Leading up to a steamy, hot and humid Chicago weekend, I had planned to spend a quiet couple of days relaxing around home with my fiancé, Casey Purta. Between busy work schedules and planning our late-summer wedding, we both needed some time to ourselves to relax, maybe make some meals and share a bottle of wine.
Then a text quickly changed that.
My childhood friend, Nicollette Canovas, reached out to say she and her fiancé, Collin Coltman, wanted to visit and, in addition to spending quality time together, suggested the four of us spend a day really taking in all Chicago has to offer.
Without a lot of time or a huge budget to plan a blowout day, I had the idea to use Groupon to save money on a variety of activities and meals, and also to pull together some suggestions for what we could all do together. We all wanted a variety of dining experiences and fun activities, and knew it would be hot, so we wanted to stay indoors.

Our day together began with brunch. We met at a comfortable, upscale restaurant just off Michigan Avenue in Streeterville. The restaurant’s Groupon voucher allowed for each of us to pick an entrée like chicken and waffles or burgers and a handcrafted brunch cocktail like a Bellini and mimosa off the menu. Usually this would cost $100, but this brunch cost just $67 — saving us 33 percent.
We then hopped into a ride-share car that whisked us up to the Lakeview neighborhood for a matinee of a lively, colorful theater performance with lights, music and a lot of laughing. Despite the fairly last-minute decision to catch this show, thanks to Groupon we saved nearly 40 percent on tickets that normally would have cost a little more than $375. Our cost? Just $238.
Since we were both getting married in September, Nicollette and I wanted to do a little shopping for the big day. We went to a Macy’s on Michigan Avenue and had a blast trying on different jewelry pieces while the guys chimed in with their opinions. Ultimately, we both went home with a pair of earrings using a 25-percent-off Groupon coupon, and when I look at those glimmering earrings in my wedding photos, I always remember our fun urban adventure.

Next up: game time! We walked a few blocks to test our wits in an escape room where you have to solve puzzles, riddles and brainteasers to get out. None of us had ever been to an escape room and didn’t know what to expect. I was surprised at how exciting and fun it was. The best part? We saved nearly 30 percent with our Groupon, which brought the cost down from $140 to $99. We all want to do it again.
All that scheming worked up an appetite, so we headed to a River North Japanese restaurant for sushi, ramen, sake and more. A night out for four in this neighborhood could easily cost $150 or more per couple. Here, we budgeted $200 total and with a Groupon+ More Top Picks Best Wine Making Kits For Beginners
All in all, the fun day with longtime friends would have cost us nearly $1,000, but we were able to save almost 30 percent — $270 — by using Groupon.
I don’t think we would’ve done as much if we weren’t getting discounts, and I don’t think I would’ve thought to do those things if they weren’t already there on Groupon. Purchasing through Groupon made it feel like our money was going further and we could do more without feeling guilty. We got more bang for our buck.
—Produced for Groupon