- Chicago's chock full of awesome museums, but popular, quality museums in big cities usually mean large crowds and high entrance fees. Check out the Chicago Cultural Center as a free alternative (this is also home to the Chicago Visitor Center.
- There's plenty of beaches along Lake Michigan in Chicago to choose from. If you're looking for crowded and active, go to North Avenue Beach. But if you're looking for nice, green space, a place to grill and have a picnic, and plenty of amenities, then consider going to Montrose Harbor Beach. Parking is free, too!
- If you want to know what's going on in the music and arts scene in Chicago, make sure you pick up The Reader to find out what's going on when you're there. Tons of great local recommendations.
- Chicago can be extremely cold in the winter, so if you find yourself there during the frigid months, head on over to the Garfield Park Conservatory, a massive greenhouse that is referred to as "landscape art under glass."
- Chicago has some great architecture and neighborhoods in and around the city. If the weather is nice, get out of the downtown area and explore Logan Square, Chinatown, Lakeview, and Uptown.
Why you should add Chicago to your RTW travel list
- Deep-dish pizza.
- Cheer for the Cubs in the right field bleachers of historic Wrigley Field.
- This is the home of the blues.
- Great public transport options
- Deep dish pizza.
- Incredible architecture in the downtown loop.
- Shop till you drop on Michigan Avenue, the Magnificent Mile.
- See some of the best museums in the world on free days.
- Rollerblade or cycle along the banks of Lake Michigan.
- Stuff yourself silly at the taste of Chicago.
- Tailgate party!... then freeze your butt off at a Bears game in January.
- Friendly people, especially compared to the citizens of other large cities in the US.
- Did we mention deep dish pizza?
Why you should not add Chicago to your RTW travel list
- It's expensive
- It's in the middle of the country, making travel to other popular US destinations expensive
- The winters are absolutely freezing with a lot of snow
Chicago isn't an obvious choice when picking a vacation city, but it's very rare to hear anyone who's disappointed after visiting. The city doesn't have many of the superstar attractions that draw people to Los Angeles, New York City, or Miami, but it does have great architecture, history, culture, and nightlife that will leave no visitor bored. It also has a hard-to-describe charm those other cities lack. The locals seem friendlier and things seem cozy even though it's a huge city.
What To Do
The Sears Tower is certainly the most visible attraction in town. The tallest building in the US has amazing views and the observation deck is far less crowded late in the afternoon. It's a great place to start your visit to properly get the lay of the land. The Art Institute of Chicago is one of the world's finest art museums. It contains American Gothic among its many famous works on display. Chicago has more than its fair share of museums and galleries including the small yet interesting Museum of Holography.
Chicago's food scene is also legendary. The Taste of Chicago festival in early July is a huge event and a major highlight, but you can do your own version any time of the year. The city center is very easy to deal with and contains many ethnic neighborhoods with plenty of authentic restaurants to match. The usual suspects of China, Italy, and Greece are represented, but neighborhoods representing Poland, Germany and Sweden are also nearby.
Being near the middle of the country, Chicago is a great stop if you've decided to rent a car and take a road trip. Train service is also frequent and reliable if you aren't in much of a hurry and particularly if you are heading to or coming from the east. But most people will want to book a flight into Chicago O'Hare (code: ORD). A commuter train goes from the center to the airport round the clock and takes 45 minutes. There are two other smaller airports near Chicago, Midway (code: MDW) and Gary (code: GYY) and some smaller carriers fly discounted flights into those, but usually the better deals are into O'Hare.
If you need to go to the airport by car you can save both time and money by paying for your Chicago airport parking ahead of time. Or you can choose the Chicago airport shuttle to take you to the airport.
Where To Stay
Chicago has a concentrated center, but it's still huge. Public transportation is very good, but it's still usually worthwhile to pay a bit more to be near the center rather than getting a cheap place and spending hours on the train each day. There are several hostels in Chicago and loads of hotels in Chicago. Prices tend to be high, but there are bargains and they sell out well in advance so plan ahead.