Vacation rentals in Cook County

5 out of 5 average rating, 23 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.

4.86 out of 5 average rating, 116 reviews

Apartment in Forest Park

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

Guest suite in Brookfield

5 out of 5 average rating, 99 reviews

Charming Chicago suburb! 1 bedroom apartment.

Enjoy your stay just west of Chicago in our 1880 updated 1st floor of a 2 flat. You get a one bedroom apartment with queen bed, private kitchen and bath, separate office for work, plus 2 porches for you to enjoy. Brookfield is a charming village with unique restaurants, bars, salon and day spa, coffee shops, library and the train to Chicago--all within a 5 minute walk. We want you to feel at home; but before you book understand that you may not smoke ANYTHING in the unit or on the property.

Private room in Des Plaines

4.88 out of 5 average rating, 331 reviews

R1 Delightful room overlooking the wild forest

My wife and I really like to create coziness in the house and we tried very hard to make our guests like it. We tried so that you not only get a good rest, but also enjoy the beautiful view on the Lake with a lively forest of our guest room. We really love our area of the house because there are many beautiful parks and unusual restaurants. In the end it is a peaceful place to live and in a lovely neighborhood. There may be other guests in the house, so it can be noisy during the day.

4.74 out of 5 average rating, 324 reviews

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

Private room in North Riverside

4.93 out of 5 average rating, 211 reviews

The Albany Park Room at the Cape Cod in Riverside

The Cape Cod in Riverside is 10 miles from downtown Chicago, accessible via METRA and CTA Blue Line. It's a block from a trail entrance, a mile from Brookfield Zoo, and close to Riverside's historic downtown and Loyola University Medical Center. O'Hare Airport is 18 miles away, and Midway is 9 miles. The Albany Park Room, one of two Airbnb listings, is on the second floor and accommodates two guests. The property supports sustainability with partial solar energy for heat and hot water.

Private room in Woodridge

4.86 out of 5 average rating, 495 reviews

Private floor with Bedroom, bathroom, living rm

We are close to all major highways, easy access to go anywhere. Public transportation w/in minutes. Designated parking spot in driveway, also street parking is available. We are next to walking/running trail & parks. Shopping, movies & restaurants are w/in walking distance. Quiet & very safe neighborhood. Shared full kitchen w/ all cook ware available. Private full size fridge/freezer, coffeemaker, toaster oven & microwave. Wifi, streaming, & cable TV. Free on-site laundry & toiletries.

4.9 out of 5 average rating, 157 reviews

Private room in Lyons

Room REN room is Bright and spacious

17 minute drive from Lake Michigan then you’ll be home. The second you walk into this second floor private room named Ren, you'll take a deep breath and feel at home. Ren is 110 sq feet. Has an adjustable work desk, There is an electronic keypad for easy entrance. High Speed WIFI, 26" LCD TV with a firestick. Don't worry about parking. There is a private lot on the property.There is a second washroom and Washer/ Dryer 2 flights of steps downstairs for your convenience.

4.99 out of 5 average rating, 225 reviews

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Condo in Chicago

5 out of 5 average rating, 3 reviews

Chic Chicago Spa Retreat – Luxe & Light-Filled

Experience top-floor luxury in this fully remodeled Avondale condo. Soak in the spa-style bath, bask in natural light from skylights, and relax with cozy furnishings, a king-size bed, and oversized smart TVs. Cook with ease in the sleek, fully stocked kitchen, or explore nearby Logan Square gems and Milwaukee Ave’s dining scene. Garage parking is included, and the Blue Line offers a direct ride to downtown or O’Hare—city access, minus the hassle.

Private room in Richton Park

4.85 out of 5 average rating, 237 reviews

Urbal retreat

On the cusp of urban and rural, urbal. To the north, the sprawling and windy city of Chicago. To the south, farmland and more open spaces. Small bedroom in a nice house on a quiet street. Living space shared with me, my boyfriend, Dillon and my 10 year old son and dog Chase. Walking distance from the train to downtown Chicago. 5 min drive to highway and area with shopping and restaurants.

4.83 out of 5 average rating, 538 reviews

Private room in Chicago

The Blue Room

A spacious single-family home; minutes away from Midway Airport (train station), within walking distance from gorgeous and dog-friendly parks, and walking distance of plentiful of supermarkets and convenience stores. Downtown Chicago is just about 40 minutes away from a train ride.

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Popular amenities for Cook County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Cook County

5 out of 5 average rating, 54 reviews

Home in Schaumburg

Great location-King beds-Kids playroom

SteveRating, 5 stars6 days ago

This Memorial Day some of my family stayed at Ninna's place and they absolutely loved the house! There were 4 spacious bedrooms, a beautiful children's room and the whole house was beautifully set up by Ninna. Would definitely book again!

5 out of 5 average rating, 16 reviews

Home in Chicago

Alluring Avondale Abode

MindyRating, 5 stars2 weeks ago

Beth was an amazing host! Super easy to work with! The place was beautiful, immaculate and comfortable. Would definitely stay there again!

Superhost

Home in Maywood

4.76 out of 5 average rating, 123 reviews

Maywood Relaxation

MadiRating, 5 stars1 day ago

We came for The Weeknd concert in the city, so we got ready there, then spent the night and morning in the house. It was a beautiful house and felt super peaceful and safe! The beds were insanely comfy and we all slept so well! So much space! Everything was just so homey and comfortable.

Superhost

Cottage in Gary

4.92 out of 5 average rating, 50 reviews

Miller Beach Cozy Cottage with indoor fireplace

MattieRating, 5 stars6 months ago

Anna was a responsive & kind host. The house was just as described and the check in was a smooth process. We would enjoy to stay here again in the future.