Apartment holiday 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!

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.

Humboldt Park Traveler's Lodge

Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed -> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

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)

Chic Wicker Park Flat • Near Blue Line

Our stylish 2B/2B Wicker Park condo is perfect for families, event-goers, and business travelers seeking comfort and convenience. Enjoy a mature, elegant, and modern space 5min walk to Damen Blue Line. This private, newly condo features luxury upgrades throughout — a Wolf gas range, Sub-Zero double refrigerator & premium appliances! On Wolcott Ave btwn Milwaukee & Division, you’re steps from top restaurants, boutiques, and everything Wicker Park has to offer. Registration #: R20000058371

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

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. Travel RN friendly, rate negotiable, PM us for info!

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Ukrainian Village 3BR/3BA • Private Patio, Parking

Welcome to Ohio St — a beautifully designed 3-bedroom, 3-bathroom private home in the heart of Ukrainian Village. Featuring a jet tub in the master bath, front patio with hammock, back porch with gas grill, and rare gated private parking for 2 cars. Sleeps 7 comfortably. Steps from Wicker Park, Bucktown, West Town & Downtown Chicago. The entire home is yours — no shared spaces, no surprises. Perfect for families, groups, and extended stays.

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.

Chic and Charming Vintage Condominium in Lincoln Park

View the city skyline from the windows and balcony of this lovely bright property in the heart of Chicago's safe and historic Lincoln Park neighborhood. With old-style elegance, wood floors, and an open fireplace, simple color schemes are delightfully offset by eclectic and inviting art. Let us introduce you to everything Chicago has to offer from the comfort of your own private getaway!