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Chicago

The Chicago 5! Don’t waste your trip on anything else.



If you are heading to Chicago for the weekend or vacation or for a conference there are dozens of things you can do and enjoy in the city. Here we go through my favorite things to do in Chicago. From the Art Institute of Chicago to the Field Museum to taking in a Cubs Baseball game there is a lot of travelers to enjoy in Chicago.
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49 Comments

  1. DO NOT listen to this guy. only a tourist would tell you touristy things to do instead of telling you to go to places and see things that only locals would know about. NEVER listen to a tourist and yes I am from Chicago area

  2. I’ll say it over and over, the best place for a hot dog is Home Depot. I’m absolutely dead serious!

    The architectural boat tour is also a hard YES! I’ve lived in this city for 46 years and have only done it 2 or 3 times, not nearly enough! Need to take the kids soon.

  3. I am so glad you mentioned the ghost in the darkness! I was getting ready to comment that! That’s one of the main reasons why I plan on going and checking out Chicagothis late fall. I’m seriously having a hard time coming up with stuff to do in Chicago, unlike New York or DC or wherever just I don’t know that much about Chicago other than the movie the fugitive. But I did know about the lions.

  4. Lived in Chicago for over a decade, totally agree with these top 5. One thing I would add would be to rent a divvy bike and ride up the lakefront path to Lincoln Park Zoo, always a must do activity for me when I visit in the summer. Also would add the Shedds Aquarium. And of course, for eats, an Italian beef sandwich from Al’s is always amazing.

  5. Chicago resident here. Yes and no. If you really want to get a feel for Chicago you have to get out of downtown, off the museum campuses, and out into the neighborhoods. Go to Clark Street in Lakeview. Go see all the new snooty restaurants in Fulton Market. Walk down 18th street in Pilsen. You will only know tourist-Chicago if you don't leave the loop (and I say this as somebody who lived in the loop for 6 years).

  6. Word of advice don’t go to Chicago. If you prefer gambling in the state of Nevada Sin City, Las Vegas, Nevada for picky travelers I went on Norwegian cruise line and tell yourself to stop teaching me Chicago people are actually really friendly and there’s beautiful girls in Chicago.

  7. Chicago is also great for seeing live Blues. I personally always love going to Kingston Mines as they have 2 live stages every night and the music is fantastic to hang out, have fun and enjoy a few drinks with. If you have kids they have a rainforest cafe downtown. If you are into Gangster and mafia history, I recommend going on a gangster tour where they will show you where the bullet hole from the St Valentine Day massacre still line the wall. If you want to have a bit of entertainment when you have teenagers I recommend going to Dicks last resort where the staff treat you like dicks but in a funny and entertainment way if you can get the idea. Its also right on the Chicago River and offers great views. Navy Pier in my opinion is a bit too touristy although FYI the view of the skyline from the Ferris wheel is really awesome. If you are looking for that one souvenir to bring home from a trip to Chicago it's Garrets popcorn. In my opinion it's the best Popcorn on earth and it will change your life and your views on popcorn.🍿 The cheddar caramel mix called the Garret mix is definitely the star of the show. I have even ordered some online to my home in Montreal before because it's that good. Another good souvenir idea is if you are into hot sauces. Chicago has every condiment you can think of under the sun ranging from sweet and savory sauces that are not spicy at all to some sauces that even a microdrop will have you running to the bathroom to put your mouth under the sink for a week. Restaurant wise Chicago has absolutely everything you can think of but obviously the best Chicago staples as well such as Italian beef and Deep dish pizza. If you travel in summer Chicago has some of the best festivals such as Lollapalooza or taste of Chicago if you want to try different foods. Are there parts of Chicago you should be concerned about? Short answer, yes but they are out of the downtown loop. One thing I want to point out and stress to you all is the safety of the city. There are many areas such as Wicker park where crime is not a serious issue but you have other areas such as Washington park or Greenfield park which I would even be concerned for the safety of nightclub bouncers in. To make it short, should you avoid all of Chicago or considering travelling to Chicago because of its crime reputation? In my opinion No. Chicago is a great city to visit with many things on offer. I do however definitely research the so called "red zones" of the city to make sure you stay far away from them.

  8. Go to Shitcago , And get robbed , murdered and beaten up by Thug's , I grew up on the South side , And it's really changed in the last 50 years It's gotten Worse than ever , Year after year after year after year , Rest in Eternal Peace John Daly , Former mayor ♦️♦️♦️‼️

  9. Just came back from Chicago! So, Chicago theatre is outstanding. If you can't make it to see NYC shows, Chicago offers beautiful theatres for hosting Broadway tours. Some shows even have long runs there, like Hamilton was there for about 3 years. Just be careful out there. Follow the same awareness and safety as you would with any big city❤

  10. Great video! Do grab a hot dog because they're easy to do right and hard to screw up. Italian beef on the other hand…

    Grab a drink at Miller's Pub. Or the Berghoff, opened by German immigrants over 100 years ago and the first post-prohibition liquor license in Chicago. Get a drink at the Green Door, built right after the Chicago Fire; a beef at Mr. Beef, which people might recognize from its fictional twin on The Bear; or cross the street for old school Italian at Club Lago, which is as Chicago as it gets. That's all before you leave the center of the city to see the neigborhoods!

  11. This should be a nice location to add to my must visit bucket list, traveling is just so much fun, I am really happy I was introduced to Mrs. Anne Marie Martin, I must say, financially she turned my story around

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