The "Chicago" colorway is arguably the most iconic in Air Jordan history. It is the palette that introduced the world to the signature line and the one that continues to shape how people view the brand today.
With so shoes models carrying that familiar red, white, and black mix, each tells a slightly different story about the era it came from. Some pushed design forward. Others kept things simple and stayed close to the original blueprint.
With the Air Jordan 40 "Chicago" arriving earlier this month, it felt like the right time to take a step back and rank the 8 best "Chicago" Air Jordans ever released.
8. Air Jordan 40 "Chicago"
The Air Jordan 40 "Chicago" lands at number eight because it's still new. The shoe dropped earlier this month and brought a modern twist to a legendary color story.
The design pulls small cues from past silhouettes without leaning too hard on nostalgia. That makes the "Chicago" colorway feel fresh again. The red accents sit clean on the white base while the black details tie everything back to the Bulls era.
It is a new chapter for the Jordan line and a reminder that "Chicago" themes are still here. This pair will likely grow on people as more colorways release and the model gets real court time. It is early, but the potential is there.
7. Air Jordan 10 "Chicago Bulls"
The Air Jordan 10 "Chicago Bulls" sits at 7 because it captures a moment that often gets overlooked. The 10 was a celebration of Michael Jordan’s career at the time, with his accomplishments listed on the outsole.
The "Chicago Bulls" colorway fits this story well, of course. The white leather upper pairs with black and red details to create a simple but sharp look. The model never reached the cultural height of the 1 or 11, but it has a loyal following.
People appreciate its clean build and easy wearability. This pair feels tied to the heart of the Bulls years without trying too hard. It is an underrated entry in the "Chicago" line that has aged well.
6. Air Jordan 2 "Chicago"
The Air Jordan 2 "Chicago" remains one of the most divisive shoes in the entire Jordan lineup. Some people swear by its Italian-inspired luxury feel. Others struggle to connect with its wildly different design.
Still, the "Chicago" colorway gives life. The white leather base looks crisp with the red heel details and black trim. The shoe carries a certain luxury that no other early Jordan offers. It fits a specific outfit and has a specific audience.
That is part of its charm and the 2 is finally getting proper respect again with new retros and collaborations. This"Chicago" version stands above the rest because it defines the model’s identity better than any other release.
5. Air Jordan 13 "Chicago"
The Air Jordan 13 "Chicago" brings a different energy to the list. The white leather upper keeps everything clean, while the red suede adds the pop people expect from a "Chicago" pair.
The hologram on the heel makes the shoe recognizable very quickly. The 13 always feels connected to late-career MJ and the final Bulls run. The "Chicago" colorway works because it balances flash with maturity.
It does not need loud details to stand out. It simply looks right every time. This model sits comfortably in the middle of the ranking because it is loved but not overdone. It's returning again in 2026, so this look could see a revival.
4. Air Jordan 1 High x Union LA "Chicago Shadow"
The Union LA "Chicago Shadow" climbs to number 4 because it reimagines the "Chicago" story without losing its soul. This pair blends "Chicago" colors with the "Shadow" look, and the result feels surprisingly authentic.
The exposed stitching, vintage styling, and mismatched tones give the shoe a worn-in character. It almost looks like something pulled from an old collector’s closet. Union managed to honor the original while creating something new.
The design is playful but still grounded in Jordan history. The collaboration was also made headlines in the sneaker world. Mixing two iconic colorways had never been seen this way before, and Jordan & Union LA hit it out of the park.
3. Air Jordan 1 High x Off-White "Chicago"
The Off White "Chicago" earns the third spot because it changed sneaker culture. Virgil Abloh took one of the most famous sneakers ever and rebuilt it with a raw, broken-down aesthetic.
The exposed foam, bold text, and stitched Swoosh signaled a complete shift in design. This pair turned the "Chicago" colorway into something experimental without disrespecting the original. It sparked a wave of deconstruction across the industry and cemented Virgil’s place in sneaker history.
People still view this shoe as a turning point for modern collaborations. Its influence is impossible to ignore. It is not just a remix, it's a cultural marker that represented a new era.
2. Air Jordan 1 Low Retro OG "Chicago"
The Air Jordan 1 Low Retro OG "Chicago" sits at number 2 because it gives the "Chicago" colorway a different feel. The Low is lighter, more casual, and easier to wear daily.
The color placement still carries the same energy as the High, but the profile changes everything. This model has become a favorite for people who want iconic history without the bulk of a high top. The 2025 retro helped bring new attention to the pair.
It looks great with almost anything and stays true to the original design. The Low delivers a relaxed version of the "Chicago" theme without losing any of the impact that defines the colorway.
1. Air Jordan 1 OG 1985 "Chicago"
The 1985 "Chicago" sits at number one without any debate. This is the shoe that started everything. The leather, the shape, the color placement, and the story remain unmatched.
Every "Chicago" release traces back to this moment. The original pairs hold a presence that is impossible to replicate. The aging leather and vintage shape tell a clear story of the era.
This shoe represents the beginning of Michael Jordan’s signature line and the birth of modern sneaker culture. Nothing since has surpassed its importance. The 1985 "Chicago" is the blueprint for what a legendary sneaker looks like. It is the obvious choice for the top spot.
