Chicago Flag Men Long Sleeve Cycling Jersey

~~€53,00 EUR~~ €37,10 EUR

In stock - Ready to be shipped

Estimated delivery between 11 June and 14 June. Order within .

Quantity

Height (cm) & Weight (kg) — Sizes XXS to XL
Size	XXS	XS	S	M	L	XL
Height	148–155	153–160	158–165	163–170	168–175	173–180
Weight	40–45	45–50	50–55	55–60	60–65	65–70

Height (cm) & Weight (kg) — Sizes 2XL to 6XL
Size	2XL	3XL	4XL	5XL	6XL
Height	178–185	183–190	188–195	193–200	198–207
Weight	70–75	75–80	80–85	85–90	90–100

Tops Measurements — Sizes XXS to XL
Size	XXS	XS	S	M	L	XL
Chest (A)	79	84	89	94	100	106
Front (B)	49	51	53	55	57	59
Back (D)	61	63	65	67	69	71

Tops Measurements — Sizes 2XL to 6XL
Size	2XL	3XL	4XL	5XL	6XL
Chest (A)	112	118	124	130	136
Front (B)	61	63	65	67	69
Back (D)	73	75	77	79	81

Pants Measurements — Sizes XXS to XL
Size	XXS	XS	S	M	L	XL
Waist (E)	50–72	52–74	54–76	56–78	58–80	60–82
Long (F)	38	40	42	46	50	54
Inseam (G)	14	16	18	20	22	24

Pants Measurements — Sizes 2XL to 6XL
Size	2XL	3XL	4XL	5XL	6XL
Waist (E)	62–84	64–86	66–88	70–92	74–96
Long (F)	58	62	66	70	74
Inseam (G)	26	28	30	32	34

Height (cm) & Weight (kg) — Sizes XXS to XL
Size	XXS	XS	S	M	L	XL
Height	145–158	154–164	160–168	164–172	168–172	170–180
Weight	40–45	45–50	50–55	55–65	65–70	70–77

Height (cm) & Weight (kg) — Sizes 2XL to 5XL
Size	2XL	3XL	4XL	5XL
Height	173–183	178–192	181–196	185–200
Weight	77–85	85–92	92–99	99–106

Tops Measurements — Sizes XXS to XL
Measurement	XXS	XS	S	M	L	XL
Chest (A)	85	89	93	97	101	105
Front (B)	49	51	53	55	57	58
Back (D)	65	67	69	71	73	75
Sleeve (F)	68	70	72	74	76	78

Tops Measurements — Sizes 2XL to 5XL
Measurement	2XL	3XL	4XL	5XL
Chest (A)	109	113	124	130
Front (B)	60	62	64	66
Back (D)	77	79	81	83
Sleeve (F)	80	82	84	86

Pants Measurements — Sizes XXS to XL
Measurement	XXS	XS	S	M	L	XL
Waist (E)	58–80	60–82	62–84	64–86	66–88	68–90
Long (F)	92	94	96	98	100	102
Inseam (G)	58	60	62	64	66	68

Pants Measurements — Sizes 2XL to 5XL
Measurement	2XL	3XL	4XL	5XL
Waist (E)	70–92	72–94	74–96	76–98
Long (F)	104	106	108	110
Inseam (G)	70	72	74	76

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Buy 2 Cycling Sets and Get a Free Jersey

TwoSetsFreeJersey

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Chicago Flag Men Long Sleeve Cycling Jersey drew its inspiration from the iconic four-star banner that has flown over the Windy City for generations. Designed for riders who carried their civic pride through every mile, this jersey channeled the bold geometry and unmistakable color palette of Chicago's beloved flag. It became a favorite among urban cyclists and group ride crews across the city's lakefront paths and neighborhood streets.

Lightweight, breathable fabric engineered for comfort on long rides
Full-length sleeves with light blue coloring echoing the flag's iconic pale blue stripes
Red side panels add a striking contrast and nod to Chicago's civic colors
Rear panel features a detailed Chicago flag graphic with white city skyline illustration along the hem
Relaxed athletic cut suitable for layering in transitional weather
Three rear pockets for ride essentials
Machine wash cold, hang dry to preserve graphic vibrancy
Available in standard men's sizing — consult the size chart for a performance-oriented fit

The four red stars and pale blue stripes of Chicago's municipal flag have become one of the most beloved and widely recognized city symbols in all of America, proudly worn by Chicagoans on everything from tattoos to water towers. This long sleeve jersey channels the fierce civic pride of the Windy City, wrapping riders in those iconic bands of blue and white with bold red stars standing for pivotal moments in the city's storied history. Along the lower hem, a silhouetted skyline evokes the lakefront panorama that has greeted countless riders pushing through headwinds on the Lake Shore Trail. Chicago has always been a cycling city at heart — from the golden age of six-day races at the old Coliseum to the modern pelotons weaving through Millennium Park. Wearing these colors on a long ride is a declaration that no matter where the road takes you, you carry a piece of Chicago with you.

Crafted with Passion, Tailored for You

At Vintage Cycling, we believe that every cyclist deserves apparel that’s as unique as their journey. That’s why every piece in our collection, from our heritage jerseys to our timeless caps and complete outfits, is made to order. This personalized approach ensures that what you wear is exclusively yours, embodying both the spirit of vintage cycling and your individual style.

Ethically Manufactured, Globally Loved

Our commitment to sustainability and quality guides every stitch and seam. Proudly manufactured independently in China, our products are the result of meticulous craftsmanship and ethical practices. By choosing Vintage Cycling, you’re not just getting apparel; you’re wearing a piece of art that tells a story, supports fair labor, and champions the environment.

Join the Vintage Cycling Family

With every order, you’re not just purchasing an item; you’re joining a community of cycling enthusiasts who value history, quality, and the bespoke craftsmanship of our made-to-order collections. Whether you’re conquering new trails or relishing scenic routes, Vintage Cycling outfits you for the journey ahead with pieces that are as enduring as your passion for cycling.

Shipment processing time
All orders are processed within 1-3 business days and made ready for shipment.
If we are experiencing a high volume of orders, order processing may be delayed by a few days. If there will be a significant delay in shipment of your order, we will contact you via email.

Delivery Times
Delivery times will depend on country, but will take a minimum of 5 days, but typically around to 7-10 days for deliveries to the UK, Europe, the United States and Canada. In some rare cases, deliveries could take up to two weeks.

Please note: Import duties, taxes, VAT, or customs fees may apply for international orders. These charges are not included at checkout and are the responsibility of the customer.

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Chicago Flag Men Long Sleeve Cycling Jersey

~~€53,00 EUR~~ €37,10 EUR

Our customers tell it better than we do!

Excellent

4.5

/ 5

Quality outfit! 😍

Quality great, received item in 10 days Quality great, received item in 10 days Quality great, received item in 10 days

Melvin Smith

Just what i needed

Brilliant retro cycle cap !! Brilliant retro cycle cap !! Brilliant retro cycle cap !!

Elliot Oxley

AAA+++

Very cool, authentic and suitable race shirt Very cool, authentic and suitable race shirt Very cool, authentic and suitable race shirt

Julain Tempfer

So nice

A vintage cycling jersey set, Comfortable and beautiful. Im so proud of it ! The history of... A vintage cycling jersey set, Comfortable and beautiful. Im so proud of it ! The history of... A vintage cycling jersey set, Comfortable and beautiful. Im so proud of it ! The history of...

Benjamin Limonet

Quality outfit

Good quality correct sizing, Will buy more in future. Good quality correct sizing, Will buy more in future. Good quality correct sizing, Will buy more in future.

Roger Webb

Peugeot Shell retro

Sono molto contendo della divisa retro Peugeot Shell Sono molto contendo della divisa retro Peugeot Shell Sono molto contendo della divisa retro Peugeot Shell

Enrico Taramasco

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Buy 2 Cycling Sets and Get a Free Jersey, Use Discount Code "TwoSetsFreeJersey"

Our latest retro cycling kits have just landed, bringing fresh additions that pair beautifully designed jerseys with matching shorts for a complete race-ready look. Each kit draws on the rich visual heritage of professional cycling, reimagining classic colour palettes, sponsor logos, and team liveries in comfortable modern fabrics. Riders love the convenience and sharp aesthetic of a coordinated set — there's something undeniably satisfying about rolling out in a head-to-toe ensemble that echoes the golden eras of the sport. Whether you're drawn to the bold graphics of the 1980s or the understated elegance of earlier decades, these new arrivals deliver instant style on every ride.

From kits inspired by famous riders' iconic team colours to designs that celebrate legendary Grand Tour stages and one-day classics, this collection showcases the very best of what we've been working on. You'll find both short sleeve and long sleeve options, each carefully matched with retro-styled shorts or tights to create a cohesive look that turns heads at every café stop. The details matter — period-accurate typography, authentic sponsor placement, and era-appropriate colour blocking all come together to honour the history behind each design. Every kit is crafted with modern performance materials, so you get the vintage look without sacrificing breathability, stretch, or comfort on longer rides.

If a particular jersey catches your eye but you'd prefer to mix and match, browse our full range of all cycling jerseys or pick up standalone retro cycling shorts to build your own custom combination. Don't forget to complete the look with a classic cycling cap for that finishing touch of peloton authenticity. We're constantly adding new designs to the shop, so bookmark this page and check back often — your next favourite kit might be just around the corner.