Chicago In A Weekend

People often ask me for advice about visiting Chicago in a weekend.

Not only did I grow up traveling there, but I also spent a year living near the city. While I will admit, living in Chicago was not the best thing I’ve ever done (we lived through one of the coldest and snowiest winters ever!)…

Chicago will always be my favorite city to visit!

So if you find yourself traveling to Chicago in a weekend with your family, here’s my top 10 list of things you shouldn’t miss:

  1. The Museum of Science and Industry: In my opinion, this is the best museum in America. It’s fun, interactive and diverse. It’s a place I could take my kids every day for a month and not only would they not get bored, but I wouldn’t either. Plan to spend as much time here as you possibly can. No one will want to leave! (Tip: There is a very nice parking deck, but it is also easy to find free or inexpensive street parking close by.)
  2. Pizza: You can’t go to Chicago and NOT get pizza at least once. Even if you don’t think you’re a fan of deep dish, most pizza places serve a more traditional style too. Ask any Chicagoan and they will have a strong opinion on which place is the best- but unless they say Lou Malnati’s, they are wrong!
  3. Navy Pier: It’s an amusement park, shopping mall, marina and so much more. Navy Pier is Chicago’s number 1 attraction. Although Navy Pier as a whole could be considered a bit of a tourist trap, riding the Ferris Wheel is definitely worth fitting into your trip to Chicago.
  4. Millennium Park: Cloud Gate, most commonly known as “The Bean,” has quickly become one of the most iconic and recognizable Chicago landmarks. It’s a great photo opportunity!     
  1. 5. The Magnificent Mile: Even if you aren’t in Chicago to shop, you need to set foot on The Magnificent Mile! It’s a Chicago landmark and walking down this section of Michigan Avenue is truly an awesome Chicago experience.
  2. 6. The John Hancock Center or The Willis Tower: Both of these buildings offer observation areas from one of their highest floors. You don’t need to do both, but depending on what you’re looking for, you should do one. It’s really quite an experience to view Chicago from 1,000 feet up.
  3. 7. Architecture Boat Tour: Just as cool as seeing Chicago from above, a tour on the river is a fabulous experience. Not only will you get a new view, by doing a guided tour you will learn all kinds of unique Chicago facts and a lot of history too.
  4. 8. Shedd Aquarium: The Shedd Aquarium sits right on Lake Michigan, and hands down the best part of the aquarium is the dolphin show. I would rate the rest of the aquarium as great, but not amazing. If you are looking to cut out an expense on your trip, this would definitely be the one I’d skip. However, if you have the time and the money- the Shedd is definitely a place worth spending a couple hours.
  5. 9. Water Tower Place: Again, even if you aren’t in Chicago to shop, walking through Water Tower Place should be on your to-do list. As you enter the building off of Michigan Avenue, make sure to ride the escalators to watch the jumping water. In Water Tower Place you will find stores like American Girl and Lego, as well as many other high end stores. Water Tower Place is also a great place to eat if you find yourself there during a meal time. If you aren’t looking for a specific restaurant experience, try Foodease. You’ll find something for everyone for reasonable prices.

10. Wrigley Field: Although Wrigley Field is considered in downtown Chicago, you aren’t going to pass it or see it without a little effort. Because it’s such an iconic sports landmark, it’s worth taking a drive north to see. If it’s baseball season, going to a game is awesome. But even if it isn’t, it’s fun to see the stadium itself. They offer tours of the stadium and if you are a baseball fan, it’s TOTALLY worth paying for the tour! 


  1. 1. Buckingham Fountain: The only reason I didn’t list this in the top 10 is because it only runs for roughly half the year. If you find yourself in Chicago anytime between May-September, you’ll definitely want to check it out!
  1. 2. Lincoln Park Zoo: Depending on how much time you have in Chicago, you could add the Lincoln Park Zoo into your itinerary. It isn’t the greatest zoo you’ll ever go to, but it’s free. And the grounds are very pretty.
  2. 3. Second City: This is NOT a family activity! It is an awesome improvisational comedy club and if you have a babysitter available, you’ll definitely want to check it out.
  3. 4. The Field Museum: Personally I don’t think that the Field Museum is THAT kid friendly. There are parts of it that my kids enjoy, and the building itself is beautiful…but it doesn’t earn a spot on my Top 10. Don’t get me wrong, it’s a great museum and if you have the time and money, definitely go there. Just don’t skip the other stuff on my list for The Field.
  4. 5. Adler Planetarium: I have the same thoughts on The Adler Planetarium as I did for The Field. Exactly.
  5. 6. Lake Michigan Beaches: Like the Buckingham Fountain, these are certainly not open year round. If you are traveling to Chicago in the summer, it’s pretty neat to be able to lay on a beach right in the heart of downtown!
  6. ANY Special Event: There are way too many to name them all, but do a quick search before you travel to find out if there are any special events going on while you’re in town. A couple notable things that come to my mind: Taste of ChicagoChicago Marathon, and the Christmas Tree in the Walnut Room.

Chicago is an amazing city.

If you have a month to spend there, I have a million more suggestions! In my opinion, this list is do-able in a weekend (okay, maybe a long weekend!) It’s a mixture of fun activities, and landmark sightings.

For those of you who have traveled to Chicago (or who live there), did I miss anything??? Anything you would add to or take off my list?

You may also enjoy reading:

Best Trips For Young Kids

Tips For Visiting The Grand Canyon WIth Kids

10 Years Of Traveling With Kids

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