Insomnia Cookies is one of The 15 Best Places for Cookies in Chicago.

1. Insomnia Cookies

8.3
2260 N Lincoln Ave (at W Belden Ave), Chicago, IL
Dessert Shop · Lincoln Park · 29 tips and reviews

Sam D.Sam Dawes: Delicious cookies! Served warm!

TammyTammy: Cookies are always fresh, hot, and chocolate chips are extra gooey. You can make your own ice cream cookie sandwich (2 different types of cookies are allowed) or an a la mode!

Maia F.Maia Feruzi: Quaint little spot open to 3am thank god to fulfill all your Kate night cravings. I had the chocolate chip cookie a la mode and it was a delicious vanilla and melted chocolate heaven in my mouth!

Sweet Mandy B's is one of The 15 Best Places for Cookies in Chicago.

2. Sweet Mandy B's

9.2
1208 W Webster Ave (at N Racine Ave), Chicago, IL
Bakery · North Side · 100 tips and reviews

Allison R.Allison Ribble: Snickerdoodle cupcakes and sprinkle sugar cookies are definitely the best! Go early in the day to get the "fresh" stuff and best selection. They also serve Intelligentsia coffee which is amazing!

RebeccaRebecca: Great Local shop, friendly service and old-fashioned treats like grandma use to make :-) Don't miss out on the best chocolate chip cookies or chocolate dipped marshmallows. Sugar Coma Beware!

AnnieAnnie: My favorite Chicago bakery! Try red velvet or any specialty of the day cupcake. Delicious banana pudding and their frosting on cookies is to die for!

Scofflaw is one of The 15 Best Places for Cookies in Chicago.

3. Scofflaw

9.3
3201 W Armitage Ave (at Kedzie Ave), Chicago, IL
Cocktail Bar · Logan Square · 149 tips and reviews

Stephanie T.Stephanie T: Homemade chocolate chip cookies at midnight and delightful cocktails!

Samantha K.Samantha Kuhn: Cute, vintage atmosphere with helpful and unpretentious servers, what more could you want at a Mixology bar? Enjoy a Diplomat's Daughter and get there at midnight for free chocolate chip cookies.

Melissa Y.Melissa Y.: Falcon Cap and Swizzle #Cinco are amazing! Free chocolate chip cookies at midnight are a great touch.

Molly's Cupcakes is one of The 15 Best Places for Cookies in Chicago.

4. Molly's Cupcakes

9.1
2536 N Clark St (btwn Wrightwood & Deming), Chicago, IL
Cupcake Shop · Park West · 207 tips and reviews

MelissaMelissa: cookie monster is delightful chocolate decadence is delicious as well

SamanthaSamantha: Amazing flavors! Cookie monster and vanilla with buttercream are to die for!

heatherheather: Try the chocolate chip cookie dough cupcake, delicious!

Chicago Diner is one of The 15 Best Places for Cookies in Chicago.

5. Chicago Diner

9.0
3411 N Halsted St (at Roscoe St), Chicago, IL
Vegan and Vegetarian Restaurant · Lake View East · 205 tips and reviews

AmiAmi: The chocolate peanut butter cookie dough milkshake is incredible.

Hannah G.Hannah G: vegan cookie dough peanut butter milkshake tastes better than any real shake youll get anywhere!!

Paras K.Paras Khara: Incredible food! Love the brunch menu. Also get the snickerdoodle cookie for dessert :) so good

BRGRBELLY is one of The 15 Best Places for Cookies in Chicago.

6. BRGRBELLY

8.5
5739 W Irving Park Rd, Chicago, IL
Burger Joint · Portage Park · 33 tips and reviews

Kelly S.Kelly S.: Decent burgers, delicious (chipotle) fries and a free cookie to top it off!

Alex L.Alex Lapenia: This place is fire. Shakes are great and you get a free cookie. Burgers and fries are excellent. Highly recommend this place. Whooooooo!

RoseRose: Our first time here. We ordered the chicken breast Leadbelly & the Easy Rider. Food was delicous! Yummy fries & you get a free cookie :) We will be back for the vodka shake & delicious food.

D'Amato's Bakery is one of The 15 Best Places for Cookies in Chicago.

7. D'Amato's Bakery

9.0
1124 W Grand Ave (at N May St), Chicago, IL
Bakery · West Town · 36 tips and reviews

Henry S.Henry S: Best Italian cookies and breads.

Smokkee S.Smokkee Singleton: Cookies!!!! Insanely addictive!

MikeMike: Best Italian bakery (and pizza!) in the entire city. You can't go wrong with a slice of sausage, or a biscotti, or a loaf of bread, or some cookies, or - anything!

Summer House Santa Monica is one of The 15 Best Places for Cookies in Chicago.

8. Summer House Santa Monica

8.8
1954 N Halsted St (btwn Armitage Ave & Willow St), Chicago, IL
American Restaurant · North Side · 134 tips and reviews

maggie m.maggie moffat: The cookies and desserts in the front are by far some of the best I've ever had. Their food is amazing also! Loved their chips and guac and their vegetables are all so good! Loved it all!

Meredith B.Meredith B: Definitely try their calamari and grab a cookie on your way out! Beautiful and relaxing atmosphere and knowledgable staff.

Max M.Max Moss: Great beer selection. The $2 slider deal was great. Get the cookie sundae.

Grand Lux Café is one of The 15 Best Places for Cookies in Chicago.

9. Grand Lux Café

8.4
600 N Michigan Ave (at Ontario St), Chicago, IL
American Restaurant · Streeterville · 349 tips and reviews

Sean M.Sean Miller: Great freshly baked cookies !

PJ Y.PJ Young: Great chocolate chip pecan cookies.

nicky w.nicky willis: Fabulous!!!!! Some of my reccomended favs; Pot roast fries and the Chocolate Chip Pecan cookies...Yummy!!!!

Letizia's Natural Bakery is one of The 15 Best Places for Cookies in Chicago.

10. Letizia's Natural Bakery

8.5
2144 W Division St (at Leavitt St.), Chicago, IL
Bakery · Wicker Park · 38 tips and reviews

AdrienneAdrienne: The espresso cookie was delicious. Pretty good chai too.

Elisa A.Elisa Ambrosini: Oatmeal chocolate chip cookie is amazing!

Serious EatsSerious Eats: Oatmeal Chocolate Chip Cookie: Sporting some beautiful lacey butter and brown sugar edges and a deliciously chewy center, this is one oatmeal cookie unmarred by the inclusion of raisins.

Potbelly Sandwich Shop is one of The 15 Best Places for Cookies in Chicago.

11. Potbelly Sandwich Shop

8.3
211 West Wacker Dr, Suite 10 (at Wells St), Chicago, IL
Sandwich Spot · The Loop · 20 tips and reviews

Alex F.Alex Flis: Huge fan of the Shakes and chocolate chip oatmeal cookies... Amazing

zfelszfels: Balance out your Farmhouse salad with an oatmeal chocolate chip cookie. 🍪

Bill P.Bill P: Probably the best sandwiches in Chicago! The roast beef is freakin' awesome! Fantastic milkshakes and tasteful cookies. Decent quantities and quality. Yummy!

Weber's Bakery is one of The 15 Best Places for Cookies in Chicago.

12. Weber's Bakery

9.4
7055 W Archer Ave (at Nottingham Ave), Chicago, IL
Bakery · Garfield Ridge · 44 tips and reviews

Jim B.Jim Baker: Very good cookies!

Lauren A.Lauren Alexandra: Cake, cookies, everything!

RiπerRiπer: Oreo Cookies & Cream and Custard filled Paçzkis are so delicious.

Panes Bread Cafe is one of The 15 Best Places for Cookies in Chicago.

13. Panes Bread Cafe

8.5
3002 N Sheffield Ave (at W Wellington Ave), Chicago, IL
Café · Lakeview · 70 tips and reviews

Elliott T.Elliott Thomas: Order the Pollo Diablo, and never, ever, ever leave without getting a monster cookie.

Jordan M.Jordan M: I can't get enough of the monster cookies here. They're amazing!

Derek K.Derek Kucynda: Sandwiches are on a whole 'nother level here! Fresh homemade bread (mmmm Tomato Focaccia) and deliciously decadent cookies! Excellent soup and sides (just avoid the dry quesadillas). It's BYOB too!

Artopolis Bakery, Cafe and Agora is one of The 15 Best Places for Cookies in Chicago.

14. Artopolis Bakery, Cafe and Agora

8.3
306 S Halsted St (at W Jackson Blvd), Chicago, IL
Greek Restaurant · Greektown · 69 tips and reviews

Marco M.Marco Morelli: Try the Greek coffee and Almond Cinnamon cake cookies.

Crain's Chicago BusinessCrain's Chicago Business: Melomakarona, cookies with honey and nuts, were quite good, but baklava was short on walnuts, vanilla and cinnamon. Read more.

Nate B.Nate Bartlett: Almond Cookies are little pieces of heaven.

Potbelly Sandwich Shop is one of The 15 Best Places for Cookies in Chicago.

15. Potbelly Sandwich Shop

8.1
55 W Monroe St Lbby 100D (at Dearborn St), Chicago, IL
Sandwich Spot · The Loop · 19 tips and reviews

Ashley Joy C.Ashley Joy Calvin Roberson: Cookies are awesome

Jillian B.Jillian Burnickas: Good soup and amazing cookies

Novel Coworking The LoopNovel Coworking The Loop: For quick service, order online and pick it up in store! The cookies are also a must!