Search Your Destination Now!

Chicago Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Update Results Reset Dates
Filter

Results: 1,000 Rentals

  • Spacious 3-bedroom Comfort Urban Chicago loft house
    From $265 per night (USD)

    VRBO

    Spacious 3-bedroom Comfort Urban Chicago loft house

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Your cozy getaway awaits in Chicago at this marvelous apartment. With three bedrooms featuring a queen, full, and twin b ...

    From $265 per night (USD)

    VRBO

    Details
  • Wonderful townhome East Lakeview near cubs 5 min walk to lake in vibrant Chicago
    From $548 per night (USD)

    Expedia

    Wonderful townhome East Lakeview near cubs 5 min walk to lake in vibrant Chicago

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This memorable townhome is the perfect home base for your trip to Chicago. Guests will find three comfortable bedrooms, ...

    From $548 per night (USD)

    Expedia

    Details
  • Newly Renovated 3BR/3BA Single Family Home Steps to Pool, Parks and River Trail
    From $550 per night (USD)

    VRBO

    Newly Renovated 3BR/3BA Single Family Home Steps to Pool, Parks and River Trail

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    *3 month minimum stays only* Welcome to your Chicago home away from home! This beautifully reimagined 3-bedroom, 3-bath ...

    From $550 per night (USD)

    VRBO

    Details
  • 2BR Avondale Apt: Free Parking + Steps to Blueline
    From $325 per night (USD)

    Expedia

    2BR Avondale Apt: Free Parking + Steps to Blueline

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Stay in a modern 2 Bedroom Apartment that sleeps 6 in a peaceful setting, just minutes from downtown and Logan Square—st ...

    From $325 per night (USD)

    Expedia

    Details
  • Fully Furnished 2BR. 5-min walk to train. In-unit laundry. Parking Available
    From $158 per night (USD)

    VRBO

    Fully Furnished 2BR. 5-min walk to train. In-unit laundry. Parking Available

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Rental Month-to-month rental with option for longer lease. Discover your perfect urban retreat in the heart of Chicag ...

    From $158 per night (USD)

    VRBO

    Details
  • 2 bedroom apartment near University of Chicago and Obama Center for your stay
    From $296 per night (USD)

    Expedia

    2 bedroom apartment near University of Chicago and Obama Center for your stay

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Stay in a stylish, private-entry 2-bedroom garden apartment in Chicago’s historic Woodlawn neighborhood, while you visit ...

    From $296 per night (USD)

    Expedia

    Details
  • Hyde Park/ Bronzeville Apartment 3E
    From $298 per night (USD)

    VRBO

    Hyde Park/ Bronzeville Apartment 3E

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    This spacious 3-bed apartment in the Bronzeville area is the center of everything that you'll need while staying here. J ...

    From $298 per night (USD)

    VRBO

    Details
  • Luxury 1BR Chicago Retreat downtown  Free Parking, Gym, Theater & Patio
    From $220 per night (USD)

    Expedia

    Luxury 1BR Chicago Retreat downtown Free Parking, Gym, Theater & Patio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Your Chicago Getaway Welcome to your stylish and comfortable 1-bedroom, 1.5-bathroom Chicago retreat, desig ...

    From $220 per night (USD)

    Expedia

    Details
  • Sweet Home Chicago- 3 BR, 2.5 BA + Game Room, Hot Tub, near O'Hare, Rosemont
    From $409 per night (USD)

    VRBO

    Sweet Home Chicago- 3 BR, 2.5 BA + Game Room, Hot Tub, near O'Hare, Rosemont

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Discover the beauty of Chicago from this unique Chicago inspired 3-bedroom house. Inside, guests find a queen bed, two t ...

    From $409 per night (USD)

    VRBO

    Details
  • Quiet Stay - Perfect for Family
    From $254 per night (USD)

    Expedia

    Quiet Stay - Perfect for Family

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Indulge in the charm of urban living at our inviting short-term rental property, where comfort and convenience blend sea ...

    From $254 per night (USD)

    Expedia

    Details
  • 2-bedroom apartment in perfect Chicago with cool AC
    From $671 per night (USD)

    VRBO

    2-bedroom apartment in perfect Chicago with cool AC

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Your Chicago adventure begins at this 2-bedroom apartment. Step into a serene space where cool air flows through the roo ...

    From $671 per night (USD)

    VRBO

    Details
  • Quiet Area - Revamped Basement
    From $247 per night (USD)

    Expedia

    Quiet Area - Revamped Basement

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your cozy retreat! Our 2-bedroom short-term rental is designed to offer you a comfortable and convenient stay ...

    From $247 per night (USD)

    Expedia

    Details
  • Stylish friendly 3BR Suite near McCormick
    From $290 per night (USD)

    VRBO

    Stylish friendly 3BR Suite near McCormick

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    🌆 Experience Downtown Comfort at The State Suite — Your Premier Chicago Stay! Wake up in the heart of Chicago at The S ...

    From $290 per night (USD)

    VRBO

    Details
  • McCormick 4BR Huge Unit w/ Pool Table | Sleeps 11
    From $307 per night (USD)

    Expedia

    McCormick 4BR Huge Unit w/ Pool Table | Sleeps 11

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Relax with the whole family or your group at this spacious and comfortable retreat in the heart of Chicago! 📣 MESSAGE ...

    From $307 per night (USD)

    Expedia

    Details
  • Spacious 3BR Smoke Ok | McCormick & UIC Campus
    From $246 per night (USD)

    VRBO

    Spacious 3BR Smoke Ok | McCormick & UIC Campus

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    🌆 Welcome and Step into the perfect blend of style, comfort, and city energy at the State Suite, your urban retreat in ...

    From $246 per night (USD)

    VRBO

    Details
  • South Loop 3BR Smoke Ok Suite Near McCormick
    From $241 per night (USD)

    Expedia

    South Loop 3BR Smoke Ok Suite Near McCormick

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    🌆 Welcome and Step into The State Suite, where city sophistication meets home-like comfort in the heart of downtown Chi ...

    From $241 per night (USD)

    Expedia

    Details
  • Lovely three bedroom Loft, University Of Chicago, Obama Library
    From $574 per night (USD)

    VRBO

    Lovely three bedroom Loft, University Of Chicago, Obama Library

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The property boasts an open and inviting floor plan, flooded with natural light, and luxurious finishes throughout, such ...

    From $574 per night (USD)

    VRBO

    Details
  • Beautiful Condo in the Middle of Andersonville
    From $169 per night (USD)

    Expedia

    Beautiful Condo in the Middle of Andersonville

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Walking Distance to Public Transit | Private Back Porch | In-Unit Laundry Experience Chicago like a local in the heart ...

    From $169 per night (USD)

    Expedia

    Details
  • Perfect 5-bedroom estate  in vibrant Chicago.
    From $1764 per night (USD)

    VRBO

    Perfect 5-bedroom estate in vibrant Chicago.

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    15

    Stay comfortably in Chicago at this amazing 5-bedroom estate. With a king bed, four queen beds, a twin bed, and a sofa b ...

    From $1764 per night (USD)

    VRBO

    Details
  • NEW! Fully Updated Jr. 1 Bed, Steps from Lincoln Park by AllSet Turnover
    From $362 per night (USD)

    VRBO

    NEW! Fully Updated Jr. 1 Bed, Steps from Lincoln Park by AllSet Turnover

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    My bright and stylish Jr. 1-bed, 1-bath condo is located in a prime Lincoln Park location. Thoughtful touches can be fe ...

    From $362 per night (USD)

    VRBO

    Details
  • The Velvet Manor | 2BR Boutique Stay
    From $488 per night (USD)

    VRBO

    The Velvet Manor | 2BR Boutique Stay

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to The Velvet Manor, a moody, designer-curated 2-bedroom retreat in the heart of Andersonville. Unwind in richly ...

    From $488 per night (USD)

    VRBO

    Details
  • Private Basement Suite-Completely separate from the rest of the house
    From $116 per night (USD)

    Expedia

    Private Basement Suite-Completely separate from the rest of the house

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Spacious & Comfortable Chicago Stay Near 95th Red Line | Fast Wi-Fi | Free Parking | Monthly Discounts Welcome to your ...

    From $116 per night (USD)

    Expedia

    Details
  • 3bd/2ba, King bd, Pets OK, Laundry, Fenced Yard, Near Downtwn, Hospitals, & Unis
    From $140 per night (USD)

    VRBO

    3bd/2ba, King bd, Pets OK, Laundry, Fenced Yard, Near Downtwn, Hospitals, & Unis

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Rental Terms: Minimum stay: 30 nights If this home doesn't suit your needs, message me. We have other homes available i ...

    From $140 per night (USD)

    VRBO

    Details
  • LIVN West Loop Chicago Classic Queen Studio
    From $276 per night (USD)

    Expedia

    LIVN West Loop Chicago Classic Queen Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Experience modern city living at LIVN West Loop Chicago, a stylish studio at 555 W Jackson Blvd in one of Chic ...

    From $276 per night (USD)

    Expedia

    Details
  • LIVN Millennium Park Downtown Chicago Superior 1BR
    From $246 per night (USD)

    VRBO

    LIVN Millennium Park Downtown Chicago Superior 1BR

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Experience the best of Chicago from this stylish, newly renovated 1 bedroom at 19 S Wabash Ave. Perfectly loca ...

    From $246 per night (USD)

    VRBO

    Details
  • LIVN Millennium Park Downtown Chicago Prem Studio
    From $246 per night (USD)

    Expedia

    LIVN Millennium Park Downtown Chicago Prem Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Experience the best of Chicago from this stylish, newly renovated premium studio at 19 S Wabash Ave. Perfectly ...

    From $246 per night (USD)

    Expedia

    Details
  • LIVN West Loop Chicago Queen Superior Studio
    From $246 per night (USD)

    VRBO

    LIVN West Loop Chicago Queen Superior Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Experience modern city living at LIVN West Loop Chicago, a stylish studio at 555 W Jackson Blvd in one of Chic ...

    From $246 per night (USD)

    VRBO

    Details
  • LIVN Millennium Park Downtown Chicago Studio
    From $223 per night (USD)

    Expedia

    LIVN Millennium Park Downtown Chicago Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Experience the best of Chicago from this stylish, newly renovated studio at 19 S Wabash Ave. Perfectly located ...

    From $223 per night (USD)

    Expedia

    Details
  • LIVN Millennium Park Downtown Chicago Superior 2 BR
    From $273 per night (USD)

    VRBO

    LIVN Millennium Park Downtown Chicago Superior 2 BR

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Experience the best of Chicago from this stylish, newly renovated 2-bedroom at 19 S Wabash Ave. Perfectly loca ...

    From $273 per night (USD)

    VRBO

    Details
  • LIVN Millennium Park Downtown Chicago 1 BR
    From $223 per night (USD)

    Expedia

    LIVN Millennium Park Downtown Chicago 1 BR

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Experience the best of Chicago from this stylish, newly renovated 1-bedroom at 19 S Wabash Ave. Perfectly loca ...

    From $223 per night (USD)

    Expedia

    Details
  • Beautifully Remodeled 2B/2BA Hyde Park
    From $255 per night (USD)

    VRBO

    Beautifully Remodeled 2B/2BA Hyde Park

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Requires walking up 2 flights of stairs. Enjoy your stay in this charming 2 bed, 1 bath apartment in the heart of Hyde ...

    From $255 per night (USD)

    VRBO

    Details
  • LIVN West Loop Chicago King Studio
    From $359 per night (USD)

    Expedia

    LIVN West Loop Chicago King Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Experience modern city living at LIVN West Loop Chicago, a stylish king studio at 555 W Jackson Blvd in one of ...

    From $359 per night (USD)

    Expedia

    Details
  • LIVN West Loop Chicago 2 BR City View
    From $448 per night (USD)

    VRBO

    LIVN West Loop Chicago 2 BR City View

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Experience modern city living at LIVN West Loop Chicago, a stylish 2 bedroom at 555 W Jackson Blvd in one of C ...

    From $448 per night (USD)

    VRBO

    Details
  • LIVN West Loop Chicago 1 BR
    From $267 per night (USD)

    Expedia

    LIVN West Loop Chicago 1 BR

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Experience modern city living at LIVN West Loop Chicago, a stylish 1 BR at 555 W Jackson Blvd in one of Chicag ...

    From $267 per night (USD)

    Expedia

    Details
  • LIVN Millennium Park Downtown Chicago 2BR
    From $254 per night (USD)

    VRBO

    LIVN Millennium Park Downtown Chicago 2BR

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Experience the best of Chicago from this stylish, newly renovated 2-bedroom at 19 S Wabash Ave. Perfectly loca ...

    From $254 per night (USD)

    VRBO

    Details
  • Retreat Near Andersonville 3BR Newly Remodeled
    From $255 per night (USD)

    Expedia

    Retreat Near Andersonville 3BR Newly Remodeled

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Requires walking up 2 flights of stairs. Enjoy your stay in this beautifully updated 3-bedroom, 2-bath apartment near t ...

    From $255 per night (USD)

    Expedia

    Details
  • Your Parkside Executive Retreat + Dedicated Office
    From $176 per night (USD)

    VRBO

    Your Parkside Executive Retreat + Dedicated Office

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Superb Executive Housing, a quiet and comfortable home away from home near historic Pullman and directly acro ...

    From $176 per night (USD)

    VRBO

    Details
  • Boulevard Stays River North Retreat Near Magnificent Mile 01
    From $213 per night (USD)

    Expedia

    Boulevard Stays River North Retreat Near Magnificent Mile 01

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Walk to the best of River North, with the Magnificent Mile, Chicago Riverwalk, Merchandise Mart, and CTA Red L ...

    From $213 per night (USD)

    Expedia

    Details
  • Mediterranean Retreat. Newly renovate 1,000 sqft.
    From $233 per night (USD)

    VRBO

    Mediterranean Retreat. Newly renovate 1,000 sqft.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Recently renovated 1ksqft apartment in historic Worker's Cottage with lush garden. The interiors have been layered by be ...

    From $233 per night (USD)

    VRBO

    Details
  • Wabash 4BR - Pool, Free In & Out Parking 2
    From $358 per night (USD)

    Expedia

    Wabash 4BR - Pool, Free In & Out Parking 2

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Summary: 🌆 Spacious 4BR/3BA in Chicago's South Loop, steps from Grant Park & Millennium Park. Sleeps up to 8 (2 Full + ...

    From $358 per night (USD)

    Expedia

    Details
  • Wabash 4BR - Pool, Free In & Out Parking 1
    From $438 per night (USD)

    VRBO

    Wabash 4BR - Pool, Free In & Out Parking 1

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Summary: 🌆 Spacious 4BR/3BA in Chicago's South Loop, steps from Grant Park & Millennium Park. Sleeps up to 8 (2 Full + ...

    From $438 per night (USD)

    VRBO

    Details
  • 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
    From $411 per night (USD)

    Expedia

    3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    9

    Welcome to Reserve Chicago 358 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ No ...

    From $411 per night (USD)

    Expedia

    Details
  • Zen City Escape | Patio + Free Parking
    From $419 per night (USD)

    VRBO

    Zen City Escape | Patio + Free Parking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to your Zen City Escape. This bright top-floor retreat offers free onsite parking, a private patio, and thoughtf ...

    From $419 per night (USD)

    VRBO

    Details
  • Cozy Urban View Retreat Near Downtown - Sleeps 7
    From $95 per night (USD)

    Expedia

    Cozy Urban View Retreat Near Downtown - Sleeps 7

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Relax in this stylish top-floor retreat designed for comfort and fun! This spacious 2BR/1BA unit sleeps up to 7 and feat ...

    From $95 per night (USD)

    Expedia

    Details
  • Wabash 4BR - Pool, Free In & Out Parking 4
    From $418 per night (USD)

    VRBO

    Wabash 4BR - Pool, Free In & Out Parking 4

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Summary: 🌆 Spacious 4BR/3BA in Chicago's South Loop, steps from Grant Park & Millennium Park. Sleeps up to 8 (2 Full + ...

    From $418 per night (USD)

    VRBO

    Details
  • 2BR/2BA · pet-friendly · workspace · residential garage parking · king beds
    From $164 per night (USD)

    Expedia

    2BR/2BA · pet-friendly · workspace · residential garage parking · king beds

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2 bed/2 bath with stainless steel appliances, king beds, standing desk, fenced backyard, dog beds/bowls, and shared laun ...

    From $164 per night (USD)

    Expedia

    Details
  • 2-bedroom Bronzeville Gem
    From $198 per night (USD)

    VRBO

    2-bedroom Bronzeville Gem

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Stay comfortably in Chicago at this 2-bedroom apartment. The space features two queen beds, offering guests a restful ni ...

    From $198 per night (USD)

    VRBO

    Details
  • Quiet and comfortable 2BR Garden Unit
    From $99 per night (USD)

    Expedia

    Quiet and comfortable 2BR Garden Unit

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Chicago is waiting for you at this 2-bedroom garden unit. Inside, guests find a peaceful space featuring one queen bed a ...

    From $99 per night (USD)

    Expedia

    Details
  • Stylish 1BR Bucktown Pad – Blue Line Access, Free Parking & Laundry In-Unit
    From $83 per night (USD)

    VRBO

    Stylish 1BR Bucktown Pad – Blue Line Access, Free Parking & Laundry In-Unit

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy effortless Chicago living in this thoughtfully designed 1-bedroom apartment in Bucktown. Just steps from the Weste ...

    From $83 per night (USD)

    VRBO

    Details
  • Lux Stay in the Heart of Roscoe Village; New space with high end amenities
    From $288 per night (USD)

    Expedia

    Lux Stay in the Heart of Roscoe Village; New space with high end amenities

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Enjoy a stylish experience in Roscoe Village at this truly one of a kind, brand new space conveniently located one block ...

    From $288 per night (USD)

    Expedia

    Details
  • Chic 2-bedroom apartment in amazing Chicago with AC
    From $763 per night (USD)

    VRBO

    Chic 2-bedroom apartment in amazing Chicago with AC

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Experience Chicago like a local in this 2-bedroom apartment. This wonderful space offers heating, AC, an iron, and a hai ...

    From $763 per night (USD)

    VRBO

    Details
  • Prime River North One-Bedroom, Steps to Dining, Shopping, Nightlife & Riverwalk.
    From $137 per night (USD)

    Expedia

    Prime River North One-Bedroom, Steps to Dining, Shopping, Nightlife & Riverwalk.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience elevated Chicago living from the 43rd floor of this premier River north/ Gold Coast high-rise! Perfectly per ...

    From $137 per night (USD)

    Expedia

    Details
  • Lux Chicago House with 6 Bedrooms / Garage / Yard / Game Room
    From $727 per night (USD)

    VRBO

    Lux Chicago House with 6 Bedrooms / Garage / Yard / Game Room

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    Highlights: 🛏 6 beautifully decorated bedrooms with designer touches 🛁 4 luxurious bathrooms with premium finishes ...

    From $727 per night (USD)

    VRBO

    Details
  • 2 Bedroom apartment free parking near transit
    From $286 per night (USD)

    Expedia

    2 Bedroom apartment free parking near transit

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Stay comfortably in Chicago at this charming 2-bedroom apartment. The space offers a cozy atmosphere with a single bathr ...

    From $286 per night (USD)

    Expedia

    Details
  • Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
    From $246 per night (USD)

    VRBO

    Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Step into a sun-drenched, top-floor sanctuary with a private roof deck and sweeping skyline views. Whether you`re here f ...

    From $246 per night (USD)

    VRBO

    Details
  • Midway Hideaway - Spacious Chicago Apartment Near Midway Airport
    From $244 per night (USD)

    Expedia

    Midway Hideaway - Spacious Chicago Apartment Near Midway Airport

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Picture this: you've just landed at Midway, grabbed your bags, and within minutes you're turning the key to your own pri ...

    From $244 per night (USD)

    Expedia

    Details
  • Logan Sq Apt | King Bed | Games | Near Blue Line
    From $269 per night (USD)

    VRBO

    Logan Sq Apt | King Bed | Games | Near Blue Line

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    **WILL BE FURNISHED BY 10/5/2026** Stay in the heart of Logan Square in this stylish, game-filled apartment just a shor ...

    From $269 per night (USD)

    VRBO

    Details
  • Golden Suite on State St | Steps to Oak St Beach & Magnificent Mile | Sleeps 4
    From $250 per night (USD)

    Expedia

    Golden Suite on State St | Steps to Oak St Beach & Magnificent Mile | Sleeps 4

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Golden Suite | Gold Coast Gem Steps from Oak St Beach Welcome to Golden Suite — Your Elevated Stay in Chicago’s Gold Coa ...

    From $250 per night (USD)

    Expedia

    Details
  • Plymouth Collection: 3BD 2BA High Floor with Gym
    From $430 per night (USD)

    VRBO

    Plymouth Collection: 3BD 2BA High Floor with Gym

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly r ...

    From $430 per night (USD)

    VRBO

    Details
  • NEW! Newly Renovated 3BR/2BA in Heart of Andersonville
    From $472 per night (USD)

    VRBO

    NEW! Newly Renovated 3BR/2BA in Heart of Andersonville

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Amazing location! Experience the unparalleled comfort and style of this brand- new, fully renovated 3BR/2BA condo nestl ...

    From $472 per night (USD)

    VRBO

    Details
  • 3-bedroom house in Chicago with AC and fitness room towels I even have foodsssss
    From $494 per night (USD)

    VRBO

    3-bedroom house in Chicago with AC and fitness room towels I even have foodsssss

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Enjoy a peaceful stay at this 3-bedroom house in Chicago. The welcoming space features three king beds and two bathrooms ...

    From $494 per night (USD)

    VRBO

    Details
  • NEW! Heart of East Village 2-Bed 2-Bath Peaceful Oasis
    From $482 per night (USD)

    VRBO

    NEW! Heart of East Village 2-Bed 2-Bath Peaceful Oasis

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy a peaceful escape at this stylish and modern home. You'll love the quaint tree-lined street that is just steps aw ...

    From $482 per night (USD)

    VRBO

    Details
  • Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
    From $241 per night (USD)

    VRBO

    Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This urban oasis is situated in a historic, tree-lined neighborhood at the intersection of Ukrainian Village and East Vi ...

    From $241 per night (USD)

    VRBO

    Details
  • ConerStone House
    From $512 per night (USD)

    Expedia

    ConerStone House

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Discover the beauty of Chicago from this marvelous 4-bedroom house. Guests will find three queen beds and one twin bed, ...

    From $512 per night (USD)

    Expedia

    Details
  • Marvelous 3-bedroom apartment with AC in vibrant Chicago
    From $150 per night (USD)

    VRBO

    Marvelous 3-bedroom apartment with AC in vibrant Chicago

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Discover this 3-bedroom apartment in Chicago. The perfect spot features a queen bed, a full bed, and a twin bed, making ...

    From $150 per night (USD)

    VRBO

    Details
  • Pool House- 4bd/ 2ba- in the city of Chicago
    From $326 per night (USD)

    Expedia

    Pool House- 4bd/ 2ba- in the city of Chicago

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Take a break and unwind at this peaceful oasis in Chicago. Whether you're playing games in the house or sitting by the p ...

    From $326 per night (USD)

    Expedia

    Details
  • Blueground | West Loop, pool, nr Union Park
    From $100 per night (USD)

    VRBO

    Blueground | West Loop, pool, nr Union Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in West Loop. It’ll be easy to simply show up and start li ...

    From $100 per night (USD)

    VRBO

    Details
  • Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
    From $246 per night (USD)

    Expedia

    Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Step into a sun-drenched, top-floor sanctuary with a private roof deck and sweeping skyline views. Whether you`re here f ...

    From $246 per night (USD)

    Expedia

    Details
  • Blueground | West Loop, rooftop, nr Union Park
    From $107 per night (USD)

    VRBO

    Blueground | West Loop, rooftop, nr Union Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this beautiful West Loop furnished one bedroom apa ...

    From $107 per night (USD)

    VRBO

    Details
  • Blueground | Near North, garden, nr Lincoln Park
    From $135 per night (USD)

    VRBO

    Blueground | Near North, garden, nr Lincoln Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Near North Side furnished one bedro ...

    From $135 per night (USD)

    VRBO

    Details
  • Blueground | Near North, fitness center, nr Lincoln Park
    From $175 per night (USD)

    VRBO

    Blueground | Near North, fitness center, nr Lincoln Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this pretty one bedroom Blueground apartment. You’ll love coming h ...

    From $175 per night (USD)

    VRBO

    Details
  • Blueground | West Loop, pool, nr United Center
    From $133 per night (USD)

    VRBO

    Blueground | West Loop, pool, nr United Center

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...

    From $133 per night (USD)

    VRBO

    Details
  • Modern 4BR Home ,Sleeps 10, 5 Beds, Free Parking Easy Access to Downtown&Lake
    From $764 per night (USD)

    VRBO

    Modern 4BR Home ,Sleeps 10, 5 Beds, Free Parking Easy Access to Downtown&Lake

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to a bright, fully renovated this year, and stylish home designed for families and friends! Enjoy 4 bedrooms, 5 ...

    From $764 per night (USD)

    VRBO

    Details
  • Great Area Logan Square Apt Games Pets - Sleeps 5
    From $231 per night (USD)

    Expedia

    Great Area Logan Square Apt Games Pets - Sleeps 5

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Escape to a fun, stylish 650 sq ft top-floor retreat in Chicago`s vibrant Avondale/Logan Square! Perfect for 4, this pri ...

    From $231 per night (USD)

    Expedia

    Details
  • Landing | Amazing 1BD, Yoga Studio, Rooftop Lounge
    From $149 per night (USD)

    VRBO

    Landing | Amazing 1BD, Yoga Studio, Rooftop Lounge

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...

    From $149 per night (USD)

    VRBO

    Details
  • Landing | Incredible 1BD, Gym, Rooftop Lounge
    From $171 per night (USD)

    Expedia

    Landing | Incredible 1BD, Gym, Rooftop Lounge

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...

    From $171 per night (USD)

    Expedia

    Details
  • Landing | Chic Studio, Clubhouse, Pool
    From $134 per night (USD)

    VRBO

    Landing | Chic Studio, Clubhouse, Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Soak up the best of River North at NEXT. Our fully-furnished homes are perfect for monthly or extended stays, featuring ...

    From $134 per night (USD)

    VRBO

    Details
  • Landing | Amazing 1BD, Pool, Yoga Studio
    From $150 per night (USD)

    Expedia

    Landing | Amazing 1BD, Pool, Yoga Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...

    From $150 per night (USD)

    Expedia

    Details
  • Landing | Stunning 1BD, Gym, Rooftop Lounge
    From $168 per night (USD)

    VRBO

    Landing | Stunning 1BD, Gym, Rooftop Lounge

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...

    From $168 per night (USD)

    VRBO

    Details
  • Landing | Stunning 1BD, Rooftop Lounge
    From $176 per night (USD)

    Expedia

    Landing | Stunning 1BD, Rooftop Lounge

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...

    From $176 per night (USD)

    Expedia

    Details
  • Landing | Beautiful 1BD, Yoga Studio, Pool
    From $145 per night (USD)

    VRBO

    Landing | Beautiful 1BD, Yoga Studio, Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...

    From $145 per night (USD)

    VRBO

    Details
  • Landing | Spectacular 1BD, Yoga Studio
    From $155 per night (USD)

    Expedia

    Landing | Spectacular 1BD, Yoga Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...

    From $155 per night (USD)

    Expedia

    Details
  • Landing | Stunning 1BD, Rooftop Lounge, Gym
    From $179 per night (USD)

    VRBO

    Landing | Stunning 1BD, Rooftop Lounge, Gym

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...

    From $179 per night (USD)

    VRBO

    Details
  • Landing | Chic 1BD, Yoga Studio, Rooftop Lounge
    From $134 per night (USD)

    Expedia

    Landing | Chic 1BD, Yoga Studio, Rooftop Lounge

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...

    From $134 per night (USD)

    Expedia

    Details
  • Landing | Modern 1BD in Lincoln Park
    From $178 per night (USD)

    VRBO

    Landing | Modern 1BD in Lincoln Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...

    From $178 per night (USD)

    VRBO

    Details
  • Landing | Amazing 1BD in Lincoln Park
    From $171 per night (USD)

    Expedia

    Landing | Amazing 1BD in Lincoln Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...

    From $171 per night (USD)

    Expedia

    Details
  • Landing | Stunning 1BD in Lincoln Park
    From $188 per night (USD)

    VRBO

    Landing | Stunning 1BD in Lincoln Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...

    From $188 per night (USD)

    VRBO

    Details
  • Landing | Stylish Studio in Lincoln Park
    From $164 per night (USD)

    Expedia

    Landing | Stylish Studio in Lincoln Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...

    From $164 per night (USD)

    Expedia

    Details
  • Landing | Incredible Studio in Lincoln Park
    From $132 per night (USD)

    VRBO

    Landing | Incredible Studio in Lincoln Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...

    From $132 per night (USD)

    VRBO

    Details
  • Landing | Stylish Studio in Lincoln Park
    From $172 per night (USD)

    Expedia

    Landing | Stylish Studio in Lincoln Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...

    From $172 per night (USD)

    Expedia

    Details
  • Landing | Modern Studio in Lincoln Park
    From $163 per night (USD)

    VRBO

    Landing | Modern Studio in Lincoln Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...

    From $163 per night (USD)

    VRBO

    Details
  • Landing | Amazing Studio in Lincoln Park
    From $164 per night (USD)

    Expedia

    Landing | Amazing Studio in Lincoln Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...

    From $164 per night (USD)

    Expedia

    Details
  • Luxe 3BR + Patio & Parking | Sleeps 9 | Lakeview
    From $461 per night (USD)

    VRBO

    Luxe 3BR + Patio & Parking | Sleeps 9 | Lakeview

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Summary: You'll feel it the moment you walk in — this isn't a typical rental. It's a sprawling, light-filled home on on ...

    From $461 per night (USD)

    VRBO

    Details
  • By Wrigley Field +Reserved Parking Space +95 Walkscore + In-Unit Laundry + Patio
    From $201 per night (USD)

    Expedia

    By Wrigley Field +Reserved Parking Space +95 Walkscore + In-Unit Laundry + Patio

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Top host approved all-new construction luxury condo in a quaint 3-unit building that sleeps 5 and offers great natural l ...

    From $201 per night (USD)

    Expedia

    Details
  • Flexhome West Town Spacious 2BR Duplex · Sleeps 8
    From $211 per night (USD)

    VRBO

    Flexhome West Town Spacious 2BR Duplex · Sleeps 8

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Discover the best of Chicago from this spacious 2-bedroom, 2-bathroom duplex apartment. Whether you`re in town for a con ...

    From $211 per night (USD)

    VRBO

    Details
  • Luxury Fulton Market Condo - Prime Location Walking distance to Riverwalk
    From $282 per night (USD)

    Expedia

    Luxury Fulton Market Condo - Prime Location Walking distance to Riverwalk

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Stay in the heart of Chicago’s West Loop. One block from Fulton Market’s award winning restaurants, bars, and cafés. Clo ...

    From $282 per night (USD)

    Expedia

    Details
  • Private Covered Garage +In-Unit Laundry+ Restaurant Row+93 Walkscore + 606 Trail
    From $148 per night (USD)

    VRBO

    Private Covered Garage +In-Unit Laundry+ Restaurant Row+93 Walkscore + 606 Trail

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Nicknamed "Midwest Headquarters of Hip" Logan Square was voted one of the coolest places in the country by Cushman & Wak ...

    From $148 per night (USD)

    VRBO

    Details
  • Top Rated w/Free Street Parking+ 2 King Beds 1 Single +In Unit-Laundry +1.5 Bath
    From $206 per night (USD)

    Expedia

    Top Rated w/Free Street Parking+ 2 King Beds 1 Single +In Unit-Laundry +1.5 Bath

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Newly renovated, Scandinavian inspired, apartment with all the amenities we have noted that guests desire in a home away ...

    From $206 per night (USD)

    Expedia

    Details
  • CHICAGO Portage Park Pad
    From $310 per night (USD)

    VRBO

    CHICAGO Portage Park Pad

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Traveling alone or with the family this apartment has the space to lounge rest or work. Located in a quite residential n ...

    From $310 per night (USD)

    VRBO

    Details
  • Blueground | Chicago Loop, pool, nr Millennium Park
    From $129 per night (USD)

    VRBO

    Blueground | Chicago Loop, pool, nr Millennium Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this spacious The Loop furnished one bedroom apart ...

    From $129 per night (USD)

    VRBO

    Details