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Apartment holiday rentals in Chicago

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Top-rated apartment rentals in Chicago

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Apartment in Lansing

4.82 out of 5 average rating, 103 reviews

The Broadway Special - 2 Bd/1 Bath Smart-Condo!

The "Suite" Escape: This is the perfect home for families or those traveling alone. Located in Lansing less than 5 mins from Indiana. Right off of I90/294 expressway for a easy commute. It's near shopping centers and restaurants. Our smart home has 65 inch Amazon Fire TVs, high-speed internet, gaming options and free streaming platforms. You can enjoy a quiet home away from the city. We look forward to you enjoying our accomodations. Monthly rentals are welcomed and longer stays are perferred.

Guest favourite

Apartment in Bridgeport

4.9 out of 5 average rating, 107 reviews

Convenient & Spacious 3BR Condo w/Free Parking

Get cozy in this spacious 3-bedroom condo, conveniently located 3 blocks from the Halsted Orange Line overlooking Palmisano Park and only 5 minutes' drive to McCormick Place. Clean, neat, modern and comfortable, the condo offers spacious living space with an open kitchen, washer/dryer, and an outdoor balcony perfect for families and groups. Hungry? Our complex offers a few delicious high rated yelp restaurant options to fulfill your appetite. We look forward to hosting you and your guests!

Apartment in Lincoln Park

4.81 out of 5 average rating, 155 reviews

Massive Old Town Home Steps to Wells St & Beach

Start your Windy City adventures in my spacious 3rd-floor duplex in the heart of Chicago's vibrant Old Town neighborhood! This 8 bed, 4 bath home comfortably sleeps up to 20 guests, making it perfect for large groups or families. Enjoy modern furnishings, a fully equipped kitchen and two cozy living areas to relax in after exploring the city. Steps from popular restaurants, bars, boutiques and the lake, you’ll be immersed in local charm. (Please note, parties and large events are not allowed)

Guest favourite

Apartment in Uptown

4.92 out of 5 average rating, 144 reviews

Stunning, Spacious, & Sunny 2bed Uptown Condo

Welcome to your home away from home in Uptown! My bright and inviting condo offers a perfect blend of comfort and convenience, with your own sunny living room to relax, fully-equipped kitchen and separate dining room, spacious private bedroom, serene sunroom with full bed for extra guests, and a workspace for business travelers. Just steps from the lakefront and Montrose Beach, and a 6-minute walk to the Wilson Red Line, this location is excellent for exploring all that Chicago has to offer.

Guest favourite

Apartment in Lincoln Park

4.91 out of 5 average rating, 100 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

This bright and airy 2 bedroom/2 bath condo has been completely renovated with a designer’s eye and creative touch. The condo comes with 2 parking spaces in the adjacent private gated parking lot. The covered patio space on the back deck offers spectacular views of the Chicago skyline – enjoy your morning coffee or evening cocktail overlooking the city. L Train Stops & tons of restaurants, bars and entertainment within walking distance. Please contact me for discounts on monthly stays!

Guest favourite

Apartment in West Town

4.92 out of 5 average rating, 109 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

Experience a calm and soothing stay in a space bathed with light and nestled amongst the trees. This top floor unit in a 3-flat condominium building offers you the serenity of a neighborhood with tree lined streets, and the convenience of being 3 miles from the heart of downtown Chicago. As a bonus, you're a 2min walk from public transportation. For something closer to home, Wicker Park and Humboldt Park offer great dining and culture steps away. We look forward to hosting you!

Guest favourite

Apartment in River North

4.98 out of 5 average rating, 127 reviews

Luxurious River North 3BR/2BA- Free Onsite Parking

Experience an urban oasis unlike any other: - Complimentary parking for one vehicle in our attached lot - Spacious, recently renovated kitchen - Immersive entertainment with large-screen TVs - Unwind with a game of poker or foosball at our dedicated tables - Conveniently located within walking distance of the Magnificent Mile - Surrounded by an array of vibrant bars, restaurants, and nightlife - Embrace our inviting patio Indulge in a memorable stay at our 3rd-floor condo!

Guest favourite

Apartment in River North

4.92 out of 5 average rating, 142 reviews

Brilliant Downtown Chicago 3-Bedroom Condominium

Situated in downtown Chicago, right next to the Godfrey Hotel, this spacious and bright 3-bedroom, 2-bathroom condominium is perfectly suited to deliver the best adventures the Windy City has to offer. Our vacation home includes four sleeping areas with 1 King & 3 Queen sized memory foam mattresses and features everything from a fully-stocked kitchen to smart gadgets like Alexa. PARKING: We offer a $30 per day parking credit. This credit pays for most or all parking costs.

Guest favourite

Apartment in West Town

4.99 out of 5 average rating, 150 reviews

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.

Guest favourite

Apartment in Uptown

4.98 out of 5 average rating, 256 reviews

Near Lake Michigan & Wrigley Field

Available 2B/2B condo with 2 King Size Beds. One block from the Aragon Ballroom and Riviera with great views of Uptown and two blocks from Lake Michigan. It’s also a perfect place to stay if your in town for a Cubs game. You can see the stadium from the rooftop deck. Walking distance to everything you need, 2 train stations, groceries, gym, restaurants/ bars. The perfect place to come and go as you please with easy key code entry.

Apartment in Wicker Park

4.83 out of 5 average rating, 335 reviews

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!

Guest favourite

Apartment in Edgewater

4.97 out of 5 average rating, 105 reviews

Steps from the Lake, Lovely 3-Bedroom Condo

Enjoy all that Chicago has to offer in this beautiful Edgewater home. Lakefront beaches are steps away, as is the red-line Granville stop. This condo is walking distance to the Loyola campus, many restaurants, grocery stores, gyms, antique stores, and more! There is ample street parking on Lakewood, often there is a space right outside the house. We provide daily parking passes for you to use during your stay.

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Popular amenities for Chicago apartment rentals

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Guest favourite

Apartment in Wicker Park

4.96 out of 5 average rating, 25 reviews

City View 3BR Condo/Garage Parki

Guest favourite

Apartment in West Town

4.96 out of 5 average rating, 46 reviews

NEW! Spacious Modern 5 BD Condo

Apartment in Wicker Park

4.84 out of 5 average rating, 181 reviews

Loft-Like Wicker Park Condo Steps from the Cta!

Guest favourite

Apartment in Lake View

4.92 out of 5 average rating, 13 reviews

Cozy, sunny, boho condo in Uptown/Sheridan Park

Apartment in East Rogers Park

4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

Guest favourite

Apartment in West Town

4.92 out of 5 average rating, 257 reviews

Modern/Spacious 2BR/2BA West Town

Guest favourite

Apartment in Chicago

4.92 out of 5 average rating, 144 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

Apartment in East Rogers Park

4.79 out of 5 average rating, 125 reviews

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach

Pet-friendly apartment rentals

Guest favourite

Apartment in Pilsen Historic District

4.86 out of 5 average rating, 126 reviews

816 PLZN Luxury Apt | Rooftop | Garage Parking

Guest favourite

Apartment in Lincoln Square

4.93 out of 5 average rating, 107 reviews

The Fox Den

Guest favourite

Apartment in Lake View

4.95 out of 5 average rating, 105 reviews

The Bagel Inn - Bright & Modern Wrigleyville 2 Bed

Guest favourite

Apartment in Chicago

4.89 out of 5 average rating, 108 reviews

Unique 2BR/2BA FREE Parking/WI-FI Minutes From DT

Apartment in The Loop

4.85 out of 5 average rating, 124 reviews

Downtown Mich Ave #7| Park View Penthouse +gym

Apartment in Lake View

4.82 out of 5 average rating, 135 reviews

Spacious Home, Incredible Lakeview Location

Guest favourite

Apartment in East Rogers Park

4.92 out of 5 average rating, 221 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Guest favourite

Apartment in Logan Square

4.91 out of 5 average rating, 329 reviews

Susie's Space. 2BR easy parking & pet friendly

Apartment rentals with a pool

Guest favourite

Apartment in Evanston

4.95 out of 5 average rating, 87 reviews

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

Guest favourite

Apartment in Evanston

4.96 out of 5 average rating, 99 reviews

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

Apartment in The Loop

New place to stay

voco: Balcony & City View

Guest favourite

Apartment in Elk Grove Village

4.95 out of 5 average rating, 78 reviews

Just remodeled apartment close to airport and mall

Guest favourite

Apartment in Evanston

4.91 out of 5 average rating, 120 reviews

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

Apartment in Uptown

4.8 out of 5 average rating, 25 reviews

Lovely condo studio

Guest favourite

Apartment in Evanston

4.96 out of 5 average rating, 93 reviews

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

Quick stats about apartment rentals in Chicago

Total rentals
1.1K properties
Total number of reviews
67K reviews
Family-friendly rentals
650 properties are a good fit for families
Pet-friendly rentals
310 properties allow pets
Rentals with a pool
90 properties have a pool
Rentals with dedicated workspaces
660 properties have a dedicated workspace

Destinations to explore