Roller skate buying guide · trending with beginners
Chicago Roller Skates: Are They Good for Beginners?
Chicago is the skate a lot of people started on: when Indy Jamma Jones, a roller skating coach, skated a pair of Chicagos through Venice in 2019, three or four strangers stopped her to say those were their first skates, and she herself says she would have skated them until they fell apart as a kid. That is the whole case for them, and it is a real one. Be clear on the other side too: none of the skaters and coaches in our compilation recommends Chicago skates by name, and the two skaters we read who bought a Chicago both say not to. Both of them had the brand’s entry-level build; the listing beginners buy most on Amazon is the leather-lined one, which is a different build on paper, and nobody we could read has skated that one. So instead of an endorsement, this page checks its published specs against what the coaches we compiled ask of a first quad skate. On paper the leather-lined Chicago meets more of them than any other trending model on this site: a leather boot, an aluminium plate and an adjustable toe stop. What it does not publish is what both skaters complained about: the wheels.
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We do not print a price or Amazon’s ratings here: both change every day and with size and colour. Check them on the listing.
Why it is on this site: what “trending” means here
The Chicago quad skate sat in the top ten of Amazon.com’s own best-seller list for outdoor roller skates when we checked on 25 October 2026, with more customer reviews than any other skate in that list’s top thirty. That is a measure of what buyers choose, not of quality. It is why the page exists; it is not why you should buy it.
How we evaluated it
We have not skated the Chicago Quad Roller Skates ourselves, and nobody tested it for this page. We took the criteria that the coaches and skaters in our buying-guide compilation give for a first quad skate, each with its source and date, and checked the published specs against them, one by one. Where a spec could not be confirmed, we say so below.
What people who skated it report
These are the reports we could find and read from people who say they actually skated it, with their limits. We did not use Amazon customer reviews, which Amazon does not allow sites to reproduce.
- Indy Jamma Jones, roller skating coach (Planet Roller Skate, about 281,000 YouTube subscribers), video of 2019; she bought the cheapest Chicago she could find in a sporting-goods store, with Matt Mickey of Intuition Skate Shop; the description carries a discount code for an unrelated brand. First impression: the boot “doesn’t look so bad”, but the wheels, plate and toe stop were hard plastic rather than urethane. Skating to Venice and back: her skate slid out from under her on every push because the wheels did not grip, the trucks were loose and “squirrely”, the boot touched the wheel on turns, and dragging the toe stop did not stop her. After about half an hour the wheels were dented and chunking and the toe stop grinding away. Her verdict: enough to roll down your street and feel the breeze, but a toy skate with a real safety question once you can turn and stop; she recommends not getting them and saving for the step up, a Candi GRL or an Impala. She adds that three or four people in Venice told her Chicagos were their first skates (source, read 25 Oct 2026)
- Lindsey Skates, a quad skater of about three years (about 13,000 YouTube subscribers), video of 2025 after six months with the skates; bought with her own money on Amazon, the listing she calls Amazon’s best-selling Chicago, in pink. Out of the box they ran large, with no padding inside. The plate was metal, which she rates as the good part; the wheels felt plasticky and did not grip, especially on a rink’s wooden floor, and the tongue kept slipping to the side. She found everything “at least 50% harder” and fell far more than in her Moxi Beach Bunnies. Usable for an occasional smooth trail with friends; not for learning, and “do not get these” for a skatepark. Her verdict: she would not recommend them to a friend, because the wheels and toe stop you would replace in the first month cost about what a better skate does. She compares them with her first pair, Moxi Beach Bunnies, which had padding and grippier wheels (source, read 25 Oct 2026)
The specs against what coaches ask for
| What coaches ask of a first quad skate | Who says it | Chicago Quad Roller Skates |
|---|---|---|
| A firm, padded boot, ideally leather or suede | Lisa J (Boardwalk Skater, 2023); Dunbeezy, whose first check for a cheap skate is a leather boot (Dunbeezytv, 12 Aug 2024) | Meets it, on paper. Leather upper and lining on the Amazon listing we link to (read 25 Oct 2026). Lindsey Skates says the Chicago she bought on Amazon was not leather: there is more than one Chicago build, and the listing colour and model name decide which you get |
| A metal plate (aluminium or magnesium), never plastic | Lisa J; Dunbeezy, second check | Meets it. Aluminium base plate with adjustable trucks (Amazon listing); Lindsey Skates confirms the plate on hers was metal |
| Soft wheels outdoors, harder wheels indoors | Lisa J; Dirty Deborah Harry (Dirty School of Skate, 21 Jun 2022); Caro Hernandez, a Moxi rider, in a video published by Moxi (7 Oct 2020) | Not published. The listing gives no hardness. Both skaters who tried the entry-level Chicago describe wheels that felt like hard plastic and did not grip, outdoors or on a rink floor |
| 62-65 mm wheels for an adult beginner | Kelly, instructor at Skate Base London (9 Sep 2024) | Just under. 60 mm on the listing we link to; other Chicago listings say 58 mm. Kelly advises 62-65 mm |
| A height-adjustable toe stop rather than a fixed one | Dirty Deborah Harry; Dunbeezy, third check | Meets it. Adjustable toe stop (Amazon listing; Walmart’s listing of the same model calls it a 5/8-inch adjustable stop). Lindsey Skates swapped hers for a softer one and says the stock one is “not the most horrible” |
Who it suits, and who should look elsewhere
It suits someone who wants the classic rink look at the lowest price the brand name allows, skates smooth floors or paths now and then, and accepts that the wheels and toe stop are the first things they will want to replace.
Look elsewhere if you intend to learn properly, skate outdoors on rough ground, or try a skatepark. Both skaters who tried the entry-level Chicago say the wheels do not grip and that everything feels harder and scarier; Indy Jamma Jones points beginners one step up, to a Candi GRL or an Impala, and says that replacing the wheels and toe stop on a Chicago costs about what the step up would. If you have not chosen between quad and inline yet, start with quad vs inline: which to buy first.
Sizing
The Amazon listing sells unisex pairs labelled with a women’s and a men’s size one number apart (a women’s 9 is a men’s 8). Lindsey Skates found hers ran large out of the box. We could not read Chicago’s own size chart on 25 October 2026. See should you size up.
What we could not check
- Chicago’s own product page: we did not find it on 25 October 2026; the specs come from the Amazon listing, with retailer listings (Academy, Walmart) read for cross-checks and not linked.
- Wheel hardness, which the listing does not give.
- Which exact Chicago model each of the two skaters had: neither names it. Indy Jamma Jones bought the cheapest Chicago in a sporting-goods store in 2019 and describes plastic wheels, plate and toe stop; Lindsey Skates bought a pink pair on Amazon in 2025, says it is not leather, and found a metal plate. Neither description matches the leather-lined, aluminium-plate listing on this page point for point.
- Bearings: the listing says “semi-precision”, with no ABEC rating, below the ABEC 7 Kelly and Viktor Hald Thorup mention.
Where to see it
Nothing on this page needs a purchase. Pick your size and colour on Amazon.
Chicago Quad Roller Skates (leather-lined)
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Questions
Are Chicago roller skates good for beginners?
On paper the leather-lined Chicago meets three of the checks the quad coaches in our compilation give: a leather boot (Dunbeezy, Lisa J), an aluminium plate (Lisa J, Dunbeezy) and an adjustable toe stop (Dirty Deborah Harry). But the two skaters we read who bought a Chicago, Indy Jamma Jones and Lindsey Skates, both had the brand’s entry-level build and both say the wheels do not grip and make learning harder. No pro skater we compiled recommends Chicago skates by name.
Are Chicago skates good for outdoor skating?
The listing does not give a wheel hardness, so we cannot say. Both skaters who tried the entry-level Chicago describe hard, plasticky wheels that did not grip on concrete or on a rink floor; Lindsey Skates says a smooth trail is the safest use. Lisa J and Dirty Deborah Harry advise soft wheels outdoors.
What is the difference between the leather-lined Chicago and the cheaper Chicago?
Chicago sells more than one quad under its name. The listing on this page is the leather-lined one, with a leather upper, an aluminium plate and urethane wheels on its spec sheet. Indy Jamma Jones’s pair from a sporting-goods store had a plastic plate, plastic wheels and a plastic toe stop; Lindsey Skates’s pink pair from Amazon had a metal plate but no leather. Check the material and plate on the exact listing and colour you buy.