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the Loop's best

Cookie shops

You have a specific craving for a cookie and you aren't settling for anything less.

Based on 518 Opinions
+515
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Updated April 2026
01
Simply Sweet Caroline's image 1
Simply Sweet Caroline's image 2
Simply Sweet Caroline's image 3
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Custom cookies feature exquisite decoration with vibrant colors and metallic accents. Friendly, professional service ensures a smooth ordering process. Each cookie is individually sealed, perfect for travel and special occasions.

Cookies come beautifully decorated and individually sealed for easy transport. Custom designs match inspiration photos perfectly, making them a hit at birthdays and showers.

People are saying

"The cookies here are beautiful and delicious."

"These cookies are adorable and delicious, a real hit for kids."

"I had cookie cakes made for our wedding weekend."

Good to know

1

The ordering process is easy and smooth for custom cookies.

2

Caroline offers cookie designs that can match your event theme.

3

Cookies are individually sealed for convenient transport.

02
Seedoโ€™s Levantine Bakery image 1

Clean, organized bakery offers a fully halal menu with unique Palestinian baked goods and a great vibe. Chocolate chip cookies deliver a rich, classic flavor, while peanut butter cookies feature tahini and jam twists. Perfect spot for a healthy lunch and breakfast with fresh, flavorful options.

Chocolate chip cookies stand out with a rich, classic flavor. Peanut butter cookies come with unique twists like tahini and jam for added depth.

People are saying

"I loved the date cake; it was rich and tasty."

"I found the lentil soup to be warming and flavorful."

"This cookie is so fresh and flavorful."

Good to know

1

The bakery is fully halal, catering to dietary restrictions.

2

Parking is limited and is paid street parking nearby.

3

Expect to find high-quality organic ingredients in all menu items.

03
Crumbl image 1
Cookie shop

Small shop with a bright, clean interior offers fresh cookies that deliver a party in your mouth. Cozy atmosphere feels inviting despite being cramped. Chocolate chip varieties stand out as the best in the game.

Cookies here are fresh and deliver a party in your mouth with every bite. Chocolate chip varieties stand out as best in the game.

People are saying

"I found the cookies here to be really fresh and tasty."

"They handled my delivery issue quickly and kindly."

"The food here is really good and fresh."

Good to know

1

Crumbl offers new cookie flavors every week.

2

Cookies cost nearly $5 each.

3

Customers must pay with cards; cash is not accepted.

04
Broadway Cafe image 1

Small space with cozy tables and street views offers a relaxed vibe with fantastic music. Chocolate chip cookies are rich and satisfying, alongside cupcakes and pastries. Late hours and peaceful surroundings make it a great spot to unwind.

Chocolate chip cookies stand out with a rich, satisfying taste. The bakery offers a variety of sweets including cupcakes and pastries, and sometimes gives out free cookies.

People are saying

"I had the best latte I ever tried here."

"I thought the desserts here were so good."

"I loved the chocolate chip cookies; they were the best I'd ever tasted."

Good to know

1

Broadway Cafe opens late, allowing for coffee and cake at night.

2

Expect no menu available for bakery items, limiting choices.

3

Prices are affordable, but some items may not be worth it.

05
Staypineapple, An Iconic Hotel, The Loop Chicago image 1

Historic building offers comfortable rooms with exceptional views and a friendly bar for a chill vibe. Guests enjoy complimentary cookies daily with coffee and a free drink. Atmosphere stays fun and welcoming throughout.

Complimentary cookies appear daily in the lobby alongside coffee and water. Each guest also receives a free drink with access to these treats.

People are saying

"This hotel's location is great for walking everywhere."

"The beds here are so comfortable and the rooms are clean."

"The staff brought us milk and cookies, and they were so kind."

Good to know

1

Happy hour offers a burger and beer or soda for $10 from 4-6 pm.

2

Every afternoon, enjoy a cookie hour with complimentary beverages.

3

Valet parking is expensive and can be problematic during busy events.

06
The Civic Opera Barber Shop image 1

Old-school barbershop offers quick, precise cuts with a vintage vibe. Enjoy authentic Italian cookies paired with espresso after your trim. Warm, welcoming atmosphere blends classic grooming with friendly chat.

They serve authentic Italian cookies alongside a shot of espresso. These come as a small treat after a haircut, paired with friendly conversation.

People are saying

"This vintage barber shop gives you a classic cut with friendly service."

"I got one of the best espressos I've ever had."

"Sam offered me Italian cookies and espresso after my haircut."

Good to know

1

The shop offers haircuts, shaves, shampoo, shoe shining, and espresso.

2

They only accept cash payments.

3

A haircut costs $40, which is reasonable for downtown.

07
Insomnia Cookies image 1
Dessert shop

Cozy spot offers warm cookies with gooey centers and crispy edges, perfect for late-night cravings. Pair treats with fresh ice cream for a rich dessert. Chill vibe attracts night owls and students, with very late delivery and simple, no-seat space.

Warm cookies arrive with gooey centers and crispy edges that melt in your mouth. Pairing them with fresh, creamy ice cream creates a rich dessert experience, especially satisfying late at night.

People are saying

"These cookies are perfectly warm, gooey, and delicious."

"It's the perfect spot for late-night chocolate cravings."

"The delivery drivers here are pretty friendly."

Good to know

1

Insomnia Cookies is open very late, making it ideal for night owls.

2

Expect long lines on weekends, especially late at night.

3

They offer multiple gluten-free cookie options for those with dietary restrictions.

08
Nutella Cafe Chicago image 1

Bright Nutella-themed decor creates a unique atmosphere with personalized jars. Nutella-filled cookies come free with drinks and pair perfectly with coffee, making them a sweet highlight. Small tables cause a crowded feel, but outdoor patio offers a quiet alternative.

Nutella-filled cookies come free with every drink and stand out over croissants and breads. The cookies pair well with coffee and Nutella mocha, making them a sweet highlight alongside ice cream.

People are saying

"You have to try the Nutella Crepe with bananas; it's very tasty."

"The waffles here are light and fluffy."

"The Nutella cookies served with drinks were delicious."

Good to know

1

Expect a wait time of 30-45 minutes during peak hours.

2

The cafe opens at 8 am daily.

3

You can personalize your Nutella with your name for a unique souvenir.

09
Crockett Cookies image 1
Wholesale bakery

Butter cookies offer a creamy buttery flavor that feels like a nostalgic throwback to classic Chicago school treats. Packaging adds to the traditional vibe, and shipping is fast and reliable, ensuring cookies arrive fresh and intact.

Butter cookies deliver a creamy, buttery flavor that feels nostalgic and fresh every time. These cookies are authentic throwbacks to original lunchroom treats, arriving unbroken and with fast service.

People are saying

"These cookies taste like childhood memories from Chicago."

Good to know

1

Shipping is fast, ensuring quick delivery of your cookies.

2

Cookies arrive unbroken if packaged properly.

3

Prices for cookies have been increasing recently.

10
The St. Regis Chicago image 1

Towering skyscraper offers epic city views and personalized butler service. Kids enjoy cookies with milk and robes, plus books arranged in rooms. Amenities include a large indoor pool and a well-equipped gym for relaxation and fitness.

Cookies come with milk and robes for kids, creating a cozy treat. Staff arrange cookies and books in rooms before arrival for a special touch.

People are saying

"Vince at the Hotel concierge desk went all out to make everything exceptional."

"The city views from the pool and terrace are amazing."

"They made my daughter's birthday extra special with cookies and milk."

Good to know

1

Every evening at 5 pm, they do Sabrage (Champagne Sabering) for guests.

2

There is a daily champagne opening ceremony with a saber starting at 5:30 p.m.

3

The hotel is located near Riverwalk, providing easy access to attractions.

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