Art, Nature, and Local Flavor: Two Days in Chicago Southland
Our Adventure Is Everywhere contains affiliate links and is a member of the Amazon Services LLC Affiliate Program. If you make a purchase using one of my Amazon or other affiliate links, I may receive compensation at no additional cost to you. Read my full privacy policy for more information.
Living just a few hours from Chicago, we visit the area on a regular basis. Typically we’ll head downtown, or maybe one of the suburbs like Oak Brook or Naperville. This summer though, my daughter and I had the opportunity to check out a whole “new to us” area of the Chicago suburbs – Chicago Southland.
Not only is Chicago Southland an easy drive from Indianapolis, but like many other visitors who just drive through on their way to Chicago, I had no idea how many truly unique experiences I was missing! I won’t be making that mistake again. And if you’re looking for an easy Midwest weekend getaway filled with art, history, outdoor adventures, local food, and a few surprises, this 2-day Chicago Southland itinerary is a great place to start.
Thanks to Visit Chicago Southland for hosting a wonderful experience. All thoughts and opinions are 100% mine.
Day 1: A Massive Quarry, Local Art, and Live Music
On our first day, we experienced something quite unique – a tour of Thornton Quarry. If this sounds interesting to you, you’ll want to make sure to plan ahead – this isn’t a spur of the moment opportunity.
Start the Morning with a Tour of Thornton Quarry
After grabbing a quick breakfast at your hotel (one of the reasons we love staying at Holiday Inn Express hotels!), head over to the meeting spot for your Thornton Quarry tour. Thornton Quarry is one of the largest quarries in the world (450 feet at its deepest point), and as a working quarry, has very limited public tour opportunities.
We were super lucky to get the chance to join the tour as some folks wait for years! On our way to the quarry, our bus stopped at a scenic overlook so we could get the big picture view first, then we headed into the quarry itself.
Until you are inside, it’s hard to really grasp the size and scope of this manmade wonder, but it truly is massive. We drove around a bit and learned a lot from our tour guide (one of the quarry supervisors), until we stopped and were able to disembark, wander around a bit, and even collect fossils!
Insider Tip: Because this is such a unique and limited experience, if it’s something you are interested in, sign up for a future tour now – they offer tours on two days a year (June and October), and some of the people we spoke to had been on the waiting list for several years before they got the call! So get on the waitlist, and then build your Chicago Southland weekend around your visit when you get the call!
Can’t snag a Thornton Quarry tour? Don’t let that stop you from following the rest of this itinerary! Start your morning exploring one of the nearby towns or grab a leisurely breakfast before heading to SoHo Shops.
Browse Local Shops at SoHo Shops at Town Center
After our time at the quarry, we drove over to the nearby Village of South Holland to check out the SoHo Shops at Town Center. This is a new community initiative where local artisans apply for the opportunity to open a seasonal shop. We strolled the grounds and discovered everything from homemade pickles (in flavors you’ve NEVER heard of) to handcrafted leather bags.
SoHo Shops are open weekends from May to December, and it’s a fantastic spot to pick up unique gifts – we did a little early holiday shopping. You’re supporting local businesses and selecting special, often one-of-a-kind gifts. Win-win!
SoHo Shops at Town Center, 16114 South Park Ave., South Holland, IL
Explore Union Street Gallery
Sticking with the art theme, next head over to Union Street Gallery. This lovely gallery has an ambitious annual series of rotating exhibits. Although artists from around the world are able to submit their art for consideration for most of the exhibits, the gallery does have a focus on supporting local artists, so you’ll always see quite a few of them showcased.
The exhibit we enjoyed was Earth & Ocean, and it had a wonderful variety of modalities, from photography to sculpture. We also spent some time chatting with several of the resident artists and admiring their works in progress. It’s inspiring to be able to enjoy so much good art in one spot!
Union Street Gallery, 1527 Otto Boulevard, Chicago Heights, IL
Spend the Afternoon at the Homewood Art & Garden Street Fair
Chicago Southland encompasses over 60 communities, which means there is almost always something happening! When we visited, it was the weekend of the Homewood Art & Garden Street Fair.
It was enjoyable to spend a few hours exploring the artist booths, enjoying the live music, and soaking up the atmosphere. I loved that all the locals seemed to be fully invested in the fair – from older couples who brought their own chairs and camped out at the stage, to families with young children painting squishies, everyone was having a great time!
Insider Tip: Take a look at the Chicago Southland calendar to see what’s happening when you are ready to plan your visit!
Dinner at Stoney Point Grill
After such a busy day full of art and the outdoors, we were starving! Lucky for us, right next to the festival music stage was a fantastic dinner spot, Stoney Point Grill. With tons of seating (inside, outside, at the bar), and an eclectic menu, it was the perfect place to fuel up.
My daughter and I consider ourselves cocktail connoisseurs, and I have to say, my spicy margarita was on point! She enjoyed an Aperol Spritz (summertime perfection) alongside her fish sandwich. I had a tasty Cajun chicken cobb salad, and we both agreed the food was a 10/10.
Stoney Point Grill, 2031 Ridge Road, Homewood, IL
End the Evening at the Lyric Theater
After dinner, it was just a short drive to Blue Island for our final stop of the day. We weren’t quite ready to end such a fun day, and lucky for us there was a Jimmy Buffett tribute concert happening at the Lyric Theater in nearby Blue Island. Instead of your typical concert venue, the theater is set up more similar to a dinner theater with tables instead of rows of seats.
The seating made for a really fun time as we got to know the couples at our table – and had a place for popcorn and margaritas! Several of the couples were long time friends and had tickets to many of the upcoming shows already purchased. The Lyric has quite the history in the town, and was recently purchased and renovated by two local residents. They have created a wonderful spot for locals and visitors alike to enjoy live music in Chicago Southland.
Lyric Theater, 12952 Western Ave., Blue Island, IL
Day 2: Nature, Chocolate, and Community Theater
Our first day was so busy that we decided to relax a little bit in the morning before we hit the road. So, after a quick workout, we had a relaxing hotel breakfast – and even played a few card games with our coffee!
Start the Day at Plum Creek Nature Center
It was a gorgeous day, but it was going to be HOT, so we headed to Plum Creek Nature Center as soon as we checked out of our hotel. Our goal? Get in a little hiking before that Midwest humidity kicked in!
Part of the Forest Preserve District of Will County, Plum Creek Nature Center is truly a gem. Both my daughter and I agreed that we would have spent MANY weekends there when she was younger if we lived nearby. Lucky for us, although the adorable kids center was geared towards younger kids (and it is really cool), there were still some fantastic hikes for older kids and adults to enjoy.
Before our hike, we explored the nature center’s current exhibit – Winged Ambassadors, and learned that these exhibits change on a regular basis. We also got to meet some of the resident wildlife in the nature center, which was a fun treat!
Plum Creek Nature Center, 27064 Dutton Road, Beecher, IL
Cool Off with Ice Cream or a Quick Lunch in Beecher
After our hike, we weren’t really hungry, but a sweet treat felt warranted, so we headed into nearby Beecher. Beecher has that small-town Midwest feel I love, and Buddy’s Drive-In fit the vibe perfectly.
In addition to ice cream, Buddy’s Drive-In also offers hamburgers and other “drive-in” food, but we just grabbed a couple scoops at the walk-up counter and sat outside on a picnic table to enjoy them before heading off to our next stop.
Buddy’s Drive In, 613 S. Dixie Hwy, Beecher, IL
Tour Historic Gayety’s Chocolates
I know we just had ice cream, but … a girl can never have too many desserts, right? Lucky for us, our next stop was Gayety’s Chocolates. Located in Lansing, Gayety’s is one of Chicago’s oldest chocolatiers (and actually used to be located in downtown Chicago).
Gayety’s has a long history in Lansing (Gayety’s is over 100 years old and most of that time it’s been in Lansing), and the current owner, Laurene, shared how much it meant to her as well as many other locals who grew up working at Gayety’s, celebrating special occassions there, and purchasing the chocolates for their holiday celebrations.
We got to sample the ice cream (outstanding) as well as several of the chocolates. Everything is made fresh on-site using quality ingredients – much of it by hand! I do want to issue a warning for you though – you may randomly start dreaming about the yumminess once you get home, so you might want to stock up before you leave!
Gayety’s Chocolates, 3306 Ridge Road, Lansing, IL
Enjoy a Performance by The Drama Group
If you time your getaway right like we did, you can end your weekend with a matinee performance at The Drama Group. We got to enjoy the community theater’s production of Clyde’s, which was fantastic.
We also spent a bit of time afterwards getting to explore the theater on a short behind-the-scenes tour with Linda, the group’s treasurer. It was fascinating to learn some of the history of The Drama Group, and it was cool to see how they stored their costumes, sets, etc.
The Drama Group, 330 West 202nd Street, Chicago Heights, IL
Where to Stay in Chicago Southland
Since Chicago Southland covers such a large area, I’d recommend staying somewhere fairly central to limit your driving. Homewood, Crestwood, and Tinley Park are all good options. We stayed at a Holiday Inn Express and loved the convenience of free breakfast and parking – two things I always appreciate on a busy weekend getaway!
Map for Your 2-Day Chicago Southland Itinerary
FAQs: Chicago Southland 2-Day Itinerary
How much driving will I do for this itinerary?
Most of the spots are 15 – 20 minutes apart from each other, but your trip to the Plum Creek Reserve is a bit longer – worth it though!
When should I visit Chicago Southland?
There are fun things to do year-round, but if you want to follow this itinerary, check whether there are current shows at The Drama Group and The Lyric Theater.
Is it safe to visit Chicago Southland?
We felt comfortable everywhere we visited during our weekend in Chicago Southland. As with any destination, pay attention to your surroundings and use the same common-sense travel precautions you would anywhere else.
Can I follow this exact Chicago Southland Itinerary?
Not necessarily – and that’s part of the fun! Thornton Quarry tours are only offered on select dates, and performances and festivals change throughout the year. Use this itinerary as a starting point, then check the Chicago Southland events calendar before your trip and plug in whatever looks fun during your visit.
Final Thoughts: 2-Day Itinerary For Chicago Southland
What surprised me most about Chicago Southland was the variety. In just two days, we explored a massive quarry, browsed local art galleries, attended a street fair, enjoyed live performances, hiked through prairie landscapes, toured a historic chocolate shop, and discovered some wonderful local restaurants. That’s a lot!
If you’re looking for a Midwest getaway that combines art, nature, local flavor, and plenty of unexpected finds without the crowds of downtown Chicago, Chicago Southland is absolutely worth adding to your list. We barely scratched the surface in two days, which just gives me a good excuse to plan another weekend!
PIN FOR LATER:
