field Museum

The highlight of my visit to the Field Museum was seeing Sue the T-rex! Sue is the best-preserved Tyrannosaurus rex specimen that has ever been found. This particular T-rex is believed to have weighed somewhere around 9 tonnes when it lived millions of years ago.

Visiting the University of Chicago campus.

Wandering through the University of Chicago campus

I kind of like visiting university campuses when I visit new places, and the University of Chicago was worth the detour. Most of the older buildings were designed in the Gothic style and walking through the ivy-covered walls of the campus is like setting foot in Europe. The Rockefeller Memorial Chapel which sits on the campus is stunning! Also, if you’re up for a little walk, President Obama’s house sits just a few blocks north from here. You won’t be able to get up close to it (the place is heavily guarded), however, you might just be able to sneak a peek at the red brick manor through the bushes!

Eating a delicious breakfast at Lou Mitchell's in Chicago.

Eating breakfast at Lou Mitchell’s

This is one diner-style joint where it’s worth getting up early – Lou Mitchell’s knows how to make one delicious breakfast! They give you free donut holes the minute you walk through the door, their fluffy omelets are served in the same skillet they’re cooked on, and their claim to serving ‘the world’s finest coffee’ really is true. I don’t even drink coffee, but I had 2 cups at Lou Mitchell’s.

Posing with sculptures at a park by the Art Institute of Chicago.

Enjoying an art filled afternoon at the Art Institute of Chicago

The Art Institute of Chicago is amazing! They have a huge collection of Impressionist and Post-Impressionist paintings, which I’m always drawn to.  Lots of Vincent van Gogh and Paul Gauguin. I also made it down to the basement to visit the Thorne Miniature Rooms. Here you can see tiny little rooms (picture dollhouses) that depict living arrangements from different periods.

The Chicago skyline at night as seen from the John Hancock Center.

Seeing the city from above all lit up at night

There are 2 buildings that offer a pretty spectacular view of Chicago. You have the Willis Tower (formerly known as the Sears Tower) and the John Hancock Centre. I went up the Willis Tower by day, and then decided to go up the John Hancock Centre by night. My suggestion is you visit either, but do it at nighttime. The city looks rather drab and grey by day, but it really comes to life in the evening when you can see the skyscrapers all lit up. Also, if you’re in the mood for a bit of an adrenaline rush, you can try Tilt! at the John Hancock Centre (where you step into a glass balcony that tilts you forward above the city), or you can try The Ledge in the Willis Tower (where you step into a glass cube that juts out of the building from the 103rd floor).

An architecture walk along the Chicago River.

Going on an architecture infused river walk

People had told me Chicago is a city for architecture lovers and now I know why. The city is home to some of the first modern skyscrapers and you can clearly see the evolution of architecture in buildings across the downtown. The most popular way to experience Chicago’s architecture is to take a guided cruise down the Chicago River, but Sam and I opted to do a river walk instead. We didn’t get the history behind each building, but it was a nice setting for a casual stroll.

The Pavilion at Millennium Park in Chicago.

Tips for travellers:

  • If you’re going to be covering a lot of the main sites in Chicago it’s worth getting a CityPASS. This grants you access to 5 different attractions across town, and it’s a lot cheaper than paying for admission at each individual place. We paid $94 for each adult pass; I know it doesn’t sound cheap, but you do end up saving 50% of the total admission price at these 5 attractions, plus you get to by-pass all the long lines – and the lines can be long!
  • Public transportation is great for getting around the city. We bought Ventra cards for the week, and we paid $28 (plus $5 for the card) for a 7-day pass which granted us unlimited access on the buses and subway system.

Here’s a little video that Sam and I made during our week in Chicago. It showcases 35 different attractions across the city, and hopefully it’ll give you a feel of what Chicago is like in the summertime:


Have you been to Chicago? 
What are some of your favourite things about the city?

Join the Conversation


  1. says: Karyn @ Not Done Travelling

    I’d love to see Sue the T-Rex. In Bali I saw the skeleton of a 10,000 year old mammoth and it blew my mind, so I can only imagine how I’d feel standing in front of Sue.

  2. says: Claire

    It’s great to see Chicago from a traveler’s view! I lived a couple hours away and used to visit all the time. I love Chicago. And pizza.

  3. says: Rachel of Hippie in Heels

    Chicago is one of my favorites! I used to visit a couple times a year in college b/c some of my friends went there. We’d order deep dish pizza to the apartment and eat it hung over until we were capable of walking.. then we’d SHOP! so fun!

  4. says: Franca

    The architecture walk along the river sounds like my thing, so interesting! I think me and Dale would have opted for the walk instead of the cruise exactly like you and Sam did, there is so much more freedom that way to stop and enjoy the view at your own pace πŸ™‚

  5. says: Olivia @ Olivia Explores

    I’d never really been too interested in visiting Chicago but this really makes me want to go! Those pictures of the cityscape are absolutely beautiful

    1. says: Audrey

      I hope you get to visit Olivia. It’s great fun in the summertime – especially with all the festival and outdoors events.

  6. Another good tip — take the water taxi! A day pass is cheap ($7?) and it starts all the way down in China Town at Ping Tom Park — there’s a parking lot in Chinatown that’s only $14 for the whole day, which is cheap for Chicago! Anyway, the benefit of the water taxi is that you get all of the amazing sights from the architectural tour (but, sadly, none of the great info) for a nominal cost.

    1. says: Audrey

      I’ll be adding pizza connoisseur to the resume. That should be some kind of distinction for anyone who passes through Chicago. πŸ˜‰

  7. says: Justine

    Chicago sounds like an amazing city. I’ve always wanted to go there. And that’s awesome you were able to catch a game at Wrigley Field. It’s so full of history. So even if you’re not a sports, it’s a pretty cool thing to experience. I’m so jealous!!

    1. says: Audrey

      It was pretty cool getting to catch a game at Wrigley. Even though I’m not really into baseball, the excitement is kind of contagious once you’re in there. πŸ™‚

    1. says: Audrey

      Thanks Rika! We’re back in Canada for a bit of summer travel, and then I think we’ll be hopping down to the Caribbean. πŸ™‚

  8. I loved Chicago too! The deep dish pizza, sunset from the John Hancock, Architecture walk (we also did our own self guided one), Millenium Park, Breakfast at Lou Mitchell’s, free improv at Second City, swimming at the many beaches – so many reasons to love that City!

  9. says: Mary @ Green Global Travel

    Looks like a trip with a ton of fun! Chicago sounds like it has an endless list of things to do and try with some really unique and interesting parts. Thanks for sharing!

    1. says: Audrey

      We were just there last week – I can’t believe we missed you, Barbara! Our paths will cross again somewhere around the world…maybe even Chiang Mai. πŸ™‚

  10. says: Jeff

    H ave never been to Chicago and I never believed if it has much offers.Thanks for sharing because that will be my next visit.Nice pictures Audrey!

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