Chicago for Eating, Cruising, and Sight-Seeing

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.