StoreDeal.ai store
Shop
  • Deals
  • Deal checker
  • Black Friday
  • Buying guides
  • Brands
  • Stores
Travel
  • Flight deals
  • Hotel deals
Company
  • Research
  • Press
  • Use in AI assistants
  • Contact
  • deal.ai apps
Black Friday 2026
  • Walmart
  • Best Buy
  • Target
  • TVs
  • Laptops
  • Headphones
  • Apple
  • Gaming
  • Vacuums
  • Kitchen
  • Toys
  • Smartwatches
  • Tablets
  • Furniture
  • Mattresses
© Deal.ai Inc.·2222 Ponce de Leon Blvd, Miami, FL 33134·support@deal.ai
TermsPrivacy
Deal.ai › Compare

Air Jordan 1 Retro High OG Shadow vs Air Jordan 1 Retro High OG Chicago

Both are Air Jordan 1 Retro High OGs with the same high-top build, leather upper and Nike Air branding, so the choice comes down to colorway and generation. The 2018 Shadow is the neutral, everyday pair and the older of the two releases. The Chicago is the louder red/white/black original and the one collectors chase, and its owners report thin insole cushioning and some pairs arriving with dry or cracked leather. Buy the Shadow to wear; buy the Chicago to own the grail colorway.

  • Choose the Air Jordan 1 Retro High OG Shadow if you want a versatile grey and black OG that works with everything and is easier to find unworn.
  • Choose the Air Jordan 1 Retro High OG Chicago if the red, white and black colorway is the point and you accept collector-grade scarcity and thinner cushioning.

Prices

  • Air Jordan 1 Retro High OG Shadow: $124.99 at Amazon (last seen Nov 13)
  • Air Jordan 1 Retro High OG Chicago: $99.97 at Shoe Palace (last seen Nov 2)
  • Difference: the Air Jordan 1 Retro High OG Chicago is $25.02 cheaper than the Air Jordan 1 Retro High OG Shadow at the latest prices (Nov 2 and Nov 13)
Jordan
Air Jordan 1 Retro High OG 'Shadow' 2018 555088-013

Air Jordan 1 Retro High OG Shadow

Air Jordan 1 Retro High OG 'Shadow' 2018 555088-013

5(8 ratings)
$124.99at AmazonChecked Nov 13
See all prices and details
Visit Amazon

Store links may earn us a commission. As an Amazon Associate, Deal.ai earns from qualifying purchases.

Pros
  • Original 1985 Shadow color blocking
  • High-quality leather upper
  • Neutral grey and black goes with everything
  • Easier to find in unworn condition
Cons
  • Less vibrant than Chicago or Bred
  • Older retro than the most recent OG releases
  • No extra lace set noted
JORDAN
Air Jordan 1 Retro High OG "Chicago"

Air Jordan 1 Retro High OG Chicago

Air Jordan 1 Retro High OG "Chicago"

$99.97at Shoe PalaceChecked Nov 2
See all prices and details
Visit Shoe Palace
Pros
  • Definitive original Chicago colorway
  • Padded collar and tongue add comfort
  • Two sets of laces included
  • Strong collector demand
Cons
  • Thin insole with little cushioning
  • Some owners report dry, cracking leather
  • Short laces and damaged boxes reported
  • Hard to find in new condition

What separates them

Air Jordan 1 Retro High OG ShadowAir Jordan 1 Retro High OG Chicago
ColorwayBlack leather with medium grey overlays and a black-and-white soleRed, white and black leather in the original 1985 Chicago palette
Release generation2018 OG retro of the 1985 Shadow2015 release, the collector-favored Chicago retro
WearabilityNeutral grey and black pairs with most outfitsBright red and white stands out and shows dirt and creasing faster
CushioningStandard AJ1 insole, no complaints reportedOwners report a thin insole with little cushioning
Leather condition reportsNo widespread leather complaintsSome owners report dry, cracking leather and short laces
Availability in new conditionEasier to find unworn as a more recent retroHarder to find unworn; mostly collector-market pairs
Collector demandSought after, but below the red-based originalsOne of the most sought-after original AJ1 colorways
In the boxStandard OG packagingShips with two sets of laces

Price history

$140.00$99.97
Nov 2Nov 13
  • Air Jordan 1 Retro High OG Shadow: lowest $124.99 on Nov 13 at Amazon.
  • Air Jordan 1 Retro High OG Chicago: lowest $99.97 on Nov 2 at Shoe Palace; $119.95 on Nov 12.

Prices at every store

Air Jordan 1 Retro High OG Shadow

  • GOATNew

    In stock

    $246.00+ $14.95 shippingChecked Nov 13
    Visit GOAT
  • Stadium GoodsNew

    In stockReturn policy

    $317.00Checked Nov 13
    Visit Stadium Goods
  • Chicpouchy StoreNew

    In stockReturn policy

    $317.00Checked Nov 13
    Visit Chicpouchy Store
  • AmazonNew

    Availability unknown

    As an Amazon Associate, Deal.ai earns from qualifying purchases.

    $124.99Free shippingChecked Nov 13
    Visit Amazon

Store links may earn us a commission.

All 4 stores and price history →

Air Jordan 1 Retro High OG Chicago

  • WalmartNew

    In stock

    $119.95Checked Nov 12
    Visit Walmart
  • Shoe PalaceNew

    Availability unknown

    $99.97Checked Nov 2
    Visit Shoe Palace
  • StockXNew

    Availability unknown

    $109.00Checked Nov 2
    Visit StockX
  • eBayNew

    Availability unknown

    $109.99Checked Nov 2
    Visit eBay

Also available at

  • WalmartCheck price at Walmart

Store links may earn us a commission.

All 8 stores and price history →

Specs compared

SpecAir Jordan 1 Retro High OG ShadowAir Jordan 1 Retro High OG Chicago
Brand—Jordan
Athletic shoe type—Basketball
Color—Red
Shoe category—Men's Shoes
Shoe width—Medium
Shoe closure—Lace-Up
Sport—Basketball
Insole material—Best Quality Material
Material—Best Quality Material
Gender—Male
Age group—Adult
Shoe collar height—High
Show all 25 specsShow fewer specs
SpecAir Jordan 1 Retro High OG ShadowAir Jordan 1 Retro High OG Chicago
Toe style—Closed Toe
Model—Air Jordan 1
Athlete—Michael Jordan
Casual & dress shoe style—Lace-Ups
Shoe heel style—Block
Heel height style—Flat Heel
Shoe sole material—Rubber
Pattern—Solid Print
Shoe size system—US Men's
Product line

What reviewers say

Air Jordan 1 Retro High OG Shadow

Owners of the 2018 Shadow praise the neutral grey-and-black look and the OG shape and branding. Many call the leather solid for a general release, though some find it stiffer than earlier OG retros. Complaints center on creasing and on paying more than for non-OG colorways.

What people mention
  • ColorwayPraisedOwners like the neutral black and grey look because it works with almost any outfit.
  • LeatherMixedMany find the leather solid for a general release, but some say it is stiffer than earlier OG retros.
  • CreasingCriticisedWearers report the toe box creases noticeably after regular use.
  • ShapePraisedBuyers say the 2018 pair keeps the OG high-top shape and Nike Air branding.

Air Jordan 1 Retro High OG Chicago

Reviewers are split on the Air Jordan 1 Chicago. Some praise the look, fit and comfort; others report poor quality, damaged pairs and thin cushioning.

What people mention
  • LookPraisedOwners say the red, white and black colorway looks better in person than in photos.
  • FitPraisedMost buyers report the shoe fits true to size.
  • ComfortMixedThe padded collar and tongue help, but the insole is thin and offers little cushioning.
  • Leather qualityCriticisedSome buyers describe the leather as dry and prone to cracking.

Questions and answers

Which is better for everyday wear?
The Shadow. Its grey and black upper hides creasing and dirt better, and owners do not report the thin cushioning or dry leather that some Chicago buyers mention.
Which colorway is more collectible?
The Chicago. It is the original red, white and black 1985 colorway and draws more collector demand than the Shadow, which is why unworn pairs are harder to find.
Do they fit the same?
Yes. Both are the same Air Jordan 1 Retro High OG last in US men's sizing, and owners say the Chicago fits true to size. The Shadow follows the same pattern.
Is the Chicago worth stepping up to over the Shadow?
Only if the colorway matters more than wearability. You get the grail look and an extra lace set, but thinner cushioning and more reports of dry leather than the Shadow.
Which has better build quality?
The Shadow has fewer quality complaints. Chicago owners report thin insoles, short laces and some pairs with dry, cracking leather, though many praise the look and fit.
Are these real basketball shoes?
They are basketball-styled high-tops with rubber soles and lace-up closure. Neither is a modern performance shoe; the cushioning is basic, especially on the Chicago.

Ask our shopping agent

It checks today's price at every store, compares the alternatives and answers in about a minute.

Enter to send, Shift+Enter for a new line

More comparisons

  • Air Jordan 1 Retro High OG 'Shadow' 2018 555088-013 vs Jordan Air Jordan 1 Retro High OG "Chicago Lost & Found"
  • Air Jordan 1 Retro High OG "Chicago" vs Jordan Air Jordan 1 Retro High OG "Chicago Lost & Found"
  • Jordan 1 Retro High OG SP Union LA Chicago Shadow vs Air Jordan 1 Retro High OG 'Shadow' 2018 555088-013
  • Jordan 1 Retro High OG SP Union LA Chicago Shadow vs Air Jordan 1 Retro High OG "Chicago"
—
Air
Theme—White
Insole color—White
Color category—White