Holiday rentals with outdoor seating in Wicker Park

Gorgeous Penthouse with Stunning Views from Private Rooftop

Welcome! We are young professionals opening up our 2 bedroom apartment to warm and down-to-earth travelers. We'd like to help you fall in love with Chicago! LIVING SPACE: Top floor condo with a great view of the neighborhood tree-lined street. Moderately large open space with hardwood floors, a comfortable and inviting atmosphere, and plentiful natural light. You can also relax on our private rooftop. KITCHEN: You are free to use the full kitchen. BEDROOMS: Two bedrooms with ample natural light and large closets. Fresh sheets, pillow, bath soap, and bath towels will be provided. BATHROOMS: 2 bathrooms (1 is a master bathroom with shower and bathtub) for guests. Central A/C is provided in the warm months and central heat during the cooler months. We live in Chicago and are happy to help if you need something. Beautiful walking-friendly Wicker Park showcases Chicago's culture, arts scene, and food and entertainment. Explore diverse nightlife and bars, historic buildings, countless vintage shops and boutiques, and street festivals in the warmer months. TRANSPORTATION: The condo is approximately a 30+ minute direct train ride from O'Hare airport and ~40+ minute train ride from Midway airport (1 transfer) using the "El" train. Getting to our condo from O'Hare is direct as we live right off the 'DIVISION' stop on the BLUE LINE. From Midway, you would need to transfer from the ORANGE LINE to the BLUE LINE. We are a fairly quick train or bus ride to the Loop and River North (for access to "downtown" cultural and city attractions) as well as other popular Chicago neighborhoods such as Ukrainian Village (walking distance), Bucktown (walking-bike distance), Gold Coast, Old Town (1 single bus, no transfers), Greektown, West Loop (quick Uber), Lincoln Park, Lakeview (bus), and Logan Square (quick "El" train ride). PARKING: Free parking can be found on Augusta Blvd (with exceptions on certain hours/days for street cleaning). Additional free parking can be found just a bit further on Cortez and Paulina. We look forward to providing you with the Wicker Park and Chicago neighborhood experience. Once you arrive, you'll get an even better picture of how phenomenal this location is.

Spacious Studio w/Balcony in Bucktown/Wicker Park

My place is in the heart of one of Chicago's Hottest and Hippest neighborhoods(Wicker Park/Bucktown) with everything you need or want within a short walk - Transportation(Blue Line Train) which is a direct shot to and from O'hare airport, Dining, Nightlife, High End boutique shopping. 15 minutes to the Magnificent Mile, Millennium Park, Wrigley Field. Perfect for couples, solo adventurers, and business travelers with Internet and Cable TV included. Sleeps 2 adults comfortably w/sleeper sofa.

Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!

Located in the heart of Wicker Park, just a 5 min walk to the Damen blue line stop. This phenomenal location allows you to access EVERYTHING Chicago has to offer without having to rent a car. Experience the best of Chicago, all within a short walk from your stay. World class bars, restaurants, and shopping all within walking distance. Want to explore downtown or catch a Cubs game at Wrigley? Hop on the "L" train and use the CTA to go anywhere in the city. This cozy garden apartment has it all.

Private coach house near transit shops & nightlife

This renovated coach house comfortably accommodates 3 adults but can sleep 4. Only a 7 minute walk from the "L" train (CTA blue line to O'Hare airport & downtown). Close to Chicago's Wicker Park and Logan Square neighborhoods with lots of nightlife and dining options within a 10-15 minute walk. The two story, ~750 sqft space features a bedroom and office upstairs; the ground floor has a combined kitchen/living room and one bathroom. 4 guest limit based on city of Chicago occupancy ordinances.

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

Ukrainian Village Garden Retreat | Free Parking

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is a small historic district of Chicago filled with historic architecture. Access the apartment via a smart lock, the apartment includes everything you need for a comfortable stay, including a queen-sized bed, full kitchen, fiber high-speed internet (100+ Gbps up and down), smart TV, modern bathroom, in-unit washer & dryer, and free garage parking.

Colorful Bucktown Garden Apartment

Enjoy a stylish experience at this centrally-located apartment. Close to all of the neighborhood amenities including the 606 trail, shopping district, highly reviewed restaurants, blue line "el" train, neighborhood parks, and more. Walk to everything you need or jump on the blue line to get downtown quickly. Our colorful space is perfect for your city stay. Enjoy comfortable spaces including an oversized bedroom, cozy living room, fully appointed bathroom, dining area, and a kitchenette.

Stylish 2-bedroom flat in Vibrant Bucktown.

* Please be aware the city of Chicago is currently renovating its lead pipes. Construction is inevitable and noise. Its a city there will be noise. Hello and welcome to Bucktown! One of Chicago's most popular neighborhoods. Bucktown is centrally located, just a short commute to downtown and surrounded by the best dining and entertainment options Chicago has to offer. We are also half a mile from the expressway and 1 mile away from the Blue Line which directly connects to O'hare airport.

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.

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)

Luxe, Private Suite w/Own Entrance-2023 Renovated

Newly remodeled private city oasis! Professionally designed suite with private keyed courtyard entry & small lighted covered patio w/table and chairs (work outside!) New ensuite bathroom w/heated floor, bespoke vanity & fab water pressure. Quiet tree-lined street with free parking, great restaurants, old pubs, shops & transport walkable. Great launch to all Chicago has to offer while enjoying charming Bucktown. Close to Downtown, Wrigley, DePaul, Zoo, Lincoln Pk, United Ctr, Lakefront.

𓃥Wicker Cozy Corner w/Parking on site

Welcome to our charming Wicker Park getaway! Located just a 5-minute stroll from the Damen blue line stop, our cozy abode offers the perfect blend of convenience and comfort. Enjoy peace of mind with driveway parking. Explore the vibrant neighborhood with ease – you're just a short walk away from coffee shops, restaurants, bars, unique shopping boutiques, and so much more. Whether you're here for business or leisure, our prime location ensures you're never far from the action.