Yes, it’s true summertime in Chicago is magical. But Fall in Chicago is just as amazing! The air is crisper, the tourist crowds have finally died down making it easier to get in to attractions, and it’s perfect for road trips and to explore the suburbs and outerlying areas. Fall is officially underway and there are so many activities to do and places to explore in and around Chicago. With the weather being as great as it is before we have snow days, it’s best to seize as much outdoor time as we can. Here is how I spent a perfect 4-day Fall weekend in and around Chicago. I’m sharing my itinerary for you to explore each amazing place as I have. Compared to my last blog post for Summertime Chi, you will need a car to visit some of my recommendations, but I promise you it will be worth it!

While I largely walk throughout Chicago and take public transportation, I rented a car this weekend through Avail Car Share. I tend to book rental cars through Enterprise, or Orbitz but I recently learned about Avail Car Share, and with a promo code they had the cheapest rates for the weekend. The car share company has cars at 15 airports across the U.S. and their cars can also be found in neighborhoods throughout Chicago and Denver. If you’d like to try them out, use this link to book your next car rental.

Day 1

Brunch at Frances’

Starting on day one, you can begin the day with brunch obviously. Head up to Lincoln Park for Frances’ Brunchery. Frances’ is a Black owned French-themed brunch and deli restaurant with indoor dining and an enclosed patio space. Frances’ is known for their mimosa tower and French Toast flight, featuring a rotating monthly French Toast flavor. I got the French Toast flight which included blueberry crumble, strawberry, apple pie, lemon curd, and the special for the month was mango and pineapple. Hands down the strawberry and apple pie French Toasts were my favorite! We also ordered a bacon flight that came with 5 pieces of bacon and included Canadian Bacon, turkey bacon, hickory smoked, and a hot jalapeño bacon. There are over one dozen juice options to choose from for your mimosas, but the crowd favorite is cotton candy. If you want to share a mimosa of the same flavor, you can order a pitcher of mimosa as well. Whatever you choose to order here, you cannot go wrong!

Take in panoramic views at Skydeck

Whether you’re local to Chicago or visiting, you have to stop to admire the beauty and view of the city. Heading to rooftops and observation decks in the Fall and cooler months are much easier than in the summer when everyone wants to be outside. Sears Willis Tower was once the tallest building in the world during the 1970s - 1990s, and the tower is an iconic staple in Chicago’s skyline. We went to Skydeck at Willis Tower on a Friday afternoon and the crowd was manageable. The layout from entry to the Skydeck is designed to keep you entertained and engaged for an hour with all of the exhibits and picture-taking opportunities that are available as you walk through before you finally take a few elevators up to the Skydeck on the 103rd floor.

We were 2 hours late to our ticketed reservation, but the staff didn’t notice nor did they say anything. I guess as long as you purchase a ticket for the correct day, you can still enter.

Located 1,300+ feet in the air, the Skydeck is on the 103 floor of The Willis Tower and The Ledge is a glass box that extends from the 103rd floor that’s 4 feet wide and has 1.5” of glass to hold you.
Because we went on a Friday afternoon in October, the admission line was not terribly long. You can purchase upgraded tickets for a fast track experience, but I would 100% recommend people to NOT purchase it. The only fast track portion is waiting in line to get your ticket scanned. After you get your admission ticket scanned, you still have to maneuver through the props and exhibitions, as well as ride the elevator up with everyone else to The Skydeck. Lastly, there is no fast track line to skip people or reserve a ledge to take pictures on The Ledge— so I’d say just save the $10 extra per person and wait a few extra minutes with everyone else.
Once you do arrive at The Ledge, there is a one (1) -minute maximum per group on, and the staff does time you with an iPad and the alarm will sound when your time is up. We looked at Instagram for inspiration poses, but once I got on the ledge I was terrified to move once I got on the glass box. My friend and I had to get in line 3 times to make sure we had enough pictures and poses, and it still didn’t seem like enough to capture the perfect picture.

I would say overall, it was a nice experience and one of those things you have to do once.
If I only had time and money to choose between going to Skydeck and the 360 Observation Deck in Water Tower Place, I’d say that 360 was less of a hassle to reach the main attraction, the views were better in my opinion, there were better fun facts such as the time capsule available for viewing, and there’s a bar. Skydeck is in a historic building and taking pictures in a completely glass ledge is pretty iconic. So if lines and time limits don’t bother you, then purchase your tickets for Skydeck. If you purchase a Chicago CityPass for admission to attractions, you won’t have to choose between the two towers, and you can visit both for one price!

End the day at a professional sports game

Professional games are in season during the fall— the regular season for the White Sox and Cubs ends by mid-October, preseason basketball for the Bulls is at the beginning of October, preseason hockey for the Blackhawks begins late September, the Chicago Fire soccer team plays through early November, and preseason football for the Bears begins in August.
If you do decide to attend a Bears football game, I recommend going in the Summer or Fall. If you’re not a diehard Bears or NFL fan, I would completely skip seeing them play in the winter since Soldier Field is an open-roof stadium.

If you don’t want to be a spectator, the Chicago Marathon runs during the second weekend of October. Since I can never wake up early enough to see the runners for the Chicago Marathon, we ended up going to see the Chicago Bulls play the Denver Nuggets during preseason.

Day 2

Go apple picking, to a pumpkin patch, and through a corn maze

We headed to Jonamac Orchard in Malta, Il. located a little over one hour west of downtown Chicago. Onsite parking is free, but it is recommended that you arrive early (before noon) and purchase your tickets in advance online because weekends book fast. They update their website and Facebook page if they stop accepting walk-in customers for the day, but if you’ve already purchased your ticket for the day, you can still enter. Jonamac sells tickets online by time slots, but no one was checking what time slot we purchased, and once you’re in, you can stay as long as you’d like. Admission tickets if purchased online are $7 per adult and include so many activities! A pumpkin patch, apple trees, a corn maze, a sunflower patch when in season, flower fields, wagon rides, an onsite bakery, access to a cider house to purchase apple wine bottles, and glasses of wine as well as tasting flights are all included in the admission ticket. There is also the Tiny Town Play Area for kids and adults to play on and take pictures, including slides, a bubble barn, a hay pile, and a few other installations. In addition, you can purchase apple tokens for a few add-ons, which include an apple launcher, an apple cannon, pony rides, a petting zoo, and a 5-minute ride on an apple train.
Besides having an onsite bakery selling cider, apple varieties by the 5 lb bag, and every apple dessert you can imagine, there are also food trucks on-site and a cider house selling kettle corn, ice cream sundaes, cider slushies, and various snacks.

We stood in line for ~45 minutes to enter the Cider House to order a flight of ciders, hard cider, apple wine, and beer from local breweries. From left to right we ordered the sunrise slushie, caramel apple wine, Jonasmack Honeycrisp hard cider, and pumpkin wine. My friend enjoyed the slushie, but I was not a fan of any of the wines or ciders we ordered. I found them to all be very sweet. I wasn’t sure what foods to pair them with, because I couldn’t see myself pouring a glass of caramel apple wine and drinking it with dinner. I guess because I didn’t know what to pair the wines with and them being so sweet, we couldn’t finish the flight, so I didn’t bother to buy bottles to bring home.
Inside the Cider House are snacks that should go with the wine like cheese curds, sausage, apple cheddar cheese, and kettle corn.

Jonamac is a family-owned apple orchard where you can pick your own apples from over 20,000 trees on their property. Besides apple picking, you can also pick your own pumpkins and pay an additional cost for any apples and pumpkins you take home. Jonamac is definitely family-friendly — great for kids, families, friend groups, and dates. Additionally, if you have a large group or want to have a party, there are campsites that include grills and firepits for rent!

Visiting Jonamac was probably the highlight of my year because there are so many activities to do! My favorite activities were the apple cannon, bubble barn station, and the jumping pillow.

New York Style Pizza for Dinner

After spending the day at Jonamac, it’s time to get dinner. I’m sure you’ve probably had your fair share of Chicago’s deep dish and tavern-style pizza by now. Head back up north to ZaZa’s Pizzeria in Lakeview. ZaZa’s recently opened in 2021, and is such a neighborhood joint. They no longer offer delivery and aren’t on third-party sites, so you have to either dine in, or place an order over the phone for pickup. We dined in, but there are ~5 tables with seating for max 20 people, so it’s a great option to bring your order back home. If you do choose to dine in, they are BYOB.
We started off with their garlic twists which were so good as well as the Chicago-style salad — think of a Chicago hot dog but in salad form minus the weiner and mustard.
We also ordered a pepperoni and sausage pizza. The crust is perfectly crisp with the right amount of sauce-to-cheese ratio. They only serve whole pizzas so be prepared to share, or have leftovers.

See a Comedy Show

After ZaZa’s pizza, end your night with a Chicago classic — standup comedy at The Laugh Factory. Laugh Factory has locations throughout California, Vegas, and Chicago. Famous comedians that have graced one of Laugh Factory’s stages include Tiffany Haddish, Paul Mooney, Richard Pryor, Arsenio Hall, and Dave Chapelle to name a few. Located in Lakeview East and a few blocks away from ZaZa’s. Laugh Factory has shows nightly, and on the weekends the latest show starts at 11:30 pm. They are very strict about their 2-drink minimum per person for every show! Alcoholic and non-alcoholic drinks qualify for the minimum. 18% gratuity is added to each order, and they check your receipts upon exiting to ensure everyone purchased 2 drinks.

Chicago has a deep stand-up comedy culture with many of your favorite comedians starting their careers in one of Chicago’s many comedy clubs. Besides Laugh Factory, I’ve seen a few shows at House of Blues featuring local acts and the famous Second City which has tons of improv shows and cheesy comedians. I always check out Eventbrite to find new comedians doing shows, and introduced to new comedy clubs through that site.

Day 3

Brunch at Honeybear Cafe

The first two days were pretty action packed, so feel free to take the rest of your time in Chicago slowly. Start your day off in Rogers Park at Honeybear Cafe. I’d wanted to try Honeybear for a while but refused to ride the Red Line for an hour or pay $60 for an Uber each way.
For whatever reason I thought they did not accept reservations, until the day of I realized they did and tried to call in for a table and was unsuccessful. We got there and put our name on the waitlist for a table, and had to wait about an hour to be seated. So, take my advice and make a reservation in advance!
Honeybear is a family-run restaurant with hearty breakfast and lunch options that make for unique menu offerings. Their decadent lattes have been all over my Instagram. They have unique flavors like s’mores, caramel apple butter, Nutella + graham cracker, honey coconut, as well as traditional coffees. I’m not a coffee girl, but I had to try a latte! My friend and I both ordered the cookie butter hot latte and it was so good! So good in fact that I recreated the drink the following week at home.

The portion size here is huge, so you’ll definitely share or bring home leftovers. The offerings range from pancakes, waffles, and thick french toast, to sandwiches, omelets, benedicts, and grit bowls. My friend ordered the breakfast sandwich on waffle and she loved it. I was pleasantly surprised to see fried catfish and grits on the menu, so you know I had to order it along with a biscuit. Everything was so good, I want to become a regular at Honeybear!

Make candles at Aura

After eating, you have to do something relaxing, so how about making candles?! I’ve been to Aura Candle Bar a few times, and it’s always an enjoyable experience. First of all, it’s in Southport and I’m obsessed with the neighborhood, the staff is great and so friendly, and there are so many scent options for you to choose from to create something unique. Because the process is interactive and customized, making candles is perfect for any occasion - if you’re with a group of friends, if you’re having a friend date, a romantic date, or if you’re solo and need to kill some time.
There are over one hundred scents to smell to create your custom fragrance, be it in candle form, wax melts, or a diffuser. You also choose the vessel that your fragrance is held in. You do have to make a reservation, and they are closed on Mondays. Candles take a few hours to set, so if you want to bring home a candle same day, I suggest not going late on a Sunday, or close to closing time.

The process begins with you smelling their candle scents and choosing all of the scents that you like. You’re then given those scents in oil form to smell to make sure you still like them and you can fiddle with multiple combinations, but your top 3 favorite scents will be used for your fragrance. The employees give you all of the tools you need - a shot glass, a spoon, and a plate. You’ll mix the oils to get the right fragrance that you want, until you fill the shot glass. The oil mixture is then transported to your end product, either mixed with wax for the candles and wax melts, or blended with alcohol for the diffuser.
We made diffusers and wax melts. My diffuser is bergamot, aujou pear, and Chardonnay. Since I put it in the bathroom, I wanted something fresh, light, and crisp, and I nailed the scent; it’s exactly what I was trying to execute. My wax melts are sandalwood, whipped cream, and mahogany. Before discovering actual wax melts, I was such a candle girl and would burn candles religiously but found that I was always left with the wax after the wick had burned out. I thought the best way to reuse the candle wax was to put it in wax warmers, but the fragrance wasn’t super potent and didn’t really travel through the whole house. The wax melts that I made at Aura is perfect! Initially, I only wanted to melt the wax in my bedroom, going for a warm, sexy, cozy vibe. I now have the wax melts melting throughout my home and as soon as you enter, the scent gives off the vibes that I was going for, and feels so inviting.

Visit a Haunted House

End the night at a haunted house to really celebrate Fall and Halloween! There are many haunted houses in the suburbs and a few spooky pop-up experiences in the city. Also, if you stay out late at a pumpkin patch or corn maze, at night the corn mazes usually turn “haunted”. At Jonamac Orchard, beginning around sunset on Fridays and Saturdays you can go through their haunted corn maze. I don’t know anything scarier than navigating a corn maze in pitch black in the middle of nowhere, so it would definitely give off haunted vibes.

For a more traditional haunted house, there is 13th Floor Haunted House out in Schiller Park. You can take the Blue Line to Rosemont, then take a Lyft or Uber to 13th Floor if you choose not to drive. 13th Floor was my first haunted house experience last year, and it wasn’t too scary. You can purchase a fast past ticket to bypass the line, but again I don’t recommend because the entry line moves pretty fast. There were scary costumed performers outside the admission line with fake chainsaws and masks scaring people, so that prepared you for what was inside. Once inside, the entire experience lasted maybe 20 - 30 minutes and it was filled with your usual fog, monsters jumping out to scare you, and the occasional serial killer coming out with a chainsaw. The animations, costumes, and makeup were really well executed here. Even for someone as scary as I am, and it was my first time at a haunted house, I would say that 13th Floor is pretty tame and is good for first-timers.
I would really like to go to the Old Joliet Prison Haunted House. Although Old Joliet and 13th Floor are run by the same parent company, I’ve been told that Joliet is more frightening. If anyone has been to either, or both haunted houses, let me know your experience down in the comment section!

If you prefer something a bit more tame, and wouldn’t want to pee your pants, Chicago bars and nightclubs often have seasonal popups. Deuces Bar in Wrigleyville hosts Nightmare on Clark Street and it is an annual favorite. Normally Deuces is just a regular sports bar where you can watch the Cubs play, but beginning October 1, Deuces transforms into a haunted house experience.
They completely deck out the bar and patio areas with lights, Halloween decorations and props. They still serve bar food, but the drink menu changes to feature more festive and spooky concoctions. You can order cocktails as a regular serving or you can order them monster goblet-style to share with your friends. My friend ordered the butter beer cocktail and I ordered Freddy’s Tequila, which was a spicy margarita. You have to make reservations in advance if you want to dine in.
Deuces also has a haunted experience, located on their second floor and tickets for the haunted experience have to be purchased in advance.

Now if spooky nor cocktails are really your thing, JoJo’s Shake Bar in River North or Naperville should be up your alley. JoJo’s is an experience year round, and they decorate and go all out for each holiday and season. JoJo’s was the first place I went to when I moved to Chicago, and it’s a great Fall experience. JoJo’s is known for their intricate pop-ups and their extreme milkshakes that feature slices of pie or cake, whole caramel apples, candy, cookies, toasted marshmallows, and other seasonal treats. They also serve food — bar snacks, burgers, sandwiches, etc. You can go to their walk-up window or bar to purchase a milkshake, extreme hot chocolate, or dessert to-go without a reservation or getting a table.

Day 4

Spend the day in Chinatown

Hopefully you were able to spend a long weekend in Chicago, or a few days during the week. We’ve visited many neighborhoods throughout the city and even ventured to the suburbs, but I think one of the most culturally rich neighborhoods in Chicago is Chinatown. Located off of the Red Line, Chinatown is home to hundreds of local businesses including restaurants, bakeries, karaoke bars, souvenir shops, beauty stores, jewelry shops, markets, a few hotels, and even a library. The Nine Dragon Wall as well as The Chinatown Gate are sculptures that welcome visitors and residents to Chinatown.

There is a parking lot next to the Cermak/Chinatown Red Line stop, and many retailers in Chinatown will validate your parking with a paid purchase. With validation, parking is $2 for 3 hours. But I found a hack from TikTok that the parking garage connected to Noodle Creation on S. Archer & Canal is completely free, and just an 8 minute walk down to the majority of restaurants and shops off of Cermak.

In Chinatown, boba tea should be your first stop. Joy Yee Plus has dozens of boba and bubble tea options to order, as well as unique smoothies and ice cream flavors. I ordered the mango pineapple green tea with boba balls, and it was so tasty and refreshing! Joy Yee Plus is the stand-alone drink spot, but Joy Yee is the full- service restaurant that also serves some of the same drink and ice cream creations as Joy Yee Plus. We ended up walking down the outdoor mall from Joy Yee Plus to Joy Yee for food. While, the service was fine, the food came out fast, and it was okay Chinese food, Joy Yee wasn’t much to write home about, and I probably wouldn’t go back again. I would prefer to try other restaurants in Chinatown. At Joy Yee my friend ordered the shrimp ramen which was terrible and would not recommend. I ordered the Mandarin chicken with fried rice and egg rolls, which also weren’t good.

Original Triple Crown Restaurant, is pretty solid, and is family/large group-oriented.

Ming Hin has a few locations throughout Chicago including Streeterville, South Loop, Lakeshore East, and of course Chinatown. They’re probably one of my favorite Chinese restaurants in the city.
Sushi Plus Rotary, while not Chinese has a location in Chinatown and Boystown, and is one of the most unique dining experiences I’ve had. They do not take reservations, so be prepared to wait. The rolls and sushi are presented throughout the restaurant on a conveyor belt and you pick up whichever plate you want from the conveyor belt. If you order something from the menu, a robotic train automatically delivers it to your table.

I’m still on the hunt to find really great food, shops, and experiences in Chinatown. If you have recommendations, or additions you’d make to this guide, I’d love to see them in the comment section!

Nov 1 Ultimate Autumn in Chicago Guide