Cook Area, Illinois Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Cook Area, Illinois on RentalSaver.com!

Cook Area Rentals

From $250 per night (USD)
VRBO
Quirky Quarters at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: I think you are just going to love my apartment. The space features wonderful large street level windows in th ...
From $250 per night (USD)
VRBO
From $382 per night (USD)
Expedia
One-of-a-Kind Apartment In Old Town!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: This unique and spacious two bedroom garden unit is the perfect place for anyone visiting Chicago! You won't r ...
From $382 per night (USD)
Expedia
From $288 per night (USD)
VRBO
Fifty Shades of Greige
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: I’m an interior designer and longtime Superhost who believes you deserve better than scratchy sheets and a sus ...
From $288 per night (USD)
VRBO
From $265 per night (USD)
Expedia
The Sassy Sanctuary at Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $265 per night (USD)
Expedia
From $230 per night (USD)
VRBO
The Shingle Life near Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: I took a perfectly nice little flat on a beautiful street and filled it with great things...I want my guests t ...
From $230 per night (USD)
VRBO
From $234 per night (USD)
Expedia
The Lilac Loveshack at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $234 per night (USD)
Expedia
From $245 per night (USD)
VRBO
Campy! Wrigley Campground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $245 per night (USD)
VRBO
From $217 per night (USD)
Expedia
A Hand-some Place Near Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: I’m an interior designer and longtime Superhost who believes you deserve better than scratchy sheets and a sus ...
From $217 per night (USD)
Expedia
From $341 per night (USD)
VRBO
The Fratterhorn at Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $341 per night (USD)
VRBO
From $230 per night (USD)
Expedia
No Place Like Gnome at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This is such a lovely spot and I think you will quite like it. The space features wonderful large windows in a ...
From $230 per night (USD)
Expedia
From $229 per night (USD)
VRBO
A Novel Situation at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This is such a lovely spot and I think you will quite like it. The space features wonderful large windows in a ...
From $229 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Keepin’ it Golden at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $250 per night (USD)
Expedia
From $308 per night (USD)
VRBO
The Codfather at Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $308 per night (USD)
VRBO
From $393 per night (USD)
Expedia
The Ivy Flat | Designer 4BR Steps to Wrigley Field
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: This 4BR/2BA apartment is a 7-minute walk from Wrigley Field and perfect for groups. There's tons of room to s ...
From $393 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Sunnyside Up! • Vintage 1 Bed at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: My new place has lots of room to spread out and all of the quirky charm that vintage buildings offer up. The l ...
From $254 per night (USD)
VRBO
From $403 per night (USD)
Expedia
The Mason - Luxe 2BR Designer Flat in Bucktown/WP
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: We invite you to spend your next trip in this beautifully remodeled 2BR flat in Chicago's iconic Wicker Park n ...
From $403 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Feelin’ Blue-tiful at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This is such a lovely spot and I think you will quite like it. The space features wonderful large windows in a ...
From $240 per night (USD)
VRBO
From $229 per night (USD)
Expedia
Taj Ma-small at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: I think you are just going to love my apartment. The space features wonderful large windows in both rooms and ...
From $229 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Tickled Pink • Vintage 1 Bed at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: My new place has lots of room to spread out and all of the quirky charm that vintage buildings offer up. The l ...
From $254 per night (USD)
VRBO
From $1444 per night (USD)
Expedia
Gold Coast Home - Rooftop - PoolTable - Parking - Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious Gold Coast Townhome – Offers Indoor Games, Rooftop, Parking & More! Experience the best of Chicago in this st ...
From $1444 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Pristine Chicago Home - 3BD - 2BA - Free Parking - 2
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Free Parking!! Step into luxury in this modern loft with 3 bedrooms, and 2 bathrooms & experience the feeling of being a ...
From $342 per night (USD)
VRBO
From $627 per night (USD)
Expedia
Pool Table! Pet-Friendly Haven 6 Mi to Rate Field
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1 Mi to Red Line | Main Living Area + Social Lounge | Spacious Backyard | 10 Mi to Downtown Designed for groups who lov ...
From $627 per night (USD)
Expedia
From $725 per night (USD)
VRBO
2,400 SF 4BR + 2 Parking | Steps to Wrigley
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Experience The Clubhouse at Wrigley Thoughtfully designed for gathering, relaxing, and making memories, The Clubhouse a ...
From $725 per night (USD)
VRBO
From $222 per night (USD)
VRBO
The Gilded Grid | Sleeps 8
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience modern luxury just moments from Wrigley Field in this brand-new 4-bedroom, 3.5-bath duplex that sleeps up to ...
From $222 per night (USD)
VRBO
From $342 per night (USD)
VRBO
Pristine 2BD - 2.5BD Duplex - Chicago - Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover comfort and privacy in our stylish duplex apartment just steps from Lake Michigan. This 2-bedroom, 2.5-bath hom ...
From $342 per night (USD)
VRBO
From $613 per night (USD)
Expedia
Elegant Historic Duplex in Old Town • Lincoln Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience the charm of Chicago’s historic Old Town from this beautiful duplex on a quiet, tree-lined street. Steps to W ...
From $613 per night (USD)
Expedia
From $106 per night (USD)
VRBO
Cozy 1 bed, furnished apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the beauty of Wrigelyville in this furnished 1-bedroom apartment. Step into a peaceful space where comfort meet ...
From $106 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Spacious 4 bedroom/3 full bathroom Family Friendly Perfect for Group& Long Stays
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
★ 4 Bedrooms, 3 full bathrooms ★ Can sleep 9 people ★ Rest peacefully in a king-size bed ★ Open Kitchen Floorplan ★ Stay ...
From $292 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Luxury Wrigley Getaway | 2BR + Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience the best of Wrigleyville in this stylish 2-bedroom retreat with free parking. Perfect for couples, small fami ...
From $479 per night (USD)
VRBO
From $157 per night (USD)
Expedia
Vibrant Getaway in the Windy City of Chicago
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy a peaceful stay at this 3-bedroom one bath apartment in Chicago offers the perfect blend of city proximity and res ...
From $157 per night (USD)
Expedia
From $209 per night (USD)
VRBO
2-bedroom condo in serene Broadview with AC for relaxing stays
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Your Broadview adventure begins at this 2-bedroom condo. Inside, guests find a nice king bed and a queen bed, perfect fo ...
From $209 per night (USD)
VRBO
From $421 per night (USD)
VRBO
Memorable Vacation, Short Drive To Arlington Heights Historical Museum!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Stay close to George Clayson House Museum and Legoland Discovery Center! This listing is for 2 separate rooms within a ...
From $421 per night (USD)
VRBO
From $227 per night (USD)
VRBO
Beautiful 32' RV located in Chicago's South suburb - A unique experience!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience Alsip like a local in this charming one bedroom mobile home. Whether you are looking for a romantic getaway ...
From $227 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Chicago O’Hare Modern Hotel‑Style Stay w/parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to your stylish hotel‑inspired getaway near Chicago’s O’Hare Airport! This bright and spacious 1‑bedroom condo i ...
From $334 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Beautifully furnished one bedroom loft located in Chicago's South side suburb
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Unwind in Alsip at this cool house perfect for a relaxing getaway. With one comfortable bedroom and two bathrooms, guest ...
From $344 per night (USD)
VRBO
From $620 per night (USD)
Expedia
Wrigley Luxe Stay | 3BR | Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy the comfort of our beautifully designed 3-bedroom home just minutes from Wrigley Field! Perfect for families, frie ...
From $620 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Luxury 4BR Home with Spa Tub & fire place Near UChicago & Obama Center
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, g ...
From $426 per night (USD)
VRBO
From $154 per night (USD)
VRBO
2-bedroom 1 bath stylish apartment in nice Chicago for relaxing stay
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This memorable apartment is the perfect home base for your trip to Chicago. Guests will enjoy two comfortable bedrooms, ...
From $154 per night (USD)
VRBO
From $256 per night (USD)
VRBO
Charming 3-bedroom townhome in vibrant Evanston - 30 day min.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly designer-remodeled 3-bedroom, 2.5-bath corner townhome in a quiet residential neighborhood, just a short walk to E ...
From $256 per night (USD)
VRBO
From $574 per night (USD)
Expedia
Stunning 3bdrm, steps to North Eastern University, Luxurious, Gourmet kitchen🌟
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Greetings from “The Bernard at Hollywood Park” located on the Northside of Chicago! Our luxury three bedroom, one bath a ...
From $574 per night (USD)
Expedia
From $417 per night (USD)
VRBO
Stunning 4-bedroom house with 2 living areas perfect for relaxing stays
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Your cozy getaway awaits at this gorgeous house. With four bedrooms, each featuring a queen bed, guests can relax comfor ...
From $417 per night (USD)
VRBO
From $115 per night (USD)
VRBO
Detached, private, spacious, free garage, fast wifi, 5min to metra in Ravenswood
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Fully renovated in July 2025, this charming detached coach house from 1897 blends historic character with modern comfort ...
From $115 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Beautiful Mid-Century Oasis in South Shore.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This mid century masterpiece is one of kind, offering a beautiful open living space with lots of natural light through a ...
From $531 per night (USD)
VRBO
From $686 per night (USD)
Expedia
3 Units | Near Chicago River | Downtown Location
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in Chicago's River North neighborhood, this hotel offers convenient access to the vibrant dining and nightlife s ...
From $686 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Pool, Gym & Basketball Court: Olympia Fields Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Quiet Neighborhood w/ Wildlife Sightings | Day Trip to Chicago | 3,200 Sq Ft Make the most of your South Suburbs escap ...
From $320 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Space: Welcome to our beautiful Logan Square apartment! Experience Chicago like a local in this spacious 2-bedroom, ...
From $328 per night (USD)
Expedia
From $393 per night (USD)
VRBO
Lovely 3-bedroom condo Walking Distance to United Center and Futon for extra bed
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Chicago is waiting for you at this 3-bedroom condo. Inside, guests find two full beds and one queen bed, also included a ...
From $393 per night (USD)
VRBO
From $308 per night (USD)
VRBO
Spacious 3BR near United Center: Deck & Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Experience ultimate comfort in this charming home, steps away from the United Center. Catch a game or concert, ...
From $308 per night (USD)
VRBO
From $384 per night (USD)
VRBO
Luxury Penthouse Collection PH1 - Fulton Market
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: BRAND NEW PENTHOUSE IN FULTON MARKET! Enjoy your new private penthouse in one of Chicago's newest and mos ...
From $384 per night (USD)
VRBO
From $485 per night (USD)
Expedia
Luxury Penthouse Collection PH4 - Fulton Market
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: BRAND NEW PENTHOUSE IN FULTON MARKET! Enjoy your new private penthouse in one of Chicago's newest and mos ...
From $485 per night (USD)
Expedia
From $276 per night (USD)
VRBO
2 Stylish Rooms Close to Green Lake, Pet-Friendly & w/ Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
We offer a relaxing retreat with modern rooms featuring flat-screen TVs, a refrigerator, and a microwave. Conveniently l ...
From $276 per night (USD)
VRBO
From $145 per night (USD)
VRBO
Affordable Pet-Friendly Room w/ Free Parking – Ideal Family & Group Stays
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We offer a relaxing retreat with modern rooms featuring flat-screen TVs, a refrigerator, and a microwave. Conveniently l ...
From $145 per night (USD)
VRBO
From $145 per night (USD)
VRBO
Charming Pet-Friendly Room w/ Free Parking - Near South Holland Metro
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We offer a relaxing retreat with modern rooms featuring flat-screen TVs, a refrigerator, and a microwave. Conveniently l ...
From $145 per night (USD)
VRBO
From $276 per night (USD)
VRBO
2 Pet-Friendly Rooms Near South Holland Metro | Convenient I-94 Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
We offer a relaxing retreat with modern rooms featuring flat-screen TVs, a refrigerator, and a microwave. Conveniently l ...
From $276 per night (USD)
VRBO
From $123 per night (USD)
VRBO
Pet-Friendly Room w/ Free Parking – Great for Solo & Business Travelers
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
We offer a relaxing retreat with modern rooms featuring flat-screen TVs, a refrigerator, and a microwave. Conveniently l ...
From $123 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Cozy Coach House - Step Outside to Frank Lloyd Wright Architectural Icons!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Private coach house in the heart of Oak Park’s Frank Lloyd Wright Historic District. Tucked away and peaceful, yet just ...
From $220 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Near UChicago, 3BR Apt, Parking, W/D, 2 Workspaces
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Work-ready 3BR, 2BA apartment located just minutes from UChicago and several major hospitals. Once inside, everything is ...
From $255 per night (USD)
VRBO
From $306 per night (USD)
VRBO
Pilsen Retreat: 4BR 3BA near Downtown Chicago
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Discover one of Chicago's most vibrant neighborhoods from this stylish 4-bedroom retreat in vibrant Pilsen. St ...
From $306 per night (USD)
VRBO
From $373 per night (USD)
VRBO
3-bedroom house in beautiful Des Plaines with cool AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Unwind in Des Plaines at this marvelous house. With three cozy bedrooms featuring two queen beds and one twin bed, guest ...
From $373 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Brown Line Lounge | Curated Moody
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space Welcome to Brown Line Lounge. Samantha and I designed this 3BR/2BA North Center apartment around every ...
From $243 per night (USD)
Expedia
From $148 per night (USD)
VRBO
Near O’Hare Airport + Breakfast. Shuttle. Pool.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Steps from the Allstate Arena and minutes from O'Hare International Airport, Staybridge Suites Chicago O'Hare offers the ...
From $148 per night (USD)
VRBO
From $157 per night (USD)
Expedia
Close to O’Hare Airport + Free Breakfast & Shuttle
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Steps from the Allstate Arena and minutes from O'Hare International Airport, Staybridge Suites Chicago O'Hare offers the ...
From $157 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Bright & Cozy Homewood 3 Bed with Arcade Game!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our spacious and comfortable 3-bedroom, 2 bath home in the charming village of Homewood, Illinois—perfect for ...
From $264 per night (USD)
VRBO
From $364 per night (USD)
Expedia
Modern 3BR Apt Near United Center
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this brand-new, stylish 3-bed, 2-bath Chicago apartment! Featuring a chic contemporary design with plush velve ...
From $364 per night (USD)
Expedia
From $417 per night (USD)
VRBO
Aqua House - Stylish Modern Home Yard & Deck Schaumburg O'Hare
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Experience a modern and quiet retreat in our big 4 Bedroom 2.5 Bathroom Split level house. Perfect blend of comfort and ...
From $417 per night (USD)
VRBO
From $835 per night (USD)
Expedia
Spacious 7-bedroom house in gorgeous Lincoln Park Chicago with AC
Bedrooms:
4
Bathrooms:
7
Sleeps:
18
Your Chicago adventure begins at this 7-bedroom house. This charming home features a mix of cozy beds, including 4 queen ...
From $835 per night (USD)
Expedia
From $158 per night (USD)
VRBO
Hip Music area 2-bedroom Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Discover the action of Berwyn's - Oak Park's Music Veltway from this 2-bedroom apartment. The space features a king bed ...
From $158 per night (USD)
VRBO
From $502 per night (USD)
Expedia
Creek Retreat on 1 acre / Game Room / Fire Pit
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Welcome to your perfect getaway, where modern comfort meets nature. Escape to a beautifully remodeled home set on a pri ...
From $502 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Near Parks & Eats! Elegant Southwest Chicago Home
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Quiet Suburban Neighborhood | Ideal for Traveling Medical Professionals Feel at home from day one at this beautifully a ...
From $172 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Logan Square Boho Getaway - Sleeps 6 - Remodeled
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to this cheerful, pet friendly 700 sqft Chicago retreat for 4-6 guests! Newly renovated garden apartment and in a ...
From $314 per night (USD)
Expedia
From $839 per night (USD)
VRBO
Retreat House with Outdoor Hot Tub & Barrel Sauna
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to this pleasant house in Chicago. With three bedrooms featuring a king bed, two queen beds, and a pack n play, ...
From $839 per night (USD)
VRBO
From $3640 per night (USD)
Expedia
Sleek New 6BR Greystone - Rooftop, In-Law Ste, Walk to Wrigley & Block to Train
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Welcome to your ultimate Chicago getaway. This brand-new, ultra-spacious Greystone sits perfectly at the intersection of ...
From $3640 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Cozy 4BR 2BA Worth Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Worth is waiting for you at this 4-bedroom house. Inside, guests find a pleasant space with four full beds and two bathr ...
From $436 per night (USD)
VRBO
From $390 per night (USD)
VRBO
Private Brookfield Apartment with Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3-bedroom apartment is perfect for your escape to Brookfield. Featuring one king bed and two queen beds, it comfort ...
From $390 per night (USD)
VRBO
From $144 per night (USD)
VRBO
Stylish 2BR Near UChicago – Easy Downtown Access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Modern and stylish 2-bedroom apartment near the University of Chicago. Fully furnished with a stocked kitchen, blackout ...
From $144 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Cozy 1 Bedroom Apartment 20 Minutes from Downtown Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to your private Chicago retreat! Conveniently located just 20 minutes from Downtown Chicago and 5 minutes from t ...
From $455 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Game Room
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Why Guests Love It: Peaceful. Well-Appointed. Immaculate. ~ 4-min walk to train - 25 minutes to Chicago ~ 2BR spac ...
From $368 per night (USD)
VRBO
From $205 per night (USD)
Expedia
2-bedroom apartment in awesome Chicago with cool AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to The Cozy Study — Apartment 1: a private, fully furnished 2 bedroom, 2 bathroom unit in Bronzeville, perfect f ...
From $205 per night (USD)
Expedia
From $408 per night (USD)
VRBO
Wrigleyville Oasis • Modern Comfort Steps from Wrigley Field
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your Wrigleyville Oasis—an inviting, thoughtfully designed apartment perfect for travelers seeking comfort, c ...
From $408 per night (USD)
VRBO
From $260 per night (USD)
Expedia
Music-Inspired 2BR Garden Flat in Historic Uptown Near Legendary Music Venues
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Tucked away on a quiet, tree-lined street in Chicago’s Uptown / Sheridan Park, this beautifully renovated 2-bedroom, 1-b ...
From $260 per night (USD)
Expedia
From $85 per night (USD)
VRBO
City Vibes 2BR - 20 min to DT, 15 min to Midway!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to our stylish 2-bedroom condo - thoughtfully designed to provide an authentic Windy City experience! Located ju ...
From $85 per night (USD)
VRBO
From $177 per night (USD)
VRBO
Studio Plus at Hilton Grand Vacations Club Chicago Magnificent Mile Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located between Chicago's Magnificent Mile and Navy Pier, Chicago Magnificent Mile, a Hilton Grand Vacations Club, offer ...
From $177 per night (USD)
VRBO
From $185 per night (USD)
VRBO
Cozy 2BR Near McCormick & Wintrust with Optional Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
When you step inside this bright South Loop suite, the energy of the city fades away. Sunlight fills the space, creating ...
From $185 per night (USD)
VRBO
From $311 per night (USD)
Expedia
Chicago Gem Near Downtown Steps from La Catedral Café : Family and Pet Friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Casa De Alma Enjoy a comfortable Chicago stay in a convenient neighborhood location with easy access to downt ...
From $311 per night (USD)
Expedia
From $113 per night (USD)
VRBO
Blueground | Edgewater, gym, nr Lake Michigan
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this sophisticated two bedroom Blueground apartment. You’ll love c ...
From $113 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Expansive 4BD - Steps from downtown - Oak Park
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience a refined stay in one of Oak Park’s most walkable pockets. This large-scale apartment provides a quiet reside ...
From $459 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Chic & Comfy 3-bedroom apartment in Logan Square, family friendly
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Welcome to our home, situated in a charming residential area of Logan Square, a vibrant neighborhood. Enjoy being walkin ...
From $295 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Luxurious Brand New 3BR -Walk Downtown Brookfield and Metra
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Brand-new, beautifully constructed home in the heart of Brookfield. This bright and spacious 2.5 bedroom residence featu ...
From $247 per night (USD)
Expedia
From $408 per night (USD)
VRBO
Luxury 3BR Apartment- Steps to Downtown and Metra
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Get ready to relax in this 3-bedroom apartment in Brookfield. The space features one full bed and two queen beds, perfec ...
From $408 per night (USD)
VRBO
From $189 per night (USD)
VRBO
Cozy Apartment in Forest Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A comfortable, updated, and completely private second-floor apartment in the heart of Forest Park. You'll be steps from ...
From $189 per night (USD)
VRBO
From $406 per night (USD)
VRBO
Lux New Hyde Park Apt by U Chicago, Museum of Science & Industry w/Peloton
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Your Luxury Hyde Park Retreat — Just Steps from History, Culture & UChicago Luxury 3BR/2BA apartment in a fu ...
From $406 per night (USD)
VRBO
From $268 per night (USD)
Expedia
Near Brookfield Zoo - King Bed - Sleeps 6
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Westchester unit near Brookfield Zoo & Oakbrook Center — sleeps 6, 20 min to downtown Chicago! *2 bedrooms ...
From $268 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Oakley: 3BR-2.5BT Home. Main level B+B & Fully Fenced yard!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Get ready to relax in this 3-bedroom house in Oak Lawn. The peaceful space features two king beds and one queen bed, Per ...
From $280 per night (USD)
VRBO
From $128 per night (USD)
Expedia
Cozy King bedroom + queen daybed near Arlington Heights
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your cozy getaway awaits in Palatine at this stylish condo. Inside, guests find one bedroom with a king bed and a living ...
From $128 per night (USD)
Expedia
From $434 per night (USD)
VRBO
Relax & Unwind Private, Comfortable, & Convenient
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3-bedroom apartment is perfect for your escape to Chicago. Featuring three queen beds, it offers a marvelous space ...
From $434 per night (USD)
VRBO
From $893 per night (USD)
Expedia
The Boho House • Two Private Suites + Parking
Bedrooms:
4
Bathrooms:
1
Sleeps:
12
Two private suites. One unforgettable stay. Perfect for groups who want to be together—without sacrificing space. Enjoy ...
From $893 per night (USD)
Expedia
From $817 per night (USD)
VRBO
Designer 3BR Near Beach & Obama Center
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Experience Chicago's most distinctive designer retreat. The Dorchester blends grand Victorian architecture with magazine ...
From $817 per night (USD)
VRBO
From $808 per night (USD)
Expedia
Private Yard Near Beach & Obama Center
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience Chicago's most distinctive designer retreat. The Dorchester blends grand Victorian architecture with magazine ...
From $808 per night (USD)
Expedia
From $914 per night (USD)
VRBO
The Zen Duplex: Two Private Suites for Groups
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Experience the "Adjoining Suite" life. This dual-level Zen retreat offers the perfect balance for families or groups: st ...
From $914 per night (USD)
VRBO
From $1026 per night (USD)
Expedia
Designer Home | Steps to the Obama Center & Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Experience Chicago's most distinctive designer retreat. The Dorchester blends grand Victorian architecture with magazine ...
From $1026 per night (USD)
Expedia

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