Fall and winter are great times of the year in Chicago, whether you are a resident or a tourist planning a trip. Cooler weather in Fall is ideal in Chicago, not too hot or too cold, and less humid. Temperatures range from the 40s to around the mid-seventies, so its great weather for sightseeing. September and October also get less rain than the summer months so there are more opportunities for outdoor activities. However, in many years, these nice temps extend well into November and December, making romantic nights and bustling days all the more fun in the city.

School has started up so the crowds won’t be as bad. You can get better deals on both flights and hotels as well, if you’re a tourist. The foliage is also at its peak, so it’s a great time to visit the parks in the city.

#1 Sight Seeing Tours
If you’re looking to do some sightseeing, fall and winter are ideal. There are a lot of sightseeing tours available year round, but they often sell out quickly during summer months. You can wait until the last minute to book your place during cooler months. Other activities such as zoos and museums are great to visit in the fall. Kids are in school so there are fewer crowds. Many of the museums are free to enter, or have free days during the slower months. Museums such as the Museum of Contemporary Art, the Field Museum of Natural History and the Adler Planetarium are all great choices.

#2 Indoor Activities During Cold Months
There also plenty of indoor activities for rainy days. Chicago is world famous for its shopping. The city has everything from high-end designer boutiques to some of the best thrift stores you’ll find, and with the coming holiday season, many stores offer extended hours. There are also a lot of great sales going on in the fall, so you can get your holiday shopping done early.

#3 Take In A Show
Cold autumn evenings are a great opportunity to check out Chicago’s theater scene and live music venues. There are interesting shows all over the city and you can often buy tickets for smaller shows on the day of the show at a discount.

If you’re looking for something to do around Halloween, the historic city of Chicago is a great place to be. There are a number of popular ghost tours that run throughout the month of October. Even if you don’t believe in ghosts, the tours are interesting and informative.

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