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

Chicago Rentals

$Modern 2BR Furnished Apt w\/In-Unit Laundry!$
From $187 per night (USD)
VRBO
Modern 2BR Furnished Apt w\/In-Unit Laundry!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your perfect retreat nestled in the heart of Chicago. Our fully furnished 2-bedroom apartment is a stylish fu ...
From $187 per night (USD)
VRBO
Click For Pricing
VRBO
Beautiful 2 bedroom 2 bathroom condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This 2 bedroom 2 bathroom condo is perfect for your Chicago stay. We offer all your essentials such as; toiletries, dish ...
Click For Pricing
VRBO
From $255 per night (USD)
VRBO
Chicago Rental - Vernon Ave
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
2600 SF renovated unit in the South suburbs, and only 30 minutes south of Downtown Chicago! This property has 5 bedrooms ...
From $255 per night (USD)
VRBO
$Spacious 3BR Apt w\/ In-Unit Laundry$
From $282 per night (USD)
VRBO
Spacious 3BR Apt w\/ In-Unit Laundry
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Discover comfort and style at our fully furnished 3-bedroom apartment. This modern home offers convenience and elegance ...
From $282 per night (USD)
VRBO
From $200 per night (USD)
VRBO
Modern 3-Bedroom Condo with Artistic Flair in Historic Bronzeville
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our spacious and stylish 3-bedroom, 3-bath condo located in the vibrant, historic Bronzeville community of Ch ...
From $200 per night (USD)
VRBO
From $1457 per night (USD)
VRBO
The Grand Kimball Lodge, Logan Square, Sleeps 14
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
The Grand Kimball Lodge is filled with enormous windows, a large, open concept layout, and Wes Anderson inspired decor. ...
From $1457 per night (USD)
VRBO
From $104 per night (USD)
VRBO
Stunning Suite 2 @ Hotel Nemo Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Hotel Nemo is a boutique, corporate guest house stylishly designed for those who want to stay just around the c ...
From $104 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Chicago Rental - W 64th St
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
2200 SF renovated unit in the suburbs of Chicago, and only 30 minutes south of Downtown Chicago! This property has 5 bed ...
From $289 per night (USD)
VRBO
From $269 per night (USD)
VRBO
Spacious, Clean and Steps from Wrigley Field!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Enjoy this beautiful space, just minutes away from the very best Chicago has to offer! This condo is walking distance fr ...
From $269 per night (USD)
VRBO
From $135 per night (USD)
VRBO
South Shore Home Near Lake for long-term stays, corporate travelers, and nurses
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to our charming brick home in the picturesque South Shore community of Chicago! This fully furnished property of ...
From $135 per night (USD)
VRBO
$Chicago Rental - W Berwyn Ave\n$
From $288 per night (USD)
VRBO
Chicago Rental - W Berwyn Ave\n
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
1800 SF renovated unit in the North suburbs, and only 20 minutes to Downtown Chicago! This property has 4 bedrooms, & 2 ...
From $288 per night (USD)
VRBO
$Gold Coast Luxury Condo w\/ Rooftop Pool$
From $199 per night (USD)
VRBO
Gold Coast Luxury Condo w\/ Rooftop Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Summary: Enjoy a stylish experience at this centrally-located place.Located in the heart of Gold Coast, Chicago's most s ...
From $199 per night (USD)
VRBO
From $92 per night (USD)
VRBO
Midway Airport 2 Bedroom with full Kitchen
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Summary: Steps from Midway Airport, our unit offers two bedrooms, a bathroom, a full kitchen with all your necessities a ...
From $92 per night (USD)
VRBO
From $286 per night (USD)
VRBO
Chicago Rental - Narragansett
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
2000 SF renovated unit is 7 minutes away from Midway Air and 20 minutes from downtown! This property has 4 bedrooms, & 2 ...
From $286 per night (USD)
VRBO
From $1143 per night (USD)
VRBO
Luxurious 8 Bed Retreat State of the Art Theater
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Welcome to our opulent 5-bedroom sanctuary, where luxury meets entertainment in the heart of the city! Nestled ...
From $1143 per night (USD)
VRBO
From $413 per night (USD)
VRBO
Chic 4-Bedroom Haven: Designer's Dream Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: Welcome to our Chic 4-Bedroom Haven in the heart of Ukrainian Village, Chicago! This meticulously curated home ...
From $413 per night (USD)
VRBO
$Ideal South Loop 2BR w\/ Pool, Gym & Rooftop, nr L, by Blueground$
From $303 per night (USD)
VRBO
Ideal South Loop 2BR w\/ Pool, Gym & Rooftop, nr L, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this bright South Loop furnished two-bedroom apart ...
From $303 per night (USD)
VRBO
Click For Pricing
VRBO
The Way, just minutes from local attractions.
Bedrooms:
2
Bathrooms:
3
Sleeps:
15
The whole group will enjoy easy access to everything from this centrally located place. We are minutes away from a local ...
Click For Pricing
VRBO
$Stylish West Loop 1BR w\/ Pool & Gym, nr Union Park, by Blueground$
From $153 per night (USD)
VRBO
Stylish West Loop 1BR w\/ Pool & Gym, nr Union Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this lovely West Loop furnished one-bedroom apartm ...
From $153 per night (USD)
VRBO
From $65 per night (USD)
VRBO
Chic Retreat Steps from University of Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Discover the ultimate urban haven at 5461 S Drexel Ave in Hyde Park a true gem that beckons to both industrious professi ...
From $65 per night (USD)
VRBO
From $104 per night (USD)
VRBO
Cozy Well Maintained Bronzeville 2 Bed 1 bath Condo! 5 min to U of C
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Quiet & Cozy Condo in Bronzeville. Updated with all new stainless steel appliances, this is the perfect getaway. This pr ...
From $104 per night (USD)
VRBO
From $147 per night (USD)
VRBO
East Lincoln Park gem
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Contemporary open kitchenStylish curtains Samsung stainless steel microwave Outdoor space Exquisite granite countertops ...
From $147 per night (USD)
VRBO
$Sunny Lakeview 1BR w\/ Rooftop & Gym, nr Lincoln Park, by Blueground$
From $116 per night (USD)
VRBO
Sunny Lakeview 1BR w\/ Rooftop & Gym, nr Lincoln Park, 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 $116 per night (USD)
VRBO
$Open Lakeview 2BR w\/ Gym & Grills, nr Lakefront Trail, by Blueground$
From $267 per night (USD)
VRBO
Open Lakeview 2BR w\/ Gym & Grills, nr Lakefront Trail, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two-bedroom Lakeview apartment with balcony views over the city. It’ll be easy t ...
From $267 per night (USD)
VRBO
$Dreamy Streeterville Studio w\/ Pool & Gym, nr Navy Pier, by Blueground$
From $127 per night (USD)
VRBO
Dreamy Streeterville Studio w\/ Pool & Gym, nr Navy Pier, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one-bedroom Streeterville apartment with high floor views over the city. It’ll b ...
From $127 per night (USD)
VRBO
$Deluxe Loop 1BR w\/ Gym & Doorman, nr L & Grant Park, by Blueground$
From $98 per night (USD)
VRBO
Deluxe Loop 1BR w\/ Gym & Doorman, nr L & Grant Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this charming one-bedroom Blueground apartment. You’ll love coming ...
From $98 per night (USD)
VRBO
$Open Loop 2BR w\/ Lounge & Gym, nr Chicago Riverwalk, by Blueground$
From $182 per night (USD)
VRBO
Open Loop 2BR w\/ Lounge & Gym, nr Chicago Riverwalk, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this pretty two-bedroom Blueground apartment. You’ll love coming h ...
From $182 per night (USD)
VRBO
$Amazing Streeterville 2BR w\/ Gym & Pool, Ohio St beach, by Blueground$
From $202 per night (USD)
VRBO
Amazing Streeterville 2BR w\/ Gym & Pool, Ohio St beach, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Streeterville furnished two-bedroom ...
From $202 per night (USD)
VRBO
$Bronzeville Haven: 2BR\/2BA Oasis, 10 Mins to Downtown$
From $117 per night (USD)
VRBO
Bronzeville Haven: 2BR\/2BA Oasis, 10 Mins to Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Bronzeville, where history and modernity converge in our inviting 2-bedroom, 2-bathroom condo. Situated just ...
From $117 per night (USD)
VRBO
$HUGE Luxury Loft in Downtown Chicago w\/ Gym, Skydeck, Theater, Game Room$
From $140 per night (USD)
VRBO
HUGE Luxury Loft in Downtown Chicago w\/ Gym, Skydeck, Theater, Game Room
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This furnished apartment is located in Streeterville. Home to iconic landmarks like Navy Pier and the Magnificent Mile, ...
From $140 per night (USD)
VRBO
From $202 per night (USD)
VRBO
2BR near Hyde Park UChicago Medical Museums Robie House Large & Comfortable
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Spacious vintage floor w/ 2BRs available inside in-progress Oasis for travelers in S. Hyde Park near UChicago Med. 300Mb ...
From $202 per night (USD)
VRBO
From $136 per night (USD)
VRBO
Taste the Best of Chicago is a cozy stylish nook in the perfect location
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Located in prominent and historic community, this stylish apartment is just across the street from the South Shore Cultu ...
From $136 per night (USD)
VRBO
$Cozy West Loop Apartment w\/Private Patio$
From $159 per night (USD)
VRBO
Cozy West Loop Apartment w\/Private Patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to this stunning West Town Apartment, located close enough to all the attractions Chicago has to offer ...
From $159 per night (USD)
VRBO
$Designer Dreams: A Luxurious Escape w\/1 car garage$
From $354 per night (USD)
VRBO
Designer Dreams: A Luxurious Escape w\/1 car garage
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to our luxurious and spacious abode! Nestled in the heart of the city, our full-size vacation home is t ...
From $354 per night (USD)
VRBO
From $275 per night (USD)
VRBO
Family Fun Escape: With 2 Free Parking Spaces!
Bedrooms:
2
Bathrooms:
3
Sleeps:
14
Summary: As soon as you step inside, you'll be struck by the open floor plan and sleek design. The living room is the pe ...
From $275 per night (USD)
VRBO
From $299 per night (USD)
VRBO
Family Fun Haven Summ
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to this stunning West Town Apartment, located close enough to all the attractions Chicago has to offer ...
From $299 per night (USD)
VRBO
$Sunny West Loop Jr 1BR w\/ Rooftop & Dog Run, nr I-90, by Blueground$
From $139 per night (USD)
VRBO
Sunny West Loop Jr 1BR w\/ Rooftop & Dog Run, nr I-90, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy West Loop furnished one-bedroom apartmen ...
From $139 per night (USD)
VRBO
$Trendy West Loop 2BR w\/ Lounge & Pool, nr Union Park, by Blueground$
From $236 per night (USD)
VRBO
Trendy West Loop 2BR w\/ Lounge & Pool, nr Union Park, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this stylish two-bedroom Blueground apartment. You’ll love coming ...
From $236 per night (USD)
VRBO
$Deluxe Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground$
From $119 per night (USD)
VRBO
Deluxe Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, 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 $119 per night (USD)
VRBO
$Lovely Uptown 1BR w\/ Gym w\/ Boxing Ring, close to Beach, by Blueground$
From $156 per night (USD)
VRBO
Lovely Uptown 1BR w\/ Gym w\/ Boxing Ring, close to Beach, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Uptown furnished one-bedroom ap ...
From $156 per night (USD)
VRBO
$Stellar West Loop 2BR w\/ Rooftop & Gym, close to L, by Blueground$
From $218 per night (USD)
VRBO
Stellar West Loop 2BR w\/ Rooftop & Gym, close to L, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this lovely two-bedroom Blueground apartment. You’ll love coming h ...
From $218 per night (USD)
VRBO
From $96 per night (USD)
VRBO
Modern Chicago Vacation Rental ~ 14 Mi to Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stay in style at this 2-bedroom, 1-bath vacation rental apartment in the heart of Chicago, IL. With its convenient locat ...
From $96 per night (USD)
VRBO
From $365 per night (USD)
VRBO
Sonder The Burnham | One-Bedroom Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Burnham is anything but a traditional red brick building. Step inside for modern upgrades with stainless steel appli ...
From $365 per night (USD)
VRBO
From $393 per night (USD)
VRBO
2BR Modern South Loop Suite With Views & Gym
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Nestled in the heart of Chicago's vibrant cityscape, we offer a luxurious urban haven that embodies modern livi ...
From $393 per night (USD)
VRBO
From $659 per night (USD)
VRBO
Splendid Corner 3BR in the Loop | City Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Stylish 1,300+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fa ...
From $659 per night (USD)
VRBO
From $400 per night (USD)
VRBO
Cozy luxury apartment-home located in the beautiful neighborhood of Bronzeville.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Indulge in the epitome of luxury living with this extraordinary apartment-home located in the highly coveted neighborhoo ...
From $400 per night (USD)
VRBO
$Gorgeous South Loop 2BR w\/ Jacuzzi & Rooftop, nr Colleges, by Blueground$
From $167 per night (USD)
VRBO
Gorgeous South Loop 2BR w\/ Jacuzzi & Rooftop, nr Colleges, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two-bedroom South Loop apartment with balcony views over the city. It’ll be easy ...
From $167 per night (USD)
VRBO
From $50 per night (USD)
VRBO
Cozy private bedroom within shared space in Woodlawn,15 minutes from everything!
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Historic Chicago fully furnished room for rent within a 4 bed/2bed shared space in Woodlawn, 15 minute away from everyth ...
From $50 per night (USD)
VRBO
$Great Location in Norwood Park\/Edison Park Area! Workstation!$
From $209 per night (USD)
VRBO
Great Location in Norwood Park\/Edison Park Area! Workstation!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
- Upper unit within two unit building -5 miles to O’Hare Airport 10 minute drive without traffic -Blackout curtains -Upd ...
From $209 per night (USD)
VRBO
From $367 per night (USD)
VRBO
UNIQUE VERSACE LOFT DOWNTOWN CHICAGO RiverNorth
Bedrooms:
2
Bathrooms:
1
Sleeps:
5
Indulge in the ultimate luxury experience at our Versace-themed loft in downtown River North, Chicago. This one of a kin ...
From $367 per night (USD)
VRBO
From $723 per night (USD)
VRBO
Modern Townhome With King Suite & Private Patio
Bedrooms:
3
Bathrooms:
2
Sleeps:
9
Welcome to Bucktown! This property lives like a single family home and consists of a private patio, 2 spacious living ro ...
From $723 per night (USD)
VRBO
Click For Pricing
VRBO
Paris Meets Chicago-Gem Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
9
Welcome to our spacious and modern condo located in the heart of River North, Chicago! Our beautiful condo can comfortab ...
Click For Pricing
VRBO
$Hip South Loop 1BR w\/ Gym & Game Room, nr Top Schools, by Blueground$
From $150 per night (USD)
VRBO
Hip South Loop 1BR w\/ Gym & Game Room, nr Top Schools, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one-bedroom South Loop apartment with high floor views over the city. It’ll be e ...
From $150 per night (USD)
VRBO
From $500 per night (USD)
VRBO
Charming 3-BR House in Logan Sq
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Discover this exquisite treasure nestled in the heart of Logan Square. Guests adore this residence for its 2-level, glas ...
From $500 per night (USD)
VRBO
From $235 per night (USD)
VRBO
Cozy, Bright and a Great Location!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Centrally located in Logan Square, this beautiful bright and airy space is overlooking one of the coolest streets in Chi ...
From $235 per night (USD)
VRBO
From $299 per night (USD)
VRBO
Cozy Modern Duplex 4 Bedroom Condo less then 5 mins from Hyde Park
Bedrooms:
2
Bathrooms:
4
Sleeps:
31
10-15 minutes from The United Center, Soldier Field, Shedd Aquarium, Museum of Science and Industry. Downtown Chicago is ...
From $299 per night (USD)
VRBO
From $273 per night (USD)
VRBO
Cozy Garden Unit Located in North Center
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
My home is located on a charming tree-lined street in the North Center/Lakeview neighborhood. The featured space is a qu ...
From $273 per night (USD)
VRBO
From $275 per night (USD)
VRBO
The Neighborhood Hotel - Little Italy One Bedroom - ADA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 KING BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM ADA This airy, one bedroom suite exudes a mid-century Italian meets slee ...
From $275 per night (USD)
VRBO
From $210 per night (USD)
VRBO
The Neighborhood Hotel - Little Italy Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
1 KING BED + 1 BATHROOM This airy studio exudes a mid-century Italian meets sleek urban loft vibe. Pops of color compli ...
From $210 per night (USD)
VRBO
$The Neighborhood Hotel - Little Italy Two Bedroom w\/ Balcony$
From $428 per night (USD)
VRBO
The Neighborhood Hotel - Little Italy Two Bedroom w\/ Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1 KING BED + 1 QUEEN BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM + BALCONY This airy, two bedroom suite exudes a mid-centur ...
From $428 per night (USD)
VRBO
From $417 per night (USD)
VRBO
The Neighborhood Hotel - Little Italy Two Bedroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
1 KING BED + 1 QUEEN BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM This airy, two bedroom suite exudes a mid-century Italian ...
From $417 per night (USD)
VRBO
$The Neighborhood Hotel - Little Italy One Bedroom w\/ Balcony$
From $347 per night (USD)
VRBO
The Neighborhood Hotel - Little Italy One Bedroom w\/ Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 KING BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM + BALCONY This airy, one bedroom suite exudes a mid-century Italian meet ...
From $347 per night (USD)
VRBO
From $372 per night (USD)
VRBO
The Neighborhood Hotel - Little Italy Two Bedroom - ADA
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
1 KING BED + 1 QUEEN BED + 1 QUEEN SLEEPER SOFA + 1 ADA BATHROOM This airy, two bedroom suite exudes a mid-century Ital ...
From $372 per night (USD)
VRBO
$The Neighborhood Hotel - Little Italy One Bedroom w\/ Patio$
From $315 per night (USD)
VRBO
The Neighborhood Hotel - Little Italy One Bedroom w\/ Patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 KING BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM + PATIO This airy, one bedroom suite exudes a mid-century Italian meets ...
From $315 per night (USD)
VRBO
Click For Pricing
VRBO
Perfect 4 Bedroom + 2 Bath unit on 2 separate floors, Free parking, CUBS
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Enjoy Chicago in this lovely and very spacious home! Entire 2 floors of space for guests to enjoy! 4 total bedrooms with ...
Click For Pricing
VRBO
From $299 per night (USD)
VRBO
Custom 5 Bedrooms, Family Friendly, Centrally Located, WITH YARD and Parking!
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
A beautiful 5 bedroom family home, located on the tree lined streets of Lakeview. A large, open-plan layout includes a 1 ...
From $299 per night (USD)
VRBO
From $48 per night (USD)
VRBO
Home sweet home in Northwest Chicago, almost a sole unit for you, great location
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Full cozy, clean, and private garden suite for a pleasant stay. The home is located on a beautiful tree-lined residentia ...
From $48 per night (USD)
VRBO
From $150 per night (USD)
VRBO
Beautiful town house
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Beautiful town house sits in meticulously maintained courtyard with two private outdoor spaces. Freshly painted first f ...
From $150 per night (USD)
VRBO
From $339 per night (USD)
VRBO
Fremont St. Guesthouse - Unit 1
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Classic Chicago Brownstone, updated 3 bedroom and 2 bathroom high end, 1st floor condo. Located on beautiful Fremont Str ...
From $339 per night (USD)
VRBO
From $520 per night (USD)
VRBO
Pilsen Paradise l 3 miles to DT
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Summary: Welcome to our 2-in-1 retreat in Pilsen! Two side-by-side apartments with modern, sleek finishes and fully stoc ...
From $520 per night (USD)
VRBO
From $199 per night (USD)
VRBO
Sleek Urban Retreat Steps from IL Med District
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Welcome to our charming 2-bedroom retreat near IL Medical District! Modern elegance and abundant natural light ...
From $199 per night (USD)
VRBO
From $125 per night (USD)
VRBO
2 Bed l 5 min from Med District l Free Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Summary: Looking for a place to stay while you're in town on business? Or maybe you're a traveling nurse or another prof ...
From $125 per night (USD)
VRBO
From $390 per night (USD)
VRBO
Chic River North Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Welcome to our Chic River North Retreat, a hidden gem in vibrant River North, Chicago. Discover a rare 2-bedroo ...
From $390 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Beautiful Downtown 3BR with Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
A beautiful and modern three bedroom two bath apartment located in the heart of Fulton Market in downtown Chicago. You'l ...
From $428 per night (USD)
VRBO
$STYLISH-LOCAL-COMFY-SAFE \/ 5 night min. stay$
From $407 per night (USD)
VRBO
STYLISH-LOCAL-COMFY-SAFE \/ 5 night min. stay
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
-Please don't ask for less than 5 nights... we do not accept reservations under 5 nights ever.. Located in Chicago’s ...
From $407 per night (USD)
VRBO
From $343 per night (USD)
VRBO
Near To Gold Coast, Michigan Avenue, And Downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Situated on quiet side street across from 19c. church, steps from popular bars, restaurants, and public transportation. ...
From $343 per night (USD)
VRBO
$Luxéry Stay South Loop - McCormick\/WinTrust Area$
From $428 per night (USD)
VRBO
Luxéry Stay South Loop - McCormick\/WinTrust Area
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Looking for a beautiful oasis in the midst of the city? Look no further, as this beautiful 3 bedroom gives you ...
From $428 per night (USD)
VRBO
From $249 per night (USD)
VRBO
Airy & Clean 2BR Apt.+ Free Covered Garage Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Indulge in the perfect extended stay experience in Chicago with our fully furnished and spacious 2-bedroom, 2-bathroom u ...
From $249 per night (USD)
VRBO
$Relaxing & Roomy 2BR Apartment w\/ On-Site Laundry!$
From $298 per night (USD)
VRBO
Relaxing & Roomy 2BR Apartment w\/ On-Site Laundry!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our cozy fully furnished 2-bedroom apartment. Nestled in a vibrant urban setting, our thoughtfully designed s ...
From $298 per night (USD)
VRBO
From $222 per night (USD)
VRBO
Complete Furnished & Modern 1BR Apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your chic urban retreat! Our fully furnished 1-bedroom apartment offers a stylish living space in the heart o ...
From $222 per night (USD)
VRBO
From $162 per night (USD)
VRBO
3BR Apartment close to Beach Park Loyola
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Experience the ultimate in privacy and convenience with our modern 3-bedroom apartment. Relax in a comfortable bed, cook ...
From $162 per night (USD)
VRBO
From $173 per night (USD)
VRBO
2BR Apt near Shops Dining Loyola University
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy a comfortable and convenient stay in our modern 2-bedroom apartment. With plush beds and a fully equipped kitchen, ...
From $173 per night (USD)
VRBO
From $178 per night (USD)
VRBO
Airport Proximity Paradise: 2BR Spacious Apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Pamper yourself with a sumptuous stay in our generously-sized 2-bedroom apartment, characterized by its contemporary and ...
From $178 per night (USD)
VRBO
$DTown Penthouse - 4bd\/4ba +Parking, Gym$
From $1261 per night (USD)
VRBO
DTown Penthouse - 4bd\/4ba +Parking, Gym
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
Welcome to our Two 2-Story Downtown Penthouses with Million Dollar Views. Guests love staying with us because: -Central ...
From $1261 per night (USD)
VRBO
From $292 per night (USD)
VRBO
50th Floor Mag Mile Studio VIEW, Pool, Gym, Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
"Step into the vibrant heart of River North, where your window frames forever views and the sky blushes with the best s ...
From $292 per night (USD)
VRBO
$Classic Lakeview 2BR w\/ Deck, Pool & Gym, nr Lincoln Park, by Blueground$
Click For Pricing
VRBO
Classic Lakeview 2BR w\/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this pretty two-bedroom Blueground apartment. You’ll love coming h ...
Click For Pricing
VRBO
From $283 per night (USD)
VRBO
The Logan Square Guest House - Classic Vintage Comfort With Free Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
You will be transported when you stay with us in this hip and charming space in Chicago's most vibrant neighborhood! Enj ...
From $283 per night (USD)
VRBO
From $518 per night (USD)
VRBO
Downtown Penthouse 2bd +Parking, Gym, Private Patio
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our 2-Story Penthouse with beautiful views. Guests love staying with us because: -Central location near Gran ...
From $518 per night (USD)
VRBO
From $468 per night (USD)
VRBO
Downtown Penthouse +Parking, Gym, Private Patio
Bedrooms:
3
Bathrooms:
2
Sleeps:
7
Welcome to our Downtown Penthouse. Guests love staying with us because: -Central location near Grant Park, Art Institu ...
From $468 per night (USD)
VRBO
From $488 per night (USD)
VRBO
Romantic 3 Bed Home In the Heart of the Park
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Limitless option in this chic GREYSTONE event space in the Heart of historic Washington Park. Whether hosting an off-si ...
From $488 per night (USD)
VRBO
From $185 per night (USD)
VRBO
Quiet Spacious 2BR Apt walk to Train, near Shops
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience the ultimate comfort in this immaculate, tranquil, and fully furnished two-bedroom apartment located in a fam ...
From $185 per night (USD)
VRBO
From $282 per night (USD)
VRBO
Luxe Ranch & Spa House Retreat! Pets Welcome
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Note: for the winter we now have the newly renovated spa house off the winter patio. Enjoy the indoor Hot Tub & Steam Ro ...
From $282 per night (USD)
VRBO
From $99 per night (USD)
VRBO
University Of Chicago Lux Pad 10 mins to Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a luxurious stay in this centrally-located condo close to restaurants, museums, White Sox stadium, University of C ...
From $99 per night (USD)
VRBO
$Trendy Streeterville Studio w\/ Pool & Gym, nr Navy Pier, by Blueground$
From $120 per night (USD)
VRBO
Trendy Streeterville Studio w\/ Pool & Gym, nr Navy Pier, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this sophisticated one-bedroom Blueground apartment. You’ll love c ...
From $120 per night (USD)
VRBO
$Sleek Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground$
From $86 per night (USD)
VRBO
Sleek Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Edgewater furnished one-bedroom apartmen ...
From $86 per night (USD)
VRBO
From $146 per night (USD)
VRBO
Lovely 3-bedroom apartment in Bronzeville
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our spacious 3-bedroom, 2-bathroom apartment on the 3rd floor of a multi-unit walk-up. Enjoy the convenience ...
From $146 per night (USD)
VRBO
$Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier\/Loop.$
From $197 per night (USD)
VRBO
Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier\/Loop.
Bedrooms:
4
Bathrooms:
4
Sleeps:
4
Book your Holiday-Get-away! This luxury space is elegantly adorned with central air, ample room for living, entertaining ...
From $197 per night (USD)
VRBO
$McCormick Place luxurious 6 bed\/3 bath HUGE Suite for groups$
From $1176 per night (USD)
VRBO
McCormick Place luxurious 6 bed\/3 bath HUGE Suite for groups
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
• Please MESSAGE US for SPECIAL WINTER RATES • Steps away from McCormick Place • 4 KING size / 2 QUEEN size beds • Mich ...
From $1176 per night (USD)
VRBO
$Sleek Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground$
From $122 per night (USD)
VRBO
Sleek Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Edgewater furnished one-bedroom apar ...
From $122 per night (USD)
VRBO
From $171 per night (USD)
VRBO
lovely and cozy vintage two bedroom, 🐾friendly apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Comfy and cozy, second floor apartment located in an incredibly beautiful & safe neighborhood on chicago’s northwest sid ...
From $171 per night (USD)
VRBO

Search Your Destination Now!

Chicago Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals