Chicago things to do this weekend are genuinely some of the most fun options of the entire summer. The Savannah Bananas bring Banana Ball to Wrigley Field for three games, and yes, tickets are technically sold out but resale is available. Benson Boone’s Wanted Man Tour plays Allstate Arena in Rosemont both Friday and Saturday nights. Wicker Park Fest takes over Milwaukee Avenue all weekend with 50-plus artists. And the WNBA All-Star Game tips off at the United Center on Saturday. Grab the free 2026 Chicago Summer Festival and Concert Guide if you have not yet and let’s get into this weekend.
🗓️ THIS WEEKEND IN CHICAGO
Savannah Bananas at Wrigley Field: Banana Ball Comes to the Friendly Confines
🍌 SOLD OUT · RESALE AVAILABLE ON THIRD PARTY SELLERS · ALL THREE GAMES AT WRIGLEY
📅 Fri July 24 · 7pm · Sat July 25 · 4pm · Sun July 26 · 3pm📍 Wrigley Field, 1060 W. Addison St., Wrigleyville🎟️ Sold out but resale from ~$112 on SeatGeek · thesavannahbananas.com📺 ESPN2, ESPN App, Disney+ and YouTube if you cannot get tickets
The Savannah Bananas are bringing their Banana Ball World Tour to Wrigley Field this weekend for three games and it is going to be absolutely wild. If you have never seen the Bananas play, here is what you need to know. Banana Ball is fast-paced, chaotic, endlessly entertaining baseball with a two-hour time limit, fans catching foul balls for outs, points instead of runs and choreographed dances on the mound between pitches. It is part baseball, part circus and entirely unlike anything else you will see at a ballpark.
The official games are sold out on the Savannah Bananas website but resale tickets are widely available. Prices start around $112 per game on SeatGeek and go up from there depending on the seat. All three games are also being broadcast on ESPN2, ESPN App, Disney+ and YouTube so if resale prices are not in the budget, you can watch from home. But honestly, Banana Ball at Wrigley Field is a bucket list experience. We are feeling super lucky to be able to go this year and can’t wait to experience it!
🏡 Realtor Mom Take: Wrigleyville is one of the most emotionally connected real estate markets in Chicago. Buyers who grow up going to games at Wrigley Field consistently want to live within walking distance of that feeling. And the fact that an event like this draws a global audience to this neighborhood only reinforces what we already know. If Lakeview and Wrigleyville are on your radar, the inventory right now is worth a serious look. We have one of the best priced luxury single family homes Wrigleyville adjacent in Southport Corridor. Check it out here: 3711 N. Magnolia Ave
Benson Boone: Wanted Man Tour at Allstate Arena
🎤 TWO NIGHTS · ALLSTATE ARENA, ROSEMONT · WANTED MAN TOUR
📅 Friday July 24 and Saturday July 25 · 8pm both nights📍 Allstate Arena, 6920 Mannheim Rd., Rosemont🎟️ Tickets at ticketmaster.com · Special guest Olivia O’Brien
We are going to Benson Boone this weekend and honestly we cannot wait. The Wanted Man Tour plays Allstate Arena both Friday and Saturday nights with special guest Olivia O’Brien. If you have been sleeping on Benson Boone, this is the moment to catch up. The energy he brings to a live show is genuinely electric and the Allstate Arena is the perfect size for this kind of performance, close enough to feel intimate, big enough to feel like a real event. We saw him at the United Center last year and he put on an amazing show! Seriously, can’t wait to see him again!
Two nights at the same venue means there is still a real chance to get tickets for Saturday if Friday has sold out. Check Ticketmaster and SeatGeek for availability. This tour has been selling out everywhere so do not wait if this is on your list.
🏡 Realtor Mom Take: Allstate Arena is a quick trip from the North Side and a reminder that some of the best concert experiences in the Chicago area happen just outside the city limits. If you have ever thought about the northwest suburbs as a place to land, Rosemont and the surrounding communities offer real value with easy city access. Worth knowing about. Plus they have the Fashion Outlets with spectacular luxury designer stores, Jenni Finch Way pro Softball and the Chicago Dogs.
Wicker Park Fest: Milwaukee Avenue Comes Alive All Weekend
🎵 50+ ARTISTS · MILWAUKEE AVE · PET FEST · KID-FRIENDLY SPACES
📅 Friday July 24 through Sunday July 26📍 Milwaukee Ave. between Damen and Wolcott, Wicker Park🎟️ Free · wickerparkfest.com · All ages · Leashed pets welcome
Wicker Park Fest is one of the best street festivals in Chicago and this weekend it takes over Milwaukee Avenue with 50-plus local and nationally recognized artists across multiple stages. The lineup spans indie rock, hip hop, electronic and everything in between, curated by the same people who bring you Do Division and some of the best independent music programming in the city. There are also kid-friendly spaces, a dedicated Pet Fest component and local food vendors from the neighborhood’s outstanding restaurant scene throughout.
Go Friday evening for a laid-back start to the weekend. Go Saturday for the full festival energy, walk Milwaukee Avenue and stay for dinner at one of the great spots on Damen or Division. Go Sunday to close it out. All of it is free. All of it is Wicker Park at its best.
🏡 Realtor Mom Take: Wicker Park buyers are chasing exactly what this festival represents every single weekend. Independent neighborhood culture, walkable dining, community investment and a street energy that is genuinely hard to replicate anywhere else in the city. The real estate here reflects that demand and right now the market in this pocket is showing us something interesting.
🗺️ ALSO THIS WEEKEND
🏀 WNBA All-Star Weekend · United Center
Friday July 25 · 3-Point Contest and Skills Challenge · Saturday July 25 · All-Star Game 7:30pm · United Center · chicagosky.com
The 2026 WNBA All-Star Game comes to Chicago this weekend at the United Center and it is a genuinely big deal for the city. The 3-Point Contest and Skills Challenge run Friday evening with the main All-Star Game on Saturday night. WNBA basketball in Chicago is a world-class live sports experience and this weekend it is at its absolute best.
🎸 Jack White · The Salt Shed Outdoors
Friday July 24 · 6:30pm · The Salt Shed, 1357 N. Elston Ave. · Sold out · Resale from ~$209 on StubHub and Vivid Seats
One of the greatest guitarists alive plays The Salt Shed Outdoors on Friday night. Sold out on official channels but resale tickets are available starting around $209. The Salt Shed at dusk on a warm July evening with Jack White on stage is about as good as Chicago live music gets. If this is your thing, go find those resale tickets now.
🏮 Chinatown Summer Fair
Saturday July 25 and Sunday July 26 · Chinatown, South Side · Free · All ages
One of Chicago’s most vibrant and authentic neighborhood street fairs returns to Chinatown with lion dances, live music, traditional and contemporary culinary offerings and cultural performances. A beautiful free weekend destination on the South Side.
🏛️ Pullman Railroad Days
Saturday July 25 and Sunday July 26 · Pullman National Monument, Far South Side · pullmanillinois.org
Step back in time at Chicago’s first National Monument with guided tours of historic railcars, live music and programming celebrating the legacy of the Pullman community. A genuinely unique and historically significant Chicago weekend destination.
🛍️ Randolph Street Market
Saturday July 25 and Sunday July 26 · Near West Side · randolphstreetmarket.com
The best antique and vintage market in Chicago returns this weekend with fashion, art, home decor and one-of-a-kind finds from vendors across the country. A great Saturday morning destination before the afternoon heats up.
The Open House Gatekeeping Conversation. What Do You Actually Think?
Something happened this past weekend that has been on my mind and I want to talk about it honestly. Because after 22 years in this business, some things still do not sit right with me, and this is one of them.
The Strategy: Hold Showings Until the Open House
More and more listings are hitting the market with a very specific instruction. No showings until the open house. Period. The listing goes live, interest builds and everyone waits for the designated day. I understand the strategy. A seller has every right to consolidate foot traffic, create urgency and generate competitive offers. Done right, it works. I have used it myself on the listing side and it can be incredibly effective.
I have also been on the winning end of it as a buyer advisor. Earlier this year I had buyer clients who wanted a property badly. No photos existed anywhere. None. They were going on completely blind faith in me and my read of what the home could be. They trusted me enough to bid $200,000 over asking without ever stepping foot inside, without a single image to go on. Just trust. That agent did everything right. When the seller accepted our offer, he reached out to every other agent who had planned to attend and let them know. People were disappointed but they understood. They were respected. That is how this is supposed to work.
What Happened This Past Weekend Was Different
This past weekend my buyer clients had a private time slot scheduled during the open house where instructions were specifically called out that no showings would be prior to this. The listing agent knew days in advance we were coming. That is not a surprise visit. That is a confirmed appointment. My clients had seen the photos, loved the location, were genuinely excited and showed up ready to engage seriously with this property.
We walked in and it was already under contract. Someone had gotten in the night before, made an offer and the seller accepted it. And the listing agent never picked up the phone. No text, no email. He let us show up, walk through the door and find out at the moment of arrival that it was gone. He was only looking for backup offers. If that agent had picked up the phone and said “I have an offer the seller is seriously considering, get over here now if you want to compete,” we would have been there in twenty minutes. That call could have created more competition, potentially a better outcome for the seller and a fair shot for our buyers and likely several others.
I have heard agents explain situations like this by saying they were following the seller’s direction. That may sometimes be true. But sellers also rely on us to explain the consequences or benefits of each decision and recommend a process that protects both their interests and the integrity of the showing experience.
Once an offer has been accepted, confirmed appointments should be notified. At minimum, buyers and their agents deserve the opportunity to decide whether they still want to attend as a potential backup. That small act of communication respects everyone’s time, manages expectations and maintains trust in the process. The issue for me is not that another buyer got the house. That happens, and competition is part of the market. The issue is that a simple phone call, text or email could have handled the situation professionally and transparently.
So What Do You Think?
Do you like the open house only showing model? As a buyer or agent does it feel fair or does it frustrate you? And what do you think about agents who let confirmed appointments show up to an already accepted offer without a heads up? Would you prefer agent accompanied showings prior to a public open house even if it means waiting until Monday for an offer deadline? I think this is the way to go, buyers and their brokers get in first, everyone else gets to tour during the open house over the weekend. Wouldn’t it be nice to be able to see the property twice too? I genuinely want to know your thoughts. Drop a comment below. This conversation is worth having.
And if you are a seller thinking about listing, the right showing strategy for your home is one of the most important conversations we have before you go live. Done right it creates competition and maximizes your result. Done poorly it burns bridges and leaves buyers bitter. We know the difference. Find out what your home is worth today and let’s talk about the right approach for your specific situation.
📞 773.732.1063 | yt@yeagerteam.com | yeagerteam.com
Banana Ball at Wrigley. Benson Boone in Rosemont. Music on Milwaukee. This Is Chicago Summer.
Three games of the most entertaining baseball you have ever seen at the Friendly Confines. One of the hottest young artists in the world playing two nights in the suburbs. Fifty-plus artists taking over Milwaukee Avenue for free all weekend. WNBA All-Stars at the United Center. Jack White at the Salt Shed. Chinatown in full summer bloom. And a real estate market that is telling a nuanced, interesting story for anyone paying close attention. Go enjoy all of it this weekend.
Drop a comment below and tell me where you are headed.
Enjoy Chicago, Juliana