Top 5 Chicago Tourist Attractions – Must See Sights

chicago, top attractions, sight seeing, most popular, top rated, sights, chicago lakefront, downtownI was asked yesterday what the top 5 things were that someone has to see if they have never been to Chicago. I also get asked “where the bean is”, “how to get to the Art Institute”, “can you go up in the Sears Tower?” and “who makes the best Chicago Pizza?” a lot. I thought for a moment and realized I have been giving this tour to my friends and family when they come to town for years and I should share it with all of you.

There are a lot more than 5 things you can do in Chicago that are a lot of fun, and it can fill more than a weekend of a few days, so if you can stay longer and want a longer list, I will work on that too. For now, these are the top 5 things that people either want to see when they come to Chicago or should see when they come to Chicago. There is a slight difference.

Top 5 Tourist Attractions in Chicago:

1. The Sears Tower. Everyone seems to remember that from 1973 to 1998 the Sears Tower was the tallest building in the world. (previously it was the World Trade Center in NYC, now it is the Petronas Twin Towers in Kuala Lumpur Malaysia) They think also that like the Empire State Building it somehow was built for tourists. In fact it was not. It is more of a working office building than a tourist attracttion and is only open for tour visits during working hours. So I have never even been up in the Sears Tower and I live here.

What you should see instead: The John Hancock Building. The John Hancock tower is a tall enough building to get a good view of the city in all 4 directions and they had the sense to make a restaurant on the 95th floor called “The Signature Room” in addition to the observatory level on the 94th floor. It is open until 11 pm and that is good because you want to be able to go in the evening to see the city lights. I feel like the John Hancock Center was more in tended to be shared with the public and has a better consumer experience.

2. Chicago Pizza. Everyone has different ideas of what Chicago Restaurant has the best Chicago Pizza. There are several that seem to get the public buzz for being the best in Chicago and have regular crowds. Pizzarina Uno (good), Giordano’s (very yummy), Lou Malnotti’s (good) and Gino’s East (good). The deep dish pizza is the standard for out of towners because you can’t find it in other cities, but thin crust pizzas at all these restaurants are great too. There is also a smaller local brand called Home Run Inn that just does the thin crust pizza, that I think is the best thin crust pizza because of their rich salty buttery crusts. You can find them mostly in the suburbs though, the only Home Run Inn that is in the city is not near downtown. It’s more the working class man’s pizza, which is why my family knew it from the 50′s and still prefers it today.

What you should do instead: If Pizza isn’t your thing, Go to the original Billy Goat Tavern under Michigan Avenue and have a double or tripple cheeseburger, or go to Portillo’s for a Chicago Hot Dog or a Maxwell Street Polish. (notice none of the foods we are known for are healthy or expensive.) There are plenty of expensive restaurants in Chicago with everything from Brazilian Beef to exotic sushi but the fast fatty foods seem to still be the most popular norm.

3. The Art Institute of Chicago. It is the biggest and best Fine Art museum in the state and probably the Midwest. The museum is known for its collections of Impressionist, Post-Impressionist, and American paintings. There are special exhibitions several times a year ranging from Monet (they own over 30 Monet painings from in adition to Van Gogh and Picasso) to Photography. You have the best in world of art from historical dark ages (swords, knight’s armor, ancient chinese pottery and egyptian jewelry are all there too)  until the present (mid century modern furniture and Georgia O’Keefe paintings) available to view at at any time you visit the museum. The special exhibits are a bonus on top of that. They even let you take pictures (in the regular exhibits), which I was suprised about. The Art Institute of Chicago is located on Michigan Ave close to Millennium Park. The staff is knowledgable and friendly and there is so much there to see that you can spend 2-3 hours walking around.

What you should see instead: They have this one right, there is no comparsion. Go see the Art Institute of Chicago. If you like more modern avant garde works, the Museum of Contemporary Art (MCA) is also good, but nothing compares to the Art Institute of Chicago.

4. The Shiny Coffee Bean thing. (cloud gate by Anish Kapoor) The bean is a very cool artistic monument type thing that you should go see, but it takes about 15 minutes to take it all in and then what? Well you are in the middle of Millennium Park, which has some things to do, but I always have thought of Millennium Park as Chicago’s answer to New York City’s Central Park. It is about lounging on break from work and not really about tourism. The only things to really do there are to have lunch or dinner at the Park Grill (which is a little snobby if you ask me), go Ice Skating on the outdoor rink if it is winter time or go see a concert at Pritzker Pavillion. Most times you need tickets for the concerts though, so if you are a tourist just here one day or weekend, you may not have anything to see there.

What you should see after the 15 minute Bean viewing and photo taking session: If there isn’t something going in Grant Park to see like Taste of Chicago, Lollapalooza or a Free Movie Night you can always wander over to Summerdance in the evenings (Thursday-Sundays) all summer (just south of the Art Institute on Michigan Ave) or go on a Chicago Boat Tour (wendella boat tours have been around the longest) of the lakefront and the Chicago River or a double decker bus tour of the downtown area. Most of these tours set off early in the morning (10 am) to around mid afternoon (3pm) on the corner of Wacker and Michigan Ave.

5. Shop on the Magnificent Mile. Everyone thinks that this area of Michigan Avenue has something unique and you must shop there when you visit Chicago.  In the old days before cars, airplanes and the internet it really did. You would go to the Mag Mile to see the best that stores and retailers had to offer. All the best department stores and ritzy fancy brand name stores were there (Chanel, Prada, Coach, the Apple Store) Now I wonder if there is anything there that you couldn’t find at a normal local big mall like Woodfield or Oak Brook? The crowds that shop there now are usually people who work or live downtown and they do more out of convienience because it’s world class shopping within walking distance. (there is an american girl store though that draws people from several neighboring states)  So it’s interesting to see, but a lot of what made the Magnificent Mile a draw has been made moot by the internet and the growth of high end shopping all over the country. We are no longer the shining OZ capital in the large and flat prarie that people ride trains to go do their twice yearly shopping like in the late 1800s and early 1900s.

What you should see instead: There is always something going at Navy Pier. If nothing else, ride the ferris wheel and view the city from the only piece of land in the lake. Or if you prefer a more high tech way to view the city, the latest craze is the guided Segway Tours. I think people go on them just to ride a segway really. (I would) They are expensive and long though. Expect to pay from $70-$100 and spend from 2-3 hours on a segway listening to a tour guide. It is all the novelty right now to tell people that you rode around Chicago on a segway. (our police force also uses them a lot, as an alternative to horses, although you do still see some horse cops around occasionally)

6. Honorable Mention – People used to ask to go see the Marshall Fields on State Street, but now that it is a Macy’s I am not sure people feel the same way about it. They have preserved a lot of the traditions and activities that Marshall Fields had, but it’s still much less about Chicago now.

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9 Responses to Top 5 Chicago Tourist Attractions – Must See Sights

  1. Pingback: My Chicago Summer Vacation Time | Chicago Weekend Fun!

  2. kathy says:

    Thanks! This was really helpful

  3. Pingback: Where to travel after visiting Chicago? | Chicago Hotel Reservations

  4. Dave says:

    Nice list. However, Wrigley Field should definitely be added to this list. It’s breathtaking beauty and magnificent history make it a must see!!!

  5. Jen says:

    Exactly what I was looking for! Thanks!

  6. Luanne says:

    Thanks for the info! We are going to be visiting soon and these suggestions will be so helpful!

  7. Pingback: Chicago Sightseeing Recommendations « Travel Ganas

  8. Shawna says:


  9. aida says:

    have yet to go to all these places . thanks for the info .

    i will visiting chicago on 3/9/2011 and grateful for the info.