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.

Last checked by Aisles: from to  (the latest check was 43 hours before this page was generated).

This is the range of check times on this page; each listing has its own check time. Most stores are checked daily. A listing past its check window shows as unknown. Stock is what each store reported, not a live shelf count, and can change after a check.

Products compared
82
Lowest price
$94.99
Stores checked
1
About this data (1 note)

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

Show all 25 rows
ProductSizeLowest priceWhereAvailability
Dr Martens Men's 939 6-Eye Ben Boot - Gaucho2 sizes/colors$119.99Alamo Shoes Andersonville, ChicagoIn stock
Johnston & Murphy Johnson & Murphy Men's Calder 175th Anniversary Chukka Boot - Tan Oiled4 sizes/colors$119.99Alamo Shoes Andersonville, ChicagoIn stock
Keen Men's Hightrail Waterproof Hiking Boot - Martini Olive/Dark Olive6 sizes/colors$119.99Alamo Shoes Andersonville, ChicagoIn stock
Merrell Men's Speed Strike 2 Mid Waterproof Boot - Drab10 sizes/colors$119.99Alamo Shoes Andersonville, ChicagoIn stock
Stacy Adams Men's Berkshire Chelsea Boot - Black9 sizes/colors$119.99Alamo Shoes Andersonville, ChicagoIn stock
Stacy Adams Men's Berkshire Chelsea Boot - Brandy10 sizes/colors$119.99Alamo Shoes Andersonville, ChicagoIn stock
Columbia Sportswear Company Columbia Men's Fairbanks Omni-Heat Boots - Kettle5 sizes/colors$124.95Alamo Shoes Andersonville, ChicagoIn stock
Spring Step Men's Cevo Boots - Black4 sizes/colors$124.95Alamo Shoes Andersonville, ChicagoIn stock
Columbia Sportswear Company Columbia Men's BugabootTM III Waterproof Boot - Graphite4 sizes/colors$129.99Alamo Shoes Andersonville, ChicagoIn stock
Columbia Sportswear Company Columbia Men's Fairbanks Omni-Heat Boot - Graphite9 sizes/colors$129.99Alamo Shoes Andersonville, ChicagoIn stock
Merrell Men's Speed Eco Mid Waterproof Boot - Black2 sizes/colors$129.99Alamo Shoes Andersonville, ChicagoIn stock
Merrell Men's Speed Strike 2 Mid Waterproof Hiking Boots - Rock11 sizes/colors$129.99Alamo Shoes Andersonville, ChicagoIn stock
Rockport Men's Northfield Plain Toe Waterproof Boot - Black23 sizes/colors$129.99Alamo Shoes Andersonville, ChicagoIn stock
Rockport Men's Northfield Plain Toe Waterproof Boot - Chocolate24 sizes/colors$129.99Alamo Shoes Andersonville, ChicagoIn stock
Dr Martens Men's Combs Poly Casual Boot - Black5 sizes/colors$139.95Alamo Shoes Andersonville, ChicagoIn stock
Cole Haan Men's Chamberlin Grand Boot - Black8 sizes/colors$139.99Alamo Shoes Andersonville, ChicagoIn stock
Merrell Men's Moab Adventure Chelsea Pull On Waterproof 100G Insulation Boot2 sizes/colors$139.99Alamo Shoes Andersonville, ChicagoIn stock

All 82 products in Men's Boots →

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.

Page generated . Stock is as each store reported it when we last checked.

Also available as Markdown and JSON (same data).