Chicago Bucket List


I took advantage of the Easter weekend to visit a new place. We researched about the closest and affordable city to go from Montreal (in terms of flight duration), two hours later we landed at Chicago O'Hare International airport, ready to explore the windy city.

I did not realise how big the city was until we started walking around downtown.
We stayed at Freehand hostel on East Ontario Street, just 3 minutes walk from Grand station - Red Line. That location is just perfect, close to restaurants, shops, etc... and the hostel is very nice, clean. I recommend it 100%. I really liked visiting Chicago and we will not mind going back there during Summertime.

Facts about Chicago

  • Chicago, Illinois is the largest city of the American Midwest and was founded in 1830.
  • An estimated 2.705 million of residents in 2016
  • 237 square miles of land
  • More than 250 theatres, 225 music venues and 200 dance companies
  • Chicago has 26 miles of public beaches that offer a refreshing respite from the summer heat
  • The Deep-dish pizza was invented in Chicago.
  • The four stars on the Chicago flag represent Fort Dearborn, the Chicago fire, the World's Columbian Exposition, and the Century of Progress Exposition.
  • Chicago's nicknames include The Windy City, City of Big Shoulders, The Second City, and The City That Works.
  • More than 125 art galleries and 20 neighbourhood art centres

View from Cindy's Rooftop restaurant

The Bucket List

Depending on your budget and how long you are visiting Chicago, you can;

  • Glide along the river on an architectural boat cruise tour.
  • Learn about the history of the city at the Chicago History Museum.
  • Walk the Magnificent Mile which is an avenue with many stores along.
  • Take a photo at The Bean (good luck to get a picture with less than 8 people behind you).
  • Try the Deep-Dish Pizza (order a small size because it is heavy).
  • Admire the skyline from the 360 Chicago Observation deck or the Skydeck.
  • Ride the big wheel at Navy Pier.
  • In summer, attend a concert or watch a movie at Millenium Park.
  • Experience the taste of Chicago Blues or Jazz.
  • Visit the Lincoln Park Conservatory and learn about more than 40,000 plants representing around 200 species.
  • Try the Chicago hot dog.
  • Happy Hours at Cindy's rooftop, The Hampton social.
  • Attend a slam poetry show at the Green Mill Cocktail lounge.


Always have the exact change when you buy a bus/metro ticket ($US3 for a single ticket at the machine and $US2.50 for a bus ride - no physical ticket given).
Get your three days pass at the airport ($20). In the city, it costs $25.

The line up is long at the Skydeck, optimize your time accordingly.

Best time to take a photo at the Bean is early morning. There are fewer people.

 The Canadian dollar is so weak that your trips to most countries will cost you a lot.

In Winter or Spring you will need; a warm jacket, gloves, a toque, a big scarf (see my picture above), warm socks, and comfy shoes.
I believe Summer is the best time to visit Chicago, it must be so nice to be there.
Have you ever been to Chicago? Share your thoughts with me in the comment section and feel free to post the link to your blog if you have one.

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