When to Visit Chicago: Visit Chicago in the Fall

Last Updated on October 21, 2022 by JaimeSays

As a part-time blogger and full-time small business owner, I try to correspond with my readers and with fellow travelers a couple of times during the week.  I was with a Twitter follower recently who told me she had wanted to visit Chicago in October but was told it was not a great time to visit.  As a native to this dramatic, and somewhat tortured city, the notion that October isn’t a perfect time to visit unsettled me.  She mentioned she heard it was too cold in October, which just made me laugh out loud.  No, it’s not California, but October being too cold?  False!  March in Chicago is usually too cold, but not autumn. Chicago in the fall and autumn is such a lovely time to visit.  The days are still long enough to pack,full of activities, the colors are beautiful, it’s marathon season, and the summer crowds have thinned out.  If you’re still not convinced when to visit Chicago, consider some of these activities for what would be an ideal trip to Chicago in the fall.

First, May as Well go for a Healthy Stroll

Fall mornings in Chicago brisk and peaceful.  If you plan on maintaining a fitness regimen while on your trip, taking a long walk or a jog on the lakefront path and riverwalk  is the best way to see the city skyline while on your trip.

Another one of my favorite places to go for a stroll or jog is in Humboldt Park.  While the western neighborhood doesn’t have the same city skyline views, its boathouse and lagoon are quite stunning.  The prairie grass and native grasslands with wildflowers seave along the path and the historic buildings of the park district can make you forget that you are in 21st century Chicago.  Some of the sights you will see on your jaunt include the following:

The boathouse was part of the original design of the park as put forth by the father of landscape architecture and park design, Jens Jensen.  Construction of the park began in 1906 and included the Jensen Formal Garden and lagoon.

The National Museum of Puerto Rican Art and Culture is my favorite building in Humboldt Park.  It is housed in the former Humboldt Park Stables and Receptory, dating back to the late 1800s.  I like to think this building is the Chicago equivalent of Pemberley. It’s no banausic Mies Van Der Rohe skyscraper, but a classical Dutch looking expanse of a home with beautiful archways and stone trim.

Time for a Mid-Morning Meal

Now that you’ve worked up an appetite and earned some calories, food is in order.  I’ll admit: I am not a brunch person. If you go to a restaurant because you are hungry, with the crowds and “no reservation” policies, it is hours until you are actually sat.  What usually happens with me is that I get irritable and am generally an unpleasant companion for whoever is with me. What does work, however, is getting to wherever you want to be right before it opens.  Some of the places I like are Beatrix,  Cantón Regio, and Cafe Robey.  Beatrix takes reservations, Cantón Regio is cash only and a beautiful space in Pilsen, and Cafe Robey is the perfect antidote to a 90 minute wait at Little Goat.

If you think that to visit Chicago in the fall means to be completely bundled up and stuck indoors, you might be right. Frequently, October is absolutely beautiful with daytime highs in the low 70s and evenings in the 50s. You’ll find al fresco dining in full force on the warmer, sunnier days.  While it isn’t the same level of dedication that you might see in Amsterdam, it is just as thriving during the autumn months.  Heat lamps and patio heaters are commonplace but I also enjoy bringing an oversized scarf that can double as a blanket.

A Visit to Chicago in the Fall may Require Taking in a Game

Chicago in the fall is a city dominated by football. That’s because it isn’t late enough in the season to give up hope! Walking down the street on a Friday or Saturday morning, expect to see Notre Dame apparel and swarms of apparel for their opponents.  That’s because Notre Dame always gets primetime night games, whether their record warrants it or not. You’ll also see Northwestern Wildcat packs decked out in purple roaming the blocks menacingly (I kid).  Neither DePaul nor Loyola have football teams, but they both have competitive soccer teams and you’ll find the Depaul soccer field visible just east of the Fullerton “L” stop.

On Sundays, you’ll know if the Bears are home or away based on the density of South Loop traffic. Even if you don’t have tickets for the game, heading over to one of the surrounding lots for tailgating is quite the experience.  In my opinion, the most convenient areas to tailgate are near the park or right off the walking path. West of Lake Shore drive, the parking lot at the corner of 14th Street and Wabash Avenue starts tailgating around 8AM on game days.  It has a large, multicolored mural good for photos, plentiful food, and a moderate noise level. To get closer to Soldier Field, I like the South Garage.  It is more boisterous and crowded than the 14th Street lot, but it’s also pretty fun. Each time I’ve been, a drum line–of three to four people–stomps through to get fans in the spirit of the game. As a bonus, it has a higher vantage point than any other parking lots so you can see the lake, southern Lake Shore Drive, and McCormick Place.

By Foot, Bus, or Boat: You Must Tour

Whether you prefer to avoid organized tours or not, I really must insist that any visitor to Chicago takes at least one docent led tour. I’m partial to an architecture boat tour as the oppressive sun of summer is no longer a deterrent to sitting outside. I like the boat tours because you can cover more ground than on foot and encounter less traffic than you would in a bus. Some of my favorite city photos are from boat tours:

When it comes to walking tours, there are either indoor or outdoor tours.  For outdoor tours, I’ve got a great Prairie District Chicago Walking Tour for you to follow.  If you hit the ones that include building interiors, it’ll bring you inside in case it is a little too windy, cold, or rainy when you visit Chicago in the fall. Secondly, it gives you access to buildings that you normally wouldn’t consider entering as a tourist.  Office buildings and financial institutions aren’t usually high on my “must-see” lists but they often have elaborate art and interiors. Bus tours are a nice option when visiting areas outside of the major traffic areas.  Neighborhoods like Pilsen and Buena Park offer smaller, party bus style modes of transportation to get around easier.

If you choose a different theme than architecture, say a food tour or a brewery tour, you’ve still made a good decision. If you are visiting for a weekend or for a week, consider at least one guided tour on your way. Then visit the museums and other attractions you had on your radar.

You Best Wash up Before Dinner

I tend to need a little down time at a hotel between a day of exploring and dinner.  When you visit Chicago in the fall, the days will be getting shorter.  I like to take time before dinner or first thing in the morning to explore the property where I stay. While I occasionally stay at AirBNBs, I tend to prefer hotels for the accoutrements and the hospitality. There have been a few properties on my radar recently, and I hope to stay at them this winter for getaways.

First is the Alise Chicago, a StayPineapple Hotel.  This brand of hotels is known for quirky, boutique decor for cosmpolitan travelers in urban locations.  What piques my interest here is the historic aspect of the building. A Daniel Burnham building from the late 19th century, the majesty of the outside of the building is matched with its interiors.

Another hotel where I’ve wanted to go for a staycation is the Intercontinental Chicago. I’ve been frequenting the wine bar at the hotel a little more regularly recently (oh look, a discount code for you too!), and finally noticed the artistry of the building. Sweeping double staircases and romanesque carvings make way to beautiful views. Then there is this pool:

“You Don’t Have to Worry about Your Waistline Anymore Because it’s the Fall.”

My fiancé uttered this phrase about why someone should visit Chicago in the fall.  And of course, to an extent, he is correct.  This food-obsessed city is the perfect spot to visit…after swimsuit season.  First, there is the phasing out of boating and bringing the party indoors.  Saturdays in the playpen transform into football games indoors with beer and wings. Eddie introduced me to Lockdown for wings, and I truly think they dethrone Jake Melnick’s. While I crave salads in the summer, I go full carnivore by the time autumn rolls around. The chicken liver mousse at Café Marie Jeanne makes my mouth water as I type this, and the coziness of The Duck Inn‘s interior, and exterior, is the right spot to order a 72 hour peking duck. If you are looking for a place to take a vacation strictly to explore the food scene, Chicago is the place to be.

Only in the Fall Events

My two absolute favorite weekends to be in Chicago are fall only events: Chicago Gourmet and Open House Chicago.The first involves the finest chefs and sommeliers in the world descending upon Millennium Park with new gadgets, food stations, cooking demonstrations–the works.  It’s prodigality abounding, and it’s quite the scene.  Then there is Open House Chicago.  For the architecture enthusiast, or even just city explorer, this is the weekend to visit.  200 “cool places” open their doors to the public to tour for 48 hours. FOR FREE.  This is not a drill. You’ll get to see museums, private offices, the top floors of skyscrapers….it’s amazing. If nothing else, this event is the reason to visit Chicago in the fall.

What do you think? Have you ever visited Chicago in the fall or autumn? Let me know by leaving a comment!

Many thanks to Choose Chicago for helping to arrange access to attractions involved in this post. As always, all opinions are my own. This post contains affiliate links.

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JaimeSays

WSET Level 2 Certified Wine Lover, DuPage County Brand Ambassador. DME + Orthotics By Day, Adoring Home Life and Travel by Night.

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