Rick Steves 21inch carry on bag - replace the 2 wheels

Can't help with Chicago but have you checked Amazon?. They actually sell replacement wheels for luggage.

Did you ask Rick? I don't have their luggage, but they seem to have a generous replacement policy - or maybe they can recommend a repair shop.
Before buying replacement wheels, unzip the lining and check whether the current wheels are plastic clipped into place, or bolted/screwed on. The latter should be replaceable.

Both of our rolling carry on bags had the wheels worn out. RS store had no solutions for us. My husband is a jack of all trades and replaced the wheels. I think he unzipped the interior and got to the worn out wheels. I took one to Goodwill and bought an old bag with good same size wheels. They then were installed. If you have to replace any screws be sure they are stainless steel. Our at home solution cost less than $5. Worn out wheels show you have done a lot of traveling. Our bags have been all over the world. Be sure to get a price for wheel replacement. A new bag may be just a little more. Our old bags,20 years, are actually just a little too big for the newer European carry on size.

Irv's luggage store moved up to Vernon Hills. They do repair also and used to be (and may still be) the one that O'Hare airlines would send things to. I have never had repair by them but I have bought luggage from them when they were in their old spot and they were very knowledgeable and helpful in my search.

Have had repairs done by Irv's and they do a nice job. But as mentioned above you might want to check the cost before making a decision...a replacement might be a better idea.

Look inside the bag. There should be a manufacter's tag that will tell you who made the bag. (As an example, for the last few years Rick's bags have been made by Ricardo of Beverly Hills.) Contact the manufacturer on the tag and ask if they can recommend someone.

I also agree that you should get a price before getting the job done. It might turn out that for a little bit more, you can buy a new bag when it goes on sale.

Thomas, if you have 2-wheeled bags (we do and LOVE them), there's been a lot written about replacing broken wheels with in-line skate wheels. Look for a shop which repairs in-line skates and/or skateboards or do it yourself. You can do your own research for what's available locally for you but just a little background....

https://www.simplemost.com/heres-flight-attendants-say-suitcase-wheels-easier-travel/

Our 14 year-old Travel Pros have been through the mill and are still going strong (yay!) but since we're unlikely to find new bags with their perfect (for us) configuration again, we'd go with skate wheel replacements if they needed repairs.

My sister was a flight attendant and always had her rolling suitcase wheels changed to skate board wheels. Had forgotten about that upgrade. She flew Beijing and Hong Kong so had low cost replacement. Don’t know why suitcases don’t come standard with quality wheels. Maybe the RS store should take note of this simple upgrade.

Maybe a dumb question, but since I rarely use a two-wheeler, how exactly do the wheels typically fail? Worn out? Come off the axles?Crack in the hub? I'd be interested in knowing what the replacement entails.

The outside plastic cover gets thin, cracks and then just partially falls off. It almost doesn’t roll so much effort to pull. This takes place over time gradually. We don’t look at our wheels but you definitely know there’s a problem when it gets bad.

The wheel-destruction process will be massively accelerated if the frame of the bag gets slightly bent, causing the wheel not to be in the original rolling position. At that point you're likely to be dragging the wheel rather than rolling it, and it will no longer be round. I suspect the frames of cheap bags are less sturdy than those of more expensive bags, but even a good bag can probably be ruined if a very heavy bag is dropped on its edge.

One other thing: Surfaces other than smooth sidewalks are an extra challenge to luggage wheels. It has seemed to me that this issue is worse if the bag is very heavy. I often lift my bag over minor rough spots, and I certainly never roll it down stairs or even down curbs.