[All content and prices updated August 2013]

Why you should add Chicago to your Indie/RTW trip

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.

  • 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.
  • Cheer for the Cubs in the right field bleachers of historic Wrigley Field.
  • This is the home of the blues.
  • Great public transport options
  • Incredible architecture in the downtown loop.
  • See some of the best museums in the world on free days.
  • Rollerblade or cycle along the banks of Lake Michigan.
  • 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.
  • 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.

Indie travel tips for Chicago

Even though places like the Willis Tower (formerly Sears Tower), the Navy Pier, and Michigan Avenue are high on the tourist radar, they are all still very cool sites and worth checking out. But if you’re looking to have more of an indie travel experience in Chicago, check out the following places.

  • The Willis Tower (formerly 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.

  • 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.


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.


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 as well. Prices tend to be high, but there are bargains, and they sell out well in advance so plan ahead.

Photo credits: Mike Boehmer