From the most beautiful summers to the coldest days you might ever experience in your life, Chicago is one of the best cities in the US to visit.
From the airport
The most affordable way is taking the CTA Blue Line to the city. The ride costs only $5 dollars. The train ride takes about 40 minutes to downtown Chicago.
I'd recommend the Gold Coast, or downtown area to stay. Both you are walking distance to many attractions. Chicago is a great city to explore walking.
Chicago is known the "Hollywood of Architects. The city is so rich in architecture, where you will see from the old to the new modern styles.
If you are visiting the city in the winter, make sure to check the forecast before you travel. Besides the cold, actually the frigid temperatures (cold is an understatement), the wind can be also brutal. Make sure you are prepared to beat the temperatures. Even in the winter, the city is beautiful, with a great number of outdoors ice skating rinks and other activities.
Chicago is simply wonderful in the summer days. Known to be one of the most beautiful large cities in the U.S., Chicago has a lot to offer in the summer days.
The city in the summer has numerous of street festivals, free concerts, street markets; it's hard to keep track of all that is happening.
One of the top options is the Millennium Park. Hosting pretty much every week movies, concerts, international artists, dance and music festivals like the Blues and Jazz. The Millennium Park is perfect to enjoy the beautiful summer evenings with a nice picnic while enjoying some free cultural programming.
If you are in the city during the month of June, maybe you are lucky to be there during the Wells Street Art Fest and the Taste of Randolph. Street festivals are a must, always double check online if there are any in town during the time of your visit.
The museums also offer great entertainment/cultural opportunities like Jazzin' at the Shedd. Nothing is nicer than to enjoy a great jazz outdoors with the beautiful views of the Chicago's skyline and the Lake Michigan.
Another fun activity is the Chicago SummerDance. From June through September you can experience a dance class following by live music where you can dance for hours! The magic of it is the great diversity of the artists and styles... you might be dancing Tango on a Thursday, Salsa on a Friday and some Irish set dancing on a Saturday!
If you are planning your trip to Chicago during the month of August, the Air and Water Show is something you don't want to miss. Thousands of people come to Chicago for this amazing experience. You can already start seeing the jets flying on the Friday, when they are practicing for the big shows on Saturday and Sunday. Best spots to watch the show are North Ave Beach and Oak Street Beach.
Chicago is offers so much fun for all ages. The beaches on the summer months are full of activities, from yoga, to jet skiing, to rollerblading to volleyball. The beaches are very lively, and certainly a must when visiting the city. Either Oak Street Beach or North Avenue, you can grab a bite to eat while people watching and enjoying the beautiful breeze from the lake.
The boat architecture tours are very interesting, but it is a little heavy to your pockets, If you want an alternative way for a boat tour, I'd suggest taking the boat taxi from Navy Pier to Willis Tower, or vice-versa. It usually takes 20 minutes and it's less than 1/3 of the cost of the architecture tour.
If you have kids with you, don't miss taking them to play on the Millennium Park Crown Fountain, and then walk on the beautiful BP Bridge to the Maggie Dailey Park. Your kids won't want to leave this place, so make sure to take some refreshments to spend a good amount of time there. The park is open until 11pm at night, which is nice during the summer nights.
One thing I really enjoy in Chicago is that we can have some amazing food in my favorite restaurants for happy hour prices. Great options are Morton's, Gyu-Kaku and Ruth's Chris Steakhouse to name a few. Hub51 has great a great Sushi happy hour every day! Check on their websites the happy hour times. You will eat very well, and your stomach and wallet will be very happy.