Best Chicago Vacation Rentals for Cubs Fans

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As of post time, it’s just 33 days to opening day at Wrigley Field, and the city of Chicago couldn’t be more excited.

Because while the Cubs have shown a less-than-stellar performance season after disappointing season, the fans can still find enjoyment in sitting in the sun, beer in hand, with the ivy-covered walls reminding them all that spring has indeed arrived in the Windy City.

If you’re a die-hard baseball fan, the only place to be–and stay–is Wrigleyville.

Handsome brick, multi-story flats are standard lodging in the fabled neighborhood, where the all-American pasttime is celebrated the whole length of Clark Street. When you’re not chowing on Chicago-style dogs at Wrigleyville Dogs, you’re parading your red, white and blue uniforms from bar to bar, whether that’s Merkles or Murphys Bleachers. Don’t forget scene-y places, too, like Rockit Wrigleyville, and if you’re willing to explore beyond the main drag, head to Southport, where the real locals linger over pints and comfort food like the creamy mac ‘n cheese at Cullen’s Bar & Grill.

Now that you have an itinerary, it’s time to find a Chicago vacation rental. If you’re only going to be here for a quick visit, I’d zero in on Wrigley to avoid that added expense of cabs, which can rack up–especially if your tomfoolery extends into the wee hours, when public transit, while available, isn’t the smartest idea at 3am.

The Southport suite above offers five nights for the price of four, and a prime location just 4.5 blocks from the Friendly Confines. The 1,200-square-foot space is fairly emblematic of other Chicago graystones with its period touches, including the gunshot-style layout, hutches and carved wooden pillars that frame the den.

You’ll feel right at home in the apartment, especially when you hear that crack of the bat outside your open windows.

Cubbies, let’s get some runs!

Posted in Family vacation spots, Mancations, Midwest vacations

About Valerie

Valerie Moloney is your resident blogger and the Expansion Markets Editor for, who oddly enough, feels panicked when asked, "What's the best place to eat in Chicago?" or her favorite, "It's my birthday. Where should we go with a party of six?" No stranger to travel--and traveling with kids--she is a young mom who ODs on the Internet when it comes to planning family trips or buying clothes. Here's hoping she finds you the vacation you deserve.

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