1. Irazu
8.8
1865 N Milwaukee Ave (at N Oakley Ave), Chicago, IL
Latin American Restaurant · Bucktown · 106 tips and reviews
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.: Definitely try the oatmeal (with milk) shake, it's amazing!
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....
2. Portillo's
9.0
100 W Ontario St (at Clark St), Chicago, IL
Hot Dog Joint · River North · 667 tips and reviews
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 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 Jackson: The chocolate shake,bacon cheeseburger,and chocolate cake are completely amazing!☺😊😀
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 Miner: Try their delicious soy ice-cream milkshakes and potato skins ... mmm
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 Miller: The shakes, Reuben, country fried everything, everything is good. Make sure to get the mac&cheese
4. Tiztal Cafe
8.9
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!
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 Presslak: Order the onion chips and try (yes, try) to sip a chocolate shake through the straw.
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.
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 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.
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 Ulibarri: Double cheese and strawberry shake is where it's at.
Time 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: 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 :)
12. Fred & Jack's
8.5
7600 S Yale Ave (btwn 76th & Vincennes), Chicago, IL
Mexican Restaurant · West Chatham · 46 tips and reviews
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 Hartford: love their strawberry milkshakes
Blucexy: 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!
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. -JJ Read more.
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.
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!