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Chicago Trip Tips – Locals Advice For Exploring the Windy City


Chicago Trip Tips – Locals Advice For Exploring the Windy CityMy passion for Chicago is never-ending. I love exploring the city and some locals were kind enough to share some Chicago trip tips and give their advice for exploring the Windy City.

The Bean

The iconic sculpture is actually called Cloud Gate, but everyone affectionately refers to it as “The Bean.” Make sure to hit this touristy spot, but go at sunrise. The early hour lets you explore and snap photos without battling a crowd and the sunlight shining underneath the sculpture will be even more beautiful.

Related: Kid-Friendly Chicago Restaurants With a Patio – Dine Alfresco Family Style


While Chicago is known for deep dish pizza hot dogs, the dessert scene is equally delicious. Do-Rite donuts is a favorite of locals, but you’ve got to try the chocolate cake at Portillo’s. Don’t be afraid to try some of the local food tours as a newbie and never underestimate those little homespun stands. They often house some of the best eats in the city.


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The Pizza Secret

Deep dish pizza is an art and takes time to make. Locals know the spots that will let you order while you wait for a table, cutting your wait time practically in half. Ask the hostess if you can put your order in before you get to your seat, and chances, your deep dish heaven will be delivered shortly after you sit down.

Related: Cheap Must-Try Eats, Drinks, and Entertainment In Chicago

Lincoln Park Zoo

The zoo admission is free, but parking hovers around the $20 range. So, instead of driving, make sure you take the bus or walk to enjoy the year-round zoo and its many festivities.

Do you have some advice for exploring Chicago? Let us know your tips and tricks for saving time, enjoying the scenes, or navigating the city in the comment section below.

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  1. Stacie @ Divine Lifestyle says

    This is such a great resource! I love it when business brings me to Chicago, so this is getting a bookmark.

  2. Pam says

    I loved Chicago when I visited. Cloud Gate was cool but I would love to check out the zoo someday.

  3. Kristin says

    FUN!! I loved Chicago when we visited, my husband and I rented bikes and we ate the most delicious foods. Such a wonderful trips, love this post!

  4. Catherine Sargent says

    I went to Chicago years ago and the deep dish pizza was amazing! I would love to go back for another visit.

  5. Kelly says

    It has been a while since I visited Chicago but it is always a lot of fun. I make sure to get myself a deep dish every time.

  6. Liz Mays says

    This is great! We lived near Chicago and we brought the kids to the city many times. There is a lot to do!

  7. MAKEBA GILES says

    I love all of the tips that you share here! I’ll actually be traveling to Chicago this weekend, and these will come in handy!

  8. Amanda Love says

    It’s been a while since I last went to Chicago and it would be so awesome to go there again! I love Chicago for their food and their architecture as well. It’s just an awesome place to go to.

  9. Carol Cassara says

    This is awesome! I love Chicago and it’s one of my favorite places! They just really know how to eat especially when it comes to pizza and desserts! I think these are things you must not miss when your’e there.

  10. Louise Bishop says

    We absolutely love visiting Chicago. Any time we get the chance, this city has our imaginations.

  11. Kita Bryant says

    I don’t live too far from Chicago. I’ve been meaning to take the kids.

  12. BRIANNE says

    I’m so dying to get to Chicago this summer with the kids! It’s a pretty close flight from NYC!

  13. Kristi says

    Not sure if they still have the option but last time we went to Chicago we went to the Science Museum and they had sessions where you could dissect cow eyeballs. Our girls LOVED it. Super fun and very educational.

  14. Our Family World says

    The Cloud Gate looks awesome. I know now why people call it “the bean.” I agree with you about Chicago’s deep dish pizza. I tried it once and I found it very good! I wish I had a chance to go back to Chicago!

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