Chicago's Best Milkshakes

A “milkshake break” is the ideal time-out from a busy day sightseeing or shopping. Whether you’re looking for a
simple vanilla shake, a booze-laced version, or one that’s topped with a mini
sundae, Chicago has a frozen treat to fit every craving.

Burger Bar
 (2954 N. Sheffield Ave.)

Though known for their burgers and creatively topped fries (like sweet potato
fries with lemon Tabasco aioli), DMK makes a terrific, thick milkshake. They
stick with classics like vanilla, chocolate, espresso, and peanut butter, and
there’s also a monthly flavor, like May’s birthday cake shake.

Burger Shop
 (2218 N. Lincoln Ave. and 1571 Sherman Ave.,

The burger joint has locations in Lincoln Park and Evanston and turns out
creamy shakes alongside thin, griddled patties and extravagant cheese fries.
The Nutella flavor has achieved cult status in Chicago, but there’s also
banana, hot fudge, Oreo, maple, coffee, vanilla, and other flavors as well.

Allium (120 E. Delaware Pl.)

For a fancier milkshake–though it’s still just $5–Allium at the Four Seasons
has a miso butterscotch milkshake that strikes an ideal balance between salty
and sweet flavors. Get it split in two, or risk being too full to finish the
housemade, Chicago-style hot dog Allium is best known for.

 (161 E. Huron, 5 W. Ontario, 100 W. Randolph, and 835 N.

M Burger’s milkshake menu simply offers vanilla, chocolate, and strawberry
flavors, and while these are very good, ask for the secret, off-menu shakes.
Past flavors have included espresso, butterscotch, and blueberry.

Lickity Split Frozen Custard Sweets (6056
N. Broadway St.)

Edgewater’s adorable ice cream parlor makes milkshakes by blending frozen
custard with a choice of toppings. Start with vanilla or chocolate custard, and
then add in hot fudge, butterscotch, or Oreos.

25 Degrees (736 N. Clark St.)

When milkshake and cocktail cravings collide, 25 Degrees is the place to go.
The burger and boozy shake joint offers giant, decadent milkshakes like salty
caramel, with Maker’s Mark, butterscotch, vanilla ice cream, and Hawaiian red
sea salt, and a Guinness shake, with Guinness, chocolate sauce, and vanilla ice
cream. For an insider’s look at their shakes, check out the clip from our friends at You Me This Morning.

The Chicago Diner (3411 N. Halsted
St. and 2333 N. Milwaukee Ave.)

The Diner, which has locations in Lakeview and Logan Square, offers vegan
milkshakes that taste exactly like they’re made with ice cream and milk
(they’re actually made with Temptation Vegan Ice Cream and sweetened with beet
sugar). The chocolate peanut butter gets all the attention, but there are also
flavors like vanilla chai, mocha, and lucky leprechaun mint.

Scooter’s Frozen Custard (1658 W. Belmont

And for those times when both a
milkshake and sundae are required, head to Scooter’s for the Boston Shake,
which tops a milkshake with a scoop of custard, chocolate sauce and whipped
cream. Though the origin of this treat is unknown, it pops up occasionally
around the Midwest and elsewhere.

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