Vacation rentals in Chicago

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Top-rated vacation rentals in Chicago

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Guest favorite
A spacious living area features two grey sofas, one with an attached chaise lounge, arranged around a rustic wooden coffee table. Soft lighting is provided by a ceiling fan above, while a textured area rug adds warmth to the tiled floor.
Cabin in Waterloo
4.86 out of 5 average rating, 87 reviews

Charming riverfront house

This quiet & serene riverfront house is the perfect setting for a family, nature lovers, fishermen, anniversaries, friends retreats, or honeymooners! Newly remodeled in 2018, we can sleep up to 12. Located just a couple of miles outside of Elkhorn & directly on the Elkhorn River, this is a nature-lovers haven! Local restaurants, shopping & other amenities in Elkhorn, Omaha & Waterloo are within a few minutes drive! Our place is a smoke & pet free home! Smoking is allowed in outdoor areas only.

Guest favorite
A covered patio area features wooden posts supporting a slatted roof. Comfortable seating is arranged around a wooden table. A view of the lush green lawn leads to a wooded area beyond, providing a sense of privacy and connection to nature.
Guest suite in West Omaha
4.88 out of 5 average rating, 170 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?

Top guest favorite
A modern, single-story home features a welcoming front porch with two chairs positioned on a neatly landscaped lawn. The exterior combines sleek white siding and stone accents, complemented by a spacious driveway and a dark-colored garage door.
Home in Omaha
4.98 out of 5 average rating, 91 reviews

King Bed- Pool Table- Arcade Games - West Omaha

This luxurious West Omaha Home has everything you need for the perfect family Vacation. Featuring smart TVs in every room (both living room TV's are 85" & 75" with sound bars), board games, pool table with ping pong table topper, 14' trampoline, corn hole, large kids play-set W/ swings, BBQ and outdoor seating, double water heater, whole home filtration & a reverse osmosis system. The kitchen is fully stocked and we provide extra cooking appliances in the pantry. Minutes to parks & rec areas.

Guest favorite
Home in Omaha
4.95 out of 5 average rating, 55 reviews

Family Fun Basement Retreat w/ Hot Tub Near Dining

Spacious Basement Retreat – Private Entrance This rental is for the basement level only, with a private entrance and a locked door separating it from the upstairs. 2 private bedrooms, a daybed with trundle, 1 full bath, living room with TV, and bar area that seats 4. Fun extras: foosball table, shuffleboard, hot tub, outdoor TV, and board games. The backyard backs up to trees, offering a peaceful and quiet escape. Just minutes from local attractions, dining, shopping, and family fun!

Top guest favorite
A two-story home is framed by lush green trees and shrubbery. The exterior features a mix of dark siding and a steep roof. An inviting pathway leads to the front porch, where soft lighting highlights the entrance. A well-maintained lawn enhances the curb appeal.
Guest suite in West Omaha
4.91 out of 5 average rating, 119 reviews

Private Space, Walk-Out Basement of suburban home.

Our cozy, quiet, home backs to walking trail, creek & prairie. Easy access to interstate, restaurants & shopping. You have private access to our walk-out basement w/bedroom, living room, bathroom, and kitchenette, + board games, books, ping pong, our backyard and a nearby park. The bedroom has a Cal King bed & dark, cool sleeping. The family room includes two twin beds and a twin mattress on floor, plus our large comfy sofa and floor to ceiling windows showcasing our green space.

Top guest favorite
A ranch-style home is depicted with a well-maintained lawn and shrubs. A two-car garage is visible on the left, and large windows provide natural light to the living areas. The clear blue sky enhances the inviting appearance of the welcoming exterior.
Home in Omaha
4.92 out of 5 average rating, 169 reviews

Inviting Place To Call Home For A While

This is a lovely home, in a very family oriented neighborhood. The rooms are all good sized. My home has been freshly painted. I have the carpet cleaned, and also top to bottom, thorough cleaning done on a regular basis. I am not in the airbnb business. Two of my children live in Nebraska, everyone else is in NJ. So we go back and forth. Our home is located in Western Omaha, a very quiet area, yet within 20/30 minutes of everything. Including the zoo, downtown, and the outlets.

Top guest favorite
The exterior of a two-story house is depicted, featuring a light brown siding and a brown shingle roof. A concrete driveway leads to a garage, while steps invite entry to the front door. Lush greenery surrounds the home, enhancing the inviting appearance.
Home in Waterloo
4.91 out of 5 average rating, 107 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, 130 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!!

Top guest favorite
An expansive living area features large windows that provide a view of the surrounding landscape. High ceilings are complemented by wooden beams. A comfortable seating area includes a dark sofa, and a foosball table is visible in the space, enhancing the recreational atmosphere.
Home in Omaha
4.96 out of 5 average rating, 103 reviews

Hangar 1 with a river view

Large secluded home with a private drive and an amazing view! This three bedroom, three full bath home with an aviation theme, has plenty of space with a view of the Missouri River and a hot tub off of the master. Three queen beds, a twin with a twin trundle, and a pull out couch can sleep up to 10. Foosball and air hockey tables. There is a bike path at the end of the driveway and only a 7 min drive to Eppley Airfield.

Guest favorite
Home in Omaha
4.95 out of 5 average rating, 310 reviews

*Romantic* Rose Cottage with Hot Tub in Benson

Romantic Rose Cottage, north Benson. Minutes from UNMC, Downtown, CWS, CHI Center, Zoo, Dundee & Benson Restaurants. Beautifully designed space, perfect for short getaways and comfortable for long term stays . Wood floors, Essential cooking items, Breakfast nook with table for dining/work space. Large off street parking for 2 cars. Washer & Dryer in basement. Furry family members welcome. Fully fenced back yard.

Top guest favorite
A newly remodeled kitchen is visible, featuring light-colored cabinets and a marble countertop. Stainless steel appliances, including a refrigerator and gas stove, are present. A small kitchen island with stools adds extra seating, while a rug enhances the room's warmth.
Home in Omaha
4.9 out of 5 average rating, 105 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
A spacious living area showcases a large, L-shaped sectional sofa in a rich brown hue. A wooden coffee table is centered on a textured area rug, with light streaming in through multiple windows. A television and entertainment unit complement the cozy space.
Home in Omaha
4.96 out of 5 average rating, 134 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.

Popular amenities for Chicago vacation rentals

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