In 1872, Immediately following the Great Chicago Fire of 1871, James McCole built this two-story balloon frame wooden structure with a detached cottage in the rear.
In 1921, Vito Giacomo opened the restaurant on the 1st floor and many of the bar fixtures installed in the 20’s still exist in the present bar & restaurant.

Over the years, the restaurant was sold and renamed the Green Door Tavern, which was originated because if the door of a restaurant was painted green during prohibition indicated the presence of a speakeasy in that establishment.

Today, the Green Door remains true to its historic Chicago roots.

Photo by Off The Beaten Track

Killgubbin vacation rentals

We found 695 vacation rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

July 2025

August 2025

Discover a selection of 6 homes and other vacation rentals in Killgubbin that are perfect for your trip. Whether you're going on vacation with family or friends, vacation homes have the best amenities for spending time at your vacation home, which might include parking and a fireplace. No matter what you're looking for, you'll be able to choose a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Killgubbin

Showing deals for:Oct 17 - Oct 24

Exceptional

(7 reviews)

Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago

Chicago, IL

9% off

Includes all fees

Enter into our large 1800 sq. ft. condo, featuring a game room. Perfect for you!

Exceptional

(27 reviews)

City Center, River North Condo HUGE 3BR, Patio, Parking(2x)

Chicago, IL

13% off

Includes all fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Killgubbin

Stylish River North Suites: Luxury Living Near Chicago’s Best Shopping&Nightlife

Sleeps 6 · 2 bedrooms · 2 bathrooms

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Sleeps 22 · 5 bedrooms · 3+ bathrooms

Top rated rentals - Killgubbin

Premier Host

The View!

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
Learn more

Find out more about Killgubbin

Frequently asked questions

What is the most popular type of vacation rental accommodation in Killgubbin?

The most in-demand types of vacation rentals in Killgubbin are apartments. Looking for something different? Vrbo has many options to match our guests' requirements, so you'll see vacation properties in all shapes and sizes, and for all budgets. The ideal fit is ready and waiting for you --- find yours today.

How much does it cost to rent a vacation rental in Killgubbin?

The average price for a vacation rental in Killgubbin can vary depending on factors like property type, length of stay and time of year. Whether you prefer a sprawling villa with space for extended family or a quaint cottage just enough for two, just enter your travel dates to find stays with exceptional value.

How much does it cost to rent a beach house in Killgubbin?

Prices for beach houses in Killgubbin vary depending on the style and size of the property and when you're traveling. Simply enter your travel dates into Vrbo and how many guests to see available options and prices. From there you can use our filters to refine your search by amenities, nearby activities, ratings and more.

Are there pet-friendly vacation rentals in Killgubbin?

Pack a travel bag and a bone for your pooch because Killgubbin has eight vacation homes that welcome pets with open arms. Let your happy hound join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check the "Pets allowed" filter box.

Can I rent a house with a pool in Killgubbin?

Add another level of fun to your adventure by booking your family into one of the five houses with a private pool in Killgubbin. Use our search filter to find properties with pools on Vrbo, then spend carefree days playing and splashing in a swimming pool that's all your own.

What are popular rental amenities in Killgubbin?

The most popular rental amenities people are searching for in Killgubbin are a sauna, a barbecue grill and a firepit. Whether you're going on vacation with your besties, family or even pets, Vrbo vacation homes have the best amenities for starting a new adventure with the people that matter most.

Are there large group vacation rentals in Killgubbin?

With three properties that can sleep 10 guests or more in Killgubbin, you don't have to leave anyone off your invite list. From fun family get-togethers to events like anniversary parties and weddings, Vrbo will help you find a large group rental to suit the occasion.

Are there vacation rentals in Killgubbin that welcome kids?

Gather your whole crew for an epic adventure in Killgubbin at one of our eight family-friendly properties. These stays feature conveniences that are ideal for trips with children, including laundry facilities, multiple bedrooms and pools. Simply click on the "Properties good for families" filter and choose your favorite.

Are there one-bedroom vacation rentals in Killgubbin?

Yes, you can take your pick from three one-bedroom rentals in Killgubbin. Whether you're looking for an apartment or a fancy condo, our one-bedroom rentals are great if you don't require tons of space. One of the best things about having your own pad? You won't ever have to share your adventure with strangers.

Can I find two-bedroom vacation rentals in Killgubbin?

Gather your loved ones and relax in total privacy and comfort in one of the two two-bedroom vacation homes Killgubbin has to offer.

Are there vacation rentals with WiFi in Killgubbin?

There are seven vacation rentals with WiFi in Killgubbin. If you'd like to disconnect from the world during your break, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Killgubbin?

Killgubbin has seven vacation rentals where you can spend your days in air-conditioned comfort. To locate a property on Vrbo that offers this amenity, enter your desired travel dates and use the filters to select the "air conditioning" box.

How old do you have to be to rent a vacation rental in Killgubbin?

The minimum age allowed can vary across properties on Vrbo, so double-check the rules of the vacation rental in Killgubbin you want to book. But usually, it's 16, 18 or 21.

How long can I rent a vacation rental in Killgubbin for?

It's really down to the Killgubbin property. To browse a list of options offering extended stays, just enter your travel dates and number of guests into the Vrbo search page. You can enjoy having the entire place to yourself, along with the comforts of home like a fully-equipped kitchen and an outdoor space where your little ones can play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.

Does Vrbo offer discounts for vacation homes in Killgubbin?

Whether you're after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to score some fabulous deals and discounts on Vrbo. From weekend retreats to extended getaways, we've got the ideal place for your next Killgubbin escape.