chicago guide

Best Ways to Spend a Chilly Fall Day in Chicago

Easy ways to get cozy on an autumn Chicago day


FALL 2018 – There’s something pretty magical about October and November in Chicago. Temperatures start to slip, people have started to let go of their wonderful summer escapades and start to fully embrace everything Chicago can offer in the fall. This means chunky sweaters and cool boots, delicious cocktails with bourbon, darker rums and smoky mezcals, meals with root vegetables and braised meats and sitting around a fireplace with friends sipping some robust red wine.

With all Chicago has to offer, there’s no skimping on a great fall day — and there’s nothing better than a sunny afternoon hanging out in the city, even when it’s in the 40s or 50s. Bundle up, because we’re taking you on a fun little romp around Chicago in autumn.

Start by booking a fall getaway package at the Chicago Athletic Association hotel. Rates start at $199, but when you book multiple days, you get to save. Book two nights, take off 5 percent and get a $25 per day food and beverage credit good to use at Cherry Circle Room, Drawing Room, Milk Room, Game Room, Cindy’s and in-room dining. Book three nights, take off 10 percent or book four and take off 25 percent — and yes, you get that $25 per day credit for every day you’re with us. Make extra special use of those credits where you can cozy up near a grand, stone fireplace that dates back to 1893 in the Drawing Room, or near a firepit on the terrace at Cindy’s. Book in advance to nab one of eight coveted seats in Milk Room – where during Prohibition, CAA club members used to sneak their whiskey – but now you can enjoy cocktails made with rare and vintage spirits.

Starting Nov. 16, head over to Daley Plaza for the annual Christkindlmarket. This German-style outdoor market welcomes visitors to stroll its booths, drink mulled wine or beer, eat sausages with sauerkraut and potato pancakes and ogle cuckoo clocks and Christmas ornaments that you can buy. Afterward, pop down to the Riverwalk to check out Tiny Tapp’s insulated tents or City Winery’s river domes where you can sip wine, craft cocktails, fall beers, specialty coffee and enjoy light bites deep into fall and the start of winter.

Plan a fun day trip outside of the city to visit an apple orchard. Many of the farms start to tie up the season in early November, but you can still check out places like Apple Holler in southern Wisconsin, Honey Hill Orchard in Waterman, Ill., about 60 miles east of the city or All Seasons Orchard in Woodstock in northern Illinois, where you can also stroll a pumpkin patch or a corn maze.

From The Vault

Let's Go For a SPiN Plan Your Holiday Party With Us! Before Navy Pier Had Tourists Drink Among Animals Get Thee to Christkindlmarket When You Could Ice Skate in Lincoln Park Cindy's Wine List is Going All Natural Cindy's Now Serving Brunch!