Condo vacation rentals in Wicker Park

Sunny Getaway Steps from Bucktown + Wicker Park

Enjoy a relaxing and chic experience steps aways from the lively, sought-after Wicker Park and Bucktown! Our home is on a quiet, tree-lined street with its own private walk-up entrance and FREE parking space. Public transportation is also very accessible. There are endless options of restaurants, bars, and shopping. The 606 trail is also steps away! We are centrally located which makes it easy and convenient to explore Chicago! Come make some memories for the weekend or as long as you'd like!

Location · Value · Check-in

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Family · Location · Sleep quality

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Escape into this spacious, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Family · Location · Checkout

Luxuriously bright 6-bedroom duplex: The Treehouse

Experience a calm and soothing stay in a spacious duplex-up bathed with light and nestled amongst the trees. This home is the top two floors of a 4-flat building which offers 6 bedrooms, 4 bathrooms, and two outdoor spaces. Enjoy free street parking, and a location just 3 miles from downtown Chicago. You're also a 2 min walk from public transit. For something closer to home, Wicker Park and Humboldt Park offer great dining and culture steps away. We look forward to hosting you!

Value · Location · Accuracy

Modern/Spacious 2BR/2BA West Town

Light, airy and luxurious, our duplex has a self-contained, 1400 sq. ft. 2nd floor with a private street entrance. There are two bedrooms and two baths. The master bedroom has a fireplace, a private balcony and a huge bathroom ensuite. In addition there is a dining room and living room. Minimal kitchen facilities include small fridge and micro. Easy commute downtown- 20 by car, 25 by bike and 30-40 minutes via public transportation. Close to hwy and public trans.

Family · Location · Condition

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Location · Value · Outdoor spaces

Modern stay in lively Wicker Park neighborhood!

Centrally located in Wicker Park, Chicago, our property is steps from public transportation and a 15-minute drive to downtown. Ideal for couples, small families and groups, solo adventurers, or business travelers exploring the vibrant city. Please note: our main street location near a hospital may have some unavoidable city noises. Our unit can house 3-5 guests, please review the sleeping arrangements prior to booking.

Family · Value · Quiet

Two Bedroom w Porch in Wicker Park

Spacious two bedroom apartment with custom wood shelving and hard wood floors. Bay windows and great natural light. Gorgeous furnished porch for when the weather is nice. Quiet, tree lined street that's close to all the best bars and music venues. Short walk to Milwaukee avenue, two blocks from the Division Street blue line station which runs direct from O'hare, only two stations to downtown.

Location · Value · Nearby

Modern Izakaya Studio in Wicker Park

The Izakaya Studio is a sleek, design-forward space in the heart of Wicker Park, with a secret whisky room inside. Inspired by the intimate atmosphere of a Japanese izakaya: warm, curated, a little unexpected. The kind of place where you settle in, pour something good, and stop thinking about your plans for a while. Spacious for a studio, and comfortable enough for a longer stay in Chicago.

Family · Value · Amenities

Stunning Wicker-Park Flat with Parking!

Enjoy a stylish experience at this centrally-located gem. Beautifully renovated 3 bedroom, 2 bath full floor flat. While quietly situated on the 3rd floor, you can walk out your front steps to all that Wicker Park and Division street has to offer. Coffee shops, bars, unlimited restaurants, green space, farmers market, gyms, grocery stores, and so much more. Easy and nearby public transit.

Value · Location · Nearby

Old Town Condo: Private Terrace & Garage Parking

Experience vibrant Chicago from this modern 2-bed, 2-bath Old Town condo. Perfect for families or professionals, it features a private terrace, gourmet kitchen, dedicated workspace, and a rare dedicated parking spot. Soaring 13-ft ceilings and stylish design create a light-filled urban retreat just steps from Lincoln Park, Second City, and North Avenue Beach. Comfortably sleeps 4.

Family · Value · Accuracy

Wicker Park/Bucktown condo with large balcony

This freshly remodeled condo with European flair is set in the trendy yet peaceful neighborhood of Bucktown - a perfect base for exploring Chicago. A short walking distance to 2 Blue line CTA stops (Western and Damen), it is surrounded by quaint neighborhood bars, restaurants, and coffee shops as well as grocery stores and trendy shopping.

Family · Value · Comfort