Chicago Rentals
From $220 per night (USD)VRBO
Downtown Chicago Apt Near Old Town & Lincoln Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: LOCATION! LOCATION! LOCATION! DOWNTOWN CHICAGO! The perfect crash pad (*NO PARTIES*) to explore the he ...
From $220 per night (USD)VRBO
From $353 per night (USD)Expedia
Urban Oasis - Walk to Restaurants, Transit & More!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: This is a sunny and cozy 2BR coach house at the border of two of Chicago's most sought-after neighborhoods, Li ...
From $353 per night (USD)Expedia
From $940 per night (USD)VRBO
\"Holy Cow\"! 4bed 4bath Duplex Penthouse w/ 2,000 sqft Private Roof-Deck!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
"Wow" Step outside & be face-to-face with the iconic Wrigley Field, home of the Chicago Cubs!! Best Space in Wrigley! ...
From $940 per night (USD)VRBO
From $785 per night (USD)Expedia
Dramatic Wrigley Loft +PRIVATE Rooftop, Center of Wrigley, Ranked GUEST FAVORITE
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
Say "WOW" in this top floor, DRAMATIC SPACIOUS Loft condo w/ PRIVATE ROOFTOP overlooking skyline! Completely REFRESHED w ...
From $785 per night (USD)Expedia
From $626 per night (USD)VRBO
Wrigley Oasis! Steps from the Field! - 3DR/1BA
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
***COVID-19 RESTRICTIONS: Due to COVID-19 Restrictions by the City of Chicago, no more than 6 guests can be on the premi ...
From $626 per night (USD)VRBO
From $351 per night (USD)VRBO
LUX CONDO NEAR DOWNTOWN and now offering car rental service.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The whole group will enjoy easy access to everything from this centrally located place. Three stylish bedrooms with priv ...
From $351 per night (USD)VRBO
From $362 per night (USD)VRBO
Designer 3BR Luxury Penthouse in Heart of Fulton Market | Featured In Architectural Digest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Summary: Spectacular 2,500 square foot brick-and-timber penthouse with 15 foot ceilings located in the heart of the vib ...
From $362 per night (USD)VRBO
From $803 per night (USD)VRBO
Spectacular Fulton Market Penthouse, Sleeps 24 in Style | Featured In Architectural Digest
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 24
Summary: 2 side-by-side designer penthouse apartments comprising 5,000 square feet (the entire top floor) of a brick-an ...
From $803 per night (USD)VRBO
From $483 per night (USD)VRBO
Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Summary: Stunning 2,500 square foot brick-and-timber luxury penthouse with 15 foot ceilings located in the heart of the ...
From $483 per night (USD)VRBO
From $167 per night (USD)Expedia
Suite 1 on Southport 4 Queen Beds!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Check out our brand new construction Suite on Southport Ave. Centrally located in the world famous Lincoln Park ...
From $167 per night (USD)Expedia
From $129 per night (USD)VRBO
Chic, Cozy home, by Blue Line Train Stop + Free parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relax in this chic and artfully designed condo. This sun-kissed 1-bedroom apartment in Irving Park is located in the cit ...
From $129 per night (USD)VRBO
From $468 per night (USD)Expedia
Lovely getaway 2BR 2BA Apartment near Wrigley Field
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your getaway location in the heart of the Roscoe Village neighborhood of Chicago! A short walk to Wrigley Fie ...
From $468 per night (USD)Expedia
From $411 per night (USD)VRBO
LUXURIOUS LINCOLN PARK Home w/ Rooftop +parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Escape into this Lincoln Park Masterpiece! Guests love this home because: - Surrounded by top-notch restaurants/retai ...
From $411 per night (USD)VRBO
From $784 per night (USD)VRBO
Smart Home in Logan Square by the 606 Trail
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This property is a smart home with 3 bedrooms and 2 1/2 bathrooms, with a garage for a small to medium size SUV, which c ...
From $784 per night (USD)VRBO
From $303 per night (USD)VRBO
Luxury Home Away From Your Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is a newly rehab house remodeled a year ago this house is your home away from home!! Upstairs Downstairs All Bedroo ...
From $303 per night (USD)VRBO
From $317 per night (USD)Expedia
Downtown Lake VIEWS, Mich Ave, Museums 2bd/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $317 per night (USD)Expedia
From $319 per night (USD)VRBO
Vintage Wrigleyville Apartment + Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious apartment in the heart of Wrigleyville, two blocks to public transportation. Located in an 1911 graystone, priv ...
From $319 per night (USD)VRBO
From $298 per night (USD)Expedia
Downtown Penthouse #1 | Vintage 2bd (+Gym)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! We are a short walk to MillenniumPark, Sk ...
From $298 per night (USD)Expedia
From $105 per night (USD)VRBO
Beautiful Streeterville 1BR w/ Gym, Pool, near Navy Pier, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Streeterville with high floor views over the city. It’l ...
From $105 per night (USD)VRBO
From $343 per night (USD)VRBO
2 Rooftops, 2 Car Garage, 4 Stories
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: Why pay $$$ Chi parking when you have a 2 CAR GARAGE DOWNTOWN? Our 4br/3.5ba rowhome has 4 levels & 2 ROOFTOPS ...
From $343 per night (USD)VRBO
From $391 per night (USD)VRBO
Chicago Riverhouse with private fenced in oasis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the ...
From $391 per night (USD)VRBO
From $143 per night (USD)VRBO
Trendy River North 1BR w/ Gym, Pool, near L stop & Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $143 per night (USD)VRBO
From $487 per night (USD)VRBO
Private Historic Coach House Wicker Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Location, location, location! Private quiet clean coach house with two bedrooms and one bath in the heart of Wicker Park ...
From $487 per night (USD)VRBO
From $601 per night (USD)Expedia
The entire FLAT. Stay Like You Own! Central AIR. TWO FULL BATHROOMS. Unique.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Designer urban feel - completely rehabbed - reclaimed wood beams - full walk in glass master shower with an exposed bric ...
From $601 per night (USD)Expedia
From $109 per night (USD)VRBO
Cozy Loop 1BR w/ Deck, Gym, W/D, nr. West Loop & the L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in The Loop with views over the city. It’ll be easy to sim ...
From $109 per night (USD)VRBO
From $434 per night (USD)Expedia
MICH AVE Downtown 2bd, Grant Park Museums 25
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $434 per night (USD)Expedia
From $407 per night (USD)VRBO
MICH AVE, Downtown, Grant Park 2bd/2ba #23
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $407 per night (USD)VRBO
From $449 per night (USD)Expedia
MICH AVE Downtown, Park, Museums 2bd #4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $449 per night (USD)Expedia
From $311 per night (USD)VRBO
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $311 per night (USD)VRBO
From $339 per night (USD)Expedia
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $339 per night (USD)Expedia
From $864 per night (USD)VRBO
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Perfectly located in the heart of Chicago in the River North neighborhood. You will experience Chicago easily from here ...
From $864 per night (USD)VRBO
From $106 per night (USD)VRBO
Lovely West Loop 1BR w/ Gym & Pool in heart of Greektown, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Greektown with views over the city. It’ll be easy to si ...
From $106 per night (USD)VRBO
From $123 per night (USD)VRBO
Trendy West Loop 1BR w/ Gym & Pool in heart of Greektown, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Greektown furnished one bedroom apartmen ...
From $123 per night (USD)VRBO
From $104 per night (USD)VRBO
Bright Loop 1BR w/Gym, Roofdeck, W/D, nr West Loop & the L 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 $104 per night (USD)VRBO
From $109 per night (USD)VRBO
Amazing West Loop 1BR w/ Gym & Pool in heart of Greektown, 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 $109 per night (USD)VRBO
From $97 per night (USD)VRBO
Sunny West Loop 1BR w/ Pool, Coworking & Gym, 1 block to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this beautiful one bedroom Blueground apartment. You’ll love comin ...
From $97 per night (USD)VRBO
From $123 per night (USD)VRBO
Ideal West Loop 1BR w/ Pool, Coworking & Gym, 1 block to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this spacious one bedroom Blueground apartment. You’ll love coming ...
From $123 per night (USD)VRBO
From $148 per night (USD)VRBO
Ideal West Loop 2BR w/ Gym & Pool in heart of Greektown, 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 $148 per night (USD)VRBO
From $160 per night (USD)VRBO
Walk to Wrigley Field/Monthly Discounts Available
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
My place is close to Wrigley Field, the Metro, Smart Bar, Uncommon Ground, Lakeview, Wrigleyville. You'll love my place ...
From $160 per night (USD)VRBO
From $108 per night (USD)VRBO
Bright Gold Coast 1BR w/ Doorman & Gym, 2 blocks to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Gold Coast furnished one bedroom apart ...
From $108 per night (USD)VRBO
From $157 per night (USD)VRBO
Airy Gold Coast 2BR w/ Gym, Pool, near. Oak St. Beach, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Gold Coast furnished two bedroom apar ...
From $157 per night (USD)VRBO
From $132 per night (USD)VRBO
Sleek Loop 1BR w/ Gym, Pool, W/D, nr. Millennium Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful The Loop furnished one bedroom apar ...
From $132 per night (USD)VRBO
From $112 per night (USD)VRBO
Bright Loop 1BR w/ Gym, Pool, nr. Financial District, 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 $112 per night (USD)VRBO
From $309 per night (USD)Expedia
Spacious Townhome! 3 bedrooms & 2 complete bath and 2 outdoor Patios, Near Train
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Spectacular Entire Townhome in the hearth of the city! 3 stories and 1900 sq feet of living space for guests with 3 bedr ...
From $309 per night (USD)Expedia
From $301 per night (USD)VRBO
Amazing & Spacious 3 bed / 2 Bath Townhome Near Downtown, Steps from the train!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Urban Oasis in the hearth of the city enough space for the full Family! Amazing 3 level Spacious Townhome with gated fr ...
From $301 per night (USD)VRBO
From $204 per night (USD)Expedia
Spacious 3BR Duplex for Groups-Near Airport & Downtown-Cozy & Quiet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Chicago — Your Perfect Weekend Escape Rated 10/10 by past guests! They loved the fully stocked kitchen, cozy ...
From $204 per night (USD)Expedia
From $177 per night (USD)VRBO
Retro-Chic Urban Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Entire top floor apartment with private entrance in a charming two-story building. Two bedrooms and 2 queen beds can hos ...
From $177 per night (USD)VRBO
From $123 per night (USD)VRBO
Smart Loop 1BR w/ Gym, Pool, W/D, nr. Millennium Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this spacious one bedroom Blueground apartment. You’ll love coming ...
From $123 per night (USD)VRBO
From $153 per night (USD)VRBO
Spacious Gold Coast 2BR w/ Doorman & Gym, 2 blocks to L, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Gold Coast with views over the city. It’ll be easy to s ...
From $153 per night (USD)VRBO
From $743 per night (USD)Expedia
Only Urban Beach House in Chicago
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Chicago’s ONLY Urban Beach House combines the best of beach life and urban life! Perfect for couples, students, faculty, ...
From $743 per night (USD)Expedia
From $447 per night (USD)VRBO
Stunning 3BR Penthouse in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: [NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Winter/Spring 2027. The ...
From $447 per night (USD)VRBO
From $279 per night (USD)Expedia
Cozy Charming •Art 🎨 • Food🌮 Close to Train 🚉 • Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Called one of the 12 coolest neighborhoods in the world! - Forbes Magazine 2018-Pilsen- Google it for yourself!! Wake up ...
From $279 per night (USD)Expedia
Click For PricingVRBO
Downtown Printer Row district Hotel style room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Situated in downtown Chicago’s urban Printer's Row district, Hotel Blake offers a relaxing retreat and easy access to e ...
Click For PricingVRBO
From $527 per night (USD)Expedia
River North's Rock N' Roll - In The Heart of the City
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2 bed, 2 bath, second floor of 3 flat above French Bistro. High Ceilings, Hardwood Floors, Fully Equipped Ki ...
From $527 per night (USD)Expedia
From $277 per night (USD)VRBO
The Neighborhood Hotel - Lincoln Park 302 - One Bedroom w/ Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
A refreshing, sophisticated oasis with added flare like vibrant, oversized works of Chicago memorabilia. Ideal for a co ...
From $277 per night (USD)VRBO
From $161 per night (USD)Expedia
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
The space is two bedrooms with a common area and bathroom. The common area has a sofa (that can be used if there are mor ...
From $161 per night (USD)Expedia
From $441 per night (USD)VRBO
Modern 3BR Penthouse in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: [NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Winter/Spring 2027. The ...
From $441 per night (USD)VRBO
From $763 per night (USD)Expedia
EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
2400 sf 4-story home in Chicago's East Village. 5 baths, spacious living rooms, fireplace, en-suite spa bath, 2 terraces ...
From $763 per night (USD)Expedia
From $458 per night (USD)VRBO
NEW LUXURY PENTHOUSE CONDO
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
OVERVIEW: This is a spacious penthouse condo with an amazing city skyline view on private rooftop terrace. Comfortably s ...
From $458 per night (USD)VRBO
From $1106 per night (USD)VRBO
THE COMPOUND Large Exquisite House Private Yard ''Best Location'' Well Appointed
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 32
Walk to everything Chicago has to offer- Downtown and Mag Mile; North ave beach, zoo and Lincoln park, restaurants, bars ...
From $1106 per night (USD)VRBO
From $416 per night (USD)VRBO
Spectacular Corner 3BR in the Loop | City Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Stylish 1,400+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and f ...
From $416 per night (USD)VRBO
From $1880 per night (USD)Expedia
The Orleans - Entire Building - With Rooftop Deck!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Summary: This property can be rented out and you would have access to the entire building which consists of 4 individual ...
From $1880 per night (USD)Expedia
From $262 per night (USD)VRBO
LOCATION!! 2b/2b Condo, 51st Floor AMAZING Views, Pool and other Amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Luxury condo in a FANTASTIC location! Remodeled upscale condo located on the brink of River North/Gold Coast/Streetervil ...
From $262 per night (USD)VRBO
From $221 per night (USD)VRBO
Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully furnished Three Bedroom, Two Bath. Walking distance from the lakefront, and a short bus ride to Michigan Av ...
From $221 per night (USD)VRBO
From $138 per night (USD)VRBO
Airy West Loop 1BR w/ Pool, Pet Spa, near Restaurant Row, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this spacious one bedroom Blueground apartment. You’ll love coming ...
From $138 per night (USD)VRBO
From $588 per night (USD)VRBO
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful bright & sunny Wicker Park 3 bedroom, 2 bath 1,500 square foot apartment located on the top floor of a private ...
From $588 per night (USD)VRBO
From $126 per night (USD)VRBO
Luxe West Loop Studio w/ Gym, Pool, Coworking, walk to UIC, 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 $126 per night (USD)VRBO
From $215 per night (USD)VRBO
Luxe South Loop 2BR w/ Spa, Pool & Gym next to Grant Park, 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 $215 per night (USD)VRBO
From $602 per night (USD)VRBO
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 22
Unique opportunity to rent an original Victorian home in historic Old Town. Only listing of its kind! Walk to almost eve ...
From $602 per night (USD)VRBO
From $316 per night (USD)Expedia
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Roscoe Village Inn offers charming vacation rental homes in Chicago's trendy Roscoe Village neighborhood 5 miles north o ...
From $316 per night (USD)Expedia
From $565 per night (USD)VRBO
Woodlawn Oasis...10 Minutes to Dining & Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Fun times with family and friends at this stylish beautiful home located 10 mins from Hyde Park, (Tiger Woods) Golf Cour ...
From $565 per night (USD)VRBO
From $1088 per night (USD)Expedia
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to the Wrigleyville Inn, where you can catch a fly ball from our front porch! Recently built from the ground up ...
From $1088 per night (USD)Expedia
From $345 per night (USD)VRBO
Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your home away from home nestled in the Village within the City – Roscoe Village in Chicago, IL. Roscoe Vil ...
From $345 per night (USD)VRBO
From $190 per night (USD)Expedia
The Bright Retreat in Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in the heart of Andersonville when you book this bright, newly renovated condo. The home is one block from Clark St ...
From $190 per night (USD)Expedia
From $125 per night (USD)VRBO
Spacious Loop 1BR w/ Pool, Gym, nr. the L & Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming The Loop furnished one bedroom apart ...
From $125 per night (USD)VRBO
From $276 per night (USD)Expedia
The Avondale Guesthouse
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This is a private three bedroom house you will be reserving in the Avondale neighborhood. Plenty of available free stree ...
From $276 per night (USD)Expedia
From $249 per night (USD)VRBO
Retro Apartment in Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stay in this perfectly situated apartment in the heart of vibrant Andersonville and find out why TimeOut Magazine calls ...
From $249 per night (USD)VRBO
From $371 per night (USD)Expedia
2 Suites, 2 Floors in Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: You will get 2 separate Suites that are directly above one another. Each Suite has 2 bedrooms and 1 bathroom. T ...
From $371 per night (USD)Expedia
From $1812 per night (USD)VRBO
PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME!!! ABSOLUTELY NO PARTIES OR LARGE GATHERINGS! We reserve the right t ask ...
From $1812 per night (USD)VRBO
From $122 per night (USD)VRBO
Premium Lakeview 2BR w/ Patio, W/D, walk to Wrigley Field, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Lake View East with balcony views over the city. It’ll ...
From $122 per night (USD)VRBO
From $197 per night (USD)VRBO
Cubs Apt, Near Wrigley!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Summary: A short 10 minute walk from Wrigley Field (0.8 miles) , and everything the popular Wrigleyville has to offer. ...
From $197 per night (USD)VRBO
From $149 per night (USD)VRBO
Hip River North 1BR w/ Pool + Roof Deck near Mag Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Near North Side furnished one b ...
From $149 per night (USD)VRBO
From $647 per night (USD)VRBO
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
Finally, a home that actually fits the whole group! Our stunning, newly-constructed Logan Square retreat was designed fo ...
From $647 per night (USD)VRBO
From $1584 per night (USD)Expedia
New Construction Building in River North!
- Bedrooms:
- 10
- Bathrooms:
- 11
- Sleeps:
- 16
Summary: This listing is perfect for your Chicago visit. You will get 4 brand new construction units (finished Septembe ...
From $1584 per night (USD)Expedia
From $285 per night (USD)VRBO
A home away from home! <No events allowed>
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
vacation rental cleaning protocol Major surfaces are sanitized and disinfected. Major surfaces include countertops, ...
From $285 per night (USD)VRBO
From $408 per night (USD)VRBO
Upgraded,Spacious 3 Bedroom Apartment.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Bright and beautiful top floor 1200 sq. ft, 3 bedrooms apartment located in Jefferson Park,9 minutes from O hare Interna ...
From $408 per night (USD)VRBO
From $296 per night (USD)VRBO
NEW LUXURY CONDO WITH PATIO DECK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
OVERVIEW: This is a high end first floor condo that comfortably sleeps 5 persons. Luxury bathrooms. Fully equipped chef’ ...
From $296 per night (USD)VRBO
From $884 per night (USD)Expedia
Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our luxurious 2-bedroom, 2-bathroom townhouse located in the heart of south loop Chicago! This home is perfec ...
From $884 per night (USD)Expedia
From $179 per night (USD)VRBO
Mod West Loop 2BR w/ Gym, Pool, W/D, nr. Fulton Market, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in West Loop with balcony views over the city. It’ll be ea ...
From $179 per night (USD)VRBO
From $135 per night (USD)VRBO
Mod River North 2BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Gold Coast with high floor views over the city. It’ll b ...
From $135 per night (USD)VRBO
From $146 per night (USD)VRBO
Hip River North 1BR w/ Pool + Roof Deck near Mag Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Near North Side with views over the city. It’ll be easy ...
From $146 per night (USD)VRBO
From $82 per night (USD)VRBO
Open River North 1BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Gold Coast with high floor views over the city. It’ll b ...
From $82 per night (USD)VRBO
From $111 per night (USD)VRBO
Roomy Loop 1BR w/ Pool, Gym, near Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful The Loop furnished one bedroom apar ...
From $111 per night (USD)VRBO
From $121 per night (USD)VRBO
Hip River North 1BR w/ Pool + Roof Deck near Mag Mile by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $121 per night (USD)VRBO
From $115 per night (USD)VRBO
Lux River North 1BR w/ Gym, W/D, near Magnificent Mile, 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 $115 per night (USD)VRBO
From $116 per night (USD)VRBO
Lux River North 1BR w/ Gym, W/D, BBQ, Pool, near Mag Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this spacious Near North Side furnished one bedroo ...
From $116 per night (USD)VRBO
From $123 per night (USD)VRBO
Smart West Loop 1BR w/ Pool, Gym, nr. Restaurant Row, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated West Loop furnished one bedroom ...
From $123 per night (USD)VRBO
From $176 per night (USD)VRBO
Ideal Gold Coast 2BR, w/ Gym, Lounge, W/D, nr Oak Street by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this charming two bedroom Blueground apartment. You’ll love coming ...
From $176 per night (USD)VRBO
From $533 per night (USD)VRBO
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In the heart of Lakeview, still close to downtown, museums and McCormick Place. A quick stroll to Lake Michigan and the ...
From $533 per night (USD)VRBO
From $587 per night (USD)Expedia
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 18
Most incredibly located, sun-filled home with designer kitchen, marble baths, and open-concept living areas—perfect for ...
From $587 per night (USD)Expedia