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    Windy City Sweets

    4.3 (226 reviews)
    Closed 11:00 am - 10:00 pm
    Updated 1 month ago

    Order Windy City Sweets Takeout or Delivery

    Windy City Sweets Photos

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    Recommended Reviews - Windy City Sweets

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    Peanut butter cup (handmade version of resse's)
    Jim D.

    Place was old school, prices were on the higher end of moderate but not like current overcharging. Definitely some nostalgia but doubt I'd make the trek solely for this place. Solid choice but nothing out of the ordinary.

    So so so Delish!
    Michelle M.

    Seriously. The BEST little dessert shop. That have ALL the goods. And I had such a difficult time trying to decide. Ultimately, I went with their coffee ice cream AND a caramel apple with nuts. My son got a milkshake and my husband got a scoop also. All so good. The helpers are super patient and kind. And helpful. Paid street parking.

    David J.

    My most favorite ice cream in the whole world is Häagen-Dazs' Chocolate Chocolate Chip and when I tell you that Windy City Sweets' Chicago Pothole is a much much better version of my favorite, I mean it. It might just be the perfect ice cream.

    Amaretto cherry
    Brooke L.

    I can see how Windy City Sweets won an award for best candy store and a separate award for cutest ice cream shops in the United States! This place is adorable and made me feel like a little kid again. There's tons of candy - chocolate, jelly beans, sours, etc. They also had some funky candy that would make fun gifts. I'm an ice cream girl so that's what initially drew me in. They have all of the classic flavors and some summery ones - amaretto cherry and Georgia peach are currently featured. This spot is perfect on Broadway!

    Windy city fudge ice cream
    Daniel M.

    Nice experience visiting this local sweets and ice cream shop! The lady who served me (who I assume is the owner) double conned my ice cream since the first cone broke - very considerate! Was able to try a few flavors before making a decision. They offer lots of different sweets/chocolates/fudges that also looked pretty good. Not many places to sit but a good spot to stop by if you're looking for a sweets fix.

    Double scoop brownie sundae
    Kristen C.

    Huge assortment of treats! Helpful staff! Ice cream was good but not the best I've had. The brownies and chocolate are the main attraction here! This place is pricey....not sure my brownie sundae was worth almost $9.

    Rachel was so kind and thoughtful in helping me make a "retro" candy box for a 65th birthday celebration. She took the time to walk around the store with me to pick out the candy - she was so enthusiastic to help. She also took the time to box/wrap it so nicely! Thank you for bringing my vision to life in making a special gift!!

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    Photo of Mark T.
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    2 months ago

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    8 months ago

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    10 months ago

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    3 years ago

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    2 years ago

    Staff is always pleasant. The ice cream is the best in he neighborhood! Try the Chicago pot hole.

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    4 years ago

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    2 years ago

    I really love this candy shop. I always go there when celebrating special days. Great cherry cordials and fun candies from my childhood

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    4 years ago

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    9 years ago

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    3 years ago

    Just got some milk chocolate bars and they were delicious! Also some of the friendliest service I've ever had!

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    3 years ago

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    Page 1 of 6

    Ask the Community - Windy City Sweets

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    It'Sugar

    It'Sugar

    3.7
    (42 reviews)
    3.4 mi

    Today on Christmas Day, when almost all the stores on Michigan Avenue were closed, It'Sugar was…read moresurprisingly open. It felt nice to find a colorful and lively place while everything else around was quiet. The store had a cheerful holiday vibe with bright lights and shelves full of candies, chocolates, and fun treats. There were some really good deals going on, with many items on 50% and even 75% discount, which made it a great time to shop. You could find a mix of classic candies, chocolates, and fun novelty items at reasonable prices. Even though it was Christmas, the store was not very busy, so it was easy to walk around, browse comfortably, and take your time choosing items. The staff was friendly and helpful, and the overall atmosphere was fun and relaxed. Overall, It'Sugar on Michigan Avenue was a nice surprise on Christmas Day -- colorful, cheerful, and perfect for picking up sweet treats or small gifts while enjoying the holiday mood.

    I spent about $14 on cherry sours from this location and was very disappointed. The candy was…read moremarketed as sour, but in my opinion it wasn't sour at all, (also, had the validation of 3 other people), I returned the next day, (today), hoping to exchange it for a different candy or receive store credit for the unused portion. The store manager told me he couldn't offer either and said it would require approval from a general manager. What frustrated me most wasn't being denied a refund, it was the lack of effort to help find a solution. No exchange, no store credit, and no attempt to escalate the issue. I left feeling like my concerns weren't taken seriously as a customer. I understand stores have policies regarding food items, but better customer service and a willingness to address product concerns would have gone a long way.

    Photos
    My Candy Assortment Purchase-08/23
    My Candy Assortment Purchase-08/23
    My candy purchase assortment-08/23
    My candy purchase assortment-08/23
    It'Sugar

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    Sugar Factory - River North

    Sugar Factory - River North

    3.0
    (981 reviews)
    3.6 mi
    $$$

    SERIVCE Server was cool. Fun, sugary, colorful, elegant…read morevibes as usually - it's supposed to be. is it for kids? Is it for adults? Is it for both? Maybe so! This is not my first time here. Parking is a pain because it's located downtown but you can utilize the parking structure nearby. They add a 20% fee on your bill, no tipping. My first visit was in Vegas years back and really loved it there. FOOD Ordered the rainbow sliders and they taste great to me. I added some bbq sauce as always with any burger. Great portions. Also ordered the Smash Burger. WELL I will return anytime.

    The Sugar Factory is... interesting. They obviously cater to kids and kids-at-heart by making the…read moreexperience feel like a celebrity walking the red carpet (why? No clue). The TVs also show nothing else but self promotion of celebrities visiting various Sugar Factory locations. Their other theme is attention-grabbing shakes and desserts. Ones that BEG others to "Look at me!" (and order one for themselves...). We partook because, well, "When in Rome!" And, honestly, it had some fun to it. The food wasn't half bad and neither were the shakes we had. The portions were decent but prices were inflated. We didn't buy-in fully but we still enjoyed our meal and didn't regret the visit (just not sure we'd be back to this one trick pony).

    Photos
    The birthday "celebration" that they advertise to be lively and fun with music, dancing, and singing.
    The birthday "celebration" that they advertise to be lively and fun with music, dancing, and singing.
    Sugar Factory - River North
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    Lollipop Passion

    Windy City Sweets - candy - Updated June 2026

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