---
title: "Men's Boots on sale in Chicago, IL: up to 47% off | Aisles"
description: "13 products in Men's Boots reported in stock below their regular price in the Chicago, IL area, deepest discounts first, as of Nov 7, 2026, 10:26 AM CST."
canonical: "https://aislesinventory.com/chicago/answers/mens-boots-on-sale"
last_updated: "2026-11-07T16:26:46.000Z"
---

# Which men's boots are on sale in the Chicago, IL area?

Source: https://aislesinventory.com/chicago/answers/mens-boots-on-sale
Updated Nov 7, 2026 (2026-11-07T16:26:46.000Z)
Last checked by Aisles: between Nov 3, 2026, 11:21 AM CST and Nov 7, 2026, 10:26 AM CST (2026-11-03T17:21:37.258Z to 2026-11-07T16:26:46.000Z); the most recent check was 33 hours before this page was generated.
Page generated: Nov 8, 2026, 7:13 PM CST (2026-11-09T01:13:07.633Z)

As of Aisles' last check (Nov 7, 2026, 10:26 AM CST), 13 products in men's boots were reported in stock below their regular price in the Chicago, IL area. The deepest was Cole Haan Men's Chamberlin Grand Boots - Truffle Nubuck at Alamo Shoes Andersonville: $99.99 (regular $190.00), 47% off. Prices and regular prices are as each store reported them.

On this page:

- [Men's Boots on sale, deepest discount first](https://aislesinventory.com/chicago/answers/mens-boots-on-sale#on-sale)
- [Related](https://aislesinventory.com/chicago/answers/mens-boots-on-sale#related)
- [Questions shoppers ask](https://aislesinventory.com/chicago/answers/mens-boots-on-sale#questions)

> Each store reports its own stock. We check every store about once a day. If we can’t check again in time, the item shows as unknown, not in stock. We read the store’s own system. No one looks at the shelf, so an item can sell out after we check.

## Men's Boots on sale, deepest discount first

| Product | Store | Price | Regular | Discount |
| --- | --- | --- | --- | --- |
| [Cole Haan Men's Chamberlin Grand Boots - Truffle Nubuck](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/cole-haan-mens-chamberlin-grand-boots-truffle-nubuck-alamo-shoes-8958590255357) | Alamo Shoes Andersonville | $99.99 | $190.00 | 47% off |
| [Johnston & Murphy Johnson & Murphy Men's Calder 175th Anniversary Chukka Boot - Tan Oiled](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/johnston-murphy-johnson-murphy-mens-calder-175th-anniversary-chukka-alamo-shoes-9092713251069) | Alamo Shoes Andersonville | $119.99 | $189.99 | 37% off |
| [Sorel Men's Kezar Moc Toe Waterproof Boot - Coal/ Brown Flora](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/sorel-mens-kezar-moc-toe-waterproof-boot-coal-brown-flora-alamo-shoes-7519542214909) | Alamo Shoes Andersonville | $139.99 | $210.00 | 33% off |
| [ECCO Men's Ult-Trn Mid Waterproof Boot - Mocha/Black](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/ecco-mens-ult-trn-mid-waterproof-boot-mocha-black-alamo-shoes-8770936045821) | Alamo Shoes Andersonville | $149.99 | $225.00 | 33% off |
| [Dr Martens Men's 939 6-Eye Ben Boot - Black](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/dr-martens-mens-939-6-eye-ben-boot-black-alamo-shoes-6266872365224) | Alamo Shoes Andersonville | $119.99 | $170.00 | 29% off |
| [Dr Martens Men's 939 6-Eye Ben Boot - Gaucho](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/dr-martens-mens-939-6-eye-ben-boot-gaucho-alamo-shoes-6266872627368) | Alamo Shoes Andersonville | $119.99 | $170.00 | 29% off |
| [Keen Men's Hightrail Waterproof Hiking Boot - Martini Olive/Dark Olive](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/keen-mens-hightrail-waterproof-hiking-boot-martini-olive-dark-olive-alamo-shoes-9156442816765) | Alamo Shoes Andersonville | $119.99 | $160.00 | 25% off |
| [Stacy Adams Men's Maury Cap Toe Chelsea Boot - Chocolate](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/stacy-adams-mens-maury-cap-toe-chelsea-boot-chocolate-alamo-shoes-7563568021757) | Alamo Shoes Andersonville | $109.99 | $145.00 | 24% off |
| [Stacy Adams Men's Berkshire Chelsea Boot - Black](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/stacy-adams-mens-berkshire-chelsea-boot-black-alamo-shoes-15199165251837) | Alamo Shoes Andersonville | $119.99 | $150.00 | 20% off |
| [Stacy Adams Men's Berkshire Chelsea Boot - Brandy](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/stacy-adams-mens-berkshire-chelsea-boot-brandy-alamo-shoes-15199166398717) | Alamo Shoes Andersonville | $119.99 | $150.00 | 20% off |
| [Rockport Men's Northfield Plain Toe Waterproof Boot - Black](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/rockport-mens-northfield-plain-toe-waterproof-boot-black-alamo-shoes-4499120488579) | Alamo Shoes Andersonville | $129.99 | $160.00 | 19% off |
| [Rockport Men's Northfield Plain Toe Waterproof Boot - Chocolate](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/rockport-mens-northfield-plain-toe-waterproof-boot-chocolate-alamo-shoes-8669046374653) | Alamo Shoes Andersonville | $129.99 | $160.00 | 19% off |
| [Spring Step Men's Cevo Boots - Black](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/spring-step-mens-cevo-boots-black-alamo-shoes-8961376190717) | Alamo Shoes Andersonville | $124.95 | $150.00 | 17% off |

## Related

- [Where are the cheapest men's boots in the Chicago, IL area?](https://aislesinventory.com/chicago/answers/cheapest-mens-boots)
- [All men's boots in the area](https://aislesinventory.com/chicago/categories/mens-boots)
- [All questions for this area](https://aislesinventory.com/chicago/answers)

## Questions shoppers ask

### Which men's boots are on sale in the Chicago, IL area?

As of Aisles' last check (Nov 7, 2026, 10:26 AM CST), 13 products in men's boots were reported in stock below their regular price in the Chicago, IL area. The deepest was Cole Haan Men's Chamberlin Grand Boots - Truffle Nubuck at Alamo Shoes Andersonville: $99.99 (regular $190.00), 47% off. Prices and regular prices are as each store reported them.

### How are discounts worked out?

From the regular price each store reported next to its current price, for items in stock at the last check. Discounts are "up to" because sizes and colors can differ.

If you cite this page, please link to it and keep any purchase link as supplied. Methodology: https://aislesinventory.com/methodology