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Ten Places to Shop on a Weekend Trip to Chicago

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Chicago is known for being an expansive grid of quirky neighborhoods, ranging from the honkey-tonk hipster hood Pilsen on the south to the neo-granola gayborhood Andersonville on the North Side. And then there's the centrally located luxury shopping districts in the Gold Coast and Streeterville along Michigan Avenue.

What if you're a beginner or intermediate Chicago shopper, and you want to find unique shops, close to your hotel that you can't find elsewhere?

After the jump, Racked Chicago suggests ten stores worth visiting on a weekend trip to Chicago — some aspirational, which are great for scoring investment pieces, and others that are totally rad and affordable to load up your carry-on bag. Click through for a rundown of each.


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1. Rsvp gallery

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1753 N Damen
Chicago, IL 60647
(773) 770-6666
Visit Website
If Linda Farrow, Junya Watanabe and Jeremy Scott were to sit at a round table eating grilled cheese sandwiches emblemized with Chanel logos, this is the place it would happen. Bright luxury streetwear and fun weekend statement pieces are what this Bucktown sub-level shop is known for. And theres no better time than right now to shop for such things.

2. P.45

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1643 N Damen Ave
Chicago, IL 60622
(773) 862-4523
Visit Website
A women's playground. Always on point with brands like 3.1 phillip lim, Rachel Comey and Hansel from Basel. The boutique's prices are a tad aspirational if you want to go on a haul, but otherwise great if you want one or two great investment pieces.

3. AKIRA Bucktown Women's

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1814 W North Ave
Chicago, IL 60622
(773) 489-0818
Visit Website
Now that Akira has something like 13 stores around Chicago, it's easy to say this shop is a no-brainer, but this women's location on North Ave in Bucktown is definitely worth the stop. As one of the original locations, and right next to the men's store, this has the largest selection of brands as well as Akira's own brand. It also has styles and more sale merchandise that the other boutiques don't have. Pieces run low and high so expect prices to match.

4. Una Mae's Freak Boutique

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1528 N. Milwaukee Ave
Chicago, IL 606222
(773) 276-7002
Visit Website
Smack dab in the middle of Milwaukee Avenue where there's tons of cool shops, Una Mae's is great because everything is so casual and fun-looking. Shop denim and t-shirts to high-low dresses and brightly colored spring patterned skirts all for the most part under $90. The apothecary section is worth a gander, too.

5. Penelope's

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1913 W Division St
Chicago, IL 60622
(773) 395-2351
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One of those shops that epitomizes the young Chicago style. Brands are never post-peak and (most always) priced reasonably. Men's and women's and a well-curated selection of arty hipster books. Spoiler: there are smushy-faced pugs involved.

6. Dovetail

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1452 W Chicago Ave
Chicago, IL 60642
(312) 243-3100
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Shop fun flouncy vintage as well as new clothing, jewelry and accessories from Chicago-based workwear makers. Owner Julie Ghatan, a youngster with attitude is always there and super helpful.

7. Greer

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1657 N Wells St
Chicago, IL 60614
(312) 337-8000
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You've never found such a welcoming shop filled with inspiration, brimming with great design and staffed with smiling women. The shop carries thousands of cards, curious items, pens, ribbon, buttons, nice pencils and even customizes stationery.

8. Luxury Garage Sale

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1658 N Wells
Chicago, IL 60614
(312) 291-9126
Visit Website
Designer everything. Discounted everything. We're talking Hermes, Giambattista Valli, Louis Vuitton, vintage designer jewelry, Judith Leiber, Burberry, Pucci, Bottega and more. The staff is super chill and they allow babies and dogs to shop like everybody else does.

9. Judy Maxwell

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(312) 787-9999
Visit Website
So you're feeling lucky and you want to be surprised? Here you have it, folks. Owned by none other than Joan Cusack this ever-changing shadowbox storefront has just transformed into a general store. Seriously, it wasn't a general store two weeks ago. There's now a wood burning stove, a cage of finches, they're working on getting the soda fountain working (the cash wrap) and a tea service. The only thing it's missing are an old man on the front porch in a rocking chair.

10. Ikram

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15 E Huron St
Chicago, IL 60611
(312) 587-1000
Visit Website
No trip to Chicago would be complete without a visitation to the palace where dreams are made. Affectionately coined "The Red Box", inside Ikram the tables are clustered with thousands of pieces of jewelry and the racks are packed everyone from Proenza to Margiela. Lots is a little out of reach, unless you're shopping sale, so if you want to check it out and not drop major coin, have lunch in the upstairs cafe. The salmon is delicious and so is the chef.

1. Rsvp gallery

1753 N Damen, Chicago, IL 60647
If Linda Farrow, Junya Watanabe and Jeremy Scott were to sit at a round table eating grilled cheese sandwiches emblemized with Chanel logos, this is the place it would happen. Bright luxury streetwear and fun weekend statement pieces are what this Bucktown sub-level shop is known for. And theres no better time than right now to shop for such things.
1753 N Damen
Chicago, IL 60647

2. P.45

1643 N Damen Ave, Chicago, IL 60622
A women's playground. Always on point with brands like 3.1 phillip lim, Rachel Comey and Hansel from Basel. The boutique's prices are a tad aspirational if you want to go on a haul, but otherwise great if you want one or two great investment pieces.
1643 N Damen Ave
Chicago, IL 60622

3. AKIRA Bucktown Women's

1814 W North Ave, Chicago, IL 60622
Now that Akira has something like 13 stores around Chicago, it's easy to say this shop is a no-brainer, but this women's location on North Ave in Bucktown is definitely worth the stop. As one of the original locations, and right next to the men's store, this has the largest selection of brands as well as Akira's own brand. It also has styles and more sale merchandise that the other boutiques don't have. Pieces run low and high so expect prices to match.
1814 W North Ave
Chicago, IL 60622

4. Una Mae's Freak Boutique

1528 N. Milwaukee Ave, Chicago, IL 606222
Smack dab in the middle of Milwaukee Avenue where there's tons of cool shops, Una Mae's is great because everything is so casual and fun-looking. Shop denim and t-shirts to high-low dresses and brightly colored spring patterned skirts all for the most part under $90. The apothecary section is worth a gander, too.
1528 N. Milwaukee Ave
Chicago, IL 606222

5. Penelope's

1913 W Division St, Chicago, IL 60622
One of those shops that epitomizes the young Chicago style. Brands are never post-peak and (most always) priced reasonably. Men's and women's and a well-curated selection of arty hipster books. Spoiler: there are smushy-faced pugs involved.
1913 W Division St
Chicago, IL 60622

6. Dovetail

1452 W Chicago Ave, Chicago, IL 60642
Shop fun flouncy vintage as well as new clothing, jewelry and accessories from Chicago-based workwear makers. Owner Julie Ghatan, a youngster with attitude is always there and super helpful.
1452 W Chicago Ave
Chicago, IL 60642

7. Greer

1657 N Wells St, Chicago, IL 60614
You've never found such a welcoming shop filled with inspiration, brimming with great design and staffed with smiling women. The shop carries thousands of cards, curious items, pens, ribbon, buttons, nice pencils and even customizes stationery.
1657 N Wells St
Chicago, IL 60614

8. Luxury Garage Sale

1658 N Wells, Chicago, IL 60614
Designer everything. Discounted everything. We're talking Hermes, Giambattista Valli, Louis Vuitton, vintage designer jewelry, Judith Leiber, Burberry, Pucci, Bottega and more. The staff is super chill and they allow babies and dogs to shop like everybody else does.
1658 N Wells
Chicago, IL 60614

9. Judy Maxwell

1151 N State St Chicago, IL 60611
So you're feeling lucky and you want to be surprised? Here you have it, folks. Owned by none other than Joan Cusack this ever-changing shadowbox storefront has just transformed into a general store. Seriously, it wasn't a general store two weeks ago. There's now a wood burning stove, a cage of finches, they're working on getting the soda fountain working (the cash wrap) and a tea service. The only thing it's missing are an old man on the front porch in a rocking chair.

10. Ikram

15 E Huron St, Chicago, IL 60611
No trip to Chicago would be complete without a visitation to the palace where dreams are made. Affectionately coined "The Red Box", inside Ikram the tables are clustered with thousands of pieces of jewelry and the racks are packed everyone from Proenza to Margiela. Lots is a little out of reach, unless you're shopping sale, so if you want to check it out and not drop major coin, have lunch in the upstairs cafe. The salmon is delicious and so is the chef.
15 E Huron St
Chicago, IL 60611