Alcala's Western Wear is one of The 15 Best Places for Boots in Chicago.

1. Alcala's Western Wear

7.8
1733 W Chicago Ave (at N Hermitage Ave), Chicago, IL
Clothing Store · East Ukrainian Village · 10 tips and reviews

BravoBravo: Opened in 1974, the Alcala family stocks 10,000 pairs of boots , 5000 cowboy hats and countless pairs of jeans, chaps, and belts. Its where I go when I need my Urban Cowboy fix. -Graham Elliot, Top Ch

The FeastThe Feast: Come here for the city's largest collection of Western gear--the quirky shop has row upon row of cowboy boots and hats to make you feel like way less of a city slicker. Read more.

Nicole V.Nicole Velazquez: Love this store!! Staff are so very friendly and eager to help!! Oh yea they have rows and rows and rows of boots!!

Dr. Martens is one of The 15 Best Places for Boots in Chicago.

2. Dr. Martens

7.7
1561 N Milwaukee Ave (at W North Ave), Chicago, IL
Shoe Store · Wicker Park · 5 tips and reviews

Lisa W.Lisa W: If you want durable high quality boots, go here. Best boot brand I've ever owned, and they have some great new designs. But you never go wrong with the classic combat boot.

Matthew C. P.Matthew C. Pantelis: Friendly and helpful staff. Get your boots on.

Chris W.Chris Wenzel: Awesome service... Definitely worth a return trip

AKIRA Bucktown Footwear is one of The 15 Best Places for Boots in Chicago.

3. AKIRA Bucktown Footwear

8.0
1849 W North Ave (at Wolcott Ave.), Chicago, IL
Shoe Store · Bucktown · 4 tips and reviews

DJ S.DJ Skeez: Staff was super nice and helpful. Great selection of heels and boots. Use the Special! Get $25 off next purchase of $100 or more

M B.M Ben-David: This location of Akira shoes has a great selection of "On Trend" shoes & the associates are super nice! They have a great sale rack here as well. :)

Lover F.Lover Face: Frances pussy is D-licious!

Independence is one of The 15 Best Places for Boots in Chicago.

4. Independence

7.6
47 E Oak St Fl 2 (btwn N Rush St & Michigan Ave), Chicago, IL
Men's Store · Streeterville · 6 tips and reviews

Phong N.Phong Nguyen: Great menswear and place to get Oak Street Bootmaker boots & shoes

MaureenMaureen: Check out the nice selection of Apolis, Post Overalls, Kapital, and other labels of outstanding quality and design. Worth the money, but make sure it fits perfect.

Renaissance HotelsRenaissance Hotels: Modern-classic American style for the refined, rugged urban outdoorsman.

TOMS Chicago is one of The 15 Best Places for Boots in Chicago.

5. TOMS Chicago

8.5
1611 N Damen Ave, Chicago, IL
Shoe Store · Bucktown · 18 tips and reviews

Shivam S.Shivam Shah: Great selection of Slippers, Shoes, Boots and much more!

Cara O.Cara Oller: love my TOMS

Makayla R.Makayla Rossi: Toms I love so much

Cadillac Palace Theatre is one of The 15 Best Places for Boots in Chicago.

6. Cadillac Palace Theatre

9.3
151 W Randolph St (at LaSalle St), Chicago, IL
Theater · The Loop · 66 tips and reviews

vanessa b.vanessa buenrostro: Very beautiful theatre to check out. The broadway shows, concerts are amazing there with even an awesome view from the balcony.

KristinaKristina: Respect the theater, dress up!

ᴡ S.ᴡ Silvestri: so excited to see Wicked

Nordstrom is one of The 15 Best Places for Boots in Chicago.

7. Nordstrom

8.3
55 E Grand Ave, Chicago, IL
Department Store · Near North Side · 95 tips and reviews

Greg W.Greg Wilcox: It's a big, beautiful NORDSTROM! What more could you ask for? Bring your Nordstrom card to earn points!

C 8C 8: It's called Nordstrom. No s and no apostrophe s. Learn this and you will go far in life.

BravoBravo: I love Nordstrom's and the girls at the Rail are the best. -John Somerville, Top Chef

Alamo Shoes is one of The 15 Best Places for Boots in Chicago.

8. Alamo Shoes

7.9
5321 N Clark St (at W Summerdale Ave), Chicago, IL
Shoe Store · Andersonville · 21 tips and reviews

Hannah ..Hannah ...: Layaway plan for winter boots!

Sam D.Sam Dicks: An excellent local shoe store. The staff are extremely friendly and helpful. Make sure to support your local businesses!

Kim Z.Kim Z: Good selection. Some of the staff are pushy yet don't want to get shoes for you to try on. Ask for Bruce for a good customer service experience.

REI is one of The 15 Best Places for Boots in Chicago.

9. REI

8.3
905 West Eastman St (at Blackhawk St), Chicago, IL
Outdoor Supply Store · 34 tips and reviews

Dana J.Dana Jensen: Genuinely friendly employees will help you make sense of the options. Great sales on occasion. The membership is totally worth it if you buy at least one big thing.

Scott B.Scott Bush: Get the membership and return anything for any reason, even years after a purchase.

SamanthaSamantha: Free parking for 90 minutes or less!

Target is one of The 15 Best Places for Boots in Chicago.

10. Target

7.9
2112 W Peterson Ave (btwn Damen & Oakley Ave), Chicago, IL
Big Box Store · West Ridge · 31 tips and reviews

Rhonda R.Rhonda Robinett: Visit Rhonda in the Boots Aisle! Stop and say hello.

Matt D.Matt Dicker: No shovels or boot trays for sale? It's February in Chicago!

L. B.L. Boogie.: Love Target!! Target is my favorite one stop shop....everything from housewares to clothing to electronics you can buy here! I will ALWAYS support Target!

The Alley Chicago is one of The 15 Best Places for Boots in Chicago.

11. The Alley Chicago

7.7
2620 W Fletcher St (at W Belmont Ave), Chicago, IL
Clothing Store · Northwest Side · 22 tips and reviews

nina m.nina morales: It's perfect for all those hard to find items we all love and as of recent my favorite tobacco shop has moved in there too! \m/ blue Havana rules

Tripp S.Tripp Stark: checking out some clothing and whatnot

Joanna W.Joanna Wahler: Ask for one of the Mikes to help with piercing. Super helpful!

Suitsupply Chicago is one of The 15 Best Places for Boots in Chicago.

12. Suitsupply Chicago

8.7
945 N Rush St, Chicago, IL
Men's Store · Streeterville · 9 tips and reviews

Henry S.Henry S: The terrace is amazing! What store in Chicago has a rooftop garden?

Fiesha L.Fiesha Lynn: Simply amazing! The guys are great and modest prices. Alterations on-sight! I'm glad I stumbled upon this new Chicago European gem!

Brandon B.Brandon Bruner: Awesome store for well dressed men

Madewell is one of The 15 Best Places for Boots in Chicago.

13. Madewell

8.8
932 N Rush St, Chicago, IL
Women's Store · Near North Side · 3 tips and reviews

Lucille F.Lucille Fisher: Excellent source of fashionable contemporary classics with quirky twist. A millennial favorite.

Christine S.Christine Solorio: All denim 40% off

Amy R.Amy Robertson: Like the low quality hipster cousin of jcrew

Mildblend is one of The 15 Best Places for Boots in Chicago.

14. Mildblend

8.2
1342 N Milwaukee Ave, Chicago, IL
Clothing Store · Wicker Park · 7 tips and reviews

Cary B.Cary Black: Phenomenal service and knowledge. Carry several made in USA brands and a solid selvedge denim selection with chainstitch hemming & denim repair services. One of the best menswear shops in Chicago.

Darryl P.Darryl Pearson: The ONLY place in Chicago you should consider buying denim. Priced great, best brands of denim and even better staff. Don't forget free hemming with the purchase of nudies or naked and famous!

MildblendMildblend: Free hemming with denim purchase.

Fleet Feet is one of The 15 Best Places for Boots in Chicago.

15. Fleet Feet

8.5
4762 N Lincoln Ave (at Lincoln Square), Chicago, IL
Sporting Goods Retail · Ravenswood · 15 tips and reviews

Dave Z.Dave Zimmer: I love this place but I am biased. Great great staff and a true belief that Running Changes Everything!

andrea m.andrea metcalf: Great peeps @fleet feet Lincoln square really genuine and nice!!

Mana I.Mana Ionescu: Did you know Fleet Feet Sports Chicago is dog-friendly? So go ahead and bring along your best friend.