Until last September, I only knew a few things about Chicago: the river is dyed green every year for St. Patrick’s Day (it’s not a prank, but an official Chicago activity!), a good friend just moved there, and it’s freezing cold in the winter (why did my friend move there?). Oh, and I’d seen one episode of Chicago Fire.

I was told that September is a great time to go – apparently not too hot and not too cold. Taking the advice, I hopped on an Alaska Air flight to visit the city.

I don’t know what I was expecting from Chicago, but I love this city! Almost as soon as I landed, I was on a river cruise (like I am in most waterfront cities). This time, it was the Chicago River Architecture River Tour. It’s fabulous. The 90-minute tour takes you down the Chicago River while the tour guide tells you everything about the Chicago skyline and the city’s 130-year history. My favourite sight: the Champagne Building (obviously!)

There’s so much to explore in Chicago: Millennium Park, little places playing jazz, and going to the top of the Willis Tower for the bird’s eye view of Chicago. I dare you to stand on the ledge up there 😊.

Another great boat cruise is on Lake Michigan, one of the five Great Lakes of North America and the only one located entirely within the United States. This massive fresh-water lake is where Chicago gets its water.

There are too many great eating spots to choose from! You won’t be disappointed. My only tip: get reservations at your preferred spot if they take them – especially for the restaurants down the Chicago River.

Chicago is an easy, tourist-friendly city, but here are a few local tips:

  • Chicago hot dogs adhere to a strict no-ketchup policy – some might say it is a criminal offense if you do! For the record, the appropriate toppings for a Chicago-style dog are yellow mustard, chopped white onions, a dill pickle spear, tomato wedges, pickled sport peppers, a dot of celery salt and a dollop of neon-green sweet pickle relish
  • Be ready to eat! Foodies will rejoice with all the amazing restaurants.
  • The Downtown Central Business District is called “the Loop” with the river bordering the north and west.
  • Get a 3-day CTA pass to get unlimited bus and train rides – a cheap way to get around. It can be purchased from the Ventra vending kiosks at either airport or at any ‘L’ station. Download the Transit App to help get around.
  • Give yourself plenty of time to get to where you need to go – traffic can be a nightmare.
  • Tipping: as usual in the United States, tipping is expected for service in restaurants and is higher than what you will find in other American cities. 20% is the expected tip.
  • Some of the cheaper dining/drinking establishments only accept cash.
  • Know the local terms. If someone advises you to take the ‘L’ that means the train. (‘L’ is short for “elevated,” which some parts of the track are.)
  • Chicago’s nickname of the “Windy City” is well-deserved! The breeze comes off the lake and the skyscrapers funnel and suck the wind between them making the streets of the Loop very gusty.
  • Prepare for traffic. In a 2015 study, Chicago had five of the 20 most congested stretches of road in the U.S.

Site-Seeing Musts:

Useful Links:

Visit Chicago Instagram Page
Visit Chicago Web Page
Culture Trip