Trip-taker: Caroline, solo-style
Type: Sight-seeing, friend-visiting
Budget: Budget travel ($500-$1000)
Where did you go?
I went to Chicago! I’d always wanted to go, and I had some unexpected time off in early January. I braved the awful winter we’ve been getting near the Great Lakes and flew out the day all the airports opened back up. This was my first trip alone after the end of my long-term relationship and after moving back home with my parents. Needless to say, the time to myself was well-appreciated. Chicago isn’t too far from my hometown, and it’s one of the last Big Cities in the US that I hadn’t yet been to. It ended up reminding me a lot of Toronto, one of my favourite places. The new-ness mixed with familiarity was just what I wanted for a solo trip.
What did you do? I enjoyed solitude for the first time in a year (seriously) in a cute boutique hotel called Hotel Felix that I got for cheap on Hotwire, a hotel room sell-off website.
I walked, a lot, and was happy to not have an itinerary in particular. I shopped when I wanted and ate where I wanted and slept when I wanted.
I had a couple of friends who I could see in Chicago, including Offbeat Bride’s own Catherine (Superman)! She drove me around parts of the town I never would have seen otherwise (we got lost a bunch and it was even more fun). She even took me out for an amazing dinner. Then we hung out in her car for like an hour talking and taking selfies because that’s what you do when you visit friends.
I organized to meet with a Chicago City Greeter. City Greeters are a completely free service that many cities around the world offer. I filled out the form online, checking off what types of things interest me when I travel — historically significant sights, off-the-beaten-path neighbourhoods, good coffee, etc. I was matched with a greeter and we started emailing a few weeks before my trip.
He organized an entire day’s worth of activities, including touring three different neighbourhoods and his favourite spots to stop for food and drinks. He based the entire day on my interests, even finding hipster boutiques he thought I’d like. He was extremely knowledgeable about his city and his enthusiasm was infectious. And it was completely free. I highly recommend checking out this service no matter what city you’re visiting.
I spent my last day at the Chicago Art Institute. It’s expensive, but worth it. Make a whole day of it and get your money’s worth while upping your culture points. And yes, I stood in front of Seurat’s Sunday Afternoon on the Island of La Grand Jatte and contemplated life.
What would you have done differently?
The weather wasn’t perfect, but being from the same climate I knew what I was in for. I’d love to see Chicago in the Spring or Fall. And if I do go back, I’ll know how to save some money: I flew from Detroit because flying from Canada to the States is prohibitively expensive most of the time. Upon returning home, I checked to see how much it would have been to take the train from Detroit, just out of curiosity. How’s four times less expensive sound? Ugh. Because of how much the train costs in Canada, I never thought it’d be that inexpensive to get to Chicago by train. And once you factored in getting to the Detroit airport and waiting for my flight, the length of travel would have been nearly the same. I can sit on a train for six hours to save $200, let me tell ya.
What advice do you have for someone travelling to Chicago?
Check prices on every available method of transportation before you leave or suffer my fate! *rattles chains*
I found a really cute hotel in a great part of town for a really good price by going off-season and by using a sell-off website. I had originally planned on booking with AirBnB, but the best room I could find was only $15 less than I paid for the hotel, and the part of town was much less central. Sometimes hotels really are better.
Definitely check out free tour guide services when you’re travelling. You’ll save money and see parts of the city you never would have otherwise. And you’ll probably get into arguments with your guide over Canadian stereotypes, but I digress…