Things to do in Chicago this weekend are especially delicious this May, and this one happens to fall on Mother’s Day weekend. First and foremost, we are devoting a full section to a Lincoln Park food crawl in two parts. Part 1 is a Saturday morning with the whole family. Part 2 is a Sunday Mother’s Day experience that every mom deserves. Additionally, we have the free Millennium Park Summer Workout Series kicking off its season, an adults-only night market and the complete summer festival calendar you have been waiting for. As your Chicago real estate family, we are out in these neighborhoods every single week. Happy Mother’s Day to every mom reading this. Let’s get into it.
🍽️ THE LINCOLN PARK FOOD CRAWL · PART 1
Saturday Morning: Bagels and Donuts on Lincoln and Armitage
Three New Lincoln Park Spots Worth Supporting This Weekend
Start Saturday morning here. Both stops are within a short walk of each other in Lincoln Park, both are independently owned and both have been generating serious buzz since opening earlier this spring. Furthermore, they are the kind of places that make a Saturday morning feel like an event. Bring the kids, grab extra and support local.
🥯 STOP 1 · OPEN DAILY FROM 7AM · I ALREADY WENT AND YES IT IS WORTH IT
PopUp Bagels · 2321 N. Lincoln Ave., Lincoln Park
Open daily · 2321 N. Lincoln Ave. · popupbagels.com | pro-tip, order ahead to avoid lines – they do sell out so order early
I went this week and walked out holding two bags and grinning like a kid. That is the “insta-famous” PopUp Bagels experience. The concept is intentionally simple. Hot, whole bagels straight from the oven, never sliced and never toasted, designed to be ripped apart and dipped into weekly rotating schmears. Furthermore, the Chicago via NYC hot spot has rotating schemers (one fruity one I was dying to try but they sold out). The five varieties, plain, sesame, poppyseed, everything and salt, come in packs of three or more. In other words, bring the whole family and share or do like I did and buy a dozen, it’s worth it!
This is the Midwest debut of one of the most talked-about New York style bagel brands in the country. Specifically, 25 Chicago locations are planned. I really love their tagline ‘Not famous, but known’. Get in now while it still feels like a neighborhood secret.
📷 Photo: Juliana Yeager / Realtor®-mom Approved
🍩 STOP 2 · SAT-SUN 8AM-2PM · REALTOR MOM APPROVED
Daly’s Donuts · 659 W. Armitage Ave., Lincoln Park
Sat-Sun 8am-2pm · Wed-Fri 7am-2pm · 659 W. Armitage Ave. · dalysdonuts.com
We are a donut family. Full stop. So when Daly’s showed up at one of our open houses this week with their signature dunkers on a marble board, I knew I had to try one and thought immediately that this belonged in the blog. I let the presenting Realtor® know that I’m forever ruined as the donuts were so so good, like oh my gahhhd good!! We can’t wait to try more this Mother’s Day weekend. Conor and Alejandra Daly started at the farmers market in 2023 and opened their first brick-and-mortar on Armitage in March. The grand opening drew a line down the block that stopped traffic.
Baked not fried, hand-made, local ingredients. Specifically, signature flavors include cinnamon sugar, chocolate dipped and chocolate churro with rotating seasonal options that sell out fast. Additionally, we highly recommend the dunkers. Therefore, go early, bring cash for extras and tell them the Yeager Team sent you.
📷 Photo: Juliana Yeager / Raising Kids in Chicago
🌸 THE LINCOLN PARK FOOD CRAWL · PART 2 · MOTHER’S DAY EDITION
🌸 SUNDAY MAY 10 · LIMITED SEATING · ADVANCE PURCHASE REQUIRED | MICHELIN RECOGNIZED
S.K.Y. at the Belden-Stratford · 2300 N. Lincoln Park West
Sunday May 10 · Mother’s Day High Tea · skyrestaurantchicago.com · (312) 846-1077 · Reserve on OpenTable
If no one has made your Mother’s Day reservation yet, consider this your sign. S.K.Y. is doing something genuinely special on Sunday and it is exactly the kind of experience that moms in this city deserve. With it connecting perfectly with Saturday morning’s crawl as a two-day Lincoln Park weekend worth remembering.
This is the Mother’s Day experience I would want someone to book for me. S.K.Y. is hosting an intimate High Tea on Sunday designed specifically to honor the mothers and mother figures in our lives. The experience is set in INTRO, their private dining space inside the Belden-Stratford, and it includes a welcome glass of bubbles, a choice of premium loose-leaf tea, seasonal pastry tiers served throughout the afternoon, a curated take-home gift and a rose for every mom at the table.
In addition, this is not a standard brunch reservation. Specifically, it is a communal round table experience designed for connection, conversation and a genuinely unhurried afternoon. Furthermore, seating is very limited and advance purchase is required. Therefore, do not wait on this one. Book now at skyrestaurantchicago.com or through OpenTable before it sells out entirely.
S.K.Y. relocated from its beloved Pilsen home to the historic Belden-Stratford in Lincoln Park in August 2025. Michelin-recognized Chef Stephen Gillanders brings a globally inspired menu to one of the most beautiful dining rooms in the city. Consequently, the setting alone makes this a Mother’s Day worth celebrating.
🏡 Realtor Mom Take: The Belden-Stratford sits directly on Lincoln Park West, steps from the zoo, the conservatory and the lakefront. Lincoln Park is defined by exactly this kind of institutional character. World-class dining, a landmark building and a community that has been one of Chicago’s most desirable addresses for generations. If you have ever wondered what your home is worth in this market, find out today.
🧒 FOR THE KIDS
Millennium Park Summer Workouts: Free Season Opener
💪🏋️♂️ FREE · SEASON OPENER · EVERY SATURDAY THROUGH SEPTEMBER 5
📅 Saturday May 9 · Morning · Every Saturday May 16 through September 5📍 Millennium Park Great Lawn, 201 E. Randolph St., Loop💰 Free · No registration · millenniumpark.org
The Millennium Park Summer Workout Series kicks off its season this weekend and it is completely free every Saturday through September 5. Specifically, the series offers cardio kickboxing, yoga, pilates and Zumba on the Great Lawn with the Chicago skyline as your backdrop. Moreover, this is one of those only-in-Chicago experiences that reminds you what an extraordinary city this is to raise kids in. Bring a mat, wear sneakers and show up ready to move.
Additionally, Millennium Park on a warm May Saturday is a full morning all by itself. After the workout, walk through the Cloud Gate, grab coffee from a nearby cafe and let the kids run the Great Lawn. Consequently, pair it with a quick trip next door to Maggie Daley Park for the climbing walls and play structures. Free, central and genuinely spectacular.
🏡 Realtor Mom Take: The Loop and Streeterville neighborhoods surrounding Millennium Park represent some of the most dynamic real estate values in Chicago right now. In particular, buyers who want lakefront access, world-class cultural institutions and true walkability in every direction are finding compelling options here in the $700K to $1.5M range. This is a neighborhood worth exploring on foot this weekend.
🍷 FOR THE ADULTS
📷 Photo: SAUCED Night Market
🌃 ADULTS NIGHT OUT · CHECK SAUCEDNIGHTMARKET.COM FOR VENUE AND TIMES
SAUCED Night Market
📅 This weekend · Confirm dates and venue at saucednightmarket.com🎟️ Tickets at saucednightmarket.com
SAUCED Night Market is one of Chicago’s most buzzed-about evening food and drink events of the spring and it is happening this weekend. Featured as a top weekend pick by Time Out Chicago, SAUCED brings together local chefs, craft beverage makers, live music and a market atmosphere after dark. Furthermore, it is exactly the kind of event that feels uniquely Chicago, independent, creative, community-driven and genuinely delicious.
In addition, the format is designed for grazing and socializing over the course of an evening rather than a sit-down meal. Moreover, the vendor lineup changes each edition so every visit feels fresh. Therefore, check saucednightmarket.com for the confirmed venue, exact times and ticket availability before heading out.
🏡 Realtor Mom Take: Events like SAUCED reflect Chicago’s independent food and culture scene at its best. Specifically, the neighborhoods that produce events like this, Fulton Market, West Town and Logan Square, are among the most attractive markets on our radar right now due to their affordability dollar per square foot. If any of those neighborhoods have been on your list, let’s talk this week.
📷 Photo: Lincoln Park Mayfest / Special Events Management
🎵 COMING NEXT WEEKEND · MAY 15-17 · PUT IT IN YOUR CALENDAR NOW
Lincoln Park Mayfest: Chicago’s Official Summer Kickoff Is Next Weekend
📅 Fri May 15 · 4-10pm · Sat May 16 · Noon-10pm · Sun May 17 · Noon-9pm📍 1000 W. Armitage Ave., Lincoln Park · Racine to Sheffield🎟️ Details at do312.com and chicagoevents.com
It is not this weekend but it is next weekend and you need to put it in your calendar right now. Lincoln Park Mayfest transforms Armitage Avenue from Racine to Sheffield into Chicago’s most beloved summer kickoff celebration. Two stages of live music run nonstop across all three days. Moreover, headliners include 16 Candles on Saturday night and Simply Elton closing Sunday. The Spring Fine Art Mart runs alongside the music all weekend with local and national artists across painting, photography and jewelry.
In addition, there is a kids’ area with activities and inflatables, a beloved pet parade and local restaurant activations from some of Lincoln Park’s best spots along Armitage. Furthermore, Chronic Flannel opens Friday night and ALT 101 closes Saturday. Doors open Friday at 4pm. Consequently, this is the unofficial start of Chicago summer and it is worth showing up for every year.
🏡 Realtor Mom Take: Mayfest has been a Lincoln Park tradition for decades because this neighborhood earns it every year. The community, the walkability, the dining and the parks all show up in full force on Armitage. Also, Lincoln Park is not only one of the most popular, but also one of the most stable neighborhood markets in all of Chicago. Therefore, if you have been on the fence about Lincoln Park, walk this festival and let the neighborhood sell itself. Then call us at 773.732.1063.
🗓️ MARK YOUR CALENDARS
Your Complete Chicago Summer Festival Guide: May through September 2026
Summer in Chicago is a sport and the 2026 festival season is genuinely stacked. Bookmark this page and check back often as we will continue adding links and updates throughout the season. Furthermore, many of these festivals are free or family-friendly, so plan ahead and get them in your calendar before the weekends fill up.
Download the List HERE
Chicago Home Prices Lead the Nation. Here Is What That Means for You This Spring.
The Numbers Are In
The S&P Case-Shiller Index just confirmed that Chicago home prices rose 5% year over year in February, leading all 20 major U.S. cities tracked. Additionally, the national average during the same period was just 0.7%. In other words, Chicago is consequently outpacing the country by a wide margin. Furthermore, inventory remains well below pre-pandemic levels, which means motivated buyers are competing hard for every well-priced listing that comes to market.
We are at peak spring market right now. Most properties in our North Side neighborhoods are therefore selling in a single weekend. By June things normalize. Specifically, the sellers who act in the next four to six weeks will command the strongest prices of the year. The window is wide open today and it will not stay that way. Which means some relief and less competition is on the horizon for buyers.
What Is Your Home Worth Right Now?
In a market moving this fast, knowing your home’s current value is the first step in any smart selling strategy. The number you knew six months ago is not the number today. Find out what your home is worth right now and let’s talk about what that means for your next move. The Yeager Team are your Chicago real estate family and we are ready to go to work for you this Spring and Summer.
📞 773.732.1063 | yt@yeagerteam.com | yeagerteam.com
Happy Mother’s Day, Chicago. You Earned This Weekend.
Bagels on Lincoln Avenue Saturday morning. Fresh-baked donuts on Armitage. A High Tea on Sunday at one of the most beautiful dining rooms in the city with a rose and a glass of bubbles. A free workout on the Great Lawn with the skyline behind you. An adults-only night market after dark. And a summer festival calendar that runs from Mayfest all the way to the World Dumpling Festival in September. Furthermore, every single thing on this list is happening in a neighborhood that tells its own real estate story. In addition, the summer festival calendar above is your guide to the entire season. Bookmark it, share it and check back often as we add links all summer long.
To every mom reading this, Happy Mother’s Day. You built the life that makes weekends like this one worth having. Finally, carbs don’t count on Mother’s Day so go get the bagels
Drop a comment below and tell me what your family has planned. I always love hearing from this community.
Enjoy Chicago, Juliana