Welcome to The Lucky Penny

Lincoln Park Bachelorette Retreat | Rooftop + Glam Bar | Sleeps 10

Planning the ultimate Chicago bachelorette weekend, bridal getaway, or girls’ trip? The Lucky Penny was thoughtfully designed for celebrating together.

Located in the heart of Lincoln Park, this stylish three-level townhome offers the perfect combination of beautiful interiors, group-friendly amenities, and easy access to some of Chicago’s best brunch spots, nightlife, shopping, and lakefront attractions.

From getting ready together at the full glam bar to sipping cocktails on the private rooftop, every detail was curated to make your weekend feel special, effortless, and photo-worthy.

The Space

Spread across three spacious levels, The Lucky Penny comfortably sleeps up to 10 guests with plenty of room for your group to gather, get ready, relax, and celebrate.

3 bedrooms | 2 full bathrooms

Sleeping arrangements:

* 1 king bed

* 3 full beds

* 1 twin bed

* 2 air mattresses

The home features:

* A luxurious king suite

* Hotel-quality mattresses and extra linens

* A private entrance

* High ceilings and boutique-inspired finishes

* Eclectic, colorful décor

* Multiple gathering spaces throughout the home

* Plenty of Insta-worthy backdrops for group photos

Whether you are planning a cozy night in, a themed pregame, or a full weekend itinerary, your group will have room to spread out without feeling separated.

The Ultimate Getting-Ready Experience

One of our most-loved features is the full glam bar, created specifically with group trips and special occasions in mind.

Your bridal party can get ready together without crowding around one bathroom mirror.

The glam station includes:

* Large mirrors with flattering lighting

* Generous counter space for makeup and hair tools

* Seating for multiple guests

* Conveniently placed outlets

* Boutique toiletries and thoughtful essentials

Put on your playlist, pour the mimosas, and enjoy getting ready together before heading out for brunch, dinner, or a night on the town.

Private Rooftop Deck + Bar

Start the morning with coffee in the sunshine or end the evening with cocktails under the Chicago sky.

The private rooftop deck features:

* A built-in bar with a mini refrigerator

* Comfortable lounge seating

* Space for morning coffee, happy hour, or late-night conversations

* A beautiful setting for bridal photos and group pictures

It is the perfect spot for matching-pajama photos, pre-dinner drinks, gift exchanges, or winding down after exploring the city.

Fully Stocked Coffee Bar

Because every great girls’ weekend needs great coffee.

Our gourmet coffee bar includes:

* Nespresso

* Keurig

* French press

* Drip coffee maker

* Coffee grinder

* Coffee, sweeteners, and brewing essentials

Enjoy a slow morning at home before getting ready for brunch or fuel up before a full day of Chicago adventures.

Amenities Your Group Will Love

* Smart TVs in every bedroom and living room

* Fully equipped kitchen with stainless-steel appliances

* High-speed Wi-Fi

* Central air conditioning and heat

* Dedicated workspace or itinerary-planning station

* Washer and dryer

* Hair dryers

* Iron and clothing-care essentials

* Welcome snacks

* Stocked household necessities

* Seamless self check-in

The Perfect Lincoln Park Location

The Lucky Penny is tucked into a charming residential pocket of Lincoln Park while keeping your group close to everything that makes Chicago unforgettable.

Walk or take a quick ride to:

* Lincoln Park Zoo

* The lakefront and walking trails

* Seasonal farmers markets

* Brunch spots, coffee shops, and restaurants

* Boutiques and shopping

* Bars and nightlife

* Wrigleyville and Northalsted

* Chicago’s most popular downtown attractions

Trader Joe’s, Target, Walgreens, and The Fresh Market are all within approximately two blocks, making it easy to stock up on drinks, snacks, decorations, and last-minute weekend essentials.

The Red, Brown, and Purple CTA lines are nearby, along with Divvy bikes, buses, taxis, and rideshare options.

Parking + Peace of Mind

* Residential zone parking sticker provided for one vehicle

* Detailed self check-in instructions

* Exterior security cameras located at entrances only

* Noise monitoring devices that measure sound levels only and do not record conversations

These features help create a smooth arrival and a comfortable stay for your group and our neighbors.

Why Guests Love The Lucky Penny

“Perfect for our bachelorette weekend—the rooftop was amazing and the location couldn’t be better!”

“The glam station made getting ready with the whole group so easy and fun.”

“Beautifully decorated, incredibly clean, and close to everything.”

“The host thought of every detail, from the coffee bar and toiletries to the welcome snacks.”

Celebrate at The Lucky Penny

Whether you are planning a bachelorette weekend, bridal celebration, birthday trip, girls’ getaway, or special Chicago reunion, The Lucky Penny gives your group a stylish home base for making unforgettable memories.

Come for the rooftop cocktails, stay for the glam bar, and leave with a camera roll full of your favorite moments.

Book The Lucky Penny and celebrate your Chicago weekend in style.