Things to do in Chicago this weekend include some of my favorite things about this city all landing at once. The Crosstown Classic is here and yes, the whole city has picked a side. Lincoln Park Mayfest finally kicks off after we teased it last week. Renegade Craft Fair takes over Andersonville. And I have a birthday story to share. Our daughter turns 13 this month and we celebrated with a Demi Lovato concert in a box suite at the United Center with three moms and seven girls. It was one of the best nights of the year. All the details are below so you can steal this idea for your own kid’s next milestone birthday.
🧒 FOR THE KIDS
📷 Photo: Chicago White Sox / MLB
Crosstown Classic 2026: The Whole City Picks a Side
📅 Fri May 15 · 6:40pm · Sat May 16 · 6:10pm · Sun May 17 · 1:10pm📍 Rate Field, 333 W. 35th St., Bridgeport🎟️ mlb.com/whitesox · Red Line to Sox-35th👦 All ages | ⚾ CUBS VS. WHITE SOX · ALL THREE GAMES AT RATE FIELD
Here is the thing about the Crosstown Classic. It is not just a baseball series. It is a full Chicago cultural event and one of the best weekends of the year to be a kid in this city. The Cubs come in leading the all-time series 77 to 75 and the South Side faithful are going to be very loud. Go Friday night for the full electric atmosphere. Go Sunday at 1:10pm for an earlier day with the kids. But go to at least one game. This is what Chicago summers are made of.
Rate Field on the South Side is also a genuinely different Chicago experience from Wrigley, and that difference is worth embracing. The neighborhood is Bridgeport, one of the most historically layered communities in the city. Taking the Red Line down from the North Side with kids is half the adventure. The train ride, the walk in, the energy of a rivalry crowd. It is the kind of Saturday that reminds you this city has so many more stories than just the one you live in every day.
🏡 Realtor Mom Take: We spend most of our time on the North Side and I love every block of it. But the South Side has real estate stories that deserve more attention. Bridgeport and the neighborhoods around Rate Field offer character, community and value that is genuinely compelling right now. Any buyer who has only looked north is leaving real options on the table.
📷 Photo: Juliana Yeager / Raising Kids in Chicago
🎉 PERSONAL STORY · TEEN BIRTHDAY IDEAS IN CHICAGO · STEAL THIS
She Turned 13 and We Did It the Chicago Way
🎂 Earlier this month · Our daughter’s 13th birthday📍 United Center | Demi Lovato Concert
Our daughter turns 13 this weekend and we wanted to do something she would actually remember. So we went all out. A Demi Lovato concert at the United Center and a night that none of us are going to forget for a very long time. It was absolutely everything.
The key to the whole evening was booking a Banner Suite at United Center. I cannot recommend this enough for a group birthday, especially for kids. The banner suites run along the upper level and if you decide to split the cost across a group of ten, they are way more affordable than you would expect. The girls had their own private space, their own entrance and a view of the stage that was just unreal. Demi Lovato put on a spectacular show and those kids were on their feet the entire night. Three moms and seven kids and every single one of us had the best time.
Alternatively, a great teen birthday idea would be hanging on Southport, which is honestly one of my favorite stretches in the city for a special night out with tweens and teens. The restaurant energy there on a warm May evening is exactly right for a birthday. Hit up any fave restaurant like Crosby’s, Coda Di Volpe, Itoko Sushi, Coal Fire, Tuco Blondie or just let the birthday girl pick again. Then, stop at Hotel Chocolat to let the birthday girl pick out whatever she wants, and maybe even double the sweets and end with Jenni’s Ice Cream or classic Dairy Queen. Don’t forget all the amazing shops on the Southport Strip for any last minute gifts, pro tip they close at 7pm so plan accordingly. The options are plentiful and all in one spot, so yes, do this. It’s an easy and memorable blueprint.
The Chicago Teen Birthday Blueprint
🎤 Banner Suites at United Center — book for any major concert, split across 8 to 10 people and they are genuinely affordable. Or go birthday style like we did for the best treat and memory. unitedcenter.com
🍽️ Dinner in Southport Corridor, Lakeview — the best stretch in the city for a special birthday dinner with teens. Walkable, vibrant, great energy on a warm night.
🍫 Hotel Chocolat — 3334 N. Southport Ave. — the most fun post dinner treat stop in the city. Let them pick everything.
🛍️ Sephora, Lululemon, Madewell, Abercrombie, Alice & Wonder – so many teen shopping spots for last minute gifts.
⭐ The verdict: 2 incredible options that is every teen girls dream birthday! Do this for your kid’s next big day.
🏡 Realtor Mom Take: Southport Corridor is one of those streets where you walk it on a warm night and immediately understand why people want to live here. The dining, the walkability, the neighborhood feeling all in one strip. It is also one of the most competitive real estate corridors on the North Side right now, and buyers who find it tend to stay. Southport Corridor lives within Chicago’s Lakeview neighborhood and if it is on your list, do not wait on this market.
🎵 IT IS FINALLY HERE · CHICAGO’S OFFICIAL SUMMER KICKOFF
Lincoln Park Mayfest: Chicago Summer Starts on Armitage
📅 Fri May 15 · 4-10pm · Sat May 16 · Noon-10pm · Sun May 17 · Noon-9pm📍 1000 W. Armitage Ave., Lincoln Park · Racine to Sheffield🎟️ Free · chicagoevents.com
We teased it last week and it is finally here. Armitage Avenue transforms into Chicago’s best street festival this weekend and there is truly no better way to feel like summer has officially arrived. Two stages of live music run all three days. 16 Candles plays Saturday night and Simply Elton closes Sunday. The Spring Fine Art Mart runs alongside the music all weekend with local and national artists. And yes, there is a pet parade. Because of course there is. This is Lincoln Park.
Go Friday after work for a relaxed vibe with great music and cold drinks on the street. Go Saturday with the kids for the full festival energy, the art mart and dinner on Armitage after. Go Sunday to close out the weekend the right way. All of it is free. All of it is worth it. Mayfest earns the title of Chicago’s summer kickoff every single year and this weekend it delivers again.
🏡 Realtor Mom Take: Mayfest exists because Lincoln Park earns it. Walk Armitage this weekend and you will understand exactly why this neighborhood commands what it does. The community, the dining, the energy and the parks are all right there on one street. If Lincoln Park is on your radar this spring, call me after the festival. I know every block.
🛍️ 250+ ARTISTS · ANDERSONVILLE · $5 SUGGESTED DONATION
Renegade Craft Fair Takes Over Andersonville This Weekend
📅 Saturday May 16 and Sunday May 17 · 11am to 6pm📍 Clark St. between Bryn Mawr and Edgewater Ave., Andersonville🎟️ $5 suggested donation · renegadecraft.com · All ages · Pets welcome
If you have never spent a Saturday in Andersonville, this is the weekend to fix that. Renegade Craft Fair has been bringing independent makers to Chicago since 2003 and the spring Andersonville edition is one of the best stops on their entire circuit. More than 250 jury-selected artists, designers and makers line Clark Street with handmade jewelry, ceramics, fashion, art prints, candles, pottery and food. Live DJs, workshops, art installations and food trucks run throughout the day on both Saturday and Sunday.
And here is what I love about Andersonville as a destination. Clark Street on a warm May weekend is a full afternoon even before the fair starts. Come for the craft vendors and stay for dinner on Clark after. It is one of those neighborhoods that earns a place on your regular rotation the moment you discover it. The $5 suggested donation supports the fair and the independent creative community it has built over more than 20 years.
🏡 Realtor Mom Take: Andersonville is one of the most distinctive neighborhoods on the North Side and one that consistently surprises buyers who discover it for the first time. The independent business culture here is unlike anything you find further south, and the housing stock offers a genuinely compelling alternative to more saturated markets, plus it is close to highly desirable schools like Rogers Park Montessori, Sacred Heart, Lycèe Francais, CPS Pierce & Chicago Waldorf. If you have never considered Andersonville, this weekend is a great reason to start.
🗺️ AROUND THE NEIGHBORHOODS THIS WEEKEND
Two more worth knowing about this weekend. Both are very different. Both are very Chicago.
🍺 Lottie’s Pub Turns 92 · Bucktown
All weekend · 1925 W. Cortland St., Bucktown · 92-cent burgers · 92-cent mimosas · Music from 1992 · lottiespub.com
Lottie’s Pub has been a Bucktown institution since 1934 and this weekend it turns 92 years old. The specials are exactly what you would want. 92-cent burgers, 92-cent mimosas and a weekend of music from 1992. And yes, if you are a Chicago Fire fan, this is the real-life bar that inspired Molly’s on the show. A bar that has been serving the same neighborhood corner for 92 years is a piece of this city worth celebrating. Go raise a glass.
🏡 Realtor Mom Take: Bucktown is one of the most sought-after North Side markets right now, especially for buyers who want walkability, the 606 Trail and that balance of neighborhood character with easy access to everything. A bar turning 92 on the same corner is the kind of community DNA that buyers are really chasing. Bucktown has it in spades.
🧘 Yoga on the 94th Floor · 360 Chicago · Every Saturday
Every Saturday · 875 N. Michigan Ave., Magnificent Mile · $55 includes cocktail or coffee plus observation deck · 360chicago.com
This is one everyone needs to put on your spring summer bucket list! Instructor Britta Eumann leads a one-hour yoga class on the 94th floor of 875 North Michigan Avenue with the entire city of Chicago stretched out below you. Your $55 includes a cocktail or coffee after class plus full access to the observation deck so you can stay and take in the view. All levels welcome. No experience required. Just bring a mat and prepare to feel very small and very grateful at the same time. This is one of the most uniquely Chicago things you can do on a Saturday morning and it runs every single weekend.
🏡 Realtor Mom Take: The view from the 94th floor is a reminder of what buyers mean when they say they want a lakefront-adjacent address. You can see exactly why the Magnificent Mile and Streeterville command what they do. If that view makes you want to talk real estate, I am just a phone call away.
Your Zestimate Is Not Your Home Value. Here Is Why That Matters.
The Problem With Automated Estimates
Here is something I tell clients all the time. Zestimates and Redfin estimates are a ballpark, not an answer. These automated tools pull comparable sales from up to two miles around your home. In Chicago, two miles bleeds across multiple neighborhoods, school districts and price points that have almost nothing to do with your specific block. A two-mile radius from a home in Lincoln Park can pull comps from Logan Square, Bucktown and Lakeview at the same time. Those are entirely different markets with entirely different buyers. The algorithm does not know that. Your local Realtor® does.
On top of that, automated estimates do not account for your specific finishes, your lot, your school district or the coffee/bagle shop that just opened on your corner. They can be off by tens of thousands of dollars in either direction. So if you are making any financial decisions based on a Zestimate alone, you are working without the right information.
Know What Your Biggest Investment Is Actually Worth
Even if selling is not on your mind today, knowing your home’s real value is smart planning. Your home is likely your single largest investment and in a market where Chicago prices just rose 5% year over year, that investment is performing. Start with an instant home value estimate right here. Then let me hone in with a precise neighborhood-specific read on what your home is actually worth today. No algorithm. No two-mile radius. Just someone who knows your block, your street and your market.
📞 773.732.1063 | yt@yeagerteam.com | yeagerteam.com
Go Enjoy This City. It Is Doing a Lot This Weekend.
The Crosstown Classic on the South Side. Mayfest on Armitage. Two hundred and fifty artists on Clark Street in Andersonville. A 92-year-old bar in Bucktown with 92-cent mimosas. Yoga on the 94th floor with the whole city below you. And a birthday blueprint you can steal for your own kid’s next milestone. Every single one of these is happening in a neighborhood worth knowing. And as someone who sells real estate in this city and raises kids in it at the same time, I can tell you that the neighborhoods in this post are some of the best places in the country to build a life. Go walk them this weekend.
Drop a comment below and tell me what your family has planned.
Enjoy Chicago, Juliana
Photo Credit:
📷 Crosstown Classic — Chicago White Sox / MLB 📷 Teen Birthday / Demi Lovato — Juliana Yeager / Raising Kids in Chicago 📷 Lincoln Park Mayfest — Lincoln Park Mayfest / Special Events Management 📷 Renegade Craft Fair — Renegade Craft 📷 Lottie’s Pub — Lottie’s Pub Chicago 📷 360 Chicago Yoga — 360 Chicago