1. Irazu
8.8
1865 N Milwaukee Ave (at N Oakley Ave), Chicago, IL
Latin American Restaurant · Bucktown · 106 tips and reviews
Janet A.: Definitely try the oatmeal (with milk) shake, it's amazing!
Rachel C.: The oatmeal shake is delicious! And they can make it vegan!
Olivia Barrett: Wow! I couldn’t recommend this place more. The casado is much like what’s served in Costa Rica. Oatmeal shake was to die for! It’s cash only, but they have an ATM. Great atmosphere and service, too.
3. Chicago Diner
8.9
3411 N Halsted St (at Roscoe St), Chicago, IL
Vegan and Vegetarian Restaurant · Lake View East · 206 tips and reviews
Amy Graff: Chicago vegan legend. Reuben gets all the love but the truffle melt really, yes, melts my heart. Seitan wings are amazing starters and the peanut butter shake is the best end to your vegan junk feast.
Pam De Silva: Fantastic vegan comfort food. The cookie dough peanut butter milkshake is a must! Concocted from soy milk and corn ice cream goodness.
Daniel Miller: The shakes, Reuben, country fried everything, everything is good. Make sure to get the mac&cheese
4. Tiztal Cafe
9.0
4631 N Clark St (btwn Wilson Ave. & Leland Ave.), Chicago, IL
Breakfast Spot · Uptown · 50 tips and reviews
Chris Hall: Probably the best chilaquiles in town and a great variety of delicious shakes and juice drinks. Open 8am-4pm every day. Also outdoor patio seating, when weather allows.
Bethany Lang: Best chilaquiles ever, and you've gotta try an oatmeal shake.
Michael Stump: Wow... The oatmeal shake is awesome. And the green chilaquiles are killer. The server was very very good as well. Kill!
5. Shake Shack
8.5
66 E Ohio St (at N Rush St), Chicago, IL
Burger Joint · Near North Side · 132 tips and reviews
Heather Williams: The fair trade shake is SUPER delicious, especially if you enjoy dark roast coffee.
David O'Connell: I was in New York for theree weeks and the line at the Shake Shack was always too long. I was very excited to see one here in Chicago. The shakes and burgers are great. "Sha-cago dog" mmmmm
Tim Porter: Shroomburger was good, get it with a milkshake for an indulgence well worth it.
6. Superdawg Drive-In
9.1
6363 N Milwaukee Ave (btwn Devon Ave & Highland Ave), Chicago, IL
Hot Dog Joint · Norwood Park · 162 tips and reviews
Lisa W: Some of the best fries in the city, and who doesn't love a perfect hot dog nestled into a special little box? Strawberry shake is amazing. Also the burgers are really solid. A Chicago classic.
Katy Thompson: The whooperdawg is delicious, and best shakes of your life, no matter the flavor.
Melissa Kane: Classic hot dogs. Their milkshakes are the best!
9. Medici on 57th
8.6
1327 E 57th St (btwn S Kimbark Ave & S Kenwood Ave), Chicago, IL
Bakery · Hyde Park · 111 tips and reviews
Anastasia Belozertseva: Strawberry lemonade is sooo refreshing in the summer! Also, the shakes are absolutely delicious.
Julia Park: Mexican milkshake, fruit tart, and strawberry lemonade :) to die for
zfels: Mexicana shake gets all the buzz, but the mocha shake is also a great bet.
13. Small Cheval
9.0
1732 N. Milwaukee Ave, Chicago, IL
Burger Joint · Bucktown · 74 tips and reviews
Emily Kane: We're not worthy. No nonsense burgers, shakes and fries that were sent straight from heaven.
Chicago Tribune: The inside is cramped and loud, so hope for a mild day and head to the back patio, where you can feast on gloriously griddled burgers and thick shakes in relative peace. Read more.
Justin White: Single cheeseburger, fries, chocolate shake. Like the Five Guys version of Au Cheval.
Time Out Chicago: Order a Boston shake, and quiver in awe as the towering milkshake topped with hot fudge and whipped cream is handed over.
Mike Hayes: Get a Boston Shake. It's a shake with a Sundae ON TOP! Amazing!
Scott Kleinberg: Simply put: There is no better ice cream in Chicago. There, I said it. Now you try it. Boston Shake is amazing. Oh heck, it's all amazing!