How to Spend a Staycation Weekend in Chicago
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Last weekend my friend came out to visit me, and since it was her first-time visiting Chicago in the summer, I turned it into a stay-cation for myself to make the most of the perfect weather we were having. Here’s a quick rundown of how we enjoyed the weekend from a local’s perspective, as well as my top recommendations for what to do if you’re planning your first trip to the Windy City.
Friday
Boxing class at Rumble
We started our morning with a 7AM boxing class at Rumble in River North. The 45-minute class is divided into ten 3-minute rounds, 5 boxing and 5 strength. Rumble has locations nationwide and definitely caters to Millennial/Gen Z women, which was perfect for us. It also happened to be the instructor’s birthday when we went, so they gave everyone health shots from a local juice bar and had raffles for prizes between rounds (I won a restaurant gift card!).
Puttshack
In the spirit of maximizing my PTO, I didn’t take any time off of work so we hung out at home all day while I worked until 5PM rolled around. Then we drove downtown to pick up Thomas from his office and headed out to the suburb of Oakbrook to go to Puttshack.
I have loved Puttshack since 2019 when Thomas and I took a trip to London and his family introduced us to it. We ended up going there 3 times during our one-week trip. I was thrilled when I heard they were expanding across the pond to America and they opened their Oakbrook location just outside Chicago in 2021.
Puttshack is a high-tech mini golf experience. The balls have chips in them to track your strokes and keep track of your score. Unlike regular putt-putt, the highest score wins and you can get bonus points for hitting certain things or getting a hole in one. Each game is only 9 holes and we played 2 of their 4 courses.
Another thing that sets Puttshack apart from regular mini golf is that it’s a full bar and restaurant as well. On a busy Friday night, you have to make reservations to get a table in advance.
Portillo’s
On our drive home, we stopped by Portillo’s, an iconic Chicago hot-dog chain for dessert. Though they originated in Illinois, they now have locations as far away as California and Florida. Many people love their chocolate cake, but what’s even better is their cake shake, which is a milkshake with an entire slice of their chocolate cake mixed in. The three of us split the small size and it was plenty.
Saturday
Breakfast at Yolk
Before Thomas and I moved to Chicago in 2019, we visited to make sure we could see ourselves living here. On that trip, we ate breakfast at Yolk’s downtown location. It’s been almost exactly 3 years but we got the chance to eat at Yolk again this weekend – this time at their Lakeview location. I got the South Beach, which is a bowl of Greek yogurt, fruit, and granola served in half a pineapple.
Yolk has locations throughout the country but also has their test kitchen in Chicago on Milwaukee Ave, where you can try unique new items not offered on menus anywhere else.
Biking Along the Lakefront
After breakfast we walked over to the lakefront where we picked up Divvy Bikes and rode down the Lakefront Trail to Navy Pier and back. The trip took about an hour and cost ~$12 per bike (they charge $1 up front and then $0.39/minute). This is a great way to get some exercise in and enjoy the beautiful views of the water and skyline.
You can unlock a Divvy Bike through the Lyft app. If you’re new to Lyft, you can use code JACKIE701637 for $8 towards your first ride.
Boating on Lake Michigan
Chicago has such a great boat culture being right on Lake Michigan, and we wanted to take full advantage of the amazing September weather and get out on the water. I rented a boat from getmyboat.com for 2 hours and our captain took us south from Diversey Harbor, around Navy Pier, to the Buckingham Fountain in Grant Park, before anchoring in Playpen for about an hour so we could swim around. The water in Lake Michigan is always pretty cold, but after a few minutes, you get used to it and are able to swim comfortably. This was definitely the highlight of the weekend!
Museum of Ice Cream
We booked last minute tickets to the Museum of Ice Cream and showed up not really knowing what to expect beyond the one Tik Tok I’d seen about the New York location. There are MOICs in several cities and the Chicago one is very much themed around the city. As you enter you walk through a pink CTA train car with a map of the city’s transit system (but instead of the stop names they’d replaced them with ice cream flavors). There are 5 chances throughout the museum for unlimited ice cream, the first of which was a Dove Ice Cream bar, which is manufactured nearby in Burr Ridge, IL. The most unique dessert they offered was hot dog flavored ice cream, which was every bit as disgusting as it sounds, but I applaud them on their creativity and dedication to the Chicago theme.
“Museum” felt like a bit of a stretch, as there were only a couple of educational points throughout. Instead, it was more of a giant Instagram-able art installation. There were lots of places for photo ops and several interactive games throughout, including 3 mini golf holes, carnival games, and a giant sprinkles pool (aka a ball pit for adults). This was certainly a unique experience, but we had a lot of fun and took a lot of photos.
Dinner at Avec River North
We managed not to completely ruin our appetites with ice cream and made our way over to Avec River North for dinner. It’s a beautiful restaurant that I’d never eaten at but had been wanting to try for a while. The restaurant asks that you order all courses at once and everything is meant to be served family style. We ordered the goat cheese as an appetizer and the tagliatelle and focaccia for our mains. The cheese and pasta were amazing, but we weren’t wowed by the focaccia.
Sunday
Breakfast at Maison Marcel
The last thing we did before taking my friend to the airport was get breakfast at Maison Marcel, a really cute French café in Lakeview. I ordered the Nutella latte and the French Breakfast, which included 2 eggs and a giant bread basket of assorted varieties, including croissants and baguette. I’ve ordered this every time I’ve been here and I don’t see myself straying anytime soon. Thomas ordered the Nutella & banana crêpe, which was also amazing.
Other things to do in Chicago
Chicago is the 3rd largest city in the United States, so it makes sense that there’s always a lot going on. One great way to see everything happening on any given day is to use the website do312.com, where you can filter to find what interests you.
Downtown Parks
Downtown Chicago has a lot of parks that are great to explore, including Millennium Park, Grant Park, and Maggie Daley Park. The Bean, the iconic mirrored sculpture that looks just as its name suggests, is located in Millennium Park and the famous Buckingham Fountain can be found in Grant Park nearby.
Museums
Chicago weather isn’t always as great as it was last weekend, so on cold or rainy days, a museum can be a great option. Chicago has plenty, including The Art Institute of Chicago, the Field Museum, the Shedd Aquarium, Adler Planetarium, and more. On a nice day, the Lincoln Park Zoo is a fantastic (and free!) choice as well.
Segway tour
A Segway tour can be a fun way to see and learn about the city. We did a Segway tour back in June through the parks to the Field Museum, Aquarium, and Solider Field and our guide gave us a good history lesson while we zoomed around. My favorite was learning about the history of the meat packing history in Chicago and how the famous Chicago-Style hot dog came to be.
Deep Dish Pizza or Chicago-Style Hot Dog
The two foods Chicago is most well-known for are definitely deep-dish pizza (which you eat with a fork and knife) and a Chicago-style hot dog. While I’m really not a huge fan of either one, they are definitely iconic and worth trying at least once. Giordanno’s and Lou Malnati’s are rival pizza shops specializing in deep dish and locals are divided on which they favor. To get a hot dog, there are plenty of street vendors around the city serving them and you can of course get them at baseball games as well.
Architecture River Cruise
I’ve taken the Architecture River Cruise multiple times and would happily go again. Chicago has so much amazing architecture with incredible history behind it and one of the best ways to see it is from the water as the guide tells you about the buildings as you pass them.
Sports game (football, baseball, basketball, hockey, soccer)
Chicago is such a big sports town being home to the Bears, Bulls, Cubs, White Sox, Blackhawks, and more. Check out the schedules to see if there are any home games when you’re here. I’m personally not a big sports fan, but I love the energy at live sporting events.
Street Festivals
In the summer, Chicago has street festivals nearly every weekend all around the city focusing on everything from the arts to gyros. Look into what’s taking place near you and it can potentially spark ideas for activities or at the very least make you aware of road closures to avoid.
Shows (Broadway, concerts, comedy, etc.)
New York isn’t the only place to see amazing shows. Chicago has its own Theatre District with rotating Broadway shows. Additionally, there are concerts and music festivals in the city along with comedy shows (especially at the famous Second City). Keeping an eye out for upcoming performances!
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