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Chicago

40 Tips I Wish I Knew Before Visiting Chicago



Here’s the exact list I share with friends visiting Chicago (my free guide): https://bit.ly/Chicago-Guide-Camden

These 40 tips to know before visiting Chicago are what I wish I knew before my trip to Chicago. Hopefully these travel tips will help you from making some of my mistakes when visiting Chicago!

Here’s the Instagram account I mentioned: https://bit.ly/cuppachicago

Every Tuesday, I share a travel tip you’ll actually use — like advice from a friend who travels nonstop — https://bit.ly/TheTuesdayTravelTip

DISCLAIMER: I only express my opinion based on my experience. Your experience may be different. Links above may include affiliate commission or referrals. I’m part of an affiliate network and I receive compensation from partnering websites. This video is accurate as of the posting date but may not be accurate in the future.

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26 Comments

  1. I love Chicago. IN THE SUMMER. I live outside Milwaukee, so I know about long cold winters. And I know like all big cities, Chicago has its problems, especially nowadays when homeless and illegals are rife. Personally, as a woman, I don't know how much I'd want to take the El. It USED to be great but, not so much any more. But I love a great big city, and Chicago has greatness in spades….but the leadership in the city as well as the state, the taxes, and all the other stuff that goes with big blue state cities, can be a very big detraction. I'd LOVE to live there – because NYC is out of the question – but there's so much about Chicago that can be a detraction. But it's a beautiful city for sure.

  2. What's wrong with visiting Cloud Gate? It’s located in Millennium Park, which I think is a great place to see if you’re in Chicago. Plus, how is Navy Pier overrated? It's a historic site with beautiful views of the lake.

    I’d also recommend visiting the Field Museum and the Adler Planetarium. Also the Buckingham Foundation or Grant Park in general. Also, a visit to the Sears Tower and the Hancock would be nice.

    100% agree on Wrigleyville. Must hangout spot!

    Portillo’s is delicious! 😁

  3. Portillo's is good but also the most commercial hot dog spot. There are hundreds of hot dog/italian beef places. You absolutely do not need to go to the most established, and a small neighborhood spot will likely have better prices, and a more authentic Chicago adventure. Weiner's Circle is massively overrated.

  4. Hey Camden. Great video. I have a question maybe you can answer or anyone else from Chicago who has some suggestions. I’m planning on being in Chicago during the World Cup and wondering what areas will be best to visit to watch games, and just feel the whole World Cup vibes. I understand this may be hard to answer as they haven’t hosted one in a long time and Chicago isn’t a host city now either. It’ll be my first time in the states from Ireland.

  5. For your safety: NEVER USE THE CTA/El. Assaults, filth, murder, robbery are all daily occurrences that you can avoid by driving/ UBER/ Cab. Our mayor only cares about the rights of illegal immigrants and dangerous severely mentally criminals.

  6. This is inaccurate. The public trans system includes buses, and they are not frequent. Certainly not a great system. Plus, no, dude, the El train is not always safe. Tourists should not casually take it to the west and north sides, especially not late at night.

  7. I LOVE Chicago, it is my favorite city on the planet. BUT…I have to say the L is not the best and the routes/taxi services leave gaps in service between L lines. You can get to a lot of places, but the spoke shape of the L map leaves a lot to be desired especially compared to NYC. But again, Chicago is the best, but the L could be made a little better.

  8. Why has no one ever mentioned Millennium Park as the world's largest rooftop park( green roof)?. Millennium Park sits atop a system of multi-story undreground parking garages that can accommodate over 9,100 cars (the second largest underground parking garage in the world after Abu Dhabi). If the parking lots at Millennium Park and Maggie Daley Park were combined, there would be over 13,000 parking spaces. Millennium Park was one of the largest engineering projects in Chicago (TARP is a larger project). Several layers of special insulation prevented the garages from flooding, and hundreds of thousands of tons of soil were brought in to ensure that everything would grow within the park. There is an active network of railway tracks under the park. And not a word about Pilsen, Lincoln Square, Bridgeport and Hyde Park, with one of the most beautiful places in Chicago, the University of Chicago, where you'll feel like you're in a Harry Potter movie. Plus Kennwood and Woodlawn. By the way, Navy Pier has the largest rooftop bar in the world – Offshore.

  9. I'm born & raised in Chicago prob 3 x your age Camden. I agree with most of what you say. .BUT…..The weather is ok for May thru Oct. Hot is June-Aug. I wouldn't use Midway Airport….-O'Hare is better & a safer neighborhood. Public transportation from O'Hare is safer than Midway. Your map at 3:06, show it's safe for the south loop-nope. I do not go into the south loop area if I can help it (and never never at night). At 11:42, you said Fulton Market is just on the outskirts of the city? Didn't you mean the downtown area. The outskirts of the city is the O'Hare area (9 miles away).

  10. Alderman Raymond Lopez 15th Ward: — "Chicagoans and say that if you rent to someone that they have just as much a right to make decisions for your property as you, the owner."

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