A Weekend Getaway From Chicago

This weekend was about the Cubs. As six figures worth of lager-wielding baseball fans crushed themselves into historic Wrigleyville, we were escaping on a long-ago scheduled trip out of town. Back then in early September, our baby was much more likely than a local World Series, so it wasn’t about baseball, but about a final weekend getaway from Chicago before the real chaos begins.

The trip was “scheduled” but not planned. Let’s begin…


6pm – The Drake Hotel, Chicago

Sure, this is in Chicago, but it was a necessary vacation pre-game. My wife and her Irving Sisters trio were there performing a few songs from the 1940’s for her great aunt’s 95th birthday. I stood by supporting both this talented trio and an $18 Old Fashioned from the upstairs bar. The latter was a good reminder why we needed to get out of the city.

7:30pm – The Phoenix Restaurant, Kenosha

When road-trip hunger strikes out of nowhere, we look to Foursquare’s directions for the nearest family-run restaurant. Hopefully, it’s a cozy spot with friendly service and locals who are as excited about the pie as I am. The Phoenix restaurant is quite a few light years from a Michelin Star, but the lasagna tasted like mom used to make it.

9pm – Shadowpool Airbnb, Outside Lake Geneva

Notice that we stayed in Fontana, outside Lake Geneva. Away from the tourists on the other side of the lake lies a quiet stretch of woods with a quaint Airbnb and a gracious host. For $75, Marlene’s renovated 19th-century cottage, fireplace and 4-post bed provided a peaceful, easy escape. We had a hard time pulling ourselves away after the morning’s feast of chicken sausages, fresh blackberries, bacon, eggs and cinnamon bread.


Upon waking up, we had zero plans and a full tank of gas. The weekend was truly two days of exploration, with no expectations other than our habit of always finding an interesting experience. With that in mind, we asked Marlene, the Airbnb owner…

US: “So, is there anything you’d recommend doing today?”

MARLENE: “There are a lot of great antique shops nearby. The nearby college has a beautiful trail around the lake. It’s very popular. Of course, Lake Geneva has a lot to do. I’d strongly recommend the Yerkes Observatory even if you don’t take the tour…”

10am – Yerkes Observatory

Five minutes from our Airbnb, the sun shone warmly onto an impressive 119-year-old dome that housed the “Birthplace of Astrophysics.” It was a quite a discovery. Surrounded by countless acres of manicured, green grass and a flaming horizon of fall foliage, the exquisitely designed building was a memorable, historic treasure we did not expect to find on our random adventure.

Carl Sagan, Edwin Hubble and many other famous astronomers built their careers using the largest refracting telescope in the world – its grounds and building funded by financier Charles Yerkes. The telescope and its largest-ever-constructed variable-height floor is still in use today. With the $8 tour, a day trip to Yerkes Observatory is highly recommended for anyone curious about the stars and how we study them.

2pm – Lake Geneva

If you’re from Chicago, then you probably know Lake Geneva is a very charming, quaint resort town that has everything you need in a standard day trip from the big city: quiet strolls along the lake, sailboat tours, fudge shops, antique stores and the requisite highly-polished pizza place that has just enough craft beers to make it feel local. Outside of town there’s enough golf, biking, spas and other activities to make it a great weekend getaway from Chicago.

We did enough peaceful rounds of ice cream, dockside exploration and lakeside walking to get excited for another happenstance adventure near our next Airbnb.

Note: We never seem to find the lonely boat captain looking for company to share his old bottle of French wine during his birthday on the lake. Yet we continue to try. 

4pm – Outside Rockton, IL / Beloit, WI

Purposefully chosen by its numerous positive reviews and location further into the country, our next Airbnb was the home of a nice couple who truly made a place for those who want to get away. Their place is complete with trees, chickens, ponds, trails, a few acres of land and a bonfire, and we were eased into a nap that lasted pleasantly too long – another benefit of having absolutely no plans or schedule.

7pm – Merrill and Houston’s Steak Joint, Beloit

Ad hoc birthday celebration. I made it to 40, I so deserved a $40 steak. When in doubt about what to do in a small town, go to the best restaurant, sit at the bar, order an 18oz rib-eye with big glass of Malbec and watch Game 5 of a Cubs/Indians World Series. Guaranteed good night out. Especially when the tab is $50 less than back home.

10:30pm till 2pm – In Pain at the Airbnb, Outside Rockton

Here’s when you wish that 18oz ribeye wasn’t the first big piece of beef your stomach has touched in months.


9am – Bushel and Peck – Beloit, WI

We learned to take it seriously when the Airbnb host suggests a place, so we spent the morning writing thank you cards over coffee and egg sandwiches in this cozy hippy’s shelter for the apocalypse community gathering place. For those who want to fill their entire kitchen with an overwhelming variety of organic, homemade goods, this will fit the (huge) bill. For us, it was our vacation porch swing with nowhere to go. The perfect start to a Sunday.

12pm – Colored Sands Forest Preserve, Somewhere Southwest of Beloit

Every weekend getaway from Chicago should include some unvarnished nature, since that’s as rare in Chicago as a clean-shaven bartender in Logan Square. We weren’t expecting stunning vistas on the northern border of Illinois, but we did find a 2-mile walk in the woods without noise, advertising and bearded hipsters from Logan Square.

The preserve is known amongst birders as one of the largest migratory bird “banding” places open to the public. During the early fall and spring, banders catch birds in huge nets, place tracking collars on them for study and release them quickly back into the wild.

Want to do something more exotic? Call ahead and take a “hawking” lesson from a local. Enough practice and you’d have an exciting way to control your neighborhood rat problem.

4pm – Edwards Apple Orchard – Poplar Grove, IL

Our last stop was this theme-park homage to the apple that we found on Foursquare – something curious to explore between our last stop and home. If fruit cults exist, I imagine there is a dark, sweet-smelling basement deep in the bowels of this farm where kids gorge on candy apples, finger paint with homemade apple butter and watch their parents get drunk on rum-infused cider before passing out on fluffy piles of delicious apple cider donuts.

Needless to say, this is another highly recommended day trip from Chicago with the family. Leave the diabetes at home.

Scroll through the photos from our weekend getaway below.

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Having traveled extensively in the past with an artist and educator schedule, I now spend my non-working hours calming a tired infant, searching for the best sazerac and getting the most out of our urban garden. As we inevitably write more about traveling with children, we'd love to read your comments about how you create the perfect comfort/adventure balancing act. Thanks for reading!

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