Please reach us at luckypennybookings@gmail.com if you cannot find an answer to your question.
To request a reservation, please visit our Booking tab and view our calendar for available dates. Once you select your preferred stay, you can submit a booking request directly through the site.
Please note that all reservations are confirmed upon availability once we review your request and respond.
If you have any questions or would prefer to book by email, feel free to contact us at luckypennybookings@gmail.com
At this time, The Lucky Penny requires a minimum stay of 2 nights. This is in accordance with City of Chicago short-term rental regulations, which mandate a two-night minimum for many licensed vacation rentals.
Additionally, during certain holidays, peak seasons, or special events, we may require a 3-night minimum stay. These extended minimums help us manage high-demand periods and ensure the best experience for all guests.
If you have questions about specific dates, feel free to reach out, we’re always happy to help!
The Lucky Penny can comfortably accommodate up to 11 guests.
The home features 3 bedrooms and 2 full bathrooms, with sleeping arrangements that include:
For additional flexibility, 2 air mattresses with bedding are also available upon request.
If you have questions about the layout or sleeping arrangements, feel free to reach out — we’re happy to help!
As much as we love our furry friends, pets are not permitted at The Lucky Penny.
This policy helps us maintain a clean and comfortable environment for all guests, including those with allergies.
Thank you for understanding!
We’re happy to offer convenient parking options for our guests. Two complimentary residential street parking passes are provided for the duration of your stay, and many guests are able to find parking in the immediate area.
If you need additional passes, we can provide them for $15 per vehicle, with a maximum of 4 total passes per reservation. Please be sure to request extra passes ahead of your booking.
For arrival and luggage, there is also a designated spot available for quick unloading. Full details and instructions will be provided with your check-in information prior to your stay.
Additional nearby parking options include:
If you have any questions about parking before your arrival, feel free to reach out — we’re happy to help!
Yes! The Lucky Penny is located in a safe, welcoming Chicago neighborhood that many guests love for its convenience, charm, and local atmosphere. Guests regularly enjoy walking to nearby restaurants, shops, and attractions.
As with any large city, we recommend using general awareness when exploring, especially later in the evening, but overall the area is one where visitors feel comfortable and at home.
We’re also happy to provide local recommendations and tips to ensure you have a great stay.
Nope! Everything is provided to our guests. You will love our boutique line of shampoo/conditioner/body wash and lotions!
Check-in at The Lucky Penny begins at 3:00 PM, and check-out is by 11:00 AM.
We may occasionally be able to accommodate early check-in or late check-out, depending on the schedule surrounding your stay. If available, these options are offered for an additional fee of $50 per hour, with a maximum of 3 hours on either end.
Please note that availability for early or late access can only be confirmed closer to your check-in date.
Feel free to reach out in advance with your request, and we’ll do our best to help!
Yes — The Lucky Penny is professionally cleaned and thoroughly sanitized between every guest stay.
Our cleaning team follows high standards to ensure the home is fresh, comfortable, and ready for your arrival.
Yes — decorations are welcome at The Lucky Penny! We love when guests make the space special for celebrations.
However, we do ask that you please follow a few guidelines:
All decorations must be completely removed at check-out. Any décor left behind or excessive cleanup required may result in an additional cleaning fee of $250 per hour, with a one-hour minimum.
Thank you for helping us keep the home beautiful for all guests!
We want you to have a wonderful stay and enjoy your time at The Lucky Penny, but parties and large events are not permitted.
To ensure a comfortable experience for everyone, we do not allow:
Guests are expected to respect our neighborhood and observe all quiet hours.
If you’re planning a small celebration during your stay, please reach out in advance so we can confirm what is appropriate.
Thank you for understanding and helping us maintain a peaceful environment for all!
If you’d like, I can make it firmer or add specific quiet hour times.
It is important to note that all bedrooms and bathrooms at The Lucky Penny are located on the 2nd and 3rd floors and are only accessible by stairs.
There is no full bathroom facilities on the first floor, so guests should be comfortable with using stairs during their stay.
Please feel free to reach out if you have any accessibility-related questions.
Exterior Security Cameras
We have security cameras located outside the property that monitor the entry door and entry walkway. These cameras help us manage check-ins and check-outs, verify the number of guests, and keep the property secure for everyone. Please note that parties and unauthorized extra guests are not permitted, as we are committed to being respectful of our neighbors.
Minut Noise Monitoring Device
We also use a Minut sound monitor inside the home. Minut is completely camera-free and only measures overall decibel levels. It does not record conversations, audio, or capture any sensitive information. This device helps prevent noise complaints while maintaining guest privacy.
If you have any questions or concerns about these devices, please feel free to reach out — we’re happy to provide additional details.
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