
Condo holiday rentals in Wicker Park
Find and book unique condos on Airbnb
Quick stats about condo rentals in Wicker Park

Total holiday rentals
Explore 20 holiday rentals in Wicker Park

Nightly prices starting at
Wicker Park holiday rentals start at $85 NZD per night before taxes and fees

Verified guest reviews
Over 2,350 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Wicker Park holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wicker Park rentals

4.8 Average rating
Wicker Park stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated condo rentals in Wicker Park
Guests agree: These condos are highly rated for location, cleanliness and more.

Chic & Spacious Bi-Level Bucktown Condo - Sleeps 8
This one-of-a-kind condo in Bucktown is ready to host! The property features a hidden staircase leading down to the in-law suite on the bottom floor! The main floor has all that you could need with a beautiful full kitchen and relaxing living room, but for when you need a bit of extra space, step downstairs into the studio-style space with a kitchenette, work station, and sleeping/living area. The blue line train stop is a 7 min walk and Ohare and Midway Aiports are a 30 minute Uber ride away.

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!

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 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

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.

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.

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!

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.

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.

Stylish & Spacious Wicker Park Airbnb!
This Airbnb is a 3-bedroom/1-bath home-away-from-home on the first floor of a historic 1890's Wicker Park landmark 3-flat on a quiet, tree-lined street. You're a few minutes' walk from the beating heart of the neighborhood, where you'll find some of Chicago's best restaurants, boutiques & art galleries. We welcome humans of all types and origins, and families with children.

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.
Popular amenities for Wicker Park condo rentals
Weekly condo rentals

Foosball, Steps from Wrigley, Private Parking

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Picture Perfect 3Bed Steps from Train and FLW

The Bagel Inn - Bright & Modern Wrigleyville 2 Bed

Logan Square Beauty with 2 Bedrooms W/parking

Two Bedroom w Porch in Wicker Park

Large Remodeled Home in Lincoln Park, Sleeps 12!

Skylit Boho Retreat in Wicker Park
Pet-friendly condo rentals

Chic and Charming Vintage Condominium in Lincoln Park

Large Chicago 3BR/3BA • Sleeps 7 • Near Downtown

Spacious 3BR • Great for Groups • Fast WiFi • Pets

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

NEW luxury Old Town 1-Bedroom condo

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

Susie's Space. 2BR easy parking & pet friendly
Condo rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Lovely 2 Bed 2 Bathroom!

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Iconic Style, Charming Lake View
When is the best time to visit Wicker Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $274 NZD | $279 NZD | $374 NZD | $365 NZD | $440 NZD | $518 NZD | $521 NZD | $575 NZD | $355 NZD | $445 NZD | $362 NZD | $330 NZD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Destinations to explore
- Rentals with a fireplace Wicker Park
- Pet-friendly rentals Wicker Park
- House rentals Wicker Park
- Fitness-friendly rentals Wicker Park
- Family-friendly rentals Wicker Park
- Rentals with outdoor seating Wicker Park
- Rentals with a fire pit Wicker Park
- Rentals with a patio Wicker Park
- Apartment rentals Wicker Park
- Rentals with a washing machine and dryer Wicker Park
- Condo rentals Chicago
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Brookfield Zoo
- Garfield Park Conservatory
- University of Chicago
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower




