Taking a vacation in Chicago is one of the best places for travel, with so many things to do during the summer and winter months, there is no chance of ever running out of fun things to do in Chicago for cheap. Chicago is by far one of my favorite vacation hot spots since my kids and grandkids live there, and since I used to live in the northwest suburbs of Chicago years ago, visiting my old stomping grounds will be a treat.

We’ve had a good time during our inexpensive Staycation vacations, but this year we decided we really needed a getaway vacation where we can fly to Chicago and enjoy the Windy City and its many attractions. Planning a cheap vacation trip to Chicago includes finding good deals on hotels, car rentals, air fare, discount event tickets and finding as many free activities as possible. When it comes to planning a vacation to Chicago or anywhere else, cheap is good, but free is better.

Deciding where to stay in Chicago, where to eat, where to park if you’re going to spend time in downtown Chicago or surrounding cities, and where all the hot spots are in or outside of the city are things that must be decided. Picking what hotels or motels we would consider for our visit to Chicago was easy with Hotels.com, and since I used to live there I know what neighborhoods are good or bad, and what areas to avoid at all cost.
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