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Lined with upscale department stores and popular retail shops, it could be considered a shopper's paradise. To escape the crowds, head instead to North Avenue for many of the same shops or to neighborhoods like Wicker Park, Lincoln Park or Lincoln Square for more quirky boutiques and independent retailers. Unless the Cubs return to their playoff form of 2003, there is no reason to try to get tickets to see the Cubs at Wrigley Field in advance.
Scalpers are always outside of the ballpark in full force and if you wait until the game has started, you can probably even grab a ticket at a discount.
This is especially true when bad weather strikes - hundreds of flights will be cancelled at O'Hare while Midway just experiences a few delays.
Fly into Midway, hop on the CTA's Orange Line train and you'll be downtown within an hour of landing.