If you are looking for a fall weekend getaway within the United States, then Chicago is a fabulous city to consider. Visiting the windy city in the fall has its charms – brisk walks around the city, indulging in deep dish pizza (and other Chicago delicacies), and cozying up with a glass of wine with a view. It is also a great chance to break out your very best fall street style. This article will walk through some fun fall activities in Chicago to consider, outfit inspiration, and some recommendations on where to eat + stay.
Fall Activities in Chicago
Explore the Chicago Riverwalk
While many think the Chicago Riverwalk is best enjoyed in the summer, I found it very charming to visit during the fall. With fewer crowds and less heat + humidity, I was able to wander and enjoy at my leisure. As you wander around and take in the views, I highly recommend visiting City Winery at the Chicago Riverwalk – with heat lamps galore and igloo options available (for a fee), you can cozy up with a glass (or carafe) of vino and soak up those river views! I recommend visiting in early Fall if you want to take the most advantage of the Riverwalk area, as some of the restaurants and bars close down once it gets too cold.
Chicago Architecture River Cruise
Speaking of the river – if you are visiting Chicago on a weekend that is earlier in the fall season, I would highly recommend booking an architecture cruise! There are many available on sites like viator. This is by far my favorite Chicago activity, as it gets you out on the water, features amazing city views, and is educational.
Sample Local Chicago Coffee Shops
While coffee is a delight to enjoy at any time, there is no better time of year than during the fall in my humble opinion! Seasonal options are out to play at this time of year, and even the trendiest of coffee shops hop on the seasonal coffee train. Two of the coffee shops that I absolutely adored while I was there were Hero Coffee Bar and Goddess and the Baker. My recommendations? At Hero Coffee Bar, make sure you grab a seasonal flavored latte (they had some unique options) and one of their almond croissants! For Goddess and Baker, grab one of their trendy coffee offerings, such as their glitter or rose matcha lattes.
Warm Up at the Art Institute of Chicago
The Art Institute of Chicago is an art museum located in Chicago’s Grant Park. Founded in 1879, it is one of the largest and oldest museums in the United States! The permanent collection offers a wide variety of subjects in art, including Pop Art, Impressionism, and the African Diaspora. Make sure that you do not miss some of their most famous and recognizable pieces, such as A Sunday on La Grande Jatte by Georges Seurat, American Gothic by Grant Wood, and The Bedroom by Van Gogh. In addition to their permanent collection, they also regularly host traveling exhibitions which might be worth checking out depending on when you visit!
Not big on art? No worries – Chicago houses several fantastic museums to choose from. Consider checking out the Museum of Science and Industry, The Field Museum, Adler Planetarium, or the Chicago History Museum.
Grab Drinks with A View
Just because it is no longer summer, does not mean the rooftop vibes have to end! Many Chicago rooftops remain open into the early fall months, which allow for an opportune time to take in sweeping views of Chicago (without the crazy crowds)! My favorite rooftop that I visited in the Fall was Cindy’s Rooftop, a rooftop bar and restaurant located at the top of the Chicago Athletic Association Hotel. In addition to amazing wine, this rooftop took the top spot as it offered views of the famous Chicago Bean surrounded by fall foliage – simply breathtaking! Be sure to pop by The Bean while you are in this part of town if you would like to grab some standard “the bean” shots.
Consider Escaping the City
Happen to have a car on your visit? While there are plenty of fall festivities to be had in Chicago proper, my last recommendation involves heading out of the city for some fall festivities in the suburbs. On my visit, we drove about an hour outside of the city center to hit up two incredible fall spots – Acquaviva Winery (Maple Park) and Kuiper’s farm. These two spots were within a 5-minute drive from one another.
Acquaviva Winery’s Maple Park location is a small little blue winery, set on a property filled with rolling hills of vines. Inside the winery it is very cozy which will keep you warm if it is a chillier day! If it is sunny out, you might prefer to enjoy some wine with a view from their outdoor seating. Either way, this winery offered incredible wine (at an affordable wine tasting price), as well as friendly service.
If you are looking for all the fall festive vibes, then look no further than Kuiper’s. This farm not only offered every local fall treat you could imagine (think freshly made apple cider donuts, pumpkin flavored treats, and local jams), they also had an in-house cidery!
What to Wear in Chicago in the Fall
When I travel, I tend to pack light. My “uniform” while in Chicago was a mix of sweaters, light jackets, jeans, a scarf, and cute boots/booties. I also brought along a packable down, which was useful on colder days. I have pulled together a few pieces for Chicago outfit + packing inspiration below.
Jackets
Tops
Accessories
Where to Stay in Chicago
I have stayed with a friend every time I have visited Chicago, however, I visited the restaurants/bars at a number of these hotels and they seemed great (and in awesome locations). I typically book hotels on Booking, but I have included direct links to a few hotels highly recommended to me by locals listed below.
Bars & Restaurants in Chicago to Try
Bars
- Bassment for fun + live music
- LH Rooftop at LondonHouse for swanky city vibes + views (open seasonally, so verify they are open on your Fall visit)
- Bub City if you are a country music fan
- Three Dots and a Dash for fun ambiance + cocktails
Restaurants
Brunch & Lunch
- Summer House
- Fremont Chicago
- Beatrix
Dinner
- Pizanos (Pizza + Pasta)
- Lou Malnati’s (Chicago Deep Dish)
- Happy Camper (Cute vibe + Pizza)
- Monteverde (Upscale Italian)
- Maple & Ash (Fancy Steakhouse)
- Momotaro (Japanese)
I hope you found this Fall in Chicago Travel & Style Guide helpful! Please let me know if you have any questions, or if there is anything you would add to the list. Looking for more travel inspiration? You can read through all of Style the World’s articles here. Happy travels xx
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