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

Chicago Rentals

From $204 per night (USD)
VRBO
Charming 4-bedroom apartment in delightful Chicago with central heat/AC, WiFi.
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Discover this marvelous 4-bedroom gem in Chicago. Step into this cool apartment and be greeted by a pleasant ambiance th ...
From $204 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Gold Coast/Downtown Hideaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
New Listing! Freshly renovated Gold Coast hideaway provides the perfect escape from the nearby shopping and restaurant a ...
From $331 per night (USD)
Expedia
From $473 per night (USD)
VRBO
Chic and Spacious Bi-level 3BD in Bucktown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This one-of-a-kind condo in Bucktown is ready to host! The property features a hidden staircase leading down to the in-l ...
From $473 per night (USD)
VRBO
From $220 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 $220 per night (USD)
Expedia
From $102 per night (USD)
VRBO
Lovely 2BR Gem w/ Outdoor Oasis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover your perfect urban retreat in the heart of Chicago's trendy Logan Square/Avondale neighborhood. This beautiful ...
From $102 per night (USD)
VRBO
From $205 per night (USD)
Expedia
The Landmark; a comfy suite near McCormick Place
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to the landmark. A cozy well appointed studio space in the heart of the historic Calumet/Giles Prairie district ...
From $205 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Modern 4BR in Hyde Park, Walk to University
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Located in the Hyde Park neighborhood on the south side of Chicago, the area is home to the University of Chicago and va ...
From $364 per night (USD)
VRBO
From $283 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 $283 per night (USD)
Expedia
From $292 per night (USD)
VRBO
Stylish 2BR Urban Retreat in River West
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Summary: Welcome to our contemporary 2-bedroom, 1-bathroom condo in lively River West. Ideal for business and leisure, t ...
From $292 per night (USD)
VRBO
From $106 per night (USD)
Expedia
Gorgeous 3-bedroom apartment in Jefferson Park, Chicago
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to this charming apartment in Chicago. This tranquil retreat offers a perfect escape for guests seeking a serene ...
From $106 per night (USD)
Expedia
From $255 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 $255 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Pulaski Mahal - Spacious 3bed/2.5bath with Game Room. Close to Hwy, train.
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 $428 per night (USD)
VRBO
From $773 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 $773 per night (USD)
Expedia
From $586 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 $586 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Charming 3-bedroom house in brilliant Chicago with WiFi, AC, plenty of sleeping.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover this fabulous 3-bedroom gem in Chicago. This wonderful house offers a cozy and inviting atmosphere that will ma ...
From $364 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Spacious 4-bedroom apartment with AC and WiFi in terrific Chicago
Bedrooms:
1
Bathrooms:
4
Sleeps:
14
Stay comfortably in Chicago at this 4-bedroom apartment. Marvelous and superb, this amazing property offers 4 queen beds ...
From $243 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Unwind in Chicago at this lovely newly renovated home! Nestled in the heart of West Town, this amazing property offers a ...
From $181 per night (USD)
VRBO
From $720 per night (USD)
Expedia
Walk to the Beach! Theater-Coffee Bar-Games-Gym
Bedrooms:
2
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 $720 per night (USD)
Expedia
From $755 per night (USD)
VRBO
Luxury Loft Collection 703 - 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 bui ...
From $755 per night (USD)
VRBO
From $1165 per night (USD)
Expedia
2-Story 4-Bedroom Condo: 3-minute walk to Wrigley Field. King Bed
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Just one block from Wrigley Field! Includes air hockey, ping-pong, foosball, and oversized Connect 4 in the basement ga ...
From $1165 per night (USD)
Expedia
From $322 per night (USD)
VRBO
Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to your perfect Chicago getaway! This spacious 3-bedroom, 2-bathroom multi-level apartment offers every ...
From $322 per night (USD)
VRBO
From $411 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 $411 per night (USD)
VRBO
From $611 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 $611 per night (USD)
VRBO
From $280 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 $280 per night (USD)
Expedia
From $242 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 $242 per night (USD)
VRBO
From $170 per night (USD)
Expedia
Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy a peaceful stay at this delightful 1-bedroom apartment in Chicago. Unit offers everything guests need for a perfec ...
From $170 per night (USD)
Expedia
$Beautiful and stylish 1 bedroom apartment in the heart of Pilsen \CASA PILSEN\$
From $64 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 $64 per night (USD)
VRBO
From $175 per night (USD)
VRBO
Stylish 2BR Apt in Irving Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Welcome to our charming basement unit in the heart of Irving Park! This inviting space is perfect for small families, co ...
From $175 per night (USD)
VRBO
From $334 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 $334 per night (USD)
VRBO
Click For Pricing
Expedia
Stay Inn South Shore- Pool Table, Arcade, Sleeps 10, Pet Friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to our stylish South Shore retreat, perfect for families and special events. This spacious 4-bedroom, 3-bathroom ...
Click For Pricing
Expedia
From $271 per night (USD)
VRBO
Walk to Lake Michigan: Chicago Apt w/ Deck
Bedrooms:
1
Bathrooms:
6
Sleeps:
4
Experience the magic of the Windy City at this 2-bedroom, 1-bath Chicago vacation rental! This apartment unit in a large ...
From $271 per night (USD)
VRBO
From $364 per night (USD)
Expedia
Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the beauty of Chicago from this 2-bed, 2-bath condo. The space offers a lovely living room with a sofa that can ...
From $364 per night (USD)
Expedia
From $180 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 $180 per night (USD)
VRBO
From $376 per night (USD)
Expedia
The Haven near Downtown, Medical District and United Center
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If you are traveling to Chicago for a special event at the united center or visiting a loved one at one of Chicago's pre ...
From $376 per night (USD)
Expedia
From $287 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 $287 per night (USD)
VRBO
From $130 per night (USD)
Expedia
Charming Chi-town 2-bedroom apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Unwind in the bustling city of Chicago at this superb apartment. With 2 serene bedrooms featuring queen beds, a welcomin ...
From $130 per night (USD)
Expedia
From $265 per night (USD)
VRBO
Game Room, Deck & Yard: Chicago Home
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Retreat to The Windy City and book this 2-bedroom, 3.5-bath Chicago vacation rental! This abode features an updated inte ...
From $265 per night (USD)
VRBO
From $679 per night (USD)
Expedia
Luxury Designer Penthouse West |Pool| Gold Coast
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center o ...
From $679 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Chic Euro City Getaway- Close to Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This newly renovated 3 bedroom/ 1.5 bath apartment is the perfect home for exploring Chicago! The closest metro station ...
From $316 per night (USD)
VRBO
From $271 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 $271 per night (USD)
Expedia
From $659 per night (USD)
VRBO
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 $659 per night (USD)
VRBO
From $257 per night (USD)
Expedia
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 $257 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Personal Gym! Luxury Balcony Condo
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 $169 per night (USD)
VRBO
From $162 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 $162 per night (USD)
Expedia
From $205 per night (USD)
VRBO
Great Old Town 1BR Gym, W/D, Lounge & A/C, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Old Town. It’ll be easy to simply show up and start liv ...
From $205 per night (USD)
VRBO
From $118 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 $118 per night (USD)
Expedia
From $252 per night (USD)
VRBO
3 Bedroomin the Medical Center!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: A couple houses off the popular Taylor St which has plenty of restaurants and bars! The Space: 3 Bedrooms 1 Fu ...
From $252 per night (USD)
VRBO
From $320 per night (USD)
VRBO
South Loop 4 Bedroom apt
Bedrooms:
1
Bathrooms:
4
Sleeps:
9
Summary: South Loop 4 bedroom apartment with 1.5 bathrooms. We are centrally located and very easy to get anywhere in th ...
From $320 per night (USD)
VRBO
From $390 per night (USD)
VRBO
Chic 2BR 2BA Condo with Balcony - River North Chicago
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Welcome to our chic 2-bedroom, 2-bathroom condo located in the vibrant River North neighborhood of Chicago! Per ...
From $390 per night (USD)
VRBO
From $196 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 $196 per night (USD)
Expedia
From $1415 per night (USD)
VRBO
Luxury Designer Penthouse Combo |South| Gold Coast
Bedrooms:
4
Bathrooms:
6
Sleeps:
20
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthouses ...
From $1415 per night (USD)
VRBO
From $2317 per night (USD)
VRBO
Six-Bedrooms in Wrigleyville
Bedrooms:
2
Bathrooms:
6
Sleeps:
16
Enjoy the combination of your own 2 apartments in Wrigleyville - the city's center of nightlife, restaurants, and baseba ...
From $2317 per night (USD)
VRBO
From $185 per night (USD)
VRBO
Wrigleyville Suites Room 3
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casu ...
From $185 per night (USD)
VRBO
From $1154 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 $1154 per night (USD)
VRBO
From $1026 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 $1026 per night (USD)
VRBO
From $185 per night (USD)
Expedia
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)
Expedia
From $275 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 $275 per night (USD)
VRBO
From $272 per night (USD)
Expedia
Chic 2-bedroom in center of Lincoln Park/Depaul/Wrigley + Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Chic garden unit in the heart of Chicago's popular Lincoln Park. Steps to public trains that will take you all over Chic ...
From $272 per night (USD)
Expedia
From $1532 per night (USD)
VRBO
Luxury Designer Penthouse Combo |North| Gold Coast
Bedrooms:
4
Bathrooms:
6
Sleeps:
20
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthouses ...
From $1532 per night (USD)
VRBO
From $248 per night (USD)
VRBO
Charming Chicago Apt
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Discover comfort and convenience in this spacious two-bedroom, two-bath apartment, ideally designed to accommod ...
From $248 per night (USD)
VRBO
From $423 per night (USD)
VRBO
Charming 1-bedroom apartment with AC, WiFi in phenomenal Park Ridge
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This memorable apartment is the perfect home base for your trip to Park Ridge. With a cozy bedroom, AC, heating, WiFi, a ...
From $423 per night (USD)
VRBO
From $240 per night (USD)
Expedia
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 $240 per night (USD)
Expedia
From $1381 per night (USD)
VRBO
Downtown Penthouse 5bd VIEWS|Parking, Gym+Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
Feel at Home, Unwind, and Enjoy the amenities you deserve at our Two 2-Story Downtown Penthouses (Combined Units) with M ...
From $1381 per night (USD)
VRBO
From $148 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 $148 per night (USD)
VRBO
From $329 per night (USD)
VRBO
3BR Prime Hyde Park Location Near University of Chicago and Dining
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Make yourself at home in this 3-bedroom Chicago retreat. This charming apartment features 3 king beds, a cozy living spa ...
From $329 per night (USD)
VRBO
From $126 per night (USD)
VRBO
Spacious apartment in Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Peaceful, zen, and serene! Great for longer stays! Under a five-minute car ride to midway airport! This is unit ...
From $126 per night (USD)
VRBO
From $391 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 $391 per night (USD)
VRBO
From $409 per night (USD)
VRBO
Chic 2-bedroom apartment in vibrant Chicago with AC, WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover the beauty of Chicago from this 2-bedroom apartment. This delightful space features 1 bunk bed and 1 full bed, ...
From $409 per night (USD)
VRBO
From $242 per night (USD)
VRBO
Gorgeous 4BDR in Chicago / 15mins from DWTN Brand New!
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
Located in Chicago, this apartment is a dream. With 4 bedrooms including 3 queen beds and 1 twin bed, guests will have p ...
From $242 per night (USD)
VRBO
From $279 per night (USD)
Expedia
The Burrow at Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Expect to find a relatively dark and moody interior filled with interesting things. The location is exceptional, with th ...
From $279 per night (USD)
Expedia
From $361 per night (USD)
VRBO
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 $361 per night (USD)
VRBO
From $277 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 $277 per night (USD)
VRBO
From $121 per night (USD)
VRBO
Minutes from Rosemont | 500+ Mbps | 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 f ...
From $121 per night (USD)
VRBO
From $1085 per night (USD)
Expedia
2 Connecting Suites at a 4⭐️ Hotel
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Delight in exclusive access to the Club Lounge in the Executive Suite at the Renaissance Chicago Downtown Hotel. This 80 ...
From $1085 per night (USD)
Expedia
From $394 per night (USD)
VRBO
Spacious 5-bedroom bungalow in delightful Chicago with AC, WiFi
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Make yourself at home in this 5-bedroom Chicago retreat. This adorable bungalow features 2 queen beds, 2 twin beds, and ...
From $394 per night (USD)
VRBO
From $312 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 $312 per night (USD)
VRBO
From $844 per night (USD)
VRBO
NEW! Large/Beautiful Home with 6BDS/4BTHS + Garage!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
NEW HOME/NEWLY FURNISHED! This 6 bed single family home is ready to host! My space accomodates 12 guests with 6 beds and ...
From $844 per night (USD)
VRBO
Click For Pricing
Expedia
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 Pricing
Expedia
From $119 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 $119 per night (USD)
VRBO
From $392 per night (USD)
Expedia
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 $392 per night (USD)
Expedia
From $61 per night (USD)
VRBO
Cozy Home Full Private 2nd Floor Apartment with AC, WiFi in Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled within the city limits, it strikes the perfect balance between urban convenience and suburban tranquility. Locat ...
From $61 per night (USD)
VRBO
From $264 per night (USD)
Expedia
Cozy 2BR-2BTH Oasis Near West Loop-Downtown Chicago!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Charming 2-Bedroom, 2-Bathroom Oasis in Prime West Town Location Discover the perfect blend of comfort and convenience ...
From $264 per night (USD)
Expedia
From $719 per night (USD)
VRBO
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 $719 per night (USD)
VRBO
From $125 per night (USD)
Expedia
Cute 2-bedroom apartment with WiFi, AC in vibrant Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your cozy and charming short term rental! This inviting apartment radiates warmth and comfort, making it the ...
From $125 per night (USD)
Expedia
From $1275 per night (USD)
VRBO
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Bedrooms:
5
Bathrooms:
10
Sleeps:
26
Come Enjoy Chicago's best rental property. We really have it all and we are in a perfect location, you won't have more ...
From $1275 per night (USD)
VRBO
From $208 per night (USD)
VRBO
Charming 2-bedroom 1 bathroom with plunge pool, new gazebo @ Bridgeport Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This Chicago unit 2 inviting bedrooms with 1 full bed and 1 bunk bed in Bridgeport . The cozy space includes new gazebo, ...
From $208 per night (USD)
VRBO
From $569 per night (USD)
VRBO
Discover Downtown from Our Well-Appointed Space | 2 Suites
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Downtown at Your Doorstep: In the vibrant Loop's heart, our boutique hotel is an urban oasis. Near the Art Institute & M ...
From $569 per night (USD)
VRBO
From $197 per night (USD)
Expedia
Chic 2-Bedroom/1 Bath Apartment in Fully Renovated Rowhouse
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Chicago is waiting for you at this lovely 2-bedroom apartment. This delightful space offers all the comforts you need, f ...
From $197 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Chic 2-bedroom apartment with AC, WiFi in vibrant Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy a soothing stay at this 2-bedroom apartment in Chicago. The cozy space features 2 queen beds, WiFi, AC, and heatin ...
From $280 per night (USD)
VRBO
From $178 per night (USD)
Expedia
Hip West Loop 1BR w/ Gym, Pet Area, Rooftop, W/D & Gym, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $178 per night (USD)
Expedia
From $183 per night (USD)
VRBO
Sweet West Loop 2BR w/ Rooftop, Spa, Pool & Gym, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this cozy two bedroom Blueground apartment. You’ll love coming hom ...
From $183 per night (USD)
VRBO
From $216 per night (USD)
Expedia
3-bedroom apt .on North Side! Great location between downtown and the airport.
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Discover this 3-bedroom gem in Chicago. Remodeled basement unit apartment in the Belmont Cragin neighborhood. Central No ...
From $216 per night (USD)
Expedia
Click For Pricing
VRBO
Chicago Urban Oasis ~ 6 Mi to Downtown!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Walkable Location | WFH Friendly | Washer/Dryer | Great for Traveling Professionals | Near Hospitals | Furnished Deck Y ...
Click For Pricing
VRBO
From $130 per night (USD)
Expedia
Chicago Apt 3 Mi to Lake Michigan!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
10 Mi to Downtown Chicago | Private Deck | 1,875 Sq Ft Get to know the Windy City up close and personal while staying a ...
From $130 per night (USD)
Expedia
From $206 per night (USD)
VRBO
Cozy 3BR Hyde Park Oasis Near UChi, Shops & Dining
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Explore our home in Chicago's vibrant Southside neighborhood, renowned for its rich culture, diverse dining options, and ...
From $206 per night (USD)
VRBO
From $668 per night (USD)
Expedia
Exquisite Chicago Modern Rooftop, Sleeps 9
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Welcome to our chic retreat in Dunning, Chicago. This modern unit sleeps 9 comfortably in 3 spacious bedrooms and 2 lux ...
From $668 per night (USD)
Expedia
From $245 per night (USD)
VRBO
Suite Dreams • Designer Style • Central • Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Your Stylish Home Base in Pilsen: Modern 3BR/2BA condo located in the vibrant East Pilsen/University Village ...
From $245 per night (USD)
VRBO
From $819 per night (USD)
VRBO
Luxury Two-Level Townhouse | Patio | Lincoln Park
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
Summary: NEWLY RENOVATED TOWNHOUSE IN THE HEART OF LINCOLN PARK! This private luxury townhouse (duplex) is perfectly lo ...
From $819 per night (USD)
VRBO
From $324 per night (USD)
VRBO
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Bedrooms:
1
Bathrooms:
4
Sleeps:
12
Spacious 1200 sqft 3BR 1BA located 10-15 min from Downtown! Tub/Shower Games for adults & kids 5 Smart TVs, free fast wi ...
From $324 per night (USD)
VRBO
From $582 per night (USD)
Expedia
Lincoln Park Haven: Balcony, Walk to Whole Foods
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Your perfect base in Chicago awaits at 'The Elm', a brand-new 2BR apartment in Lincoln Park. Enjoy stunning vie ...
From $582 per night (USD)
Expedia

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