A Local’s Windy City Food Tour

02.May 2011

Guest Authors

This is a guest post by Kim of To Uncertainty And Beyond. She takes us on a mouthwatering tour of her home town, Chicago. Belly up to the bar and be prepared to feast your eyes!

Visitors to Chicago are bombarded with glorious, calorie filled food options. There’s pizza, hot dogs, fried chicken, and great bars on every corner! (Not to mention the great dessert options!)

While there are also wonderful healthy, fresh, vegetarian, vegan, and high-end places. I thought it would be more fun to focus on the “bad for you” places that I know and love. I’ve lived in Chicago for about 6 year and have made it a priority to seek out and find the best of the best in lots of different cuisines. Hopefully my hard work (and hard eating) will help you on your next visit to the Windy City!

Deep Dish Pizza

A Chicago style pizza is deep dish, stuffed with ingredients, and lots of cheese. It’s served in what looks like a round cake pan and the buttery crust is usually about 3 inches tall. each pizza takes about 35-45 minutes to bake, so order a beer, an appetizer, and be ready to wait!

deep dish at lou malnati's

The original deep dish is said to have been invented by the guys at Gino’s East. So, that is always a popular place to go. It’s good, but always really crowded and packed with tourists. You’ll find lots of variations of Deep Dish pizza in the city. My tip? Head to Lou Malnati’s or Pequod’s for the best pizza in town.

Lou Malnati’s is one of the most popular chains in the city, and for good reason. Their pizza crust is crunchy, the ingredients are fresh, and the sauce full of flavor. Also try the Malnatti salad. Yum! Pequod’s is famous for it’s “caramelized” cheese crust. To me, it almost tastes burned, but it does have an interesting flavor. There are only two locations, but Pequod’s definitely holds its own up against the big chains.

Lou Malnati’s Locations:

  • South Loop: 805 S. State Street (near the Harrison Red Line stop)
  • River North: 439 North Wells Street (near the Merchandise Mart Brown Line stop)
  • Lincoln Park: 958 W. Wrightwood (near the Diversey Brown Line stop)

Pequod’s Location:

  • Lincoln Park: 2207 N. Clybourn Ave (15 minute walk from Armitage Brown Line stop)
  • Morton Grove: 8520 Fernald Ave Morton Grove Il (out in the burbs, you have to drive)

Gino’s East:

  • Downtown: 633 North Wells Street (near Grand Red Line stop or Chicago Brown Line stop)
  • Northwestern Campus: 162 East Superior Street (near Chicago Red Line stop)

Hot Dogs

Chicagoans don’t hesitate to line up and wait for the best hot dogs in the city. A Chicago- style hot dog is made with very specific ingredients. It begins with a boiled all-beef frank placed on a steamed poppyseed bun. This basic dog is topped with diced onion, bright neon green pickle relish, yellow mustard, tomato wedge, a pickle spear, and a hot pepper. Do not ask for ketchup, it does not belong on a Chicago dog. You will likely be ridiculed by the employees and fellow diners if you order ketchup.

You can get a fairly decent hot dog pretty much anywhere in the city. Make sure you look for the signs of a higher quality dog like the all-beef frank and poppyseed bun! If you want a higher class hot dog, give Hot Doug’s or Franks ‘n Dawgs a try. You’ll pay a lot more, but get a gourmet hot dog experience. Be prepared to wait in line for at least 45 minutes at Hot Doug’s. Especially on the weekend when he’s serving up his famous duck fat fries!

Hot Dog stand locations:

Fried Chicken

Harold’s Chicken Shack is the place to go for fried chicken in Chicago. This joint originated on the south side in the 1950′s and many of the original locations will take your order and hand your chicken over from behind bullet proof glass. It is the “dive bar” of the chicken world and it’s tasty!

The chicken is fried to order in a half beef tallow and half vegetable oil to give it a unique taste. If you’re craving some good, old fashioned, southern fried chicken. Harold’s is for you!

You can also find the southern delicacy of chicken and waffles in Chicago. The best place to go is on the south side as well, Chicago’s Home of Chicken and Waffles. How can you pass up a delicately crispy waffle topped with a peice of mouthwateringly juicy fried chicken and maple syrup? Doesn’t sound good? It’s not just good, it’s AMAZING.

Chicken n Waffles

Harold’s downtown locations:

  • South Loop: 636 South Wabash Avenue (near Harrison Red Line stop)
  • West Loop: 518 W Harrison (near Clinton Blue Line stop)
  • West Loop: 804 West Washington Boulevard (Near Clinton Green Line stop)

Chicago’s Home of Chicken and Waffles: 3947 S King Dr (near the Indiana Green Line stop, but driving is also a good option)

Beer

Chicagoans have access to some great locally brewed beer from bigger companies like Goose Island to the smaller Half Acre brewery as well as microbreweries from Wisconsin and Michigan. You can find restaurants and bars with lists so extensive that it makes your head spin.

Chicago is a great place for a beer-tasting night out with friends!

Bar and Brewery locations:

Dessert

I love dessert. Who doesn’t? Chicago also has some amazing places to tempt your sweet tooth. The best frozen custard in the midwest (believe me, I’ve nearly tried them all) can be found at Scooter’s Frozen Custard. If you’ve never had frozen custard, it’s a must when visiting Chicago. It’s a thick, creamy, version of ice cream that is just too darn good to pass up. Fozen custard joints only offer vanilla or chocolate. However, you can choose from a plethora of ingredients for concretes, which is a better version of a blizzard.

Another great ice cream option is The Original Rainbow cone, which has been a Chicago institution since 1926. They have thier unique rainbow cone as well as other yummy options.

If ice cream isn’t your think you can go the baked route. Chicago has some wonderul bakeries serving up cupcakes, cookies, cakes, sweet bread, muffins, and my personal favorite, pies.

Hoosier Mama pies is quickly becoming the hottest spot for dessert in the city. They serve up amazing sweet and savory pies with perfect crusts and fresh ingredients.

Locations for great sweets:

  • Scooter’s Frozen Custard: 1658 West Belmont Avenue (10 minute walk from Belmont Brown Line stop)
  • Original Rainbow Cone: 9233 S Western Ave (driving is your best option)
  • Original Rainbow Cone: Loop – 177 N State St (State/Lake Brown, Orange, Green Line stops, Lake Red Line stop)
  • Hoosier Mama Pie Company: 1618 1/2 Chicago Avenue (15 minute walk from Chicago Blue Line stop)
  • Molly’s Cupcakes: 2536 North Clark Street (take bus 22 or 36)
  • Bake: 2246 W North Ave (near Damen Blue Line stop)
  • Sweet Mandy B’s: 1208 W Webster Ave (10 minute walk from Fullerton Red Line stop)

Great eats in Chicago

Visitors to Chicago are bombarded with glorious, calorie filled food options. There’s a

pizza, hot dog, fried chicken, or a great bar on every corner! (Not to mention the great

dessert options!) While there are also wonderful healthy, fresh, vegetarian, vegan, and

high-end places. I thought it would be more fun to focus on the “bad for you” places that I

know and love. I’ve lived in Chicago for about 6 year and have made it a priority to seek

out and find the best of the best in lots of different cuisines. Hopefully my hard work (and

hard eating) will help you on your next visit to the Windy City!

Pizza

A Chicago style pizza is deep dish, stuffed with ingredients, and lots of cheese. It’s

served in what looks like a round cake pan and the buttery crust is usually about 3 inches

tall. each pizza takes about 35-45 minutes to bake, so order a beer and be ready to wait!

The orignal deep dish is said to have been invented by the guys at Gino’s East. So, that is

always a popular place to go. It’s good, but always really crowded and packed with tourists.

You’ll find lots of variations of Deep Dish pizza in the city. My tip? Skip Giordano’s (a

favorite for some reason) and head to Lou Malnati’s or Pequod’s. Lou Malnati’s is one of the

most popular chains in the city, and for good reason. Their pizza crust is crunchy, the

ingredients are fresh, and the sauce full of flavor. Also try the Malnatti salad. Yum!

Pequod’s is famous for it’s “caramelized” cheese crust. To me, it almost tastes burned, but

it does have an interesting flavor. There are only two locations, but Pequod’s definitely

holds its own up against the big chains.

Lou Malnati’s Locations:
South Loop: 805 S. State Street (near the Harrison Red Line stop) – MUCH LESS CROWDED
River North: 439 North Wells Street (near the Merchandise Mart Brown Line stop)
Lincoln Park: 958 W. Wrightwood (near the Diversey Brown Line stop)

Pequod’s Location:
Lincoln Park: 2207 N. Clybourn Ave (15 minute walk from Armitage Brown Line stop)
Morton Grove: 8520 Fernald Ave Morton Grove Il (out in the burbs, you have to drive)

Gino’s East:
Downtown: 633 North Wells Street (near Grand Red Line stop or Chicago Brown Line stop)
Northwestern Campus: 162 East Superior Street (near Chicago Red Line stop)

Hot Dogs

Chicagoans don’t hesitate to line up and wait for the best hot dogs in the city. A Chicago-

style hot dog is made with very specific ingredients. It begins with a boiled all-beef frank

placed on a steamed poppyseed bun. This basic dog is topped with diced onion, bright neon

green pickle relish, yellow mustard, tomato wedge, a pickle spear, and a hot pepper. Do not

ask for ketchup, it does not belong on a Chicago dog. You will likely be ridiculed by the

employees and fellow diners if you order ketchup.

You can get a fairly decent hot dog pretty much anywhere in the city. Make sure you look for

the signs of a higher quality dog like the all-beef frank and poppyseed bun! If you want a

higher class hot dog, give Hot Doug’s or Franks ‘n Dawgs a try. You’ll pay a lot more, but

get a gourmet hot dog experience. Be prepared to wait in line for at least 45 minutes at Hot

Doug’s. Especially on the weekend when he’s serving up his famous duck fat fries!

Hot Dog stand locations:
Hot Doug’s: 3324 North California Avenue (Not really near the L, take a cab)
Jim’s Original Hot Dog: 1250 South Union Avenue (15 minute walk from Roosevelt Red Line

stop)
Portillo’s: 100 W Ontario St (Near the Grand Red Line stop)
Flub a Dub Chub’s: 3021 N Broadway (Near the Wellingtong Brown Line stop)
Superdawg: 6363 N. Milwaukee Avenue, Chicago, IL (really far out there, you have to drive)
Franks ‘n Dawgs: 1863 N Clybourn (Near Armitage Brown Line stop)

Fried Chicken

Harold’s chicken Shack is the place to go for fried chicken in Chicago. This joint

originated on the south side in the 1950′s and many of the original locations will take your

order and hand your chicken over from behind bullet proof glass. It is the “dive bar” of the

chicken world and it’s good! The chicken is fried to order in a half beef tallow and half

vegetable oil to give it a unique taste. If you’re craving some good, old fashioned,

southern fried chicken. Harold’s is for you!

You can also find the southern delicacy of Chicken and Waffles in Chicago. The best place to

go is on the south side as well, Chicago’s Home of Chicken and Waffles. How can you pass up

a delicately crispy waffle topped with a peice of mouthwateringly juicy fried chicken and

maple syrup? Doesn’t sound good? It’s not just good, it’s AMAZING.

Harold’s locations:
South Loop: 636 South Wabash Avenue (near Harrison Red Line stop)
West Loop: 518 W Harrison (near Clinton Blue Line stop)
West Loop: 804 West Washington Boulevard (Near Clinton Green Line stop)

Chicago’s Home of Chicken and Waffles: 3947 S King Dr (near the Indiana Green Line stop, but

driving is also a good option)

Beer

Chicagoans have access to some great locally brewed beer from bigger companies like Goose

Island to the smaller Half Acre brewery as well as breweries from Wisconsin and Michigan.

You can find some restaurants and bars with beer lists so extensive that it makes your head

spin. Chicago is a grea3t place for a beer-tasting night out with friends!

Half Acre Brewery: 4257 N. Lincoln Ave (near Montrose Brown Line stop)
Goose Island Beer Co: 1800 N Clybourn Ave (near North/Clybourn Red Line stop)
Revolution Brewing: 1800 N Clybourn Ave (near California Blue Line stop)

Bars with Great Beer Lists:
Hopleaf Bar: 5148 North Clark Street (15 minute walk from Berwyn Red Line stop)
Map Room: 1949 N Hoyne Ave (10 minute walk from Western Blue Line stop)
Villains: 649 South Clark Street (near Harrison Red Line stop)
Clark Street Ale House: 742 N Clark St (near Chicago Red Line stop)

Dessert

I love dessert. Who doesn’t? Chicago also has some amazing places to tempt your sweet tooth.

The best frozen custard in the midwest (believe me, I’ve nearly tried them all) can be found

at Scooter’s Frozen Custard. If you’ve never had frozen custard, it’s a must when visiting

Chicago. It’s a thick, creamy, version of ice cream that is just too darn good to pass up.

Fozen custard joints only offer vanilla or chocolate. However, you can choose from a

plethora of ingredients for concretes, which is a better version of a blizzard. Another

great ice cream option is The Original Rainbow cone, which has been a Chicago institution

since 1926. They have thier unique rainbow cone as well as other yummy options.

If ice cream isn’t your think you can go the baked route. Chicago has some wonderul bakeries

serving up cupcakes, cookies, cake, sweet bread, muffins, and my personal favorite, PIES.

Hoosier Mama pies is quickly becoming the hottest spot for dessert in the city. They serve

up amazing sweet and savory pies with perfect crusts and fresh ingredients.

Scooter’s Frozen Custard: 1658 West Belmont Avenue (10 minute walk from Belmont Brown Line

stop)
Original Rainbow Cone: 9233 S Western Ave (waaaay out there, you should drive. It’s a cute

shop though!)
Rainbow Cone: Loop – 177 N State St (State/Lake Brown, Orange, Green Line stops, Lake Red

Line stop)
Hoosier Mama’s: 1618 1/2 Chicago Avenue (15 minute walk from Chicago Blue Line stop)
Molly’s Cupcakes: 2536 North Clark Street (take bus 22 or 36)
Bake: 2246 W North Ave (near Damen Blue Line stop)
Sweet Mandy B’s: 1208 W Webster Ave (10 minute walk from Fullerton Red Line stop)

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About The Author: Kim quit her job in 2010 to travel the world. She and her husband Clark went on a crazy eight month journey around the world. They visited more than 20 countries! Their blog To Uncertainty and Beyond features tips for travel, budget, food, culture, photography, videos and more! Follow them on twitter @2UNB.

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7 Responses to “A Local’s Windy City Food Tour”

  1. Keith Says:

    Hot Doug’s is TOTALLY worth the wait on the weekends, I highly recommend it. I have been there twice when I was visiting my sister in Chicago, and had an amazing lunch both times.

    Also Gillian I like the focus on amazing food and the corresponding photos for this post, although all I can think of now is what I will have for lunch despite it only being 10:30…thanks!
    Keith recently posted..My Moral Energy Hazard

  2. Lisa Says:

    Note to self: when packing for Chicago, remember appetite, antacids, and Thigh Master.

  3. Raymond Says:

    I had to do a triple take on those hot dogs. Sweet Jesus. I thought they were subs.
    Raymond recently posted..The World is Flat and You Can Be Too

  4. crazy sexy fun traveler Says:

    Should have not seen that! It’s 11pm and now I want a pizza and then an apple pie :D
    Thanks for the tips!

  5. Globetrottergirls Says:

    Bookmarked this post for our Chicago visit in September :) Great tips, we’ll make sure to try as many of these as possible.
    Globetrottergirls recently posted..Revisiting a Ghost…Ending my twelve-year love affair with Montezuma- Costa Rica

  6. Kim Says:

    Thanks everyone! Glad you enjoyed the post! There are also some healthier food options in the city. I’m working on a post about that right now. hehe.

    @Globetrotter Girls – Hey! Look us up when you’re in Chicago. We should get drinks! :o)

  7. Sean Says:

    As a native Chicagoan, I can say this list is SPOT ON. I would especially plug The Original Rainbow Cone on the far south side (although they now have a location just off State & Lake!) Truly a delicious, fun dessert experience that you can’t get anywhere but CHICAGO!