Irazu is one of The 15 Best Places for Milkshakes in Chicago.

1. Irazu

8.8
1865 N Milwaukee Ave (at N Oakley Ave), Chicago, IL
Latin American Restaurant · Bucktown · 106 tips and reviews

Amy L.Amy Le: Where else can you get the best Oatmeal Milkshake delivered right to you? Irazu Costa Rica Restaurant also has some of the best chicken & steak burritos in Chicago. The meats are perfectly marinated. Read more.

Janet A.Janet A.: Definitely try the oatmeal (with milk) shake, it's amazing!

Kris D.Kris D: Oatmeal shake is a must. Grilled steak is amazing upgrade to the authentic rice worth the buck. If you get Omar as a waiter tip him well, so makes the visit laid back....

Portillo's is one of The 15 Best Places for Milkshakes in Chicago.

2. Portillo's

9.0
100 W Ontario St (at Clark St), Chicago, IL
Hot Dog Joint · River North · 667 tips and reviews

Amanda C.Amanda Cooper: My favorite place for Chicago style hot dogs or hot dogs in general. For dessert get the cake shake, you won't regret it!

Lauren M.Lauren Meek: Amazing burgers, hot dogs, chocolate cake shake. You pretty much can't go wrong. It is always crowded, but the lines move quickly. You can call ahead with your order

Nyla J.Nyla Jackson: The chocolate shake,bacon cheeseburger,and chocolate cake are completely amazing!☺😊😀

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

3. Chicago Diner

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

Mikaela M.Mikaela Miner: Try their delicious soy ice-cream milkshakes and potato skins ... mmm

Amy G.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.

Daniel M.Daniel Miller: The shakes, Reuben, country fried everything, everything is good. Make sure to get the mac&cheese

Tiztal Cafe is one of The 15 Best Places for Milkshakes in Chicago.

4. Tiztal Cafe

8.9
4631 N Clark St (btwn Wilson Ave. & Leland Ave.), Chicago, IL
Breakfast Spot · Uptown · 50 tips and reviews

Chris H.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 L.Bethany Lang: Best chilaquiles ever, and you've gotta try an oatmeal shake.

Michael S.Michael Stump: Wow... The oatmeal shake is awesome. And the green chilaquiles are killer. The server was very very good as well. Kill!

Shake Shack is one of The 15 Best Places for Milkshakes in Chicago.

5. Shake Shack

8.4
66 E Ohio St (at N Rush St), Chicago, IL
Burger Joint · Near North Side · 132 tips and reviews

Tim P.Tim Porter: Shroomburger was good, get it with a milkshake for an indulgence well worth it.

Marwan M.Marwan Mz: The signature burger is the best and the their side by side shake is amazing

Adam V.Adam V: The cheeseburger is delicious and goes well with one of their shakes. Amazing all around.

Superdawg Drive-In is one of The 15 Best Places for Milkshakes in Chicago.

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

Scott P.Scott Presslak: Order the onion chips and try (yes, try) to sip a chocolate shake through the straw.

Lisa W.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 T.Katy Thompson: The whooperdawg is delicious, and best shakes of your life, no matter the flavor.

DMK Burger Bar is one of The 15 Best Places for Milkshakes in Chicago.

7. DMK Burger Bar

8.8
2954 N Sheffield Ave (at W Wellington Ave), Chicago, IL
Burger Joint · Lakeview · 257 tips and reviews

Anna C.Anna C: Outstanding burgers and the best peanut butter shake since the Zephyr closed down. Om nom nom!

Evan[Bu]Evan[Bu]: Bison burger with deviled eggs? Just another reason why Chicago is home to some of the world's best food. Be sure to try a S'mores shake with your meal!

Serious EatsSerious Eats: Great griddled burgers from a fine dining chef, plus crispy fries and thick shakes.

The Wiener's Circle is one of The 15 Best Places for Milkshakes in Chicago.

8. The Wiener's Circle

7.8
2622 N Clark St (btwn Drummond Pl & Wrightwood Ave), Chicago, IL
Hot Dog Joint · Park West · 130 tips and reviews

Faith R.Faith Ryder: Get the chocolate shake. Its $20 but it's big enough for at least 4 AND it's the best shake you'll ever have!

jeff s.jeff semones: Best chocolate shake ever! Ever.

Jany W.Jany Wang: Oh babe ! U gonna love their chocolate milk shake ! Can't get the same anywhere else !!! Awesome !!!! Strongly recommended ! (Worthwhile $20!)

Medici on 57th is one of The 15 Best Places for Milkshakes in Chicago.

9. Medici on 57th

8.7
1327 E 57th St (btwn S Kimbark Ave & S Kenwood Ave), Chicago, IL
Bakery · Hyde Park · 111 tips and reviews

Anastasia B.Anastasia Belozertseva: Strawberry lemonade is sooo refreshing in the summer! Also, the shakes are absolutely delicious.

Julia P.Julia Park: Mexican milkshake, fruit tart, and strawberry lemonade :) to die for

zfelszfels: Mexicana shake gets all the buzz, but the mocha shake is also a great bet.

Janson's Drive-In is one of The 15 Best Places for Milkshakes in Chicago.

10. Janson's Drive-In

8.8
9900 S Western Ave (at W 99th St), Chicago, IL
Hot Dog Joint · Beverly · 15 tips and reviews

Spencer L.Spencer Lent: Amazing banana shakes here... and the best fries I have had in YEARS.

Wendy P.Wendy Pettas: NOW OPEN. Come and check it out. banana shakes are awesome.

Andrea M.Andrea Martinez: Strawberry banana shake is amazing !!!

M Burger is one of The 15 Best Places for Milkshakes in Chicago.

11. M Burger

7.4
5 W Ontario St (btwn N State St & N Dearborn St), Chicago, IL
Burger Joint · Near North Side · 84 tips and reviews

Jeremiah U.Jeremiah Ulibarri: Double cheese and strawberry shake is where it's at.

Time Out ChicagoTime Out Chicago: Aside from the juicy burgers and chicken sandwiches, this location offers beer (like Goose Island's Green Line) and, most important, an ice-cream program featuring dipped cones, sundaes and shakes. Read more.

Lisa W.Lisa W: The key lime pie shake special during September was the best shake I've had in a long time. Should be a staple on the menu :)

Fred & Jack's is one of The 15 Best Places for Milkshakes in Chicago.

12. Fred & Jack's

8.5
7600 S Yale Ave (btwn 76th & Vincennes), Chicago, IL
Mexican Restaurant · West Chatham · 46 tips and reviews

Michele E.Michele Evans-Brock: GREAT FOOD! A Steak Burrito that will have your eyes rolling in the back of your head. Authentic breakfasts: Omelettes and Homestyle Potatoes, Shakes and Malts... You've got to check them out.

Ashley H.Ashley Hartford: love their strawberry milkshakes

BlucexyBlucexy: Been eating here for over 15 years and i never had any problems! The steak burrito is off the chain! Try it with jalepenos and a strawberry shake!

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

13. Chicago Diner

8.7
2333 N Milwaukee Ave (at W Fullerton Ave), Chicago, IL
Vegan and Vegetarian Restaurant · Logan Square · 84 tips and reviews

T S.T Sussman: The vegan milkshakes are amazing.

Heather Z.Heather Zinger: Best vegan milkshakes ever!

Jeiran H.Jeiran Hasan: Chocolate peanut butter milkshake was outstanding!

Choppers is one of The 15 Best Places for Milkshakes in Chicago.

14. Choppers

7.8
1659 N Ashland Ave (at Wabansia), Chicago, IL
Burger Joint · Bucktown · 25 tips and reviews

Mel K.Mel Kerno: Chocolate shakes are to die for!

Chicago magazineChicago magazine: Best milkshake: Mix strawberries with creamy peanut butter for the nostalgic PB&J. Read more.

Wendy J.Wendy Johnson: Choppers milkshakes are the best in the city. LOVE.

Scooter's Frozen Custard is one of The 15 Best Places for Milkshakes in Chicago.

15. Scooter's Frozen Custard

9.2
1658 W Belmont Ave (at Paulina St.), Chicago, IL
Ice Cream Parlor · Lakeview · 60 tips and reviews

Time Out ChicagoTime Out Chicago: Order a Boston shake, and quiver in awe as the towering milkshake topped with hot fudge and whipped cream is handed over. -JJ Read more.

Time Out ChicagoTime Out Chicago: Order a Boston shake, and quiver in awe as the towering milkshake topped with hot fudge and whipped cream is handed over.

Scott KleinbergScott 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!