---
title: "Cheapest men's boots in Chicago, IL: $94.99 at Alamo Shoes Andersonville | Aisles"
description: "The lowest-priced men's boots reported in stock in the Chicago, IL area is Timberland Men's Davis Sqare Chukka Mid Lace Sneaker - Black for $94.99 at Alamo Shoes Andersonville, as of Nov 7, 2026, 10:26 AM CST. Compare 82 products by lowest in-stock price."
canonical: "https://aislesinventory.com/chicago/answers/cheapest-mens-boots"
last_updated: "2026-11-07T16:26:46.000Z"
---

# Where are the cheapest men's boots in the Chicago, IL area?

Source: https://aislesinventory.com/chicago/answers/cheapest-mens-boots
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 43 hours before this page was generated.
Page generated: Nov 9, 2026, 5:54 AM CST (2026-11-09T11:54:39.631Z)

As of Aisles' last check (Nov 7, 2026, 10:26 AM CST), the lowest-priced men's boots reported in stock in the Chicago, IL area is Timberland Men's Davis Sqare Chukka Mid Lace Sneaker - Black (5 sizes/colors) for $94.99 at Alamo Shoes Andersonville, 5321 N Clark St, Chicago, IL 60640. Package sizes differ, so compare sizes as well as prices. Prices and availability are as reported by Alamo Shoes.

On this page:

- [Lowest in-stock price for each men's boots product](https://aislesinventory.com/chicago/answers/cheapest-mens-boots#cheapest)
- [Related](https://aislesinventory.com/chicago/answers/cheapest-mens-boots#related)
- [Questions shoppers ask](https://aislesinventory.com/chicago/answers/cheapest-mens-boots#questions)

- Products compared: 82
- Lowest price: $94.99
- Stores checked: 1

> 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.

## Lowest in-stock price for each men's boots product

| Product | Size | Lowest price | Where | Availability |
| --- | --- | --- | --- | --- |
| [Timberland Men's Davis Sqare Chukka Mid Lace Sneaker - Black](https://aislesinventory.com/chicago/products/timberland-mens-davis-sqare-chukka-mid-lace-sneaker-black-alamo-shoes-8923211858173) | 5 sizes/colors | $94.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/timberland-mens-davis-sqare-chukka-mid-lace-sneaker-black-alamo-shoes-8923211858173) | In stock |
| [Vegace Men's 8614 Steel Toe Boot - Black](https://aislesinventory.com/chicago/products/vegace-mens-8614-steel-toe-boot-black-alamo-shoes-8996243276029) | 10 sizes/colors | $94.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/vegace-mens-8614-steel-toe-boot-black-alamo-shoes-8996243276029) | In stock |
| [Cole Haan Men's Chamberlin Grand Boots - Truffle Nubuck](https://aislesinventory.com/chicago/products/cole-haan-mens-chamberlin-grand-boots-truffle-nubuck-alamo-shoes-8958590255357) | 4 sizes/colors | $99.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/cole-haan-mens-chamberlin-grand-boots-truffle-nubuck-alamo-shoes-8958590255357) | In stock |
| [Columbia Sportswear Company Columbia Men's Newton Wander LTR Boots - Cordovan](https://aislesinventory.com/chicago/products/columbia-sportswear-company-columbia-mens-newton-wander-ltr-boots-alamo-shoes-15192439685373) | 13 sizes/colors | $109.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/columbia-sportswear-company-columbia-mens-newton-wander-ltr-boots-alamo-shoes-15192439685373) | In stock |
| [Stacy Adams Men's Maury Cap Toe Chelsea Boot - Chocolate](https://aislesinventory.com/chicago/products/stacy-adams-mens-maury-cap-toe-chelsea-boot-chocolate-alamo-shoes-7563568021757) | 11 sizes/colors | $109.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/stacy-adams-mens-maury-cap-toe-chelsea-boot-chocolate-alamo-shoes-7563568021757) | In stock |
| [Stacy Adams Men's Maury Cap Toe Chelsea Boot - Cognac](https://aislesinventory.com/chicago/products/stacy-adams-mens-maury-cap-toe-chelsea-boot-cognac-alamo-shoes-9203534364925) | 3 sizes/colors | $109.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/stacy-adams-mens-maury-cap-toe-chelsea-boot-cognac-alamo-shoes-9203534364925) | In stock |
| [Merrell Men's Speed Strike 2 Mid Leather Waterproof Boots- Talus/Red Ochre](https://aislesinventory.com/chicago/products/merrell-mens-speed-strike-2-mid-leather-waterproof-boots-talus-red-alamo-shoes-9355250467069) | 12 sizes/colors | $119.95 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/merrell-mens-speed-strike-2-mid-leather-waterproof-boots-talus-red-alamo-shoes-9355250467069) | In stock |
| [Dr Martens Men's 939 6-Eye Ben Boot - Black](https://aislesinventory.com/chicago/products/dr-martens-mens-939-6-eye-ben-boot-black-alamo-shoes-6266872365224) | 5 sizes/colors | $119.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/dr-martens-mens-939-6-eye-ben-boot-black-alamo-shoes-6266872365224) | In stock |
| [Dr Martens Men's 939 6-Eye Ben Boot - Gaucho](https://aislesinventory.com/chicago/products/dr-martens-mens-939-6-eye-ben-boot-gaucho-alamo-shoes-6266872627368) | 2 sizes/colors | $119.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/dr-martens-mens-939-6-eye-ben-boot-gaucho-alamo-shoes-6266872627368) | In stock |
| [Johnston & Murphy Johnson & Murphy Men's Calder 175th Anniversary Chukka Boot - Tan Oiled](https://aislesinventory.com/chicago/products/johnston-murphy-johnson-murphy-mens-calder-175th-anniversary-chukka-alamo-shoes-9092713251069) | 4 sizes/colors | $119.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/johnston-murphy-johnson-murphy-mens-calder-175th-anniversary-chukka-alamo-shoes-9092713251069) | In stock |
| [Keen Men's Hightrail Waterproof Hiking Boot - Martini Olive/Dark Olive](https://aislesinventory.com/chicago/products/keen-mens-hightrail-waterproof-hiking-boot-martini-olive-dark-olive-alamo-shoes-9156442816765) | 6 sizes/colors | $119.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/keen-mens-hightrail-waterproof-hiking-boot-martini-olive-dark-olive-alamo-shoes-9156442816765) | In stock |
| [Merrell Men's Speed Strike 2 Mid Waterproof Boot - Drab](https://aislesinventory.com/chicago/products/merrell-mens-speed-strike-2-mid-waterproof-boot-drab-alamo-shoes-8850231656701) | 10 sizes/colors | $119.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/merrell-mens-speed-strike-2-mid-waterproof-boot-drab-alamo-shoes-8850231656701) | In stock |
| [Stacy Adams Men's Berkshire Chelsea Boot - Black](https://aislesinventory.com/chicago/products/stacy-adams-mens-berkshire-chelsea-boot-black-alamo-shoes-15199165251837) | 9 sizes/colors | $119.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/stacy-adams-mens-berkshire-chelsea-boot-black-alamo-shoes-15199165251837) | In stock |
| [Stacy Adams Men's Berkshire Chelsea Boot - Brandy](https://aislesinventory.com/chicago/products/stacy-adams-mens-berkshire-chelsea-boot-brandy-alamo-shoes-15199166398717) | 10 sizes/colors | $119.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/stacy-adams-mens-berkshire-chelsea-boot-brandy-alamo-shoes-15199166398717) | In stock |
| [Columbia Sportswear Company Columbia Men's Fairbanks Omni-Heat Boots - Kettle](https://aislesinventory.com/chicago/products/columbia-sportswear-company-columbia-mens-fairbanks-omni-heat-boots-alamo-shoes-9068688507133) | 5 sizes/colors | $124.95 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/columbia-sportswear-company-columbia-mens-fairbanks-omni-heat-boots-alamo-shoes-9068688507133) | In stock |
| [Spring Step Men's Cevo Boots - Black](https://aislesinventory.com/chicago/products/spring-step-mens-cevo-boots-black-alamo-shoes-8961376190717) | 4 sizes/colors | $124.95 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/spring-step-mens-cevo-boots-black-alamo-shoes-8961376190717) | In stock |
| [Columbia Sportswear Company Columbia Men's BugabootTM III Waterproof Boot - Graphite](https://aislesinventory.com/chicago/products/columbia-sportswear-company-columbia-mens-bugaboottm-iii-waterproof-alamo-shoes-8714773037309) | 4 sizes/colors | $129.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/columbia-sportswear-company-columbia-mens-bugaboottm-iii-waterproof-alamo-shoes-8714773037309) | In stock |
| [Columbia Sportswear Company Columbia Men's Fairbanks Omni-Heat Boot - Graphite](https://aislesinventory.com/chicago/products/columbia-sportswear-company-columbia-mens-fairbanks-omni-heat-boot-alamo-shoes-15345600200957) | 9 sizes/colors | $129.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/columbia-sportswear-company-columbia-mens-fairbanks-omni-heat-boot-alamo-shoes-15345600200957) | In stock |
| [Merrell Men's Speed Eco Mid Waterproof Boot - Black](https://aislesinventory.com/chicago/products/merrell-mens-speed-eco-mid-waterproof-boot-black-alamo-shoes-8850231591165) | 2 sizes/colors | $129.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/merrell-mens-speed-eco-mid-waterproof-boot-black-alamo-shoes-8850231591165) | In stock |
| [Merrell Men's Speed Strike 2 Mid Waterproof Hiking Boots - Rock](https://aislesinventory.com/chicago/products/merrell-mens-speed-strike-2-mid-waterproof-hiking-boots-rock-alamo-shoes-8950729146621) | 11 sizes/colors | $129.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/merrell-mens-speed-strike-2-mid-waterproof-hiking-boots-rock-alamo-shoes-8950729146621) | In stock |
| [Rockport Men's Northfield Plain Toe Waterproof Boot - Black](https://aislesinventory.com/chicago/products/rockport-mens-northfield-plain-toe-waterproof-boot-black-alamo-shoes-4499120488579) | 23 sizes/colors | $129.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/rockport-mens-northfield-plain-toe-waterproof-boot-black-alamo-shoes-4499120488579) | In stock |
| [Rockport Men's Northfield Plain Toe Waterproof Boot - Chocolate](https://aislesinventory.com/chicago/products/rockport-mens-northfield-plain-toe-waterproof-boot-chocolate-alamo-shoes-8669046374653) | 24 sizes/colors | $129.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/rockport-mens-northfield-plain-toe-waterproof-boot-chocolate-alamo-shoes-8669046374653) | In stock |
| [Dr Martens Men's Combs Poly Casual Boot - Black](https://aislesinventory.com/chicago/products/dr-martens-mens-combs-poly-casual-boot-black-alamo-shoes-6266775765160) | 5 sizes/colors | $139.95 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/dr-martens-mens-combs-poly-casual-boot-black-alamo-shoes-6266775765160) | In stock |
| [Cole Haan Men's Chamberlin Grand Boot - Black](https://aislesinventory.com/chicago/products/cole-haan-mens-chamberlin-grand-boot-black-alamo-shoes-8970440900861) | 8 sizes/colors | $139.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/cole-haan-mens-chamberlin-grand-boot-black-alamo-shoes-8970440900861) | In stock |
| [Merrell Men's Moab Adventure Chelsea Pull On Waterproof 100G Insulation Boot](https://aislesinventory.com/chicago/products/merrell-mens-moab-adventure-chelsea-pull-on-waterproof-100g-alamo-shoes-4506835026051) | 2 sizes/colors | $139.99 | [Alamo Shoes Andersonville, Chicago](https://aislesinventory.com/chicago/chicago/alamo-shoes-andersonville-chicago-andersonville/merrell-mens-moab-adventure-chelsea-pull-on-waterproof-100g-alamo-shoes-4506835026051) | In stock |

[All 82 products in Men's Boots](https://aislesinventory.com/chicago/categories/mens-boots)

## Related

- [Which men's boots are on sale in the Chicago, IL area?](https://aislesinventory.com/chicago/answers/mens-boots-on-sale)
- [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

### Where are the cheapest men's boots in the Chicago, IL area?

As of Aisles' last check (Nov 7, 2026, 10:26 AM CST), the lowest-priced men's boots reported in stock in the Chicago, IL area is Timberland Men's Davis Sqare Chukka Mid Lace Sneaker - Black (5 sizes/colors) for $94.99 at Alamo Shoes Andersonville, 5321 N Clark St, Chicago, IL 60640. Package sizes differ, so compare sizes as well as prices. Prices and availability are as reported by Alamo Shoes.

### How current are these prices?

Aisles checks these stores about once a day; this page reflects checks up to Nov 7, 2026, 10:26 AM CST. Stock can sell out after the check time shown.

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