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

Chicago Rentals

From $317 per night (USD)
VRBO
Chic 1 BR w Parking S
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Stunning 1 bedroom Chic Modern unit with 1 Parking Space, Private Entrance Patio, 75 inch TV, with 1 king bed a ...
From $317 per night (USD)
VRBO
From $627 per night (USD)
Expedia
Designer Apt, Billiards, Private Patio, 1 Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Stunning 3 bedroom modern garden unit apartment with 1 Gated Parking Space, Pool Table (Also a dining table), P ...
From $627 per night (USD)
Expedia
From $246 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 $246 per night (USD)
VRBO
From $552 per night (USD)
Expedia
Modern Apt, Billiards, 1 Private Patio,1 Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Stunning 3 bedroom modern garden unit apartment with 1 Gated Parking Space, Pool Table (Also a dining table), P ...
From $552 per night (USD)
Expedia
From $254 per night (USD)
VRBO
The Vibe Headquarters
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Come and enjoy your stay here at The Vibe Headquarters, where you’re sure to find peace. This condo is located in Washin ...
From $254 per night (USD)
VRBO
From $94 per night (USD)
Expedia
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 $94 per night (USD)
Expedia
From $264 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 $264 per night (USD)
VRBO
$Charming 4-bedroom apartment in delightful Chicago with central heat\/AC, WiFi.$
From $204 per night (USD)
Expedia
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)
Expedia
$Gold Coast\/Downtown Hideaway$
From $505 per night (USD)
VRBO
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 $505 per night (USD)
VRBO
From $508 per night (USD)
Expedia
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 $508 per night (USD)
Expedia
From $241 per night (USD)
VRBO
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 $241 per night (USD)
VRBO
$Lovely 2BR Gem w\/ Outdoor Oasis$
From $102 per night (USD)
Expedia
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)
Expedia
From $292 per night (USD)
VRBO
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 $292 per night (USD)
VRBO
From $440 per night (USD)
Expedia
Charming 3 bedrooms Apartment at the Medical District
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Come enjoy this beautiful updated unit in the heart of the Medical District/ Tri-Taylor. The apartment is conveniently l ...
From $440 per night (USD)
Expedia
From $628 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 $628 per night (USD)
VRBO
From $310 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 $310 per night (USD)
Expedia
Click For Pricing
VRBO
Gorgeous 3-bedroom apartment in Jefferson Park, Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to this charming apartment in Chicago. This tranquil retreat offers a perfect escape for guests seeking a serene ...
Click For Pricing
VRBO
From $220 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 $220 per night (USD)
VRBO
From $557 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 $557 per night (USD)
VRBO
From $364 per night (USD)
Expedia
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)
Expedia
From $222 per night (USD)
VRBO
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 $222 per night (USD)
VRBO
From $625 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 $625 per night (USD)
Expedia
From $1321 per night (USD)
VRBO
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 $1321 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Summary: Welcome to your perfect Chicago getaway! This spacious 3-bedroom, 2-bathroom multi-level apartment offers every ...
From $527 per night (USD)
Expedia
From $403 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 $403 per night (USD)
VRBO
From $479 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 $479 per night (USD)
Expedia
From $412 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 $412 per night (USD)
VRBO
From $161 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 $161 per night (USD)
Expedia
$Beautiful and stylish 1 bedroom apartment in the heart of Pilsen \CASA PILSEN\$
From $65 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 $65 per night (USD)
VRBO
From $271 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 $271 per night (USD)
VRBO
From $358 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 $358 per night (USD)
VRBO
$Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer\/Dryer$
From $262 per night (USD)
Expedia
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 $262 per night (USD)
Expedia
From $724 per night (USD)
VRBO
The Urban Manor “Modern luxury style”
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Urban Manor in Hyde Park neighborhood, close to charming restaurants and coffee shops, exudes luxury and comfort. Th ...
From $724 per night (USD)
VRBO
From $226 per night (USD)
Expedia
2 queen beds -Boat rental opt
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our cozy 2-bedroom apartment in the heart of Bridgeport, Chicago’s vibrant and historic neighborhood! Perfect ...
From $226 per night (USD)
Expedia
From $346 per night (USD)
VRBO
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 $346 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Chicago Apt: 4 Mi to Lake Michigan
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Looking for a comfortable home base while exploring the city? Pack your bags and head to this welcoming 4-bedroom, 1-bat ...
From $249 per night (USD)
Expedia
From $149 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 $149 per night (USD)
VRBO
From $404 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 $404 per night (USD)
Expedia
From $237 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 $237 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Rustic Cozy Haven in West Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to your cozy retreat in West Town! Nestled amidst vibrant restaurants and lively bars, this charming unit offers ...
From $349 per night (USD)
Expedia
From $130 per night (USD)
VRBO
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)
VRBO
From $381 per night (USD)
Expedia
1-bedroom apartment in awesome Chicago with AC, WiFi and 1FREE Garage Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Consider this apartment your home away from home while you visit Chicago. This charming space features a cozy bedroom wi ...
From $381 per night (USD)
Expedia
$Walk to Lake Michigan: Chicago Apt w\/ Deck$
From $278 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 $278 per night (USD)
VRBO
From $357 per night (USD)
Expedia
Game Room, Deck & Yard: Chicago Home
Bedrooms:
4
Bathrooms:
4
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 $357 per night (USD)
Expedia
From $311 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 $311 per night (USD)
VRBO
$Chicago Cityview Chic II Gold Coast\/River North$
From $231 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 $231 per night (USD)
Expedia
From $457 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 $457 per night (USD)
VRBO
From $260 per night (USD)
Expedia
Personal Gym! Luxury Balcony Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
🌟 This property is managed by @LuxuryLodgingSTR , visit us on the web before booking here for extra savings! 🌟 ✨ Much ...
From $260 per night (USD)
Expedia
From $435 per night (USD)
VRBO
The Lytle House Loft
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Lytle House Loft is a one of a kind residence located in the heart of the Edgewater neighborhood in Chicago, just bl ...
From $435 per night (USD)
VRBO
$Neat Old Town 1BR Gym, W\/D, Rooftop, BBQ & A\/C, by Blueground$
From $135 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 $135 per night (USD)
Expedia
$Great Old Town 1BR Gym, W\/D, Lounge & A\/C, by Blueground$
From $191 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 l ...
From $191 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 $182 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 $182 per night (USD)
VRBO
From $251 per night (USD)
Expedia
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 $251 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Cozy 3-bedroom apartment in beautiful Old Irving Park, Chicago with AC, WiFi
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy a comfortable stay in Chicago at this first floor 3-bedroom apartment. This delightful property features 3 queen-s ...
From $220 per night (USD)
VRBO
From $171 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 $171 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Spacious 3-Bedroom Haven Near Chicago's Top Attractions
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to this beautiful apartment at Chicago! Feel free to relax at any of the 3 bedrooms we have with queen size bed ...
From $231 per night (USD)
VRBO
From $413 per night (USD)
VRBO
2 Bed & 3 Bath Chicago Condo
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Kick back and relax in this calm, stylish space minutes away from Chicago's best attractions. Step inside thi ...
From $413 per night (USD)
VRBO
From $260 per night (USD)
VRBO
Windy City Getaway | 3BR 2BA Chicago Townhouse by RedAwning
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Experience Chicago up close and personal when you stay at this 3-bedroom, 2.5-bathroom vacation rental. Boasting stylish ...
From $260 per night (USD)
VRBO
$Spacious Roscoe Village Apt w\/ Home Office!$
Click For Pricing
Expedia
Spacious Roscoe Village Apt w\/ Home Office!
Bedrooms:
2
Bathrooms:
6
Sleeps:
6
Pet Friendly w/ Fee | Walkable Location | 2 Mi to Wrigley Field Experience the city in style when you stay at this Chic ...
Click For Pricing
Expedia
$Chic 2-bedroom in center of Lincoln Park\/Depaul\/Wrigley + Parking$
From $253 per night (USD)
VRBO
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 $253 per night (USD)
VRBO
From $400 per night (USD)
Expedia
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 $400 per night (USD)
Expedia
$Large 2-Bedroom w\/ Huge Roofdeck view of Skyline$
From $440 per night (USD)
VRBO
Large 2-Bedroom w\/ Huge Roofdeck view of Skyline
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Summary: Experience luxurious living in Chicago! This brand new, spacious 2-bedroom 2-bath penthouse apartment offers an ...
From $440 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Luxury one bedroom condo located in Chicago's Gold Coast neighborhood!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy a stylish one bedroom condo located in the heart of Chicago's famous Gold Coast neighborhood. This luxury condo b ...
From $250 per night (USD)
Expedia
From $1836 per night (USD)
VRBO
Downtown Penthouse 5bd - Parking, Gym, Pool, VIEWS
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Feel at Home, Unwind, and Enjoy the amenities you deserve at our Two 2-Story Downtown Penthouses (Combined Units) with M ...
From $1836 per night (USD)
VRBO
From $158 per night (USD)
VRBO
CozylSpaciousl 2-BR Self-checkin Apartment in Chicago l Few Steps from Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Located in Chicago, enjoy what this 2-bedroom apartment has to offer. With 2 queen beds, a cozy bathtub, and essential a ...
From $158 per night (USD)
VRBO
From $459 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 $459 per night (USD)
VRBO
From $155 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 $155 per night (USD)
VRBO
From $166 per night (USD)
VRBO
Bryant Gorgeous duplex
Bedrooms:
3
Bathrooms:
3
Sleeps:
3
Gorgeous duplex in Wicker Park/Bucktown on quiet, tree-lined ONE WAY side street south of North Ave. 2 OUTDOOR SPACES - ...
From $166 per night (USD)
VRBO
$Gorgeous 4BDR in Chicago \/ 15mins from DWTN Brand New!$
From $239 per night (USD)
Expedia
Gorgeous 4BDR in Chicago \/ 15mins from DWTN Brand New!
Bedrooms:
2
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 $239 per night (USD)
Expedia
From $419 per night (USD)
VRBO
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 $419 per night (USD)
VRBO
From $220 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 $220 per night (USD)
Expedia
$UIC \/ Little Italy - Charming 1 Bed 1 Bath Apt. WITH FREE PARKING!$
From $170 per night (USD)
VRBO
UIC \/ Little Italy - Charming 1 Bed 1 Bath Apt. WITH FREE PARKING!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
About this space: Adorable 1 bed 1 bath apartment WITH FREE PARKING located in the heart of Chicago's Little Italy neig ...
From $170 per night (USD)
VRBO
$Modern Chic Condo 7 mins from downtown Chicago!\n$
From $228 per night (USD)
Expedia
Modern Chic Condo 7 mins from downtown Chicago!\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience the Windy City from our stylish 1-bedroom condo, perfectly designed for comfort and convenience. Just a block ...
From $228 per night (USD)
Expedia
From $149 per night (USD)
VRBO
Minutes from Rosemont | 500+ Mbps | Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
🌟 This property is managed by @LuxuryLodgingSTR, visit us on the web before booking here for extra savings! 🌟 ✨ “ Sup ...
From $149 per night (USD)
VRBO
From $1162 per night (USD)
Expedia
2 Connecting Suites at a 4.5⭐️ Hotel
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Junior Suite + Superior Room 2 Double Beds at Sofitel Chicago Magnificent Mile provides added space and privacy to ...
From $1162 per night (USD)
Expedia
From $697 per night (USD)
VRBO
2 Connecting Suites at a 4.5⭐️ Hotel
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The One Bedroom Suite features a second king-size bedroom, offering contemporary decor and beautiful views of Lake Michi ...
From $697 per night (USD)
VRBO
From $1093 per night (USD)
Expedia
2 Connecting Suites at a 4.5⭐️ Hotel
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Appointed with a second, sumptuous guest room, modern furnishings and beautiful floral artwork by photographer Warwick O ...
From $1093 per night (USD)
Expedia
From $697 per night (USD)
VRBO
2 Connecting Suites at a 4.5⭐️ Hotel
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The One Bedroom Suite Double features a second king-size bedroom, offering contemporary decor and beautiful views of Lak ...
From $697 per night (USD)
VRBO
From $1067 per night (USD)
Expedia
2 Connecting Suites at a 4⭐️ Hotel
Bedrooms:
3
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 $1067 per night (USD)
Expedia
From $144 per night (USD)
VRBO
Lakeview home
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
Welcome to this hidden gem in Lakeview with a highly coveted PRIVATE 700 sf. walk out terrace/yard -wonderful for outdoo ...
From $144 per night (USD)
VRBO
$NEW! Large\/Beautiful Home with 6BDS\/4BTHS + Garage!$
From $1060 per night (USD)
Expedia
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 $1060 per night (USD)
Expedia
$Best Location\/ Designer themed\/ Patio\/ Queen beds\/ Parking$
Click For Pricing
VRBO
Best Location\/ Designer themed\/ Patio\/ Queen beds\/ Parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Walk to almost everything Chicago has to offer- Downtown, Magnificent Mile, North Avenue beach, zoo, and Lincoln park, r ...
Click For Pricing
VRBO
$Large Modern 2BD\/2BA Condo in River North- Free Parking!$
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 $145 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 $145 per night (USD)
VRBO
From $61 per night (USD)
Expedia
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)
Expedia
From $318 per night (USD)
VRBO
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 $318 per night (USD)
VRBO
$4 Mi to Dtwn Chicago: Modern Home w\/ Outdoor Space$
Click For Pricing
Expedia
4 Mi to Dtwn Chicago: Modern Home w\/ Outdoor Space
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
2,800 Sq Ft | Washer/Dryer | Deck w/ Charcoal Grill | 1 Mi to Train Station Book your next Windy City getaway at this 3 ...
Click For Pricing
Expedia
From $886 per night (USD)
VRBO
Stunning 4-Bed 4-Bath Fully Renovated Home - Dual Living Spaces in North Chicago
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to this beautifully renovated single-family home, offering luxury, comfort, and modern elegance in the heart of ...
From $886 per night (USD)
VRBO
From $126 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 $126 per night (USD)
Expedia
From $339 per night (USD)
VRBO
Dive Into Your Dream Vacation! Near Bridgehouse and Chicago River Museum!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $339 per night (USD)
VRBO
From $1485 per night (USD)
Expedia
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 $1485 per night (USD)
Expedia
$8 beds. Wicker Park Spacious Guest House wi\/Spa Bath, Fireplace, 1 Grg Spot.$
From $537 per night (USD)
VRBO
8 beds. Wicker Park Spacious Guest House wi\/Spa Bath, Fireplace, 1 Grg Spot.
Bedrooms:
3
Bathrooms:
3
Sleeps:
13
Escape to a superb 3-bedroom guest house in Wicker Park. This enjoyable retreat is a Unwind, relax, and enjoy everything ...
From $537 per night (USD)
VRBO
$Hip West Loop 1BR w\/ Gym, Pet Area, Rooftop, W\/D & Gym, by Blueground$
From $196 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 $196 per night (USD)
Expedia
$Sweet West Loop 2BR w\/ Rooftop, Spa, Pool & Gym, by Blueground$
From $357 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 $357 per night (USD)
VRBO
From $212 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 $212 per night (USD)
Expedia
From $95 per night (USD)
VRBO
Chicago Urban Oasis ~ 6 Mi to Downtown!
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Walkable Location | WFH Friendly | Washer/Dryer | Great for Traveling Professionals | Near Hospitals | Furnished Deck Y ...
From $95 per night (USD)
VRBO
From $112 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 $112 per night (USD)
Expedia
From $491 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 $491 per night (USD)
VRBO
From $635 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 $635 per night (USD)
Expedia

Search Your Destination Now!

Chicago Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals