Chicago Marathon weekend is one of my absolute favorite weekends of the entire year. The city is buzzing, strangers are cheering each other on, and there is something genuinely moving about watching 45,000 people run 26.2 miles through our streets. Whether you are running, cheering, or just soaking it all in with your kids on the sidelines, this weekend delivers. Seriously, tell me you didn’t have tears in your eyes. I have also rounded up Lincoln Park Wine Festival, a great pick for the little ones, and — because I cannot help myself — a sneak peek at a stunning new Lincoln Park listing coming to the market. Let’s get into it.
🗓️ This Weekend in Chicago
Cheer on the Chicago Marathon
📅 Sunday, October 11 | ⏰ Starts 7:30 AM | 📍 Grant Park & along the course | 💰 Free to spectate | 👨👩👧 All ages
If you have never taken your kids to cheer at the Chicago Marathon, this is the year. There is nothing like it. The route winds through 29 neighborhoods, and you can post up almost anywhere along the course with a handmade sign and watch the magic happen. My personal favorite spectator spots: Lincoln Avenue near mile 9 for the North Side energy, or the stretch through Chinatown around mile 21 where the runners need the cheers most and the crowds are incredible.
Pack snacks, bring a sign (kids LOVE making them the night before “Run Faster, We’re Hungry” is a classic), and plan to be on the route by 8 AM to catch the lead runners. The course is closed to cars but most neighborhoods are very stroller-friendly along the spectator side. This is one of those Chicago moments that will stick with you and be one of your kids core memories.
🏡 Realtor mom take: The neighborhoods along the Chicago Marathon route are having a moment and marathon weekend is genuinely the best way to feel it. We are talking Lakeview, Lincoln Square, Roscoe Village, Pilsen, Bridgeport: all neighborhoods where people actually know their neighbors, where the block associations are active, and where the restaurant scene keeps getting better. Lincoln Square just welcomed a wave of new openings including Goosefoot relocating on Lincoln Avenue near Welles Park and ET-CHI bringing Turkish fusion to the neighborhood. This is a corridor where families plant roots and stay. If you are watching the race from the sidewalk and finding yourself looking up at the greystones and two-flats and wondering what it would actually cost to live here, that is exactly the kind of conversation I love.
Chicago Cultural Center: Free Family Programming
📅 Saturday & Sunday, Oct 10-11 | 📍 78 E. Washington St., Loop | 💰 Free admission | 👨👩👧 All ages
The Chicago Cultural Center is one of the most underrated free resources in this city, and on Marathon weekend it is a perfect home base if you are downtown. The Tiffany glass domes alone are worth the trip — my kids stop in their tracks every single time. Rotating exhibits, drop-in art activities on weekends, and a beautiful space to warm up and regroup between spectating spots.
It sits right on Washington Street near Grant Park, which makes it an ideal pitstop in the morning before heading to the finish line area. Bathrooms, water, and a dose of culture — all free. That is a Chicago win.
🏡 Realtor mom take: The Loop and South Loop continue to be one of the best-value family neighborhoods in the city. Walkability scores through the roof, access to parks and museums, and price points that surprise buyers who have only been looking north. The Chicago Cultural Center is right there, which is one of those things people forget until they actually live nearby and start using it every weekend. Not many neighborhoods in Chicago are a buyer’s market right now, and this is one of them. So it is still a great opportunity to purchase with many options to choose from.
🍷 Lincoln Park Wine Festival
📅 Saturday & Sunday, Oct 10-11 | 📍 Lincoln Park, South Pond area | 🎟️ Tickets required at lincolnparkwinefestival.com | 🔞 21+
This is one of the best grown-up weekends of the fall and it happens to land on Marathon weekend, which means the energy in Lincoln Park is absolutely electric. Sip your way through pours from 30+ wineries and local favorites while surrounded by fall foliage at the South Pond. It is beautiful, it is walkable from the neighborhood, and it is exactly what October in Chicago should feel like.
Pro tip: go Saturday afternoon to avoid the post-marathon Sunday crowds and get your pick of the longer pours. Pair it with dinner at one of the Lincoln Park restaurants on Armitage or Halsted after. This is a proper adults-only afternoon.
🏡 Realtor mom take: Lincoln Park was my first Chicago home after college and I have a soft spot for it that will never go away. This festival is one of the reasons why. You are steps from the South Pond, Armitage Avenue boutiques, North Pond restaurant, and some of the best school options in the city, public and private. Schneider Deli is opening their Lincoln Park location at 1733 N. Halsted, which is exactly the kind of neighborhood institution that makes a block feel complete. The Lincoln Park Chamber of Commerce does a good job of tracking what is new and opening. The lifestyle in this neighborhood is one you really have to experience to understand. If you are here this weekend for the wine festival and you are feeling it, trust that instinct. Let’s talk about what it would actually take to make this your neighborhood.
🗓️ Also This Weekend
Marathon Finish Line Experience at Grant Park
📅 Sunday, October 11 | ⏰ Starting 9:30 AM | 📍 Finish Line, Columbus Drive at Balbo | 💰 Free with spectator registration at chicagomarathon.com
If you are not running (same, same), get yourself to the finish line area. There is something genuinely emotional about watching runners cross after 26.2 miles. People are crying, strangers are hugging, cowbells are everywhere. Chicago does the finish line experience better than anywhere in the world — the crowd energy is unreal and the skyline backdrop is chef’s kiss.
Beck at the Auditorium Theatre
📅 Thursday and Friday, Oct 9-10 | ⏰ 7:30 PM | 📍 Auditorium Theatre, 50 E. Ida B. Wells Dr. | 🎟️ From $79 at auditoriumtheatre.org
Two nights only. Beck at the Auditorium Theatre is the kind of show that feels like a gift — an iconic artist in one of the most beautiful venues in the country. If you can grab tickets for Friday night, it is a perfect start-of-weekend move. The Auditorium is stunning, the acoustics are unreal, and Beck puts on a show worth every penny.
ART on THE MART
📅 Thursday and Saturday evenings this weekend | ⏰ After dusk | 📍 Chicago Riverwalk, along Wacker Dr. | 💰 Free
One of Chicago’s most underrated fall traditions. ART on THE MART projects massive video art installations onto the facade of the Merchandise Mart along the river — it runs about 30 minutes and it is genuinely spectacular. Walk the Riverwalk after dinner, grab a drink at one of the river spots, and catch the show. It is free, it is beautiful, and it is the kind of thing that makes you fall in love with this city all over again.
🏡 Realtor mom take: River North is having a real moment and ART on THE MART is honestly just the beginning of the story. This neighborhood has always had the restaurant scene (Bavette’s, Portsmith, The Waydown) but what is happening right now is the lifestyle piece is catching up to the buzz. You can walk to the Riverwalk, to the Loop, to the Magnificent Mile, to the West Loop in under 20 minutes. Motel Bar just relaunched under new ownership with a whole Wisconsin supper club vibe, which sounds ridiculous but I promise it works. The River North Association is one of the more active neighborhood groups in the city if you want to get a real sense of community. For buyers who want true walkability and that city-at-your-doorstep feeling without being in the Loop itself, River North delivers. Come for the art installation, stay for the neighborhood tour. I am happy to give it.
Olivia Rodrigo: The Unraveled Tour
📅 Sunday, October 11 | 📍 United Center, 1901 W. Madison St. | 🎟️ Tickets at unitedcenter.com
She is here and she is not messing around. Olivia Rodrigo’s Unraveled Tour hits the United Center Sunday night and if you have tickets, you already know. If you do not, check StubHub, because this is one of those shows people will be talking about and you don’t want FOMO. Whether you are going with your teenage daughter or your best friend, this is the concert of the fall.
🏡 Real Estate Corner
COMING SOON | 1155 W. Armitage, Unit 202 — Lincoln Park | $800,000
2 Bed / 2 Bath | Corner Condo | Elevator Building | Garage Parking
Moody, sophisticated, and full of sunshine. This impeccably designed corner condo is anything but ordinary. Think custom designer wallpaper, stunning finishes, thoughtful upgrades throughout, and incredible natural light pouring in from every angle. The oversized private balcony is the kind of outdoor space that becomes your favorite room the second you see it.
Add an elevator, attached garage parking, extra storage, and a location right on Armitage Avenue surrounded by Lincoln Park’s best boutiques, restaurants, coffee shops, and wine bars — and you have a home that checks every box. Style, substance, and one of the most walkable addresses in the city. This one has it all.
Reach out before it hits the market. These Lincoln Park corner units do not last. I would love to get you in for a preview. DM me or reach out at yeagerteam.com for details and early access.
Where Rates Stand This Week
The rates are what everyone is talking about and they are definitely up and high. This is not unusual for this time of year and with midterms coming up always induces fear into the market. The 30-year fixed is running around 7.25% to 7.71%. The 15-year is closer to 6.50% to 6.95%. Jumbo loans, which is what most of our Lincoln Park and Lakeview buyers are working with, are coming in around 6.87%.
What I keep telling buyers right now is this. Fall is genuinely one of the best times to buy in Chicago. I am predicting that rates will go down in December or the new year and with that, the Spring Market arrives. Spring (January – June) gets all the attention, but spring also brings out every other buyer who has been sitting on the fence. Right now you have less competition. Serious sellers are on the market. And you can actually take a breath and make a good decision instead of writing an offer in a parking lot on your phone.
The good homes still move fast. That has not changed. But if a packed open house and an eleven-offer weekend sounds like your nightmare, fall might be your season. I would love to help you navigate your search before everyone else shows up in the new year.
For sellers: I know what you are thinking. Rates are high and buyers are scared. But here is what the data actually shows. Serious buyers do not stop buying in the fall. They stop browsing. The people walking through your door in October are not curious. They are ready. And they are doing it with less competition from other sellers too. If you have been waiting for the “right time” to list, I could argue this is a better window than you think. Every other seller is waiting until Spring. Reach out and let’s talk about what your home is worth right now. Curious what your home is worth right now? Check your home value here.
Investors: THIS is your season, don’t sit on it. Now until the end of the year.
Have a great weekend, Chicago! Marathon weekend is one of those Chicago weekends that reminds you why you live here. Get out there, cheer loud, sip something good, and soak up the fall energy before it disappears. Whether you are on the sidelines or crossing a finish line of your own, this city has your back.
Drop a comment and tell me where you are spectating! And if that Lincoln Park listing caught your eye — or if you are just ready to talk about where you want to be living, my DMs are always open. 🏡
Enjoy Chicago,
Juliana