Vacation rentals in Chicago

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Top-rated vacation rentals in Chicago

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

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Top guest favorite
An outdoor dining area is set beside a tranquil lake, featuring a dark wooden table surrounded by six black chairs. An umbrella provides shade, while the water reflects the nearby houses and greenery. A pathway leads to the water's edge, suggesting opportunities for relaxation.
Guest suite in Waterloo
4.98 out of 5 average rating, 110 reviews

Lake Life (Something For All Ages & Seasons)

Beautiful private lower level, walk-out lake front in a quiet neighborhood. Spacious living quarters. Fireplace, full kitchen, bar, dining area, big screen TV. Bedroom has a queen bed. 2nd TV area has a queen Murphy bed. Bathroom has 2 sinks & a shower. Laundry room has a washer/dryer. Outdoor space includes a covered patio & hot tub, outdoor kitchen with chef's grill, refrigerator & fire pit. Kayaks, paddle boards, 2-person canoe, floats & fishing poles are available. Event Fee varies.

Guest favorite
Guest suite in Omaha
4.89 out of 5 average rating, 161 reviews

Private Suite with Nature Views-Full Washer/Dryer

Backing to a wooded creek this home away from home is sure to be the relaxing place you are waiting for. This is a separate entrance lower level walkout apartment complete with kitchen, laundry, spacious bedroom, and 3/4 bath. Amenities include fiber gigabit high speed internet, smart TV (w/ Netflix), coffee bar able to brew ground coffee or K Cups, and dedicated off street driveway parking for two vehicles parked tandem. Please reach out if you have special requests or accommodations in mind?

Superhost
Apartment in Aksarben - Elmwood Park
4.72 out of 5 average rating, 411 reviews

Petite & Charming- Near Aksarben and Baxter Arena!

-Triplex (garden level) -Located in the Historical Aksarben neighborhood, a few Blocks from Baxter Arena, Aksarben Village, University of Nebraska at Omaha, and Creighton University Medical Center (Bergan Mercy)! -Short 5-10min Uber/Lyft to Midtown, Blackstone, Downtown! -Professionally Decorated -Loads of Character -WiFi -Roku Smart TV with Netflix and Sling tv access for streaming channels -Secured Coded Entry -Fully stocked kitchen for cooking -Limited on-site parking/no oversized vehicles

Superhost
Apartment in Omaha
4.77 out of 5 average rating, 62 reviews

Charming Dundee Fairview Apartment #10

Discover an inviting 1B/1B apartment nestled in the historic Dundee neighborhood of Omaha, within the iconic Fairview apartments designed by Henry Frankfurt in 1917. This inviting residence provides a central location with a beautifully updated interior and an outdoor balcony with courtyard views. You are a short walk from Dundee's finest restaurants and shops, 1.5 miles to the University of Nebraska Medical Center & 2.1 miles to Creighton University Medical Center. Come enjoy this space!

Top guest favorite
A cozy room features a spacious bed with a striped comforter and decorative pillows. A comfortable couch sits beside a bedside table and lamp, creating a welcoming area. A dresser is positioned against the wall, and soft lighting gives the space a warm feel.
Apartment in Papillion
4.94 out of 5 average rating, 358 reviews

Coastal Retreat Getaway, Secluded, Off 370/I-80

Step into a private and cozy space. Relax watching TV in bed or on the couch. This place is part of our walk out basement, so you may hear day to day living upstairs. For your safety there is a Ring camera installed at the entrance and will light up the entryway when it’s dark. Parking is on the well lit public street. Easily walk up our dedicated Airbnb sidewalk, no steps, walk around to the back of the house. You’ll be in a serene space that makes you feel right at home.

Superhost
Guest suite in Omaha
4.79 out of 5 average rating, 234 reviews

Nestled in Nature

A mother-in-law suite perfect for individuals to families looking to stay in the prestigious Millard area. We are steps away from gorgeous Lake Zorinsky, golf courses, shopping, and other amenities. You can expect a friendly neighborhood, a full kitchen, gas fireplace, and natural light! Our shared backyard has a large fire pit, outdoor dining, and the gorgeous NE sunset. Lastly, check in is 6p and check out is 10a. *Please expect some noise from the main residence, above*

Top guest favorite
An outdoor seating area features several wooden chairs and tables surrounding a central fire pit. The space is paved with bricks, providing a clean, defined gathering spot. Green grass and a fenced yard create a spacious and open atmosphere for relaxation.
Home in Waterloo
4.9 out of 5 average rating, 102 reviews

Comfortable, 3-bedroom home on a quiet cul-de-sac

Welcome to a home away from home, conveniently located in the "backyard" of Omaha! All of our guests have full access to the entire home, located on a large corner lot in a quiet cul-de-sac. Less than 30 minutes from downtown (think Omaha Zoo, Century Link Center, etc.). Less than 20 minutes from I-80 and popular Omaha neighborhoods like Aksarben Village, and Midtown Crossing are only 15-20 minutes away. Only blocks away from some of the best restaurants around as well!

Top guest favorite
A spacious living area is filled with natural light from large windows. A teal sectional sofa is complemented by light-colored armchairs and a round coffee table. A textured area rug covers the hardwood floor, while a decorative plant and wall clock add subtle accents.
Home in Omaha
4.95 out of 5 average rating, 124 reviews

Light & Bright 4 bedroom Home in West Omaha

Cheerful family friendly 4 bedroom home in the heart of Southwest Omaha. Close to great restaurants and shopping. All Brand new furniture/decor and super comfy memory foam beds will have you basking in these boho modern vibes. 1 mile to Zorinsky Lake with beautiful walking trails and fishing. 2 miles to Legacy village with Lifetime Fitness & great food options. 5 miles to Village Pointe for many more shopping and dining options. You'll Love it!!

Superhost
A cozy living area features a bright yellow sofa and a round coffee table placed on a decorative rug. A flat-screen television is mounted on the wall. The kitchenette, equipped with modern appliances, is visible in the background, adjacent to a bedroom area with a queen-sized bed.
Apartment in Omaha
4.84 out of 5 average rating, 135 reviews

Inviting Pet Stay, Near the Zoo and Dining!

- Enjoy your stay with a private entrance and a dedicated workspace for convenience. - Bring your furry friend to this pet-friendly unit, perfect for a home-like experience. - Centralized location with restaurants, shops, and main attractions minutes away. - Easily accessible with free parking on-site, ensuring stress-free arrivals. - Book now for a cozy, amenities-filled stay and warm hospitality from Joanne!

Guest favorite
The exterior of a two-story home features light grey siding with contrasting dark brick accents. A welcoming front entrance is illuminated by soft lighting, and manicured landscaping lines the walkway. A driveway and stairway lead to the entrance, adding to the home's inviting curb appeal.
Home in Omaha
4.9 out of 5 average rating, 96 reviews

Warm & Welcoming Home

Newly remodeled and freshly furnished! Relax with the whole family or a group of friends at this comfortable home in West Omaha. Close to shopping, restaurants, coffee shops, golf courses, park, walking trail, and more, this home is a perfect place to unwind and recharge while away. Enjoy the spacious fenced back yard, deck and chairs. Exceptional neighborhood park nearby and toys for the kids in the garage.

Guest favorite
The exterior of the basement unit features a private entrance with wooden stairs leading to an upper deck. A pathway lined with stones and greenery guides towards the entrance. The surrounding yard displays a lawn, shrubs, and trees, offering a natural and spacious environment.
Home in Elkhorn
4.98 out of 5 average rating, 125 reviews

Private Basement Unit in West Omaha

Unwind and relax in our contemporary and spacious basement unit located in the suburbs of Omaha. The home is located in the Grove neighborhood, which is very safe and has a park, splash pad, and walking paths. The neighborhood is minutes from Village Pointe shopping area, twenty minutes from Old Market and the downtown area, and half an hour from the airport.

Top guest favorite
Home in Omaha
4.93 out of 5 average rating, 120 reviews

2 bedroom villa with garage in quiet neighborhood

2 bedroom villa in a popular SW Omaha neighborhood. Near Village Point and lakeside shopping areas. Also close to many dining venues, movies, hospitals and more. 2 large bedrooms and a pull out couch in the lower level. Garage available for parking. Patio is open to the common area . Close to walking paths and park. Fully furnished with all necessities.

Popular amenities for Chicago vacation rentals

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