Just-because solo trip to freezing Chicago

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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.

Car selfie!
Car selfie!

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.

Georgia O'Keefe's Cow's skull with calico roses
Georgia O’Keefe’s Cow’s skull with calico roses

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…

Comments on Just-because solo trip to freezing Chicago

  1. I think solo trips are great. they tend to be really relaxing and, like you said, provide much needed ‘me’ time.

    I am in Canada too – and Chicago is really the last major US city i have never visited. I must get on that!

  2. Chicago in the summertime is where it’s at! Lalapalooza, Taste of Chicago, the Air Show, I could go on and on!!!

    Bravo to you for braving the horrific Chicago winters. You’ve only scratched the surface of this gorgeous town and what a good review. 🙂

    • I have to politely semi-disagree. My extended family is from Chicago and I have visited (relatively long term visits 2 weeks – a month) in most seasons. I agree there are more activities in the summer but its also really hot and very crowded. If you’re looking to go to museums and things good luck because its going to be packed! Personally I don’t mind the winters since there are less people. I think I would suggest something like going in the fall or spring when the weather is nicer and there’s still plenty to do than in the winter but its less crowded.

      • To piggyback AmeliaJane, come here (Chicago) pretty much anytime after Labor Day. Less tourists, not hellishly hot as the summer, but still warm and less humid (usually) well into October.

        Also, commuter pro-tip: if you’re into architecture along the Chicago River, hop a water taxi instead of the actual architecture tour. If you don’t mind the lack of narration, you can see the same gorgeous sights for $3 one-way. Or if you just want to get from the Loop near Union Station/Ogilvie to anywhere near the lake, take the water taxi. It also runs to Chinatown on an infrequent schedule.

  3. YAY CHICAGO POST! It’s so funny about that Seurat scene in Ferris Bueller’s Day Off — in real life, there are always tons of people standing right in front of it. 😉

    And I can’t believe that free greeter service worked out so well! What an amazing way to see things with a local (who doesn’t get lost like I do!). 😉

    I recommend coming during one of the times when the Renegade Craft Fair is going on (September is ideal). I think it would be right up your alley and lots of other festivals are going on around that time.

  4. The Amtrak Wolverine route from Detroit to Chicago is delightful! I used to commute to Michigan for work most weeks and although the train took twice as long as driving, the price was lower and it was an exceptionally relaxing ride. I’d highly recommend it!

    • The early morning or late night trains are great because there are fewer people and being rocked to sleep by train movement is the best.

      A random caution about the train though- they cannot change the thermostat while moving. When I was on it the temperature climbed from about 30 degrees F to close to 60, but the heat never turned off. Lots of sweaty bodies by the time we hit our next stop and could turn it off.

  5. Yay solo travel! I’m doing that soon. Well, I’ve traveled alone a lot, but always to go see and stay with friends. Staying in a hotel or hostel would be new. I’ve just booked tickets to Japan for a late summer trip, and I’m really excited but not quite sure what to expect. Whatever happens, it should make an interesting post.

    That Global Greeter thing sounds like an excellent idea. I’m really impressed at how much yours planned for you. (And no, I didn’t see any in Japan, but maybe there’s something similar.) Glad you had a great time!

    • Wow your upcoming trip sounds incredible! We’d love to hear about it!

      As for City Greeters in Japan, a Google search brought this up http://tokyogreeter.jimdo.com/

      “TOKYO GREETERS, which is provide by TOKYO FREE GUIDE, offers overseas visitors a free tour in and around Tokyo, which has a myriad of exciting and appealing attractions. We will take you to look around at your request, free of charge, including Kamakura, Hakone, or Nikko.”

      Not the same organization but definitely the same idea!

  6. I want to know more about this greeter biz! I would LOVE showing off my hometown to traveling peeps. In another life, I would totally be a tour guide. Maybe even in this life if I can find people who are interested in the random tidbits of info in my head.

  7. Chicagoooooooo (*sobs*) My boyfriend and I lived there last year, and we both miss it terribly. I’m glad you had an awesome trip! I totally agree that everyone needs to visit the Art Institute at least once.

    I noticed your shoutout to Toronto, which is a place I’ve always wanted to visit but I know almost nothing about. I’d love some recommendations!

    • I’ve never been to Chicago, but I’ve been living in Toronto for about a decade now. The official Tourism Toronto website: http://www.seetorontonow.com/
      If you like cultural stuff, the Royal Ontario Museum (ROM), the Art Gallery of Ontario (AGO) & the Bata Shoe Museum are pretty fun times. Ripley’s just opened a big aquarium (no dolphins/whales) but I haven’t been yet, because it is new so it is super busy. There’s the big zoo (the controversial elephants have since been handed over to a sanctuary), a small, free zoo in High Park and a working farm in Riverdale which is great for kiddos.
      The Steamwhistle Brewery downtown does tours, and it is in a historical train-related building.
      Lots and lots of festivals in the warmer months: Nuit Blanche, TIFF, Pride, Word on the Street (so many books and authors!!), etc.
      What do you like to do?

        • Toronto is fantastic, for real. It’s consistently in my top three favourite cities (and I have been to a a lot of big cities around the world). There’s just something about it. *sigh*

          My fav parts of Toronto are Queen Street West (shopping that gets weirder and cooler the farther west you go), Kensington Market (thrift stores galore), the Danforth (Greek Town), and Queen’s Park (pretty park in the middle of the city with/near historic buildings).

          • I worked at the edge of Kensington Market for five years and it was the best. All those delicious food options for lunch crammed into that little radius. Plus thrift store shopping. So good.
            Queen West is not what it was – gentrification has really gotten a good foothold the last few years, but there are still a few awesome spots left like Fashion Crimes & Misdemeanors (the Silver Snail comic shop moved to Yonge, Peach Beserk closed the physical store . . . sad face).

            Caroline, you left Chinatown (Spadina) off your list! So many low priced things and delicious noms!

  8. My favorite OffBeat hotel is in Chicago! You MUST stay at the House of Two Urns Bed & Breakfast. It has delightfully morbid decor (skulls, poetry about death, crows…), themed bedrooms, homemade breakfast, and it’s right on the Blue Line to get you anywhere you want to go in the city.

  9. Yay solo trips! Solo trips are the best. All the FREEDOM. This sounds like a really cool one.

    Also I totally forgot about being able to submit travel stories to OBH&L. I’m going on a solo trip to Budapest in the autumn and you can bet I’ll submit that!

  10. I visited Chicago with my (now ex) huband in October 2012. We took a train across about 12 US cities, and let me tell you without a doubt that Chicago was my favorite.

    Best part of the trip, the Segway tour we took across the city. We did it beginning late evening and it ended at night. It took us EVERYWHERE we wanted to see. I can’t even remember most of the places now, but it was so much fun! We learned how to use the segways, seen all the great sites of Chicago at dusk, and it was even a private tour, because there were only two of us. I guess it would be more busy in the summer, but I’d still say it’s totally worth it! We even learned some great history facts about the city while on our Segways. The guide was very professional while still being very fun and interactive!

    They have a website, and operate in other cities as well. I think they’re called City Segway tours or something like that. It’s a blue logo if you google them. Totally recommended for anyone’s trip to Chicago!

  11. I have such a love affair with Chicago. Thank you so much for mentioning the greeter thing. I consider myself travel-savvy, and I had NO. CLUE. this was a thing. None! I can’t wait to use this service the next time I travel.

  12. Sounds like a great trip! I’ve been to Chicago a few times, and I have always enjoyed my time there. Went to The Taste of Chicago last summer and watched Jill Scott perform, which was a lot of fun.

    I’m curious. What is the name of the cute boutique hotel that you stayed at? Sounds worth checking out! =)

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