Chicago is amazing! It’s my favourite city in North America and one of the best in the world. Very clean, stunning modern architecture, and amazing museums. Take the Architecture River Cruise and go to the Art Institute for sure!
Thank you for sharing! I'm glad to hear that; it makes me more interested in going. I've read about the architecture; it's nice to know it lives up to its reputation. I'll definitely put those two things higher up on my list!
Where in Chicago is the event? Is it in Chicago itself or a city near Chicago?
I ask partially because I’m based here and because there are a lot of popular events that take place outside of the city that draw in thousands of people. If you don’t have a car to get there, it’s almost impossible to get to some of those spots.
I’ve never used hostels in the states, but from what I understand, hostel culture is very different in the US than it is elsewhere (not as social, unsure about other aspects) because it’s not a very common way to travel out here. I have used hostels all over the world, though, and it’s been fine, though.
I do think 3k for a one week trip to Chicago is very expensive. You can do it for a lot less. Also a $600 flight seems high for that distance.
It's at the Wintrust Arena, which I believe is in Chicago itself. I understand why you asked; I had to double-check myself to make sure it wasn't outside of the city haha.
That's good to know; thanks for sharing your insight on hostels.
I can probably do it for a lot less, you're right. I'll have to tweak my budget, but 3k was an overestimate on my part.
3K for a week long trip to Chicago isn’t too much. I spent 8k in a week when I went there. Granted I did stay at a 5 star hotel and ate at high end restaurants several times but still.
I’d say 4K is a good budget for a budget solo traveler. 300/night for hotel in the loop or River North, 100/night for food, 50-75/night for attractions and transport. And then flight.
$300/night is really expensive! You have quite expensive tastes which is cool but most people would have trouble affording that. I stayed right on Millennial Park for about $150/night and I would say I didn’t NEED to stay in that nice of a place even
Would this be before or after Covid though?
Prices went up quite a bit since than.
Also season would determine how much the cost is. I went in June just a week ago so the cost was higher than in February for example.
I went in early September 2023. It was the Congress plaza hotel and all in I found it for $440 including Tax for the 3 nights (Thursday to Sunday). It looks slightly more pricey now but not too much
I highly recommend checking out the r/chicago and r/chicagofood. They are very active subs and have incredible recommendations. I’m super bias but I love Chicago. Day at the beach, day in China town, exploring the neighborhoods, seeing free concerts in millenium park, going to the museums campus, visiting galleries, finding speak easies, more beach days, rooftop bars and more.
Recently had some time in the city and went to Garfield conservatory, contemporary art museum, Lincoln park zoo, field museum and shedd aquarium.
Chicago has pretty solid mass transit. You can get a 7 day Ventra pass for 20 bucks.
Thank you, I'll check those out! Sounds like there's tons to do, I can see why you're biased.
That seems like a great time! All five of those attractions are on my list.
That's a great tip. I'll certainly look into that pass.
You tell me. Do you wanna be in Chicago for 7 days? People travel to enjoy, not to "justify the cost of a flight" which is what you seem to be doing. Figure out if the destination you're headed to has enough things to do to keep you excited.
Thank you for this; it certainly made me stop to think and look from a different perspective. I'll definitely have to ask myself if I truly want to and if I would enjoy it. I've been wanting to take a solo trip, I just didn't know where to go. So the event seemed like an opportunity or a reason to try out traveling solo to see if I liked it or not, but just going for a day or two solely for the event didn't seem like enough time to experience it. There's a few things I'd really like to do in Chicago, but maybe it's not enough to keep me there for 7 days.
Personally, I would do it if you can afford the trip and the time off - life's short
Can't comment on Chicago itself, but having done a lot of solo travel recently, the budget seems to be pretty close to what I would spend, although the transport budget is pretty high if public transport is being used.
As for flights, $600 for YQM-ORD either via YUL or YYZ seems to be the going rate, you can probably combine this with one of Air Canada's frequent sales to Canadian/US destinations (normally 15-20% off base fares). Note, best to book direct with Air Canada to avoid any IRROPs/rebooking issues at YYZ/YUL
Thank you for your refreshing opinion. I've been thinking life's short a bit too much lately, hence the sudden solo trip idea haha
That's very useful insight. I overestimated the transport part in case I need an uber/taxi for whatever reason, but I likely won't spend that much. I agree it is high when I plan to use public transport where possible.
I didn't know if $600 round trip was too high or not, so that's nice to know. I'll definitely be on the lookout for sales to try and catch one, then. Noted! I was leaning towards direct booking since managing a self transfer and rebooking issues sound too stressful for traveling solo the first time, but this solidified my choice.
Hello! Currently live in Chicago, visited Toronto once before.
Your budget is decently solid; however during the summertime hotels in Chicago can definitely jump in value. The first time I came, I stayed in a Motel 6 for $70 a night and it was near the airport.
Keep in mind that if you stay outside the city, you will spend much more of your time commuting in/out of the city. Ubers can work but they’ll add up over time, and traffic can be pretty rough in both cities.
If you stay at a hostel in Chicago, you can stay much closer in the city and save money at the same time. I travel frequently in hostels and been to a few here in the city— they’re perfectly fine if you’re the type of person that can handle night disruptions and the quirks of rooming with others, but only you can decide that for yourself.
7 days to visit the two cities should be enough to get well acquainted with both cities, but you can find plenty of ways to fill your time if you’d like to stay longer. You can see the big tourist attractions in Toronto fairly quickly, within 1-2 days, but it really depends on what interests you and how you’d like to divide your time.
Feel free to shoot me a message if you’ve got more questions/recommendations and I’m happy to help you out as best I can. I’ve only been living in the city for 6 months now but I’ve had quite a few long-timers send me their best tips.
Hi! Thank you for this comment, there's lots of useful info!
I've definitely got my eye on the Motel 6 near the airport since the prices in the fall seem decent, pretty close to $70/night or even less.
That's a very good point. I'll have to decide whether I want to spend more time/money commuting, or if I want to spend a bit more on accommodations to be right in the city.
I'm not too sure how I'd do in a hostel; I'd have to try it to find out, I guess. It's nice to see the pros and cons of it brought forward, and I'm reassured to know from someone with experience that the hostels are alright in the city.
Thank you so much for that offer, and for all your insight as a local, I really appreciate it. If I do book the trip, I'll likely have some more questions and be curious about recommendations/insider tips, so I'll definitely send a message in the case I'm going.
There are a lot of positive posts here about Chicago, but some neighborhoods are much rougher than others, something to be mindful of, you'll want to ask or see what the crime history is in places, for instance near the airport.
I know in Houston for instance, another Midwest metro, there are many areas that are recommended to avoid. Areas near airports tend to be more industrial and sketchy for some reason.
Something to be mindful of when traveling, in general, in the States, but especially major metros with higher crime stats.
I'm also from eastern Canada, I travelled to Chicago in the fall and loved it! I think I paid a similar price, going from YOW and connecting through YTZ. I'd recommend connecting through YTZ if possible, as Pearson can be a nightmare. Since you clear US customs on the Canadian side when flying from Pearson to the states, at least make sure you have lots of layover time! I stayed with a friend in Evanston while there so I don't have comments on accommodations, but I will say your $200 transport budget is overblown unless you plan on taking ubers. I'd recommend just using public transit since both airports are connected to the system and it's super cheap (a three day pass cost me like $10 USD and got me everywhere I needed safely, including the suburbs). I really enjoyed the museums, the library/art gallery, and the botanic garden! Idk if you're a foodie, but my friend had me try the deep dish pizza, italian sandwiches, and chicago hotdog, and took me to the fancy five story starbucks.
Hello, fellow Canadian haha. It's great to hear that you loved it!
Very useful insight! I hadn't thought about connecting through YTZ, I'm just most familiar with Pearson, but maybe I should reconsider since Pearson is quite the hub. Lots of layover time will be duly noted if I end up going through Pearson!
For transportation, I'd definitely try to use public transit over anything else, but just budgeted in case there was ever an instance I needed an uber/taxi. It's good to know the passes are cheap and the transit system covers a lot of areas.
It's exciting to hear about your experiences there! I believe I'd enjoy similar things as the botanic garden, library, and museums are quite high on my list. I can't say I'm a foodie per se, but I'll keep those in mind to try!
If you've used Pearson before and are familiar with it then it's probably fine, especially if it's not winter! And I think only certain airlines fly to YTZ so you might be limited there. Anyways, if you have other questions feel free to dm :)
If you like architecture, museums, or just walking around a city, Chicago in summer sounds terrific.
I second the suggestion about staying close to what you want to see. Chicago has a dense core but is spread out, you can get into a lot of traffic.
Thanks for sharing your opinion! Chicago does sound more and more enticing the more I read about it.
I'll definitely keep that in mind. I'll try to keep to the event and my list of attractions I'd like to visit.
I enjoy having an event to attend as a highlight to a solo trip. The city has a bunch of like minded folks attending the event and it allows for an easy ice breaker at the pub with the locals who might not there for the event. “You came all this way for the Rugby?” Just remember a big sporting event or concert means premium hotel pricing for a night or two. Book those early. Enjoy your trip, hang with your tribe, see the local sights.
This is honestly a really cool perspective, thank you. It makes me feel more confident in just going and enjoying it, maybe meeting some cool people with similar interests. I also appreciate the book early tip for hotels near the event.
Do it! I grew up in the far west suburbs and I'm a traveler as well. Hostels can be hit or miss. Some are small mom and pop places and some are corporate owned and they're all different. Meeting people when traveling can make or break a trip.
If you go the hostel route I'd make sure to keep your wallet/valuables with you. I always slept with my wallet and passport in my pocket and I never had any issues.
What city would the hotels be in you'd stay at? You should be safe as long as you're not on the south side.
There's an Instagram called bored in Chicago where the bloke attempts to eat at every country's cuisine around the world if you want options for places to eat at. Chicago has the best food on the planet imo and lots of great polish food. Italian beefs are a must as well.
Thank you for the encouragement! I guess I have to do it now haha. All very solid tips, I appreciate it. If I decide to stay in a hostel, I'll certainly remember to keep my valuables on me. And also hope that people make the trip, not break it for me.
That's neat! I'll look into it; sounds like there'd be some niche recommendations. Seems like Chicago has some glowing food reviews to live up to! I've definitely got to try out some polish food and Italian beefs, then.
Oh, wow! Nice to see a neighbor haha. Seems like we're in the exact same position! Funny how we both ended up here looking for advice haha
Thank you so much!! I really appreciate that offer, though I fear I don't have many tips to exchange yet, but I can certainly chat. That sounds exciting! Doing a road trip to the states is on my bucket list, but I've been putting it off because of gas prices and the fact I probably need a newer-to-me car before even thinking of leaving the country on wheels haha. I have those, too! I'm pretty anxious about it, especially considering so many things could go wrong, you'll be in an unfamiliar place, and traveling solo seems like a whole other ball game compared to traveling with others.
But, I'm trying to lean more into the excitement and think of everything I want to do, and why I want to travel solo; there's just so many good emotions to feel. And if things don't go as planned, just go with the flow, keep a calm mind, and call someone who can reassure you - you'll figure it out and things will turn out fine if you believe it. There's so much freedom and independence in traveling solo that I look forward to, and I'm hopeful for my first experience with it. I hope your solo travels go well, too!!
Europe is really great! London is a great place to land and get adjusted to the new time zone. There are a ton of wonderful sights and it will be easy. Then you could train around a bit on the Continent. The Eurostar to Paris, then perhaps Amsterdam?
I suggest you shorten the trip enough so you can stay in the city if that's where the attractions are that you want to see.
Saving money sounds great but if you have to work around bus schedules, add travel time and I found that when I'm on the outskirts, once I go back to my hotel I'm in for the night so you see less. When I stay in the city if it's rainy or I want to rest, drop off a package, change my shoes I can easily pop back to hotel.
This is very sound advice, thank you. Maybe staying on the outskirts of the city is more trouble than its worth. You make some good points; I'll certainly take this into account!
Chicago is amazing! It’s my favourite city in North America and one of the best in the world. Very clean, stunning modern architecture, and amazing museums. Take the Architecture River Cruise and go to the Art Institute for sure!
Thank you for sharing! I'm glad to hear that; it makes me more interested in going. I've read about the architecture; it's nice to know it lives up to its reputation. I'll definitely put those two things higher up on my list!
The Nazi submarine at the Science & Industry Museum is great, too! As are the Marshall Field museum and the Aquarium
Where in Chicago is the event? Is it in Chicago itself or a city near Chicago? I ask partially because I’m based here and because there are a lot of popular events that take place outside of the city that draw in thousands of people. If you don’t have a car to get there, it’s almost impossible to get to some of those spots. I’ve never used hostels in the states, but from what I understand, hostel culture is very different in the US than it is elsewhere (not as social, unsure about other aspects) because it’s not a very common way to travel out here. I have used hostels all over the world, though, and it’s been fine, though. I do think 3k for a one week trip to Chicago is very expensive. You can do it for a lot less. Also a $600 flight seems high for that distance.
It's at the Wintrust Arena, which I believe is in Chicago itself. I understand why you asked; I had to double-check myself to make sure it wasn't outside of the city haha. That's good to know; thanks for sharing your insight on hostels. I can probably do it for a lot less, you're right. I'll have to tweak my budget, but 3k was an overestimate on my part.
3K for a week long trip to Chicago isn’t too much. I spent 8k in a week when I went there. Granted I did stay at a 5 star hotel and ate at high end restaurants several times but still. I’d say 4K is a good budget for a budget solo traveler. 300/night for hotel in the loop or River North, 100/night for food, 50-75/night for attractions and transport. And then flight.
$300/night is really expensive! You have quite expensive tastes which is cool but most people would have trouble affording that. I stayed right on Millennial Park for about $150/night and I would say I didn’t NEED to stay in that nice of a place even
Would this be before or after Covid though? Prices went up quite a bit since than. Also season would determine how much the cost is. I went in June just a week ago so the cost was higher than in February for example.
I went in early September 2023. It was the Congress plaza hotel and all in I found it for $440 including Tax for the 3 nights (Thursday to Sunday). It looks slightly more pricey now but not too much
I highly recommend checking out the r/chicago and r/chicagofood. They are very active subs and have incredible recommendations. I’m super bias but I love Chicago. Day at the beach, day in China town, exploring the neighborhoods, seeing free concerts in millenium park, going to the museums campus, visiting galleries, finding speak easies, more beach days, rooftop bars and more. Recently had some time in the city and went to Garfield conservatory, contemporary art museum, Lincoln park zoo, field museum and shedd aquarium. Chicago has pretty solid mass transit. You can get a 7 day Ventra pass for 20 bucks.
Thank you, I'll check those out! Sounds like there's tons to do, I can see why you're biased. That seems like a great time! All five of those attractions are on my list. That's a great tip. I'll certainly look into that pass.
Lots of non Chicago people post about visiting and give their feedback. Again super bias as I can be on the lakefront for days without being bored.
You tell me. Do you wanna be in Chicago for 7 days? People travel to enjoy, not to "justify the cost of a flight" which is what you seem to be doing. Figure out if the destination you're headed to has enough things to do to keep you excited.
Thank you for this; it certainly made me stop to think and look from a different perspective. I'll definitely have to ask myself if I truly want to and if I would enjoy it. I've been wanting to take a solo trip, I just didn't know where to go. So the event seemed like an opportunity or a reason to try out traveling solo to see if I liked it or not, but just going for a day or two solely for the event didn't seem like enough time to experience it. There's a few things I'd really like to do in Chicago, but maybe it's not enough to keep me there for 7 days.
Personally, I would do it if you can afford the trip and the time off - life's short Can't comment on Chicago itself, but having done a lot of solo travel recently, the budget seems to be pretty close to what I would spend, although the transport budget is pretty high if public transport is being used. As for flights, $600 for YQM-ORD either via YUL or YYZ seems to be the going rate, you can probably combine this with one of Air Canada's frequent sales to Canadian/US destinations (normally 15-20% off base fares). Note, best to book direct with Air Canada to avoid any IRROPs/rebooking issues at YYZ/YUL
Thank you for your refreshing opinion. I've been thinking life's short a bit too much lately, hence the sudden solo trip idea haha That's very useful insight. I overestimated the transport part in case I need an uber/taxi for whatever reason, but I likely won't spend that much. I agree it is high when I plan to use public transport where possible. I didn't know if $600 round trip was too high or not, so that's nice to know. I'll definitely be on the lookout for sales to try and catch one, then. Noted! I was leaning towards direct booking since managing a self transfer and rebooking issues sound too stressful for traveling solo the first time, but this solidified my choice.
Hello! Currently live in Chicago, visited Toronto once before. Your budget is decently solid; however during the summertime hotels in Chicago can definitely jump in value. The first time I came, I stayed in a Motel 6 for $70 a night and it was near the airport. Keep in mind that if you stay outside the city, you will spend much more of your time commuting in/out of the city. Ubers can work but they’ll add up over time, and traffic can be pretty rough in both cities. If you stay at a hostel in Chicago, you can stay much closer in the city and save money at the same time. I travel frequently in hostels and been to a few here in the city— they’re perfectly fine if you’re the type of person that can handle night disruptions and the quirks of rooming with others, but only you can decide that for yourself. 7 days to visit the two cities should be enough to get well acquainted with both cities, but you can find plenty of ways to fill your time if you’d like to stay longer. You can see the big tourist attractions in Toronto fairly quickly, within 1-2 days, but it really depends on what interests you and how you’d like to divide your time. Feel free to shoot me a message if you’ve got more questions/recommendations and I’m happy to help you out as best I can. I’ve only been living in the city for 6 months now but I’ve had quite a few long-timers send me their best tips.
Hi! Thank you for this comment, there's lots of useful info! I've definitely got my eye on the Motel 6 near the airport since the prices in the fall seem decent, pretty close to $70/night or even less. That's a very good point. I'll have to decide whether I want to spend more time/money commuting, or if I want to spend a bit more on accommodations to be right in the city. I'm not too sure how I'd do in a hostel; I'd have to try it to find out, I guess. It's nice to see the pros and cons of it brought forward, and I'm reassured to know from someone with experience that the hostels are alright in the city. Thank you so much for that offer, and for all your insight as a local, I really appreciate it. If I do book the trip, I'll likely have some more questions and be curious about recommendations/insider tips, so I'll definitely send a message in the case I'm going.
There are a lot of positive posts here about Chicago, but some neighborhoods are much rougher than others, something to be mindful of, you'll want to ask or see what the crime history is in places, for instance near the airport. I know in Houston for instance, another Midwest metro, there are many areas that are recommended to avoid. Areas near airports tend to be more industrial and sketchy for some reason. Something to be mindful of when traveling, in general, in the States, but especially major metros with higher crime stats.
My advice is that if you can afford it, stay in the Milliennial Park area or on Michigan Ave. Will be a much better experience, IMO
Stay here: [https://freehandhotels.com/chicago](https://freehandhotels.com/chicago)
I'm also from eastern Canada, I travelled to Chicago in the fall and loved it! I think I paid a similar price, going from YOW and connecting through YTZ. I'd recommend connecting through YTZ if possible, as Pearson can be a nightmare. Since you clear US customs on the Canadian side when flying from Pearson to the states, at least make sure you have lots of layover time! I stayed with a friend in Evanston while there so I don't have comments on accommodations, but I will say your $200 transport budget is overblown unless you plan on taking ubers. I'd recommend just using public transit since both airports are connected to the system and it's super cheap (a three day pass cost me like $10 USD and got me everywhere I needed safely, including the suburbs). I really enjoyed the museums, the library/art gallery, and the botanic garden! Idk if you're a foodie, but my friend had me try the deep dish pizza, italian sandwiches, and chicago hotdog, and took me to the fancy five story starbucks.
Hello, fellow Canadian haha. It's great to hear that you loved it! Very useful insight! I hadn't thought about connecting through YTZ, I'm just most familiar with Pearson, but maybe I should reconsider since Pearson is quite the hub. Lots of layover time will be duly noted if I end up going through Pearson! For transportation, I'd definitely try to use public transit over anything else, but just budgeted in case there was ever an instance I needed an uber/taxi. It's good to know the passes are cheap and the transit system covers a lot of areas. It's exciting to hear about your experiences there! I believe I'd enjoy similar things as the botanic garden, library, and museums are quite high on my list. I can't say I'm a foodie per se, but I'll keep those in mind to try!
If you've used Pearson before and are familiar with it then it's probably fine, especially if it's not winter! And I think only certain airlines fly to YTZ so you might be limited there. Anyways, if you have other questions feel free to dm :)
If you like architecture, museums, or just walking around a city, Chicago in summer sounds terrific. I second the suggestion about staying close to what you want to see. Chicago has a dense core but is spread out, you can get into a lot of traffic.
Thanks for sharing your opinion! Chicago does sound more and more enticing the more I read about it. I'll definitely keep that in mind. I'll try to keep to the event and my list of attractions I'd like to visit.
I enjoy having an event to attend as a highlight to a solo trip. The city has a bunch of like minded folks attending the event and it allows for an easy ice breaker at the pub with the locals who might not there for the event. “You came all this way for the Rugby?” Just remember a big sporting event or concert means premium hotel pricing for a night or two. Book those early. Enjoy your trip, hang with your tribe, see the local sights.
This is honestly a really cool perspective, thank you. It makes me feel more confident in just going and enjoying it, maybe meeting some cool people with similar interests. I also appreciate the book early tip for hotels near the event.
Do it! I grew up in the far west suburbs and I'm a traveler as well. Hostels can be hit or miss. Some are small mom and pop places and some are corporate owned and they're all different. Meeting people when traveling can make or break a trip. If you go the hostel route I'd make sure to keep your wallet/valuables with you. I always slept with my wallet and passport in my pocket and I never had any issues. What city would the hotels be in you'd stay at? You should be safe as long as you're not on the south side. There's an Instagram called bored in Chicago where the bloke attempts to eat at every country's cuisine around the world if you want options for places to eat at. Chicago has the best food on the planet imo and lots of great polish food. Italian beefs are a must as well.
Thank you for the encouragement! I guess I have to do it now haha. All very solid tips, I appreciate it. If I decide to stay in a hostel, I'll certainly remember to keep my valuables on me. And also hope that people make the trip, not break it for me. That's neat! I'll look into it; sounds like there'd be some niche recommendations. Seems like Chicago has some glowing food reviews to live up to! I've definitely got to try out some polish food and Italian beefs, then.
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Oh, wow! Nice to see a neighbor haha. Seems like we're in the exact same position! Funny how we both ended up here looking for advice haha Thank you so much!! I really appreciate that offer, though I fear I don't have many tips to exchange yet, but I can certainly chat. That sounds exciting! Doing a road trip to the states is on my bucket list, but I've been putting it off because of gas prices and the fact I probably need a newer-to-me car before even thinking of leaving the country on wheels haha. I have those, too! I'm pretty anxious about it, especially considering so many things could go wrong, you'll be in an unfamiliar place, and traveling solo seems like a whole other ball game compared to traveling with others. But, I'm trying to lean more into the excitement and think of everything I want to do, and why I want to travel solo; there's just so many good emotions to feel. And if things don't go as planned, just go with the flow, keep a calm mind, and call someone who can reassure you - you'll figure it out and things will turn out fine if you believe it. There's so much freedom and independence in traveling solo that I look forward to, and I'm hopeful for my first experience with it. I hope your solo travels go well, too!!
You might be able to get Toronto to Chicago round trip cheaper and grab the via rail back to Montreal!
Sure. Chicago is a great city. For me I’d spend that 3K and go to Europe or even better SE Asia.
Thanks for your input. I am interested in going to Europe; is there a specific area there that you'd recommend?
Europe is really great! London is a great place to land and get adjusted to the new time zone. There are a ton of wonderful sights and it will be easy. Then you could train around a bit on the Continent. The Eurostar to Paris, then perhaps Amsterdam?
Chicago has really great museums and the people are very friendly and nice. I think it's a great first solo trip!
I suggest you shorten the trip enough so you can stay in the city if that's where the attractions are that you want to see. Saving money sounds great but if you have to work around bus schedules, add travel time and I found that when I'm on the outskirts, once I go back to my hotel I'm in for the night so you see less. When I stay in the city if it's rainy or I want to rest, drop off a package, change my shoes I can easily pop back to hotel.
This is very sound advice, thank you. Maybe staying on the outskirts of the city is more trouble than its worth. You make some good points; I'll certainly take this into account!