Chicago has been called "America's Family Friendly City", and for good reason. As the third largest city in America, Chicago has a lot of the culture and diversity of New York - with safer streets, more parking, and most importantly; lower prices. Chicago's O'Hare International Airport is a global hub that's located in the center of the country. This makes flights to and from Chicago very affordable compared with other locations. What's more, when you get to Chicago there are any number of ways to enjoy world class amenities at a fraction of the price - take a look!
You already know you can save money booking your hotel with travel websites. What you might not realize when you're booking those rooms, is how much money you can save staying just minutes from downtown Chicago. It's easy to think you have to stay downtown and sleep there just to enjoy what the city has to offer - not true! Check out hotels in nearby Northern and Western suburbs like Park Ridge and Oak Brook. Hotels in these suburbs are mere minutes from downtown Chicago, and other fascinating neighborhoods - yet will save you 25% - 50% per night on hotel fees.
Even if you can travel and sleep affordably, you still need fun things to do. The great thing about vacationing in a large metropolitan city like Chicago, is how many affordable, or even free things there are to do all over the city. Here's a quick list:
This world class zoo has animals from all over the world, including Polar Bears, Baboons, and even Silver Back Gorillas. It also happens to be completely free! Tip: don't park in the zoo's official parking lot: this will set you back about $25. Instead, park on nearby Halstead Street, or take public transit in from an area with street parking. If you're traveling around the holiday season, be sure to check out "Zoo Lights", a fantastic musical lights festival in the zoo.
Millennium Park is a beautifully landscaped park right in downtown Chicago. Also free, this park offers stunning views of downtown and fun sculptures like the world famous "bean." Summer highlights include free concerts in the Millennium Park band shell, and fireworks every Wednesday night. In the winter, the park gains a free ice skating rink (bring your own skates.)
If you're traveling to Chicago, you probably want to travel to the top of the tallest building in the US, the Willis Tower (nee, "Sears Tower".) The problem is, this can cost you around $25, per person! The Sky Bar at the top of the Hancock building north of the Willis Tower will take you up for free - only charging you one drink per adult for as long of a stay as you'd like, and just as cool of a view! The drinks aren't cheap, but $8 per beer is better than $25 per person.
If you plan your vacation right, you'll be in Chicago on one of the days each month when every museum is completely free. This sometimes changes year to year, but you can definitely find out. Again, you'll save between $15 to $20 per person visiting museums on these days. If you get started Early enough in the Morning, you can probably hit the Museum of Science and Industry on the South side of the city, and still make it back downtown to the Field Museum of Natural History and Art Institute of Chicago; both of which are very close to each other.
Self Guided Architecture Tour
One of the best parts about Chicago is the amazing downtown architecture. While you could spend hundreds joining a live guided foot or boat tour - whey not simply buy a single guide book, download a podcast, or print a map that will cite all of the best vantage points for amazing new and historic architecture? Self guided tours are the way to go; they take a bit more preparation in advance, but save major dollars down the road.