One of the best cities in the world is Chicago, IL. Okay we might be a little biased as this is our hometown. But Chicago is great city to visit with lots to offer. We recently spent the weekend here and had a great time. Since we live in Florida now, it was fun getting to be tourists! Here is our itinerary for 3 days in Chicago. Obviously you could spend much more time here, but if all you have time for is a quick weekend getaway then this is a great way to see some of the highlights of the city.

Day 1

We flew in really early on a Saturday into Midway Airport. Our flight actually landed at 8:30AM so we had pretty much the entire day to explore. We spent our first day in the Millennium Park area. It was such a gorgeous day we wandered around Millennium Park, Grant Park, and Museum Campus. Millennium Park is where you can take the famous selfie with The Bean. (The Bean’s official name is ‘Cloudgate’ but nobody actually calls it that.) We then walked down to Grant Park to see Buckingham Fountain. The lakefront looked so beautiful that we strolled along the path until we got down to the Museum Campus. This is where the Adler Planetarium, Shedd Aquarium, and Field Museum are located. Right next door is Soldier Field where the Chicago Bears play. We did so much the first day we were exhausted!

Day 2

The next day was spent at Navy Pier. Even though we have been to Navy Pier many times, they recently redid some of it so it was like going to a whole new place. They also opened up the new Centennial Wheel this year after replacing the original one. There are lots of shops and restaurants with great views of the city. This is also where you can take sightseeing boat trips, lunch/dinner cruises, and lots more. One of our favorite areas is the Beer Garden, which is located towards the end of the pier. There is usually live music and it is a fun place to grab a drink, relax, and people watch.

Navy Pier is also home to the Chicago Shakespeare Theater, IMAX Theater, kid-friendly attractions like the Chicago Children’s Museum and Chicago Fun House Maze, Stained Glass Gallery, and lots more. If you finish up everything at the Pier, the Riverwalk is a quick stroll from the entrance.

(Keep your eye out for the mural ‘Pier People‘ done by one of our friend’s cousins, Pete Nawara!)

Day 3

Take me out to the ballgame…take me out to the crowd! Today was spent in Wrigleyville and at Wrigley Field for a Cubs game! Wrigley Field is one of the oldest baseball stadiums in America and the home of our favorite team, the Chicago Cubs. (Wrigley was built in 1914. The oldest ballpark is Fenway in Boston built in 1912). The area around the park is known as Wrigleyville. There are so many bars, restaurants, and souvenir shops. This is one of the hotspots in the city for nightlife.

Even if you do not like baseball, it is worth going to see the park and Wrigleyville. If you do not want to sit through a baseball game, you can take a tour of the park for about $25 a person. The easiest way to get to Wrigley Field is to take the CTA Red Line and get off at the Addison stop.

Chicago Travel Tips

*We lucked out with great weather. However the weather can be unpredictable, so pack some layers just in case.

*Try to stay downtown. You can easily walk to so many places. If you cannot find a hotel downtown, make sure you stay near an ‘L’ station or Metra station. This way you can easily take public transportation around instead of renting a car. Parking is very expensive downtown.

*Famous Chicago foods: Chicago style hot dog, deep dish pizza from Lou Malnati’s, roast beef sandwich from Al’s, Garrett’s popcorn (None of this is remotely healthy but even we cannot pass up some Lou Malnati’s pizza.)

*Chicago in the summer is the best. There are so many festivals, street fairs, and special events going on outside. Many of these are free. We personally think that is the best time to visit the city. Check out the city’s website for what’s going on.

*Both O’Hare and Midway Airports are easily accessible by public transportation. O’Hare is closer to the North Side while Midway is on the South Side.

Have you ever been to Chicago? What are your favorite things about the city or is Chicago still on your list of cities to visit? Let us know in the comments!

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