Fall In Chicago

A Guide to Fall in Chicago: Condé Nast Traveler’s Best Big City!

Readers of CNT Vote Chicago Best Big City For Fifth Consecutive Year

The readers of Condé Nast Traveler have spoken and for the fifth straight year our hometown, Chicago, was voted the best big city. Of course, we wholeheartedly agree and the honor feels extra special in a year where a return to travel has meant so much for so many.

Though summer often gets all the shout-outs, thanks to our impressive lakefront and beach scene, fall is an equally amazing time to visit. Below, check out our picks for the top things to do in Chicago this fall, inspired by the CNT accolade, which notes our “impressive architecture, first-rate museums, brilliant chefs, and massive brewing scene.”

We’d love to be your home base for this exploration and are honored to have also been named the #3 top hotel in Chicago in the same poll with readers loving our historic lobby, gem-like Milk Room bar, spacious rooms and the best views of Millennium Park at Cindy’s Rooftop.


The Chicago Architecture Biennial returns for the fourth straight year under the theme of The Available City, which asks us to consider the impact collective space can have in cities today. Through a reinvented platform, the Biennial creates opportunities for conversations about the intersection of architecture and design and such critical issues as health, sustainability, equity and racial justice.

What better way to explore Chicago’s neighborhoods than through this program which features free, public happenings at sites in neighborhoods across Chicago and on digital platforms. Check out the upcoming programs, available through October 31, here.


Our neighbor on Michigan Avenue is the famed Art Institute of Chicago. Founded in 1879, it is one of the oldest and largest museums in the United States. This fall they welcome a limited time exhibition featuring iconic American artist Barbara Kruger, who has been a has been a consistent, critical observer of the ways that images circulate through our culture.

It’s a massive show with Kruger’s work filling the 18,000 square-foot Regenstein Hall, and it also expands to encompass Griffin Court – an 8,000-square-foot atrium running the length of the Modern Wing.


The talented team at our own James Beard award-winning space, Cherry Circle Room, is combining two of our favorite things this Halloween: scary movies and savory eats. Taking place on Halloween night, the moody vibes at CCR are the perfect backdrop for sips and a scare.


The Festival of Barrel-Aged Beers, or FoBAB as insiders lovingly refer to it, returns this November 12 and 13 with two exclusive tasting sessions. Come to celebrate wood and barrel-aged beers, featuring over 90 breweries and 300 individual beers poured at tables spread within an expanded 23,000 square foot space in UIC Forum. 

Your fall ticket to Chicago awaits! Explore our collection of special offers to get your getaway booked today.