Chicago will be your kind of town. Every time you leave, Chicago will be calling you home. It’ll say, “Don’t you wanna come back for a Chicago style dog or pie?” And no, I don’t mean actual dogs or a sweet dessert. I mean Chicago style hot dogs and pizza. When you visit Chicago, you’ll experience the blue waters and boats drifting lazily on Lake Michigan. Your mind will be blown by the Field Museum, Shedd Aquarium and the Planetarium. You’ll feel the wind ruffle your hair as you go on a boat tour of the city down the Chicago River. 

Ah, yes. Chicago. What can I say about such a grand city in the heart of the United States?A place where the people are friendly and the fashion is great. With plenty to do, Chicago will draw you in like sugar to cotton candy. If you don’t go, you’re skipping out on one of the best metropolitan cities in the heart of ‘Murica.

Chicago Slang 

You wanna act like a local? You gotta sound like one too. Here’s some quick pointers on how to fool the locals into thinking you’re one of them, As a proud Chicagoan, I find myself guilty of most things below.

  • The most important rule is how you annunciate your A. It’s a small drawn out A.
  • Replace the ‘th’ and ‘tt’ with D.
    • Example: Da BEARS and budder.
    • Example: Da El (the train) Da Loop (highway).
  • Use ‘The Lake’ for any reference to Lake Michigan.
  • Use ‘The City’ for any reference to Chicago.
  • Sandwich is pronounced sammich.
  • LSD is not a drug. Let’s get real. It means Lake Shore Drive.
  • Distance is measured in minutes.
    • Example: It’s about 20 minutes out.
  • Slur your words. (I find myself EXTREMELY guilty of this.)
    • Example: garage key= gratchkey
    • Example: Three= tree
  • It’s POP not soda.
  • Learn the Interstates.
    • I 290 = The Ike or the Eisenhower
    • I 55 = The Stevenson
    • 90-94 South of Downtown = The Dan Ryan
    • 90-94 North of Downtown = The Kennedy
    • 94 on the North side = The Edens

Now that this has been established, you may now proceed to navigating the city like a Chicagoan.

What to Do

The Sears Tower

Locals will always call it this. The Willis Tower? WTF is that? If you wanna get around like a local does, use this expression and you’ll fit right in. On a clear day, you can get a fantastic eye orgasm from the city.

Cost: Adult $22 Child $14

The Signature Lounge on the 96th Floor

If you want the breathtaking views of the city while enjoying a drink, you need to go to the John Hancock on the 96th floor. It’s busy, so you should definitely book a reservation. P.s. The women’s bathroom has the best views on the entire floor!

Cost: $7-$22

locals guide to chicago

Navy Pier

No trip to Chicago is complete without visiting this theme park on the water. While you’re there, ride the Ferris Wheel, make a candle, and have an ice-cold draft at the beer garden. Excitement alert: the brand new Ferris Wheel is opening! It’s climate controlled, bigger and better than ever. 

Cost: $20-$100

locals guide to chicago

Wendella Boat Tours

I went on this tour as a kid and much later with my boo bear when he visited me. This tour gives you a bit of the history of Chicago and you can learn a thing or two on how it became so great. I suggest the Signature Lake and River Tour. We took the later tour when the sun was setting and watched the city change from day to night. It was breathtaking. 

Cost: $36

locals guide to chicago

Millenium Park

I never get tired of selfie-ing at the Bean. If you’re there this giant bean with a reflective surface is actually quite entertaining. You can walk around the park for hours and there’s always something poppin happening from food festivals to concerts. 

Cost: $0

locals guide to chicago

The Adler Planetarium 

This is my personal favorite and way less crowded than the Shedd or Field Museum. If you dig astrology and space and shit, then you need to go here. Your mind will be blown with their awesome facilities. 

Cost: Adult $12 Child $8

LSD 

If you’re a junkie, I cannot offer you drugs, but Lake Shore Drive is a great way to see the city. LSD spans part of the Lake’s coast, where the city literally meets the sea.

Cost: Gas Money

locals guide to chicago

What to Eat

Chicago Style Pizza

Have you ever wondered what it would be like to sink your teeth into a plate of diabeetus so divine you taste purple, hear yellow, and smell blue? Look no further because this delectable delight is bound to make your taste buds sing in harmony. Chicago style pizza is a deep dish where they pack on the cheese on top of the crust and chunky tomato sauce on top of the cheese. Wanna know why Chicagoans call it a pie? Deep dish literally looks like one. While you’re in Chicago go to two famous joints by the name of Gino’s East or Giordano’s. 

Cost: $15-$35

locals guide to chicago

Chicago Style Hot Dog

What’s this? You want ketchup on your hot dog ONLY? What kind of Chicagoan does this? The answer is no one. Our unique dogs come with Vienna beef, inside a poppy-seed bun, topped with mustard, relish, onions, tomato wedges, a pickle spear, sport peppers and a dash of celery salt. To eat a hot dog with plain old ketchup in Chicago is just blasphemy. Go and get a real dog, you hooligan! lol  

Cost: $5-$8

locals guide to chicago

Portillo’s 

Besides bdubs, this is my kryptonite. Portillo’s is a fusion restaurant with all your Italian and fusion favorites. Need a beef sammich or a shake? No problem. Want an Italian sausage (don’t get dirty on me here) or a delicious burger?

Cost: $2.75- $10

Italian Ice and Lemonade 

For a long time, the city of Chicago was segregated. My dad grew up in the Italian neighborhood in the 1950s and he knew were all the great joints were. I came to love Italian ice and lemonade in the old Italian neighborhoods where the nonnas would make it fresh. One of the best places to go is Mario’s Italian Lemonade for your palatal pleasure. This is only open during spring until late fall. Don’t miss out on your chance for great noms. 

Cost: $4

locals guide to chicago
Image by Thomas Hawke

P.s. I just seriously made myself super hungry after composing this. Are you feeling hungry? I’m famished. Who would have thought Chicago is an amazingly culinary place?

Music 

Okay, so maybe I haven’t convinced you that Chicago is great because of aforementioned. But you can’t go wrong with music festivals and Chicago is home to one of the coolest summer festivals– Lollapalooza. This is a fantastic festival where everyone lights up, tokes up, gets drunked up and enjoys three days of great music and energy. We also are home to: 

Chicago Jazz Festival

Spring Awakening (an electronic music festival)

Pitchfork Music Festival (hip hop)

Riot Fest (rock and heavy metal)

As a Chicago native, I love da city more than anything. I love the food, I love the beach and the freezing cold lake all days of the year (even in summer). Chicago is a grand city that will take your breath away. A city doused in the modern with a bit of history. What are you waiting for? Let Chicago whisk you away!


And now for the GIVEAWAY! [CLOSED]

I’m super pleased to announce I have partnered with GPSmyCity which makes iOS and Andriod apps for all you travelers out there! This app features self-guided city walks in 470 cities around the world! I’m giving away 20 promo codes. Each of these ensures one free download of the app which normally costs $4.99 in the Apple and Google Play stores.I will announce the giveaway winners on my Facebook page, YouTube channel, blog and Twitter

Rules

  1. This giveaway is open WORLDWIDE!
  2. Give me a like on my Facebook page and follow me on Twitter.
  3. Leave a comment below telling me your favorite destination and favorite food to try from that destination.
  4. You can enter on my YouTube channel as well! (For a total of two times to go into the drawing.)
  5. The contest will run for 3 weeks. I will announce the winners on March 26th!
  6. If you are a winner, you have one week to claim your prize. If you do not claim it after one week, I will redraw names and give it to someone else!

     locals guide to chicago

39 Comments on A Local’s Guide to Chicago

  1. It’s hard to pick a favorite. I’d really like to go to Taiwan again. The bubble tea was my favorite food there. Thailand was also lots of fun. The fruit was so fresh and delicious there, and Thai food is so flavorful. I’ve never been to India but I absolutely love Indian food. There are so many places I haven’t seen yet that I would like to visit. So it’s really hard to choose a favorite.

    • I totally agree. The food in Taiwan is amazing! I love how a lot of their food is boiled and not fried. I love fresh and delicious fruit. It seems the further north you get any passion fruit or exotic fruit is super expensive!

  2. I love that you covered your hometown! It makes me happy to see more bloggers bringing it local… I mean, this is the place where you actually are in the know! Love your guide on the Chicago-esque “American-isms.” I think distance being measured by minutes is an unspoken rule all Americans adhere to. I really really want to get to Chi-Town. One of my friends there is getting into the food scene and really thriving so its pretty cool. Imma visit when you’re back in your stomping grounds 😉

    • The food in Chicago is so darn good. It’s one of my favorite parts about my hometown! Chi town is one of my favorite places in the world. Please come visit me! I love guests!

  3. Fantastic and in-depth post! I wanted to visit Chicago before reading this, but now I’m convinced that I HAVE to check it out. That decision could be based on the food alone. Thank you for all the interesting info about the city. Keep up the amazing work!

    • The best time to visit Chicago is at the end of the summer. Albeit very hot, the awesome festivals, food, and lake make up for it!

  4. Ahhh Chicago! Such a fun city to visit. This time of year is great to go when they turn the entire river green for St. Patrick’s Day, too. We ended up going to the Signature Lounge during a week day and there was hardly a soul in there. Though the city lights look great from there at night, on a clear sunny day, it’s really nice to have a drink up there virtually alone.

    • I loved that! It’s always fun and awesome to day drink and be merry! I would love to live in Chicago again just to experience all the awesomeness of Chicago! The Signature Lounge is legit the best. <3

  5. Great post on Chicago! Funny that I’m from nearby Cleveland, but I’ve only ever been to O’Hare airport and never been out in the city! I’d love to head there and go up the Sears Tower to see the view. I’d also love to go to one of their music festivals and check out the jazz scene there. I must try proper deep dish pizza as well! Thanks for sharing!

    • Chicago is a must go destination, especially if you’re from Cleveland! O’Hare is an awesome airport (I think it’s well organized, but maybe because I’ve lived in Chicago most of my life). The music scene in Chicago is one of the best! If you’re into jazz, you definitely have to check out the House of Blues!

  6. Such an enticing post and with great photos! My family is a pizza-eating family and we’re looking forward to that day when we can eat the authentic Chicago pizza… In Chicago! Your “the woman’s bathroom has the best view” reminds me of toilet of Top Cloud of The Jongno Tower. Nice view but your 96th floor view looks more awesome!

    • You will inevitably fall in love with Chicago deep dish. I am still waiting for the day when I can go back and eat it happily. The 96th floor view is the best!

  7. Next time I’m in the US I must visit Chicago. Good food, music, architecture and so much more. I’m especially eager to stand on the Skydeck. I’m such a tourist.. 😀

    • I’m terrified of heights, so I could never stand on the glass at the Sky Deck. I would always get sweaty hands and chicken out. Go forth and be tourist! 😉 We welcome you in Chicago!

  8. I’m probably visiting Chicago next year for work and I will definitely take advantage to have some days of vacation there! This list is just awesome! 🙂
    and thanks for organizing this giveaway!! 🙂 travel apps are so useful!! ^^

    • Don’t let it go to waste! Chicago never disappoints. You’ll love the food and check out a music festival if you can!

  9. Chicago is definitely one my top spots for a foodie tour! The Chicago style pizza picture just reminded me that I have not been in awhile and need to go again soon.

  10. One of the cities that I haven’t been to that I would love to visit. So much culture and fun. Love the Chicago slang. Would love to try the pizza and dogs, as much Chicago as hoagies and cheesesteaks are to Philly.

  11. I’ve actually done a lot of these things! Yes! I’d love to see more about the neighborhoods or doing it on a tight budget if you end up doing another post about Chicago!

  12. Weirdly I can’t recognise many US accents but I can always pick up that Chicago twang, would love to visit. My favourite destination would have to be the Galapagos, so favourite food would be gallo pinto – not the best but I lived off it for three weeks as it’s the cheapest meal around.

    • The Chicago accent is always the best accent. I’m not biased or anything. 😉 That food sounds not so bad. Would it be veggies and beans? I love pico de gallo and beans!

  13. Oh my, that pizza really speaks to me through the screen. I have never been to America but I would come to Chicago just for that pizza, haha! I didn’t know there is a Chicago slang, sammich sounds like a funny word. 🙂

    • Chicago is the best city in the world, but I’m not biased or anything. 😉 The slang is my favorite part of the city. I feel like it makes us Chicagoans unique.

  14. What we like when we travel, is to get an immersive local experience of the place and see it up close, like eating where the locals eat, etc. Chicago is a wonderful city and your guide would definitely show us the way to see the city through the eyes of a local. Millenium Towers and the Signature Lounge are what appeal to me a lot.

  15. It’s going to be my detailed guide for visiting Chicago. I particularly appreciate your jotting down the Chicago Slangs. It’s true, if you are going to act like a local, better know the local slangs first 🙂 I will try them when in Chicago.

  16. Love Chicago! Only been once, but definitely plan to come back again in the future to explore more of it. Hands down, my favourite attraction is the Wrigley Field tour. It’s amazing how much history you have in that stadium alone. I also now appreciate the difficulty of hitting homeruns in that park given the different wind patterns that can occur through the day during the entire MLB Season.

    I was also surprised that you didn’t add Garrett’s Popcorn as a place that locals check out. Unless my friend lied to me, my understanding is that it is quite popular given it’s amazing Chicago-style popcorn. So addicting! Or is this place really more of a tourist trap that Chicagoans typically avoid?

    • I wouldn’t recommend the Wrigley Field Tour because I’m a White Sox fan. Then again in Korea, there are two different fans–Cubs fans and Wrigley Field fans. Most people are fans of the field. 😉

      Alas most people do know about Garrett’s popcorn but it is a great addition to the list. It’s a bit of a tourist trap, but an oh so delicious one.

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