Tell me if this sounds familiar: you're out and about, and are craving something sweet. However, almost all places and bakeries you walk into have, at smallest, a cookie the size of one's face. I'm looking to satisfy my sweet tooth, not have a full meal in dessert form! Windy City Sweets fits the bill perfectly! They have a very wide selection of all sorts of sweet goodies! Homemade chocolates and candies, commercially made candies, ice cream, jelly beans by weight (buttered popcorn is peak, and you can't change my mind). There are likely many others, but I found what my heart was craving and went for it. Looking at their selection, there is something for everyone, even stuffed animals! (Eating these is not recommended, HA!) I suppose a candy shop has *some* appeal to the young and young at heart, so why not? I also love that they have reasonable prices, are open late-ish (until 9pm), and have friendly, welcoming service. Final verdict: To make it dead-simple: if you have a sweet tooth, and are within a couple miles of Northalsted, get yourself in here already! read more

Came here after sushi across the street at Wakamono yesterday evening. No line or wait. Service was friendly and fast. Loved the pirate's treasure with m&ms and Oreos. They also had a great selection of candy, though we didn't buy any. Will come back for sure whenever I'm in Chicago! read more

Windy City Sweets - Pirates treasure - Candy Stores Near Me - Chicago, Illinois

I love supporting small, local businesses, but I am not sure how this place survives. Stopped in here last week with my husband and he bought a junior scoop of sorbet. He said that it was the smallest scoop he ever had. Yesterday, I went in for a double scoop of sorbet. Not only were the full-size scoops ridiculously small, but the sorbet was so soft, it barely filled the tiny cup. Priced at $7.95, with tax and tip it was almost $10, and it didn't even taste that good. Just my opinion, but this is a longtime business in need of a refresh. read more

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. read more

Windy City Sweets - Peanut butter cup (handmade version of resse's) - Candy Stores Near Me - Chicago, Illinois

I happen to by this amazing store the other day and saw the sign in the window about 25 kinds of licorice. I was intrigued. Inside the store is amazing with almost every kind of sweet you could think of. A few days later, I was having a conversation and someone mentioned Dubai chocolate. Apparently, it's trendy and it is in short supply. Next time I went by Windy City sweets I popped in to ask them. They told me they didn't have any in stock but would call me when it did come in. A few days later, I received a call from the store, letting me know they had a limited amount in stock. So I walked over, they had about 10 pieces of milk chocolate based Dubai chocolate. I bought some and enjoyed it. It was really amazing. I remarked to the staff that it would be really great in dark chocolate. The enthusiastically told me they would make me some and I should come back in about 20 minutes. This is amazing customer service! The dark chocolate based version is even better. (if you prefer milk, chocolate, then you might prefer the original). What impressed me was not just the product they created, but their willingness to on a moment's notice actually make me the dark chocolate version. And on another note, the selection of licorice is amazing. After I come down from the sugar high from the Dubai chocolate I will return to sample the licorice. Overall, the store is amazing, the staff is very friendly, and they are extremely customer oriented. read more

I like Oberweiss better than Windy City Sweets for a few reasons, but Windy City Sweets is a lot closer to me. However, ahem. Seeing what I paid for two tiny scoops of ice cream doesn't make me want to return here. read more

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. read more

Windy City Sweets - So so so Delish! - Candy Stores Near Me - Chicago, Illinois

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. read more

Windy City Sweets - Candy Stores Near Me - Chicago, Illinois

Amazing old school candy store. Licorice, gummies, fudge, ice cream, nuts, and beanie babies. This store has everything you need and more. The huge glass case holds chocolates made on premises. Truly a gem in Chicago for a classic candy store. read more

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! read more

Windy City Sweets - Amaretto cherry - Candy Stores Near Me - Chicago, Illinois

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. read more

Windy City Sweets - Windy city fudge ice cream - Candy Stores Near Me - Chicago, Illinois

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

Very tasty ice cream and candy shop on the north side! I could spend over an hour just browsing the candy, then have my ice cream once I've worked up an appetite. I really like their ice cream flavors and the staff was very nice. read more

Located in The Lakeview neighborhood of Chicago, Windy City Sweets brings gourmet candy to Chicago. Great location & great service. 5 out of 5 stars. read more

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. read more

Windy City Sweets - Double scoop brownie sundae - Candy Stores Near Me - Chicago, Illinois

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!! read more

Windy City Sweets - Candy Stores Near Me - Chicago, Illinois

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Best candy shop in chicago my son goes there to spend his allowance each week! Great ice cream and great handmade chocolates . Also, we love their selection of gummies. The pigs are the best! read more

Flavors on flavors on flavors! So many different ice cream flavors, you're guaranteed to find something you like. SO glad they're offering samples because I had the hardest time trying to decide which ones sound better. Settled on Chicago Pot Hole and Gold Rush. If you also can't decide and like chocolate, just copy my picks! Hidden amongst the mountain of candy are a couple small tables next to the window. Doesn't seat many, but you'll eat your ice cream too quickly to need a long stay anyway. read more

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

I love brownies, especially the ones from here. They have fabulous peppermint bark for the holidays (my favorite bark yet), truffles of all sorts, chocolate covered Oreos (yum!), peanut butter covered Oreos (my favorite), milk chocolate covered Oreos, massive PB cups (truly massive and thick- one could feed four), and ice cream! We come in often enough to see the selection of goods changed frequently, with new provisions often beautifully displayed. My husband gets me a ridiculous amount of treats from here too often, but somehow I do not mind. The goods he picked up for VDay were over the top, though; guys- please stop sending the Scot home to me with bags of sweets... I cannot eat this much! We love the guys that run this shop, and especially the older gentleman that formerly owned WCS and remains around (except when they encourage my husband to buy the entire store)! Friendly service! Another major plus: they're open late!! read more

I have been a customer of this store since the mid 1980's. From ice cream, to hand dipped chocolate items, to traditional penny candies, to gummy candy , there is something for everyone at this classic little sweet shop You can't mix and match or serve yourself like many modern shops so when I bring my crew, we each spend a significant amount of time hemming and hawing over our final decision until we pick a treat. I love how this place hasn't changed a bit since I frequented it as a child. Recommend! read more

Just such a fun little candy shop, and everything I've tried so far (after two visits) is fantastic. It's such a great atmosphere. It feels like an old-timey candy store with treats I haven't seen in years (Bit-o-Honey!) Don't leave without getting the fudge! It's a little pricey but sooo good. The gentleman behind the counter was so very friendly and helpful, seemed so eager to not just help me, but talk with me while I was deciding which of the many goodies I'd be taking with me. read more

I recently moved down the street from this lovely store, and although everything here looks amazing, I've only tried the ice cream (so far!). This place has some of the best ice cream I've had in Chicago! Their flavors are creative with lots of texture. I've tried multiple different options, and honestly, you can't go wrong. My personal favorites include the Unicorn Stars (from what I remember, it's swirls of colorful sweet vanilla ice cream with white chocolate chunks) and the Pirates Treasure (caramel ice cream with M&M pieces and chocolate cookies). Other notable flavors I've tried too include their Birthday Cake and Banana Pudding. I look forward to trying even more and also their other products, including fudge and other candy treats. Highly recommend! read more

I always feel like I'm entering Willy Wonka's chocolate factory when I come in here! I immediately headed over for the ice cream and asked for a sample (I was also parched and asked for a water which the girl working the counter kindly gave to me). I got the birthday cake and chicago chocolate ice cream in a waffle cone and it did not disappoint! Also, the birthday cake ice cream has chunks of vanilla cake in it which was a nice surprise! If you are in the area, I would highly recommend stopping into this Lakeview gem! read more

Windy City Sweets - birthday cake ice cream and chicago chocolate ice cream in a cone - Candy Stores Near Me - Chicago, Illinois

Cute little gem of a place in East Lakeview! Friendly staff and great treat options to satisfy your sweet tooth! We went for some late night ice cream. There are a ton of flavor choices and they let me try a ton before making a decision! I went with a scoop of coffee with chocolate chips and a scoop of coconut almond chocolate chip. Both were great! I will be back to try some other flavors and to pick up one of their caramel apples that look so good! read more

I've been seeking walking destinations in the neighborhood as an excuse to get out of the house during COVID and Windy City Sweets has quickly become one of my favorite stops. Staff is very friendly and helpful, which is always a good thing but is particularly great during these times when a little bit of banter goes a long way. I've only tried the candy, but it's all delicious and it changes frequently. Dark chocolate covered pretzels are my favorite-- great chocolate to pretzel ratio. Such a neighborhood gem-- well worth a stop. read more

The following plethora of Baby Boomer references may alienate Gen X, Y, and Triple-Z progeny. Please be advised before proceeding... I believe I just saw the Beaver and his fat friend Larry Mondello hanging out and getting stomach aches from all the candy, fudge and ice cream they had. And here comes Ozzie and Harriet's boys, David and Ricky. They're meeting up with Wally, Lumpy and that jerk Eddie Haskell to buy some Pez and cruise girls. Uh-oh, now they're all gonna get it 'cause Sheriff Andy Taylor just walked in with Deputy Barney Fife. They're wondering why none of them are in school. It honestly feels like a trip to TV Land when you walk into Windy City Sweets in Lakeview. The maximally stocked store is filled to the brim with so much hard candy, jelly beans, fudge, chocolate, nuts, licorice, malt balls, cookies shaped like cartoon characters and Pez dispensers of all sizes up the wazoo. This place is as old-fashioned as a sweets shop can get, and yet the yard sale appeal makes it way too infectious to pass up ...even if you planned to be real good on your diet. I actually didn't think I needed a bag of gummy fish until it seemed to call out my name. But what really got me - even in 22-degree Chicago winter weather - was the ice cream. They don't have a huge selection, but I just had a hankering for the Pumpkin Spice milkshake. I didn't care that I was freezing my bulbous hiney not five minutes earlier on the street...it just tasted so good that I think I found myself skipping down the sidewalk on Broadway. And I could tell the bundled-up passers-by were palpably jealous of my dairy-saturated glee. There's something so Midwest cornbelt about Windy City Sweets that you can't help but explore your inner Opie here. SWEETS / ICE CREAM - 4 stars...hits the spot...even if you didn't know you had a spot to hit before you walked in AMBIANCE - 5 stars...stocked full of sugary goodies in a cluttered, old-fashioned way...hard to resist for a baby boomer if you ask me SERVICE - 4 stars...friendly and fast with the scoop TOTAL - 4 stars...I gotta go meet Whitey and Gilbert now...see ya in school, Miss Landers read more

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The Windy City Sweets store has been around for decades in neighborhood of Lakeview. The store is very accessible since it's located on Broadway. Upon entering the store, it's like a reminder of the past years. The store is large in size with wooden floors, a wall of "penny candies" and various toys / novelties. Of course, you can't forget the ice cream counter upon entering the store. You will find the ice cream or yogurt of your choice. I have never had an ice cream that I didn't enjoy. Don't be afraid to try a sample of an ice cream that you haven't had before. Customer service as always been great - the staff will go above and beyond to make sure a guest is happy. Enjoy your ice cream at one of the interior tables or on the sidewalk patio. Go enjoy. read more

Windy City Sweets - Wall of sugar - Candy Stores Near Me - Chicago, Illinois

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i absolutely LOVE this old fashioned candy store. MY son was looking for a specific candy, and after googling every place I could find, this popped up. Located somewhere near boys town ( don't quote me I'm going off signs), its on a nice road about 15 min north of downtown. Inside you enter a world of sweets, chocolate and nostalgia. Inside we were greeted by two gentlemen who were busy making FUDGE. FRESH! The other man was packaging chocolate dipped oreos and told us how we could find everything. I asked for the specific candy my son was looking for and boom it was to be found, made his whole trip. We ended up trying the birthday cake oreos, some razzles!!, some fudge and some lollipops. All in all, my experience was awesome. They were so incredibly friendly, and patient. very family friendly VERY professional and so i HIGHLY recommend this place if you have a killer sweet tooth. read more

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My general sentiment about independently owned candy stores is that they are overpriced, stale, and old fashioned creepy clownish kitschig. Windy City Sweets are none of these things! Their decadent fudge is great during the cold months and their independently made ice cream is eclectic and delights any time of year. I recommend the Chicago Pothole, an ice cream that is a chocolatey, multi-textured, messy, unorganized, hot mess of everything chocolate in one chilly scoop of ice cream, and the Salty Jack, which is a Cracker Jack themed ice cream. Yes, it is as good as it sounds. Don't be afraid of ordering one of their more esoteric scoops. If you do not want a specialty of any sort, then yes, this is also a place where you can buy offbeat cadies such as "Warheads" for the inner 90s child inside, specialty gummy bears, or taffy for someone quirky. In addition to their up to date products, the store space itself is also as relatively contemporary as a candy store could be. The staff members are also all very polite and pleasant to conduct business with. This place is a neighborhood gem in Lakeview East that adds character to the neighborhood and should be given habitual visits by locals whenever they have a sweet-tooth. read more

We frequent this candy shop as it is nearby my son's school. They have everything! It's a fun old style candy store with lots of options, ice cream and malts, and random toys like beanie babies. They have a wide option of chocolates and gummies that are pay by the pound, but also lots of items that are prepackaged. read more

When I first walked in Windy City Sweets, I was transported back to my school-age candy store, minus the stuffed animals. My 2 friends and I would stop in and get a snack or treat of penny candy. If only one of us had money, then that person would buy something that could be divided up 3 ways. At Windy City Sweets one afternoon, I was there just as school let out, and there the kids were, doing the exact same thing my friends and I used to do, 50 years ago. It was a beautiful thing to see. One girl was deliberately excluded from the rest. The person behind the counter spotted her just as I had decided to buy her treat for her. I don't like mean girls or bullies. The person behind the counter let her have her treat on the house. It brought tears to my eyes, as I thought, what a wonderful place this is. Good sweets, kind staff. Who can ask for more? Windy City Sweets, I hope you're around for a very long time. There are still children to teach about quality of chocolates and kindness to others. read more

Cant say enough about this store. Absolutely the best. Peter has to be the kindest and best sales person around. His knowledge of the City was vast. If you have never been there dont waste a minute. Fun time for the entire family...kids will experience a real candy store..one of a kind... any chocolate you try is amazing.. something you dream about...yum yum... read more

This place is exquisite! Lots of goodies! Chocolates and homemade fudges, sugars and sweets, treats from my past....candy I thought was long gone....not here! Candy from my parents childhood is here too :) Loads of fun! We're coming back for ice cream sundaes and pixie sticks... Also-- Daily Specials!! read more

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

What a lovely treat shop in the heart of Lakeview! I've walked by it several times and did not pay much attention until the summer heat came along, and I start dreaming only of ice cream. This place is kind of a childhood dream. You walk in and are surrounded by sweets, ice cream, and little gifts. We have stopped here twice in less than 24 hours for some ice cream. Last night we tried the birthday cake and peppermint ice cream in waffles cones. Today we had birthday cake and amaretto cherry. The amaretto cherry is my favorite. It is a sweet amaretto flavor with thick, crunchy chocolate shavings and big chunks of maraschino cherry. There are many other flavors including lower fat yogurt and sorbets. I have only tried the ice cream. However the fudge and other treats look delicious. They are one of the rare places that I can find juicy pear Jelly Belly's on bulk! I am looking forward to seeing what their selection is like in the winter. Maybe hot chocolate? One can dream. read more

Windy City Sweets - Birthday cake and amaretto cherry - Candy Stores Near Me - Chicago, Illinois

I have NEVER been so insulted in my life. The treatment of a woman and her child that I witnessed was inexcusable. Complaining about a child touching a glass, mocking him and his mother? Absolutely ridiculous. As a parent and a member of this community I'm beyond insulted. The treatment of this woman and child will be passed on. Not very smart with a school one block away. read more

I've been coming to Windy City Sweets since I moved to Lakeview in 2010. Always a great time and I find the coolest treats (like my favorite sour pumpkin gummies for Halloween!) This year they knocked my custom caramel apple wedding favors out of the park! Delicious and fresh, even a week later. My guests were raving about them. Would highly recommend for your next event. Thank you! read more

Windy City Sweets - Candy Stores Near Me - Chicago, Illinois

This place is amazing!! Is a huge candy store for every age and taste. So many sweets to pick from. We just came here for the ice cream and ended up trying some cookies as well. The ice cream selection is great! Is not like other small local places that only have 4 ice creams for you to pick from, here you will have many options. The staff was very friendly as well. They have indoor and outside sitting to pick from. They offer different specials each day of the week. Give it a try you will not be disappointed!! read more

Windy City Sweets - Birthday cake and pirates treasure! - Candy Stores Near Me - Chicago, Illinois

I will visit my lola and she loves sweet's. So I came to this place to look for some sweets to buy. Their place was clean. They have a lot of sweets to choose from. They have chocolate, strawberry, coffee, macha and many more flavors. The sweets were organized well. The staff are friendly and nice. They will greet you and help you. They will also recommend some flavors to taste. I bought a box of chocolate cupcakes and some candy chocolate. I'm sure my lola loves it. I choose to buy a different flavor of cupcakes. It is put in a box. It's a little bit expensive but worth the price. I highly recommend this place. read more