
Condo holiday rentals in Cook County
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Top-rated condo rentals in Cook County
Guests agree: These condos are highly rated for location, cleanliness and more.

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
Brand New Private Modern 2 bd 2bth apt for your stay in Chicago. We are located 2 blocks form the CTA line in the heart of Pilsen, a neighborhood Time Out labeled the 10th coolest in the world. Newly renovated, hardwood tiled floors throughout, chefs kitchen, toiletries, brand new furnishings including 2 queen beds, 1 twin sleeper, fresh linen, smart TV (HBO, Netflix, Hulu) wifi, tons of books,coloring books,board games & puzzles! We truly want you to feel like this is your home away from home.

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.

Private hot tub - King bed suite - Free parking
Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Inspired, luxe living in Logan Square on BLVD #1
Welcome to our Palmer Square House! In the heart of hip Logan Square. Enjoy a rare opportunity to experience Boulevard living. "Live like a local" in one of Chicago's most visited & vibrant neighborhoods. 1915 historic 2-flat has been renovated with luxurious amenities. Lots of windows provide natural light. Chef's kitchen is beautiful & functional. Option to rent PH at same time if available. Primary bathroom has serious spa vibes. NO CLEANING FEES! Very fast WiFi. 65" Smart TV QLED.

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.

Chicago Oasis | Spa Bath, Patio & Fireplace
Experience the best of Chicago from this centrally located retreat just minutes from Downtown, top restaurants, shopping, and iconic attractions. Relax in a spa bathroom with a jetted tub and rain shower, cozy up by the fireplace, and enjoy a fully equipped kitchen. A king bedroom and queen Murphy bed comfortably accommodate up to 4 guests. Finish your evenings on the private patio gathered around the fire table.

Dwtn 10 Min, Free P, PingPong, Sleeps 10
- Spacious, modern 2BR/2BA with free indoor parking, steps from the United Center - Game room with a Ping-Pong table for family-friendly fun after a day of sightseeing - Chef’s kitchen with high-end appliances and a rice cooker for convenience - Relaxing master suite with a walk-in closet, en-suite bathroom, and heated floors - Book now for a comfortable stay with easy access to major Chicago attractions

3D Tour! Designer Condo near Logan Square
Scan QR code in photos for a 3D Tour! What you’ll love: - Totally renovated garden unit, completed in 2021. Everything new. - Upscale furnishings & decor. - Gourmet, fully equipped kitchen w/ new appliances, coffee maker and spices. - Remote work station w/ super fast Wi-Fi (600mb). - Serta queen mattress in master. - Bunk beds w/ full and twin sized memory foam mattresses. - Heat & A/C.

Just remodeled apartment close to airport and mall
This is just remodeled first floor 1 bedroom apartment that has everything you need for a comfortable stay. Conveniently located 14 min from O'hare airport and 10 min from Woodfield mall that has to offer variety of stores and huge amount of restaurants. All kitchenware for cooking your meals, board games for fun, pool to relax in summer and some snacks to get most out of your stay here.

Picture Perfect 3Bed Steps from Train and FLW
Welcome to your beautiful 3 bedroom home-away-from-home! From the Insta-worthy forest room to the cozy fireplace reading nook to the modern ice crusher in the kitchen, we've put so much thought into this home that we're sure you won't ever want to leave. Welcoming and newly updated, this unit is close to restaurants, shopping, the best of Frank Lloyd Wright, and the train to the city.

Spacious Evanston Unit - Walk to Northwestern U
Welcome to my contemporary and spacious garden level unit located on a tree filled, serene residential block in Evanston. Walking distance to Northwestern University, retail areas, trains, golf, and the lovely beaches of Lake Michigan! A Walgreens and a local brewery restaurant are just a few steps away. Plentiful free street parking and free EV chargers one block away.

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 Cook County condo rentals
Weekly condo rentals

Logan Square Beauty with 2 Bedrooms W/parking

Can't Beat This 2min Walk to Wrigley!

Spacious 5-BR Apt next to transit Free Parking

Wrigleyville Updated Condo with Free Parking

Soft Leather & Warm Bricks in Stylish New Home

Spacious 4 Bedroom Condo

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

1,800ft² Parking Workspace W/D Full Kitch
Pet-friendly condo rentals

816 PLZN Luxury Apartment| Rooftop| Garage Parking

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

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

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

Private Lincoln Park Condo with 2 Parking Spots

Convenient & Spacious 3BR Condo w/Free Parking

Lincoln Square Gem!

Two Bedroom w Porch in Wicker Park
Condo rentals with a pool

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

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

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

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

Pond View, Washer Dryer, Non Smoking Community

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

Iconic Style, Charming Lake View

Pond View, Washer Dryer, Non Smoking, Pet Free
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- Wrigley Field
- Lincoln Park
- United Center
- Soldier Field
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- 875 North Michigan Avenue
- Naval Station Great Lakes
- Six Flags Great America
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Chicago River Walk
- University of Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Donald E Stephens Convention Center
- Frank Lloyd Wright Home and Studio
- Union Park
- Washington Park Zoo
- Garfield Park Conservatory
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