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Chicago
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Chicago

Book activities & Things to do in Chicago

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Chicago. The Windy City. Chi-Town. If New York is America’s head, then Chicago is its heart. An international hub for commerce, industry, and culture, Chicago draws tourists and wayward travelers from across the globe. Whether it's Chicago’s famous deep-dish pizzas, its bluesy nightlife, or something else that attracts them is anybody’s guess. What is known is that Chicago hosts well over 50 million domestic and international tourists per year. Maybe it's the internationally renowned landmarks such as the Willis Tower, Cloud Gate, and the Magnificent Mile. Ultimately, it doesn’t matter what draws you to this “City in a Garden” because “[s]he is always a novelty; for she is never the Chicago you saw when you passed through the last time.” – Mark Twain.

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Things to do in Chicago

  • Our tips for Chicago

    Our tips for Chicago
    • Fashionably Late. Wait for the first pitch before buying your Cubs ticket. Although they did win the World Series in 2016, once the Cubs start slumping, tickets can be had below face-value from your friendly local scalper.
    • Be Flexible. If the line for the Willis Tower Skydeck is never-ending and you’re looking for alternative things to do in Chicago, relax and have a cocktail in the Signature Room of the John Hancock Building, instead. The view is just as spectacular!
    • Got Beef? Chicago is known for its deep-dish pizzas and hotdogs. But, you’d do quite well to sample another original Chicagoan favorite: the Italian Beef Sandwich with au jus. Amazing!
  • Good to know

    Good to know
    Best Time To Visit The weather during a Chicago tour can be extreme and difficult to predict. But, generally speaking, May/June and September/October are the best months for Chicago sightseeing, weather-wise. A plethora of street fairs and music festivals await you during the hot and humid summer months. Chicago dazzles with holiday light displays during December and January; but, the city is sometimes called Chi-beria because of the bitter cold.
    Getting Around Put on your walking shoes! There’s no better way to see this pedestrian-friendly city than on foot. But, if want to speed things up a bit, here are some great options:
    • A Chicago attraction in its own right, the historic elevated train, or “L”, together with city buses, will drop you within walking distance of any tourist destination. Chicago’s transit system is generally safe and the fare is just a few bucks. People unaccustomed to city life should avoid using the L late at night.
    • For hassle-free Chicago day tours, consider a $5 Ventra Card. You can load it with unlimited rides on all CTA lines for 1, 3, or 7 days. The price is $10, $20, and $28, respectively.
    • For a nifty savings, avoid private parking lots. Instead, park in public lots underneath Millennium Park or near Museum Campus. it's what to do in Chicago when you’ve got your own wheels.
    Stay Safe Chicago’s gang violence has made headlines in recent years. But, don’t worry. You’ll be quite safe if you remember our following safety tips:
    • Spike Lee directed a film called Chi-Raq, depicting Chicago’s warlike violence on the south side. Avoid these neighborhoods at all costs. Tourist areas are usually rather safe.
    • Common crimes near tourist areas are pickpocketing, smartphone snatching, and gambling scams, such as Three-card Monte. Avoid gathering crowds and secure your valuables in your front pocket or money wallet.
    • Plan your travel route for a Chicago day trip ahead of time, have your ticket/passes ready, and try to appear confident and purposeful so as to avoid the attention of would be pickpocketers.

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