Cook Area Rentals
From $745 per night (USD)VRBO
East Lincoln Park Gem: Spacious 4BR apartment with modern amenities.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Experience refined living in this garden-level apartment, nestled within a distinguished historic Greystone bui ...
From $745 per night (USD)VRBO
From $638 per night (USD)Expedia
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)Expedia
From $196 per night (USD)VRBO
Downtown Delight: Chic Stay near Chicago Theater! Pets are welcome!
- 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 $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
Click For PricingExpedia
Modern Farmhouse | Yard + Pets OK | LCP Collection
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience our chic modern farmhouse in Streamwood, offering 3 stylish bedrooms, each with a luxurious king bed ...
Click For PricingExpedia
From $291 per night (USD)VRBO
Beautiful Suburban Home 30 minutes from downtown Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Alone, with friends, or with family? Whatever your needs, this house is sure to fulfill your expectations. Full house in ...
From $291 per night (USD)VRBO
From $1166 per night (USD)Expedia
3Bed/2Bath Wrigley home w/view & party deck 443 ft from Wrigley Field - 3rd Fl
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovated down to the s ...
From $1166 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 $224 per night (USD)Expedia
3 Bedroom Medical Center!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: A couple house off the popular Taylor St which has plenty of restaurants and bars! The Space: 3 Bedrooms 1 Ful ...
From $224 per night (USD)Expedia
From $225 per night (USD)VRBO
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)VRBO
From $439 per night (USD)VRBO
Charming 4BR Coach House in River West Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to our stunning 4-bedroom retreat nestled in the heart of Chicago, where urban excitement meets modern ...
From $439 per night (USD)VRBO
From $586 per night (USD)VRBO
Elegant 3-Bed, 3-Bath Home in Chicago <25-minutes to O’Hare & Downtown + Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this beautifully renovated single-family home, offering luxury, comfort, and modern elegance in the heart of ...
From $586 per night (USD)VRBO
From $238 per night (USD)Expedia
Dalia Flat - Sleeps 10 - 10 minutes to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Large 3 BR 1BA located 10 min drive from Downtown Chicago Tub/Shower Walking distance from subway/train station Directly ...
From $238 per night (USD)Expedia
From $181 per night (USD)VRBO
Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Feel comfortable in this spacious and unique 1bd space. New In-law-suite which includes a large family room. There is an ...
From $181 per night (USD)VRBO
From $508 per night (USD)Expedia
Skokie 9 bed 4 bedrooms house
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 12
4 bedrooms 1 and half bathrooms with 9 beds. Newly renovated. Magnificent Georgian- style home has been well maintained ...
From $508 per night (USD)Expedia
From $220 per night (USD)VRBO
OpulentUrban Retreat: Luxe Living
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the Opulent Urban Retreat, a luxurious escape in the city's heart. This elegant apartment features a spacious ...
From $220 per night (USD)VRBO
From $983 per night (USD)Expedia
Wicker Park Entire House, Private Yard and Parking!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Renovated 4 bed 3 bath home in the heart Wicker Park. PRIVATE FREE PARKING! Incredible backyard with outdoor kitchen and ...
From $983 per night (USD)Expedia
From $282 per night (USD)VRBO
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)VRBO
From $244 per night (USD)Expedia
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)Expedia
From $325 per night (USD)VRBO
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)VRBO
From $450 per night (USD)Expedia
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)Expedia
From $151 per night (USD)VRBO
2BD/1 BA with summer patio in quiet Roscoe Village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to a wonderful home in quiet, family-friendly West Lakeview/Roscoe Village. This is a spacious 2 bedroom+office/ ...
From $151 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 $396 per night (USD)VRBO
Book the Great Migration Guest House. Family-sized condo near the Green Line.\n\n
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
LOOK FOR THE GREEN DOOR BLACKS IN GREEN LAUNCHES NEXT LEVEL TOURISM IN WOODLAWN In homage to the legendary "Green Boo ...
From $396 per night (USD)VRBO
From $283 per night (USD)VRBO
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)VRBO
From $324 per night (USD)Expedia
Wrigleyville Suites Room 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casu ...
From $324 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 $486 per night (USD)Expedia
3BR Luxury Modern Apartment
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: This is the place to be in downtown Chicago! This new building offers you comfort and luxury in one of the most ...
From $486 per night (USD)Expedia
From $289 per night (USD)VRBO
Stylish 3bd w/ backyard patio mins from Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Funkytown! A Stylishly appointed 3 bd 2 bth w/ an idyllic backyard oasis located just mins from downtown Chic ...
From $289 per night (USD)VRBO
From $256 per night (USD)VRBO
Mid-Term 4-bedroom house in fabulous Flossmoor with a Pool Table
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this enchanting house in Flossmoor. With 4 bedrooms, including 3 king beds, 1 sofa bed, and 2 queen bed, this ...
From $256 per night (USD)VRBO
From $324 per night (USD)VRBO
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)VRBO
From $142 per night (USD)Expedia
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)Expedia
From $278 per night (USD)VRBO
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)VRBO
From $204 per night (USD)Expedia
Cozy & Colorful garden unit in Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Escape to our private 3 bedroom garden condo in trendy Logan Square. This urban retreat offers a cozy living space with ...
From $204 per night (USD)Expedia
From $167 per night (USD)VRBO
Beautiful Apartment in Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 16
Great apartment in ChicagoWhat will guests love about your area? Ghost tours, a buzzing restaurant district, or a night ...
From $167 per night (USD)VRBO
From $231 per night (USD)Expedia
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)Expedia
From $255 per night (USD)VRBO
Game Room & Outdoor Patio | LCP Collection
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Summary: Experience comfort in this beautifully remodeled 2-bedroom, 1-bath apartment in Berwyn, IL. Perfect for a small ...
From $255 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 $392 per night (USD)VRBO
Family, Groups - Convenient to Wrigley, Loop, Airport - Spacious 2200 Sq Ft
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Early Check-Ins and Late Check-Outs are difficult to accommodate. If you need additional time, please consider booking a ...
From $392 per night (USD)VRBO
From $696 per night (USD)Expedia
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)Expedia
From $570 per night (USD)VRBO
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)VRBO
From $302 per night (USD)Expedia
Modern Condo • Safe Chicago Stay Near O’Hare
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
✨ Place was clean and comfortable. Easily accessible to airport, gym, grocery stores, etc. I felt safe in the area. ✨ ...
From $302 per night (USD)Expedia
From $714 per night (USD)VRBO
4 BR • Theater Room • Gym • Walk to Lincoln Park!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 12
✨ I highly recommend this location. The home is beautiful and quaint. The location is perfect. The neighbor is very quie ...
From $714 per night (USD)VRBO
From $315 per night (USD)Expedia
5 Star Luxury Stay Near Chicago O'hare Airport, King Beds
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Chicago O'Hare Airport is just 10 minutes away. Enjoy a stylish stay with your whole family at this luxurious 5-star pro ...
From $315 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 $322 per night (USD)VRBO
Updated 3 Bedroom Chicago Historic Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Ready to stay in CHARMING Chicago? Our NEWLY UPDATED masterpiece has IMPECCABLE DESIGN, 3 bedrooms, and is step ...
From $322 per night (USD)VRBO
From $205 per night (USD)VRBO
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)VRBO
From $234 per night (USD)Expedia
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)Expedia
From $72 per night (USD)VRBO
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)VRBO
From $163 per night (USD)Expedia
Landing | Beautiful 1BD, Yoga Studio, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Schaumburg’s vibrant Veridian campus, Element at Veridian puts you minutes from Woodfield Mall, top dining sp ...
From $163 per night (USD)Expedia
From $152 per night (USD)VRBO
Landing | Beautiful 1BD, Clubhouse, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Schaumburg’s vibrant Veridian campus, Element at Veridian puts you minutes from Woodfield Mall, top dining sp ...
From $152 per night (USD)VRBO
From $284 per night (USD)Expedia
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)Expedia
From $266 per night (USD)VRBO
The Banksy-Greystone Rooftop Firepit United Center
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Banksy, this modern apartment offers 2 bedrooms, one with a king bed and a queen bed. The apartment also features a ...
From $266 per night (USD)VRBO
From $184 per night (USD)Expedia
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience the charm and convenience of our unique tiny apartment in La Vecindad, perfect for your stay in Pilsen, Chica ...
From $184 per night (USD)Expedia
From $184 per night (USD)VRBO
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)VRBO
From $250 per night (USD)Expedia
Friends-Inspired 3 BDR Escape Vintage Vibes & Private Garden Near Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Friends-Inspired Oasis with Private Garden & Pool Welcome to our one-of-a-kind duplex escape in Schaumburg—just 35 minut ...
From $250 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 $269 per night (USD)Expedia
Chicago Cityview Chic II Gold Coast/River North
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our stylish, 2-bed, 2-bath condo located in the vibrant Gold Coast/River North neighborhood. Discover the epi ...
From $269 per night (USD)Expedia
From $691 per night (USD)VRBO
Serene & Charming 5BR Des Plaines Getaway by RedAwning
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to your home away from home in beautiful Des Plaines, IL! This cozy and spacious house is ideal for families, f ...
From $691 per night (USD)VRBO
From $666 per night (USD)Expedia
Family-Friendly South Loop Escape by RedAwning
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
If you're seeking urban living, this 3 1/2-story unit is for you. A spacious townhome, it's ideally nestled between McC ...
From $666 per night (USD)Expedia
From $240 per night (USD)VRBO
Quick Drive to Downtown Chicago & Early Check-In
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Book your stay now at our modern, fully furnished condo—just minutes from downtown Chicago and the Illinois Medical Dist ...
From $240 per night (USD)VRBO
From $146 per night (USD)Expedia
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)Expedia
From $144 per night (USD)VRBO
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)VRBO
From $344 per night (USD)Expedia
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)Expedia
From $115 per night (USD)VRBO
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)VRBO
From $225 per night (USD)Expedia
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The apartment is exclusively yours, without interruption for the duration of your stay, so relax, unwind, and make yours ...
From $225 per night (USD)Expedia
From $201 per night (USD)VRBO
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)VRBO
From $215 per night (USD)Expedia
NEW modern 2BR apt near UofChicago & Hyde Park w/free Parking & pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sleek, secure, and sun-drenched! This brand-new 2-bedroom, 1-bath garden unit is your tech-savvy urban oasis with a priv ...
From $215 per night (USD)Expedia
From $946 per night (USD)VRBO
Wrigleyville 3BD Condo
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $946 per night (USD)VRBO
From $1025 per night (USD)VRBO
Wrigleyville Garden 3BR/9beds Pod
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $1025 per night (USD)VRBO
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
From $479 per night (USD)VRBO
Large 2-Bedroom w/ Huge Roofdeck view of Skyline
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience luxurious living in Chicago! This brand new, spacious 2-bedroom 2-bath penthouse apartment offers an ...
From $479 per night (USD)VRBO
From $164 per night (USD)Expedia
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
<p>Located in Oak Park, this welcoming vacation home lets you experience it all. You'll easily make the 9-minute drive t ...
From $164 per night (USD)Expedia
From $123 per night (USD)VRBO
Cozy 2BR Self-checkin unit in Chicago l Few Steps from DT I Car Rental Available
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Located within just 8 miles from Downtown Chicago, enjoy what this 2-bedroom apartment has to offer. INBOX ME FOR ON-SIT ...
From $123 per night (USD)VRBO
From $351 per night (USD)Expedia
Space&style New rehab, first flr + bsmt of duplex, driveway prkng, walk to train
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Chic + spacious w/A+ location! 2024 gut-rehab. One of two apartments a two-flat. This unit = Main floor + finished bsmnt ...
From $351 per night (USD)Expedia
From $189 per night (USD)VRBO
Three Bed Spacious Comfy Apt by Midway Airport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Discover the perfect balance of comfort and convenience in this beautifully renovated 3-bedroom, 2-bath apartme ...
From $189 per night (USD)VRBO
From $400 per night (USD)VRBO
Chic 2-bedroom condo in amazing Chicago minutes from Lake Michigan
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Kick back and relax in this calm, stylish space in the heart of Chicago’s legendary Bronzeville neighborhood. This styl ...
From $400 per night (USD)VRBO
From $125 per night (USD)VRBO
2BR • Sleeps 7 • King Bed • Prime Location
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
✨ “ Great apartment, great location. Very important too, the host is true to their word and they mean what they say. ” ✨ ...
From $125 per night (USD)VRBO
From $82 per night (USD)Expedia
King Bed | Smart TV | Historic Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 13
✨“ My partner couldn’t stop saying how much she enjoyed the space. Mattress was perfect.. so comfortable Wished we could ...
From $82 per night (USD)Expedia
From $92 per night (USD)VRBO
90s Condo| King Bed | 65” Smart TV | Arcade Game
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
✨” The apartment is very cozy and is conveniently located by the airport, stores and many places to eat. Loved it! “✨ � ...
From $92 per night (USD)VRBO
From $92 per night (USD)Expedia
Top Rated Condo • King Bed • Safe Historic Location
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
✨ “ I definitely will be booking here again. ” ✨ 👉 This luxurious condo is located in a family-friendly neighborhood ...
From $92 per night (USD)Expedia
From $72 per night (USD)VRBO
King Bed Studio | 60\" HDTV | Safe | Close to Metra
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
✨ “ I walked around all hours of the day and night and always felt safe. I will stay here again. ” ✨ 👉 Brand New Moder ...
From $72 per night (USD)VRBO
From $276 per night (USD)Expedia
Pine Beam Sloth Apartment next to Blue Line
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our charming 650 sq ft, 1-bedroom apartment! It's the perfect size for comfortable living, offering a well-e ...
From $276 per night (USD)Expedia
From $803 per night (USD)VRBO
Rainbow Guest House: Charming 3-bedroom house in great location
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Your Chicago adventure begins at this 3-bedroom house. Welcome to Rainbow Guest House. This designer owned, rebuilt and ...
From $803 per night (USD)VRBO
From $333 per night (USD)VRBO
Spacious, one-level condo next to Jackson Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this condo in picturesque Chicago. This beautiful rental features 3 queen beds spread across 3 bedrooms, ensur ...
From $333 per night (USD)VRBO
From $132 per night (USD)VRBO
Minutes from O`Hare | Safe Neighborhood | Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
✨ “ Super comfy couch (one of my favorites and we have been traveling in airbnbs for 6 months)” ✨ 👉 Entire apartment ...
From $132 per night (USD)VRBO
From $295 per night (USD)VRBO
Cozy Chinatown Apartment w free parking spot!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 1,000 square foot condo located in Chinatown, part of the South Loop/McCormick neighborhood. This 3 bedroom / 1 ...
From $295 per night (USD)VRBO
Click For PricingVRBO
Large Modern 2BD/2BA Condo in River North- Free Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our chic 2 bedroom, 2 bath condo (Parking Included) in the heart of River North, one of the most sought-after ...
Click For PricingVRBO
From $116 per night (USD)VRBO
Chic 2-bedroom apartment in fabulous Chicago with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your Chicago adventure begins at this 2-bedroom apartment. The space features two bedrooms and a third bedroom used as a ...
From $116 per night (USD)VRBO
From $307 per night (USD)VRBO
Chic Modern NEW Loft near United Center, UIC/IMD & Downtown W/ Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Discover luxury in our newly renovated 2nd floor loft in Tri-Taylor. With 13-ft ceilings, large windows, brick and moder ...
From $307 per night (USD)VRBO
From $291 per night (USD)Expedia
3-bedroom house in fantastic Hanover Park with AC, WiFi. Enjoy your stay
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Discover this terrific 3-bedroom gem in Hanover Park. This tranquil house features 1 queen bed, 1 full bed, and 1 twin b ...
From $291 per night (USD)Expedia
From $483 per night (USD)VRBO
\"Melody of Evanston\" 3BD, 2BA UrbanLux Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your Evanston adventure begins at this charming 3-bedroom condo. With a king bed, queen bed, dual twin beds, and a dorm ...
From $483 per night (USD)VRBO
From $747 per night (USD)Expedia
Stunning 4-Bed 4-Bath Home - Prime Location OHare & Downtown <25-min, Free PRKNG
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to this beautifully renovated single-family home, offering luxury, comfort, and modern elegance in the heart of ...
From $747 per night (USD)Expedia