For those of you that have been following closely on my social media sites, you know that I’ve spent most of September and October gallivanting around the US travelling for work! My first destination of many was exploring the state of Illinois, specifically in Chicago and the surrounding suburbs. I had never visited before, and I was really excited to have the chance to explore! Read on for some of my top tips for exploring Illinois.

Prepare your documents ahead of time

It had been so long since I’ve travelled internationally – since 2019, to be exact. Three years is a long time to go without those international travels, and I know many of us are in the same position due to the impact of the pandemic. I recommend giving yourself extra time for processing and ensuring you are meeting all relevant COVID protocols ahead of time. I found I had to download multiple apps and the check-in process was quite extensive, both entering and leaving the US – so make sure you do your research and have all of that prepared ahead of time! You will of course have to go through customs when you arrive, but it is helpful to do as much as you can ahead of time to speed up the process.

I also had quite the debacle with trying to get my passport in time for my travels, and it truthfully arrived just in time! I ordered my passport back in June and it didn’t arrive until September, and even then, it was a tight turn-around. After some issues with shipping and delivery, it finally arrived on the Friday before – and my flight was on Sunday! Talk about cutting it close. I definitely recommend ensuring you order any passports or visas well in advance due to the long processing time! I am hoping to eventually get a NEXUS card as well to speed up my time at airports and travelling to the US even more.

Choosing your flight location

My first flight was leaving from the Billy Bishop Airport in Toronto, which is located right downtown on Toronto Islands. I had never flown out of this airport before and was really glad I had the chance to check it out! Billy Bishop is a much smaller airport and they only fly to certain destinations, but luckily for me, the Chicago Midway airport is one of those destinations. The biggest draw of Billy Bishop for me is the view. It’s situated right on the water with views of the CN Tower in downtown, and when you fly in/out, you get to see spectacular city views. Those views are definitely a highlight, and something you don’t get to experience if you’re flying out of Toronto Pearson! For any local Torontonians looking to take a flight to Chicago, I definitely recommend flying out of Billy Bishop. It’s an excellent experience! Arriving at Chicago Midway was an overall pleasant experience. Customs went fairly quickly and I picked up my rental car, and was off!

Exploring downtown and the suburbs

Chicago is a very similar city to Toronto. Easy to drive, traffic is horrible, the downtown city centre is exciting, and the surrounding suburbs each have their own feel. I stayed in Schaumburg for the week, but I’d recommend staying somewhere a bit closer to downtown if you’re wanting to really get that city feel. Staying a bit further out just meant a bit more driving time, however, it also meant I got to see a lot more of the suburbs surrounding Chicago. I explored areas like Barrington, Vernon Hills, Lincolnshire, Lake Forest, Highland Park, Evanston, and more. Each area has its own distinct feel and amenities. Many of them were surrounded by a lot of green space, which I really liked.

I also had the chance to explore downtown Chicago a bit. I wandered around the heart of downtown near Millennium Park, which is a big highlight. Seeing all of the sculptures in that area was super neat. The big draw is “the bean”, as it’s affectionately known, which is actually called Cloud Gate. I’ve seen so many photos of this monument, so it was really cool to see it in person. There is a lot of interesting architecture surrounding that area as well. Walking along the river is also a big highlight, and seeing the lakefront. I would have loved to had more time to explore downtown Chicago, but I’m glad I had some opportunity to check it out, and feel like I saw the big highlights.

Chicago eats!

Of course, no trip to Chicago would be complete without enjoying the food they have to offer! A few highlights include Portillo’s, which offer hot dogs (I did not eat because I’m pescetarian but I did have their pasta which was delicious), and their famous chocolate cake shake – which is literally a giant piece of cake shoved into the blender to make a milkshake. I did get the shake which was good, though I’m not sure my body would be able to handle it again hahah 😛 I did have to spread it out over two days!

Another highlight I wanted to experience was deep dish pizza. Let me tell you, when they say deep, they mean it!! It was massive and SO filling. I went to Giordano’s which was really good, though I am sure there is some debate out there about where the best spot to get deep dish pizza is! Finally, getting Garrett’s popcorn was also on my list. They have the original Chicago Mix with the cheddar and caramel corn, and since original is always best, it’s no surprise that it was delicious. I picked up a bag at the O’Hare International Airport on our way back and it did not disappoint. There were very few vegetables consumed on this trip but I ain’t that mad about it… though I did dive into salads head first when I came back!

After a great time exploring in Illinois, I flew back to Toronto, this time through O’Hare International and in to Toronto Pearson. The bigger airports did take a bit more time but were still nice to check out. Having done most of my paperwork ahead of time (definitely one of my top tips), I was able to breeze through customs when landing back in Canada.

Some final tips

Here’s a few final top tips for you to make note of on your trip to Illinois, specifically Chicago!

• If you’re in Toronto, try flying from the Billy Bishop Airport to fully experience those downtown views!
• Prepare all of your documents ahead of time and ensure you check any COVID protocols – this will save you a ton of time at the airports and make sure the process goes smoothly
• Take the chance to explore some of the nearby suburbs around Chicago to take in wonderful green, park-like spaces
• Check out downtown Chicago, in particular Millennium Park and Cloud Gate
• Make sure you enjoy some of the Chicago classics like deep dish pizza, Portillo’s, and Garret’s popcorn!

I hope you enjoy your visit to Chicago if you’re heading there in the future! If I missed any must-do’s in Chicago, let me know in the comments! As always, make sure to follow our Facebook page and Instagram for the most up-to-date news, and don’t forget to sign up for our email newsletter 🙂