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From the bustle of the Loop on a weekday morning to the tranquility of Lake Michigan on a cool fall afternoon, Chicago is an experience in contrasts. Its cultural offerings and historic attractions draw seasoned international travelers, but the city's mix of family-friendly museums, beautiful parks, and iconic skyscrapers also attract vacationers of all ages. The fun -- and the challenge -- is to fit everything in one trip. You can put together a full itinerary each day and still have plenty left over for your next visit.

What you see will depend on your interests and stamina. The city's museums alone could keep you busy for at least a week. (If you don't have that much time, the top three exhibits that shouldn't be missed are the Impressionist masterpieces at the Art Institute of Chicago; Sue, the biggest Tyrannosaurus rex fossil ever discovered, at the Field Museum of Natural History; and the U-505 submarine at the Museum of Science and Industry). Come summertime, a stroll through picturesque Lincoln Park Zoo on the Near North Side is the perfect way to spend an afternoon; the setting makes it worth visiting even if you don't have kids along. (Added bonus: It's free!)

From a traveler's perspective, visiting Chicago is especially hassle-free because the majority of the places you'll want to see are in or near downtown, making it easy to plan your day and get from place to place. And because this is a town with a thriving tourist economy, you have plenty of guided sightseeing options: walking tours of famous architecture, boat cruises on Lake Michigan, and even bus tours of notorious gangster sites. If you're lucky enough to visit when the weather's nice, you can join the locals at the parks and the beaches along Lake Michigan.

Extensive public transportation makes it simple to reach almost every tourist destination, but some of your best memories of Chicago may come from simply strolling along the sidewalks. Chicago's neighborhoods have their own distinct styles and looks, and you'll have a more memorable experience if you don't limit yourself solely to the prime tourist spots. And if you really want to talk about da Bears or da Cubs, chances are, you'll find someone who's more than happy to join in.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.