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The Perfect Fall Day in the Loop


Posted  17 days ago  in  Trending, Loop List, Things to Do

2 MIN READ – Fall is arguably the best season in Chicago (or at least top two!). Cooler temps, light layers and plenty of things to do – both outdoors and in – encourage Chicagoans to step outside. If you want to paint with the colors of the wind, here are some ways to enjoy some of the vestiges of a perfect autumn day downtown in the Loop.

See the sites

A Shoreline Sightseeing Architecture River Tour makes the perfect centerpiece of a wonderful fall day in Chicago. Shoreline’s expert guides share the inside stories behind Chicago’s world-famous architecture during a relaxing, 75-minute tour along the historic Chicago River. You’ll also enjoy spectacular views and photo ops of Chicago’s scenery and landmark buildings. Tours depart from the northeast corner of the Michigan Avenue Bridge throughout the fall (weather permitting). Get a discount using Shoreline Sightseeing’s Loop Deal. Learn more.

Shoreline Sightseeing

Museum of Contemporary Photography's new exhibit, What Does Democracy Look Like? Makes the perfect indoor escape for a fall day. Leading up to the 2020 presidential election, the  MoCP  has invited seven faculty members from various departments at Columbia College Chicago to mine the MoCP’s  permanent collection of nearly 16,000 objects. Each curator interprets the museum’s collection to consider what democracy means to them, and how photographic images record and shape our understanding of current and historical events. This exhibition will not only showcase photography from the collection, but will also feature participatory elements, including onsite voter registration. Learn more.

Bruce Davidson Untitled 1991


You can also celebrate the changing of the seasons with this selection of autumnal works from the Art Institute’s collection. 

Art Institute fall day

Or, check out any of the other great tours and attractions in the Loop.

Enjoy a great meal

Soak up the year’s best patio season weather while you can! Plenty of restaurants in the Loop are serving up delicious Fall specials, including Boleo.

Boleo Semi

The temperatures are dropping, but Boleo is just warming up. Be transported to South America where the drinks flow, the music is always playing, and the food is irresistible. Come & try one of lead bartender, Sam Garcia’s Monet Inspired Cocktails in partnership with Art Institute of Chicago’s Monet + Chicago exhibition. Located on the 15th floor of Kimpton Gray Hotel Chicago. Open Wednesday and Thursday from 5-9 p.m. and Friday-Saturday from 4:30-10 p.m. Be aware that reservations are highly recommended. Learn more.

Update your wardrobe

As temperatures begin to drop and colors of the trees start to change, it means it’s time to refresh your wardrobe with the latest styles of fall. Stop in to Q Clothier and Rye 51, the side-by-side luxury men’s custom clothier brands providing top quality, hand-crafted attire tailored perfectly for individuals of every lifestyle. A new addition to the Gold Coast neighborhood, shop with seasoned experts as you browse the latest and trendiest garments. Bath in luxury as you sip on some whiskey while shopping warmly and safely! Learn more.

Or head to the Loop and check out a whole plethora of other shopping options


Treat yourself to a Loop Staycation

“Fall” into your favorite River North hotel this season at Godfrey Hotel. Not only are the savings great, but so are the rewards! During your stay, be sure to make a reservation for a Haunted Igloo at I|O Godfrey, one of the city's most popular rooftops! On Halloween, enjoy craft cocktails, costume prizes and a warm place to celebrate the spooky season. Learn more.


Hotel Essex is right across the street from Grant Park, one of the city’s most beautiful parks. Experience the city like never before in one of the newly renovated guest rooms. Fall savings await you with delicious dining experiences, and a close proximity to local shops, parks and fun! Learn more.

Hotel Essex

Take a Walk

Whether you want to watch the leaves fall, or get some cool, fresh air, check out a few of the best places to take a walk in the Loop.

EN photo blog 14

Share your perfect Fall day with us on social media: #BackInTheLoop.