
Apartment holiday rentals in Wicker Park
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Top-rated apartment rentals in Wicker Park
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WONDERFUL WICKER PARK 2BD/2BA w/ patios +parking
Escape into this spacious condo in a bustling top-notch, Chicago neighborhood! 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! - 2 private walk-out patios! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out patio - Designated parking spot! - Steps away from blue line Damen station (800 feet)

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!

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!

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.

Susie's Space. 2BR easy parking & pet friendly
Sunny and spacious, 2 bedroom apartment in Avondale near the Green Exchange/ Greenhouse Loft Flexible, self check-in Easy street parking (with provided permits) Pet fee $80 per pet Bedroom 1 with a king sized bed Bedroom 2 with a full bed Air conditioning and ceiling fans Soft linens and towels Separate dining room Fully equipped kitchen Free WIFI Smart TV for streaming Garden in back with a fire pit and charcoal grill Laundry room in basement

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
Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures 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.
Popular amenities for Wicker Park apartment rentals
Weekly apartment rentals

Int. Designer’s Lakeview Duplex w/private backyard

Welcome to the Chi! Close to Downtown

Inspired, luxe living in Logan Square on BLVD #1

Two Bedroom w Porch in Wicker Park

Skylit Boho Retreat

2-Story Luxury Condo in Wicker Park–10 Mins to DT

Remodeled Duplex in the Heart of Lincoln Park

Twin Lions Lodge • Private Hotel w/ Speakeasy
Pet-friendly apartment 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

Lincoln Square Gem!

NEW luxury Old Town 1-Bedroom condo

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

Large Remodeled Home in Lincoln Park, Sleeps 12!
Apartment 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 | $208 SGD | $212 SGD | $283 SGD | $277 SGD | $333 SGD | $392 SGD | $395 SGD | $436 SGD | $269 SGD | $337 SGD | $274 SGD | $250 SGD |
| 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 |
Quick stats about apartment rentals in Wicker Park

Total holiday rentals
Explore 20 holiday rentals in Wicker Park

Nightly prices starting at
Wicker Park holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 2,610 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Wicker Park holiday rentals include wifi access

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

4.9 Average rating
Wicker Park stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Pet-friendly rentals Wicker Park
- Rentals with a fireplace Wicker Park
- Rentals with a washing machine and dryer Wicker Park
- Flat rentals Wicker Park
- Family-friendly rentals Wicker Park
- Rentals with a patio Wicker Park
- Rentals with outdoor seating Wicker Park
- House rentals Wicker Park
- Fitness-friendly rentals Wicker Park
- Rentals with a firepit Wicker Park
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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
- Wicker Park
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Illinois Beach State Park




