Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

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

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Top guest favourite

Flat in Chicago

5 out of 5 average rating, 61 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Guest favourite

Flat in Cicero

4.96 out of 5 average rating, 342 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

Guest favourite

Flat in Berwyn

4.9 out of 5 average rating, 349 reviews

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

Guest favourite

Flat in Near North Side

4.83 out of 5 average rating, 827 reviews

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Guest favourite

Private room in Norwood Park

4.85 out of 5 average rating, 115 reviews

Private, Cozy Bedroom Near O’hare in Norwood Park

Highlights: -Beautiful hiking/biking trail nearby -Close to major highways -Downtown Chicago: 12 miles -O’hare airport, Rosemont, Donald Convention Center, All-State Arena: 3 miles -Advocate Lutheran Hospital: 5 miles -Amita Resurrection Health Center: 1.4 miles Note: this is a basement room. You’ll be sharing the bathroom and kitchen with 2 other Airbnb guests *Only one guest allowed per room. No exceptions! All guests will be asked to leave if multiple guests are present.

Guest favourite

Flat in Lower West Side

4.85 out of 5 average rating, 308 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond to our house rules.

Guest favourite

Private room in Hyde Park

4.92 out of 5 average rating, 285 reviews

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.

Guest favourite

Private room in Des Plaines

4.88 out of 5 average rating, 367 reviews

R1 Delightful room in quiet neighborhood

A cozy room located in peaceful neighborhood, a perfect place to stop after traveling from O'Hare airport! We have a beautiful wild river, lake, and forest right in the backyard and surrounding our area, with wild life creating a cozy atmosphere, amazing to take walks. We are a 10 minute ride from the O'Hare International Airport, a 5 minute ride from a Metra Station, and surrounded by all kinds of parks and interesting restaurants.

Guest favourite

Flat in Lake View

4.94 out of 5 average rating, 140 reviews

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

Guest favourite

Private room in Calumet City

4.97 out of 5 average rating, 135 reviews

Private Spacious Room in a shared house.

House located in Calumet City, not far from Franciscan Hammond hospital, 10 minutes away to Ford Plant, 19 minutes away to Horseshoe Casino, 18 minutes away to the BP Plant and Purdue University. Dining area and family room with television and WiFi. These areas are shared with other guests. Private room has a full bed, tv, closet and office desk and mini fridge.

Top guest favourite

Apartment in Noble Square

4.97 out of 5 average rating, 840 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Private room in Bolingbrook

4.84 out of 5 average rating, 203 reviews

Comfy SUPER MEM FOAM BED, EZ smart entry! Cable

Full size LUXURY MEMORY FOAM bed. MICROWAVE & MINI FRIDGE right in room! Cable TV. Beautiful nature centers, jogging paths, lakes and parks all near by! Asian and American buffets, Olive Garden, Home Run Inn, McDonald's, Burger King and much more within minutes! Beautiful, safe area, Water Park, bating range. Cakes & coffee, spring water, fruit & more.