Chicago is a great city to visit year-round, but fall offers a chance to explore with cooler temps, and before holiday crowds descend.
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With flight deals readily available, consider planning an affordable weekend escape to the Windy City. Many highly-rated, inexpensive Airbnbs are available to book for the next several weeks, ranging from $93 to $205 nightly.
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We selected Airbnbs that were rated 4.9 or higher, available on weekends October through December (many include Thanksgiving for a small price increase), nicely styled, and centrally located.
With its impressive urban landscape, innovative food and drink, ample art and architecture, and friendly residents, Chicago is exciting to visit whether it's your first or fifteenth trip.
And right now is a great time to plan a city break there before the holiday family rush and harsh winter begin.
With two major airports, it's also pretty easy to land a great deal - I found cheap fares on Expedia starting at $156 (at the time of publication) from New York for Friday to Sunday travel in October, November, and December. The more flexible you are on timing, the cheaper the flight.
Of course, you'll need somewhere to stay. Airbnb is incredibly popular in Chicago, filled with stylish, affordable, and centrally-located accommodations.
To help you plan the perfect Chicago weekend, I combed Airbnb listings based on the following criteria:
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Airbnb listing is for the entire home (no awkward hallway conversations with your host).
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The home is available on a weekend in October, November, and/or December. If you want a holiday trip, most are also available over Thanksgiving for an increase of approximately $20-30 per night.
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Listings are under $205 a night, for a range of affordable, yet upscale properties. All were available to book as of publishing time.
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All are highly-rated Airbnb listings with a review score of 4.9 or higher - no surprises here.
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Decor is well-curated and stylish. Do it for the 'gram.
Need flights? Find cheap fares to Chicago. Or, drive with Turo.
Keep reading to book any of these 10 Airbnbs for every price point, ranging from $93 to $205 per night.
