Cook Area Rentals
From $304 per night (USD)VRBO
Top floor of Historic Oak Park Home /2 Car Garage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Secluded but never isolated; 3 blocks from the L-line, next door to Hemingway's birthplace, surrounded by dozens of Fran ...
From $304 per night (USD)VRBO
From $161 per night (USD)Expedia
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This gorgeous 2bed/2bath packs a powerful punch, and more amenities than you'll know what to do with. -1 Private Parkin ...
From $161 per night (USD)Expedia
From $275 per night (USD)VRBO
Chicago's Hidden Treasure \"Evanston, IL\" Urban Luxury with comfort
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Eco-Friendly, modern, sleek, condo with modern finishes and resort-like amenities are just steps from Northwestern Unive ...
From $275 per night (USD)VRBO
From $275 per night (USD)Expedia
Half a mile from everything in the heart of Evanston, Illinois
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Northwestern Alumni, Parents, Corporate Travelers, and Evanston Adventure Seekers!! This property is all about coming t ...
From $275 per night (USD)Expedia
From $275 per night (USD)VRBO
Chicago's Hidden Treasure, \"EVANSTON, IL\"
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Northwestern Alumni, Parents, Corporate Travelers, and Evanston Adventure Seekers!! This property is all about coming t ...
From $275 per night (USD)VRBO
From $1491 per night (USD)Expedia
Nice cozy home to experience on your vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Nice 3 bedroom 2 bathroom with laundry room. Nice walkthrough garage. The house is amazing with hardwood floors and kitc ...
From $1491 per night (USD)Expedia
From $202 per night (USD)VRBO
Updated Forest Park 3 BR Bungalow
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This charming and recently updated 3BR bungalow in a friendly neighborhood is perfect for families, business travelers, ...
From $202 per night (USD)VRBO
From $329 per night (USD)Expedia
✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our apartment is located right next to the beach and a very nice path to take long walks where you can enjoy the views o ...
From $329 per night (USD)Expedia
Click For PricingVRBO
Bright and Spacious 2BR 2BA Apt., FREE PARKING, Walk to Train
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This Queen Anne home built in 1876 is located in the heart of Oak Park, just a few minutes walk to Frank Lloyd Wright ho ...
Click For PricingVRBO
From $171 per night (USD)Expedia
Angie & Mike's Nest!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated three bedroom & 1 bath apartment with stainless steel appliances. The space The apartment is in the se ...
From $171 per night (USD)Expedia
From $950 per night (USD)VRBO
Elegantly decorated spacious 4 bedroom, 5 bathroom home in historic Oak Park
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
This home is meticulously decorated with amazing opulent lighting, stain glass pocket doors, and a great floor plan. Th ...
From $950 per night (USD)VRBO
From $249 per night (USD)Expedia
Relaxing Oak Park Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This charming Oak Park Bungalow offers a quiet relaxing environment to unwind after a busy day of site seeing in Chicag ...
From $249 per night (USD)Expedia
From $369 per night (USD)VRBO
5 Star Upscale Entire Family Neighborhood Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This home is located on the River Side/ N. River Side part of Berwyn and Oak Park in a delightful quiet family neighbor ...
From $369 per night (USD)VRBO
From $240 per night (USD)VRBO
Pet-Friendly Family Apartment - Near NU Campus!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Explore the Windy City with this stylish 2-bedroom, 2-bath apartment! In walking distance, you'll find a variety of loca ...
From $240 per night (USD)VRBO
From $274 per night (USD)VRBO
Elegant|Brand New Remodeled|1BR|Next to Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our apartment is located right next to the beach and a very nice path to take long walks where you can enjoy the views o ...
From $274 per night (USD)VRBO
From $324 per night (USD)Expedia
Lincoln Park Light Filled Loft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience this unique Lincoln Park loft where you’ll love the open concept space, the floor to ceiling windows, & the c ...
From $324 per night (USD)Expedia
From $175 per night (USD)VRBO
Large, modern 2 bedroom in the heart of Forest Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Quiet and spacious lofted 2 bedroom unit steps from the heart of downtown Forest Park's Madison St. There you will find ...
From $175 per night (USD)VRBO
From $388 per night (USD)Expedia
\"Bliss of Evanston\" 180°view, 2BDR +2Bath UrbanLux
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Urban-Luxe experience at the Bliss of Evanston Condo. Elegant finishes and a sweeping terrace view, resort-like ameniti ...
From $388 per night (USD)Expedia
From $272 per night (USD)VRBO
\"Joy of Evanston\" 1BDR, KING EXEC Suite, pool+Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Eco-Friendly, modern, sleek, condo with modern finishes and resort-like amenities are just steps from Northwestern Unive ...
From $272 per night (USD)VRBO
From $416 per night (USD)Expedia
\"Unity of Evanston\" 3 BDR+2BA ModernLuxe High Rise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Modern-Luxe experience at the Unity of Evanston Condo. Elegant finishes and a sweeping view. Resort-like amenities with ...
From $416 per night (USD)Expedia
From $357 per night (USD)VRBO
Classic Oak Park Home, 11 Mi to Downtown Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
- Walk to Shopping & Dining - In-Unit Laundry Experience the best of Chicago from this 4-bedroom, 1.5-bathroom home in ...
From $357 per night (USD)VRBO
From $220 per night (USD)Expedia
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Be sure to check out the VIDEO tour push the arrow on the third photo. Happy to accommodate same day reservations pl ...
From $220 per night (USD)Expedia
From $259 per night (USD)VRBO
Beautiful & Cozy 2bd/1b Near O’Hare & Metra (MD-W)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the peaceful Galewood/Elmwood Park area of Chicago. We are in the boarder line of Chicago/Suburbs. Our Home i ...
From $259 per night (USD)VRBO
From $250 per night (USD)VRBO
Charming, light-filled 5br Wilmette home
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 6
Light and art filled 5br, 2ba, 2fp, garage, huge fenced backyard. Beautifully designed and landscaped. Kitchen boasts ne ...
From $250 per night (USD)VRBO
From $296 per night (USD)VRBO
Contemporary 2BR Flat Right Next to Wrigley Field & Transit ❤️ Cubs!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience city life; Located in Wrigley! Feel like a local! We're experienced! we've hosted more than 1000 reservati ...
From $296 per night (USD)VRBO
From $241 per night (USD)Expedia
Monthly Specials! Cozy Home away from Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
In the HOMETOWN OF OUR POPE LEO, a cozy home away from home. 7 minutes to the city of Chicago, 22 minutes to Downtown. ...
From $241 per night (USD)Expedia
From $379 per night (USD)VRBO
*Comfortable & Spacious Home Close to Downtown*
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
We are Airbnb Superhosts and have been on the platform since 2016. This is a Comfortable & Spacious beautifully furnish ...
From $379 per night (USD)VRBO
From $211 per night (USD)VRBO
Best Value, Quality Stay! Pet-Friendly Property, Close to Water Tower Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $211 per night (USD)VRBO
From $552 per night (USD)VRBO
A Place You'll Surely Enjoy! Near Chicago History Museum, Pet-Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $552 per night (USD)VRBO
From $439 per night (USD)Expedia
5-minute walk to the largest old school arcade in America! Family friendly.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Bring the whole family to this great place with lots of room for fun. We are located 10 miles from Downtown Chicago. Ple ...
From $439 per night (USD)Expedia
From $147 per night (USD)VRBO
Chicago style apt/Near Hosp/ORD/MDW/DT
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your family will be close to everything at this centrally-located place. Stay includes: *Free Street Parking *Free Wifi ...
From $147 per night (USD)VRBO
From $308 per night (USD)Expedia
Cozy retreat in a prime location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a clean and comfortable stay with a luxurious king bed and a private backyard. Located in a peaceful neighborhood, ...
From $308 per night (USD)Expedia
From $378 per night (USD)VRBO
Newly Revamped Home - For privacy lovers
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
Big family? Group getaway? We’ve got more sleeping space than you’ll know what to do with. Try finding this much space a ...
From $378 per night (USD)VRBO
From $140 per night (USD)Expedia
Lakeview Lux - Apt #2
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 9
Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...
From $140 per night (USD)Expedia
From $153 per night (USD)VRBO
Lakeview Lux - Apt #1
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...
From $153 per night (USD)VRBO
From $470 per night (USD)Expedia
St.Bens, Jacuzzi, EV Parking! 4 beds, Walk to Wrigley Field & Brown Line!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Looking for a spacious, stylish, and fully-equipped home in the heart of Chicago? Book your stay now and make this beau ...
From $470 per night (USD)Expedia
From $352 per night (USD)VRBO
Luxury Chicago 2 Story Condo: 10 Mins to Downtown
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Experience luxury in our 2 bedroom (3 bed) duplex down, spread over 2 levels, our home offers over 1800+ sq ft of room. ...
From $352 per night (USD)VRBO
From $175 per night (USD)Expedia
Charming 5 bedrooms 2 bath near Downtown Loop and Mc cormick Place, Museum
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 6
5 bed 2 full bathroom with 2,600 of living space. Property is located on a quiet street with long term ownership. Restau ...
From $175 per night (USD)Expedia
From $298 per night (USD)VRBO
Stylish Streeterville 2BR w/ Lounge & Pool, nr Riverwalk, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Streeterville furnished two bedroom ap ...
From $298 per night (USD)VRBO
From $215 per night (USD)Expedia
Upscale Streeterville Jr 1BR w/ Gym, nr Magnificent Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Streeterville furnished one bedroom a ...
From $215 per night (USD)Expedia
From $146 per night (USD)VRBO
Convenience & Comfort! w/ Airport Shuttle Service, Pet-friendly Property!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $146 per night (USD)VRBO
From $1002 per night (USD)VRBO
-Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Have fun with the whole family at this stylish place. Your family will be close to everything when you stay at this cent ...
From $1002 per night (USD)VRBO
From $633 per night (USD)VRBO
Spacious 5 BR / King Size Beds + Private Parking!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Discover Chicago from our cozy home! Just .5 mile from the Green Line CTA station, explore downtown with ease. 3 minute ...
From $633 per night (USD)VRBO
From $315 per night (USD)Expedia
Relaxing 2BR Apartment in Lively West Rogers Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Listing Description Welcome to this beautiful two-bed, one-bath apartment in the heart of West Rogers Park! Perfectly l ...
From $315 per night (USD)Expedia
From $297 per night (USD)VRBO
New renovation-1BR-Stylish-Modern-Next to the Lake\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
LISTING DESCRIPTION - Experience the best of Evanston in our cozy 1BR/1BA apartment near Lake Michigan. Enjoy a fully e ...
From $297 per night (USD)VRBO
From $299 per night (USD)Expedia
Modern Spacious New Renovation 1BR Evanston
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Listing Description Experience the best of Evanston in our cozy 1BR/1BA apartment near Lake Michigan. Enjoy a fully equ ...
From $299 per night (USD)Expedia
From $103 per night (USD)VRBO
Trendy Loop Jr 1BR w/ Game Room, nr Park & Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Chicago Loop furnished one bedroom apa ...
From $103 per night (USD)VRBO
From $391 per night (USD)Expedia
3BD West Town Gem: Explore the Windy City in Style
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our stylish 3-bed, 2-bath Condo in the heart of Chicago's vibrant West Town. Designed for your comfort, it's ...
From $391 per night (USD)Expedia
Click For PricingVRBO
Belmont Pleasures - hot tub / arcade gaming room
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
About this space Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come hav ...
Click For PricingVRBO
From $759 per night (USD)Expedia
Luxury Loft Collection 902 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...
From $759 per night (USD)Expedia
From $175 per night (USD)VRBO
Cozy 2 Bedroom unit-15mins Dwtn!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Trendy two unit apartment nested between South Loop and Bronzeville. The unit is in close proximity to McCormick,Winturs ...
From $175 per night (USD)VRBO
From $457 per night (USD)Expedia
McCormick 3B/2Ba Family Oasis up to 8 guests with Parking-Optional/Gym/Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 Queen size beds + ...
From $457 per night (USD)Expedia
From $301 per night (USD)VRBO
McCormick Patio skyline view 2b/2b with optional Parking/sleep 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Private patio • Cit ...
From $301 per night (USD)VRBO
From $499 per night (USD)Expedia
Luxurious McCormick 3be/2ba Suite/up to 8 guests w optional parking/Gym/Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 KING size bedroo ...
From $499 per night (USD)Expedia
From $1076 per night (USD)VRBO
Luxurious McCormick 6 bed/4 bath Suite for up to 12 guests w Jacuzzi/Opt parking
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Jacuzzi in the unit • 2609 sq f Luxurious unit ...
From $1076 per night (USD)VRBO
From $900 per night (USD)Expedia
Luxurious McCormick 5 bed/4 bath Suite for up to 12 guests with optional parking
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Luxurious unit for ...
From $900 per night (USD)Expedia
From $461 per night (USD)VRBO
McCormick Place 6 twin beds + Sofa bed with Optional parking for up to 10 guests
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 6 twin size beds + ...
From $461 per night (USD)VRBO
From $479 per night (USD)Expedia
Greenhouse Inn, Evanston Northwestern Loyola Chicago. Kid Friendly w/parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Explore The Greenhouse Inn in Evanston! A 3-bed, 3-bath duplex for 6 guests with 2 kitchens, in-unit laundry, and parkin ...
From $479 per night (USD)Expedia
From $370 per night (USD)VRBO
Urban Oasis - Kid Friendly - Quiet Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in a quiet and safe neighborhood, our property offers a unique blend of style, comfort, and entertainment. Step ...
From $370 per night (USD)VRBO
From $148 per night (USD)Expedia
Spacious 2BR, this hidden gem combines vintage allure with urban flair!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the charm of The Maestro, an amazing 2-bedroom, 1-bath apartment nestled within a stunning 1920’s era Chicago b ...
From $148 per night (USD)Expedia
From $187 per night (USD)VRBO
Chic 2BR Haven: Minutes from Downtown & Medical District
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Welcome to your tranquil urban oasis in the vibrant heart of Chicago, IL! Nestled on a serene block near Douglas Park in ...
From $187 per night (USD)VRBO
From $161 per night (USD)Expedia
Classic West Loop 1BR w/ Gym, near Fulton Market & I-90, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...
From $161 per night (USD)Expedia
From $638 per night (USD)VRBO
Modern, Luxe, House 20mins to Downtown, Sleeps 16, Private Rooftop, 2car Garage
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
Luxurious Modern Retreat with 1000 sqft Rooftop Welcome to the Monticello - our stunning modern new construction, desig ...
From $638 per night (USD)VRBO
From $88 per night (USD)Expedia
Dreamy West Loop 1BR w/ Rooftop & Dog Wash, nr L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Near West Side. It’ll be easy to simply show up and sta ...
From $88 per night (USD)Expedia
From $492 per night (USD)VRBO
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Bee's Knees - a vintage gem with a Hollywood-glam twist! This 4-BR Chicago bungalow home is the perfect getaw ...
From $492 per night (USD)VRBO
From $196 per night (USD)VRBO
Breath of Fresh Air! Near Willis Tower and Cloud Gate - The Bean, Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience the Windy City's elegance & charm from our central, downtown location This listing is for a room within a ho ...
From $196 per night (USD)VRBO
From $316 per night (USD)VRBO
Guest favorite Spacious Home near Chicago O'Hare Airport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
It is a lovely spacious and cozy home (recently updated) nestled in a peaceful neighborhood in the Chicago area. We are ...
From $316 per night (USD)VRBO
From $186 per night (USD)VRBO
Cozy Spacious 3br
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Nice and Spacious Cozy apartment nestled in the heart of chicago, top floor apt. With Double ovens when cooking for a ni ...
From $186 per night (USD)VRBO
From $1278 per night (USD)VRBO
New home w/view & party deck - 2nd Floor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Prime Location: Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovat ...
From $1278 per night (USD)VRBO
From $225 per night (USD)Expedia
4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This home features 4 bedrooms, 2 full baths, a living room, and a fully stocked kitchen that you can cook your own delic ...
From $225 per night (USD)Expedia
From $230 per night (USD)VRBO
Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined str ...
From $230 per night (USD)VRBO
From $282 per night (USD)Expedia
Updated Spacious Home -Near NWU- Hospitals+More
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Enjoy your stay with your friends or the whole family at this stylish recently renovated modern north shore home, 10 min ...
From $282 per night (USD)Expedia
From $244 per night (USD)VRBO
Deluxe River North 1BR w/ Gym, Pool & Roof, nr Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming River North furnished one bedroom ap ...
From $244 per night (USD)VRBO
From $325 per night (USD)Expedia
Enamored in Elmhurst
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
Enjoy your stay with the whole family at this beautifully renovated house with and open floor plan, fully stocked kitche ...
From $325 per night (USD)Expedia
From $450 per night (USD)VRBO
Haus Of Hues: MDRN Bright Peaceful Private Apt
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Peaceful and centrally-located, this flat is the perfect place to relax with the whole family or explore the city with f ...
From $450 per night (USD)VRBO
From $889 per night (USD)Expedia
Sleeps 12 Comfortably with 8 Bedrooms, 3 Full Bathrooms, 2 Kitchens and Parking
- Bedrooms:
- 3
- Bathrooms:
- 8
- Sleeps:
- 12
This House was built in 1902 and was modified into 2 apartments in the 1940's. The house has 3 levels and many stairs. I ...
From $889 per night (USD)Expedia
From $95 per night (USD)VRBO
Cozy & Comfy 2 bedroom remodeled with plenty parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to this beautifully remodeled fully furnished apartment for rent located on the south side of Chicago This 2-bed ...
From $95 per night (USD)VRBO
From $283 per night (USD)Expedia
2-bedroom apartment just 2 minutes drive to Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the heart of Chicago's vibrant North Center neighborhood in this charming 2-bedroom apartment. Situated just a ...
From $283 per night (USD)Expedia
From $367 per night (USD)VRBO
House in the Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Bring the whole family to this great place with lots of room across the street for fun fishing, golfing, bike track, val ...
From $367 per night (USD)VRBO
From $324 per night (USD)Expedia
Cozy 4-bedroom house in adorable Evanston with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Located in Evanston, enjoy what this 4-bedroom house has to offer. With 4 queen beds, our property provides ample space ...
From $324 per night (USD)Expedia
From $142 per night (USD)VRBO
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a peaceful stay at this 1-bedroom apartment in Hickory Hills. This serene and quaint property offers everything yo ...
From $142 per night (USD)VRBO
From $278 per night (USD)Expedia
Cozy apartment near zoo, DePaul, Oz Park and much more!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful brownstone in the heart of Lincoln Park. 5 minute walk to Lincoln Park zoo, lakefront, variety of restaurants/ ...
From $278 per night (USD)Expedia
From $231 per night (USD)VRBO
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Penthouse Loft in Chicago. As avid travelers and frequent VRBO users, we've infused our home with inspira ...
From $231 per night (USD)VRBO
From $235 per night (USD)VRBO
Charming 2-bedroom apartment in hip Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Chicago at this delightful apartment. With 2 bedrooms, including a king bed and a queen bed, this property is ...
From $235 per night (USD)VRBO
From $696 per night (USD)VRBO
6BR Chicago Gem: Prime, Safe, Family-Friendly Hub
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Experience Chicago in an unmatched setting: two apartments beautifully united into a grand 6-bedroom, 2-bathroom home in ...
From $696 per night (USD)VRBO
From $570 per night (USD)Expedia
Gorgeous 5 Bedroom Gem Sleeps 18 with Pool, Ping Pong, Pac Man, Tons of Games!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 18
Gorgeous gem within 10 miles of Downtown, Airport, Lake Michigan, and United Center! About 15 miles from Wrigley Field ...
From $570 per night (USD)Expedia
From $353 per night (USD)VRBO
Home Away From Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our charming Chicago rental home, " A Home Away From Home"! This vacation retreat offers a serene ambiance th ...
From $353 per night (USD)VRBO
From $205 per night (USD)Expedia
Suite 2 on Southport 4 Queen Beds
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Check out our brand new construction Suite on Southport Ave. Centrally located in the world famous Lincoln Park ...
From $205 per night (USD)Expedia
From $234 per night (USD)VRBO
Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
A spacious updated bungalow at the beginning of the beautiful quite boulevard. The house is on beautiful Wrightwood Nei ...
From $234 per night (USD)VRBO
From $72 per night (USD)Expedia
Beautiful and stylish 1 bedroom apartment in the heart of Pilsen \"CASA PILSEN\"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Casa Pilsen!! Located in the heart of Pilsen, enjoy what this 1-bedroom apartment has to offer. This fabulous ...
From $72 per night (USD)Expedia
From $284 per night (USD)VRBO
Cozy 2-bedroom apartment in welcoming Chicago in the Wicker Park area
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind in the stylish two-bedroom apt on Beach Street, a street in Chicago. The city is full of award-winning restaurant ...
From $284 per night (USD)VRBO
From $184 per night (USD)Expedia
Charming Pilsen Studio - Quick Access to Downtown Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover the charm of our unique studio apartment in La Vecindad, your perfect retreat in Pilsen, Chicago! This cozy stu ...
From $184 per night (USD)Expedia
From $146 per night (USD)VRBO
Near O`hare • Personal Gym & Balcony • Safe Area
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
✨ Much cheaper than a hotel, and definitely bigger and more comfortable than the four star hotels on the other side of t ...
From $146 per night (USD)VRBO
From $144 per night (USD)Expedia
Neat Old Town 1BR Gym, W/D, Rooftop, BBQ & A/C, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Old Town furnished one bedroom ...
From $144 per night (USD)Expedia
From $344 per night (USD)VRBO
Spacious 4-bedroom house in charming Des Plaines with AC, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience Comfort and Fun at our house in Des Plaines, IL Single family wrench in quiet neighborhood. Houses up to 8 p ...
From $344 per night (USD)VRBO
From $115 per night (USD)Expedia
1-bedroom condo next to Chicago Midway International Airport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Your Chicago adventure begins at this delightful 1-bedroom condo. The cozy bedroom features a queen bed, while the bathr ...
From $115 per night (USD)Expedia
From $383 per night (USD)VRBO
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This memorable apartment is the perfect home base for your trip to Chicago. With 3 bedrooms, including 1 king bed, 1 que ...
From $383 per night (USD)VRBO
From $201 per night (USD)Expedia
Chic 1-bedroom apartment in phenomenal Chicago with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover the beauty of Chicago from this enchanting 1-bedroom apartment. With a cozy living room featuring a futon, gues ...
From $201 per night (USD)Expedia
From $185 per night (USD)VRBO
Relaxing Chicago Vibe - Minutes away from major attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly renovated condo, perfect for up to 4 guests. This spotless space is meticulously cleaned and maintained to ensure ...
From $185 per night (USD)VRBO
From $243 per night (USD)VRBO
2 Bed & 3 Bath Chicago Condo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Kick back and relax in this calm, stylish space minutes away from Chicago's best attractions. Step inside thi ...
From $243 per night (USD)VRBO