
Cook Area Rentals
- From $636 per night (USD)
VRBO
Charming 6BD Retreat - Steps Away from Wrigley
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 13
Welcome to our *NEW* charming and spacious 6BD home—perfect for large groups seeking comfort and convenience. Just a few ...
From $636 per night (USD)VRBO
- From $72 per night (USD)
VRBO
Logan Square SRO Hotel Room 209
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Fully furnished private hotel room in a perfect Logan Square location! This room shares a bathroom with one other room a ...
From $72 per night (USD)VRBO
- From $1589 per night (USD)
VRBO
Sleeps 26 • Modern Multi-Unit • Gym • Workspaces
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 26
Welcome to Waveland Chicago 100 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $1589 per night (USD)VRBO
- From $381 per night (USD)
Expedia
2BR • Newly Furnished Modern Apt • Near O'Hare
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Potawatomie Chicago 201 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪ ...
From $381 per night (USD)Expedia
- From $397 per night (USD)
VRBO
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to Drummond Chicago 233 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $397 per night (USD)VRBO
- From $516 per night (USD)
Expedia
Walk to the Beach • Private Office • 5BR
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 13
Welcome to Columbia Chicago 655 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $516 per night (USD)Expedia
- From $255 per night (USD)
VRBO
Private Workspace • Sleeps4 • Modern Stylish Stay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Waveland Chicago 568 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $255 per night (USD)VRBO
- From $328 per night (USD)
Expedia
Modern Condo • Safe Chicago Stay Near O’Hare
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to River Chicago 442 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Note ...
From $328 per night (USD)Expedia
- From $142 per night (USD)
VRBO
Top Rated Condo •King Bed • Safe Historic Location
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to 78th Elmwood Park 453 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ ...
From $142 per night (USD)VRBO
- From $83 per night (USD)
Expedia
Top Rated Condo • 65” TV • Family-friendly 2BR
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 78th Elmwood Park 417 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ ...
From $83 per night (USD)Expedia
- From $278 per night (USD)
VRBO
2BR Fitness Pad • Private Gym • Sleeps 7
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to Waveland Chicago 268 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $278 per night (USD)VRBO
- From $446 per night (USD)
Expedia
Game Room • Fire-pit • Playground • Gym • Billiard
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Kilpatrick Chicago 600 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ ...
From $446 per night (USD)Expedia
- From $91 per night (USD)
VRBO
King Sleep Number Bed • Prime Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to 78th Elmwood Park 241 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ ...
From $91 per night (USD)VRBO
- From $313 per night (USD)
Expedia
Sleeps 7 • Huge Projector • Designated Workspace
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to Waveland Chicago 845 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $313 per night (USD)Expedia
- From $921 per night (USD)
VRBO
Sleeps 18 • 7BR • Gym • Game Room • Theater
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 18
Welcome to Waller Chicago 344 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Not ...
From $921 per night (USD)VRBO
- From $395 per night (USD)
Expedia
2BR Traveler's Favorite • Modern and Clean
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Drummond Chicago 839 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $395 per night (USD)Expedia
- From $287 per night (USD)
VRBO
Mins from O'Hare • Safe Location • Private Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to River Chicago 490 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Note ...
From $287 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Sleeps 4 • New Modern 1BR • Private Workspace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Waveland Chicago 513 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $295 per night (USD)Expedia
- From $102 per night (USD)
VRBO
King Bed Studio | 60\" HDTV | Safe | Close to Metra
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to 78th Elmwood Park 478 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ ...
From $102 per night (USD)VRBO
- From $486 per night (USD)
Expedia
2BR w/ Workspace - Coffee Bar - Near Transit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Drummond Chicago 523 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $486 per night (USD)Expedia
- From $749 per night (USD)
VRBO
Designer Retreat 2BR w Cowboy Pool, Fire Pit & Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your home away from home in the heart of Bridgeport, Chicago; a centrally located, artistic neighborhood in a ...
From $749 per night (USD)VRBO
- From $103 per night (USD)
VRBO
Blueground | Chicago Loop, rooftop, nr Millennium Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this lovely The Loop furnished one bedroom apartme ...
From $103 per night (USD)VRBO
- From $1116 per night (USD)
VRBO
Spacious Bronzeville Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy a comfortable and spacious apartment in the Bronzeville neighborhood. Walking distance from IIT and College o ...
From $1116 per night (USD)VRBO
- From $202 per night (USD)
Expedia
Modern 2BR, Private Elevator, Near United Center and Secure Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience elevated city living in this modern 2-bedroom, 2-bath condo in Chicago’s Near West Side. A private elevator o ...
From $202 per night (USD)Expedia
- From $97 per night (USD)
VRBO
Blueground | South Loop, view, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this comfortable South Loop furnished studio apart ...
From $97 per night (USD)VRBO
- From $499 per night (USD)
Expedia
Sleeps 12/Free parking+20 min to DT Chicago
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Ideal for families or groups. This listing is for 2 apartments in the same building: 1. First floor apartment has no s ...
From $499 per night (USD)Expedia
- From $482 per night (USD)
VRBO
Modern 3BR Near Downtown & Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
People say there is no place like home… but this unit was designed to feel even better. From comfort to style, every det ...
From $482 per night (USD)VRBO
- From $311 per night (USD)
Expedia
29th Floor 2BR Grant Park Suite with Balcony, Gym
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in a luxury 2BR 2BA high-rise in downtown Chicago near Grant Park, Millennium Park, and the Lakefront. Sleeps 8 wit ...
From $311 per night (USD)Expedia
- From $186 per night (USD)
VRBO
Chicago 3BR Loyola - 10 Min Walk to Beaches & CTA
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Located in Chicago’s Edgewater area near Loyola University and the lakefront, this spacious 3BR stay places you close to ...
From $186 per night (USD)VRBO
- From $234 per night (USD)
Expedia
Chicago 3BR Retreat 10 Min Access to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience Chicago from this bright retreat in Humboldt Park. Ideally located for exploring Chicago, the accommodation o ...
From $234 per night (USD)Expedia
- From $307 per night (USD)
VRBO
Walk to Wrigley! Spacious 3BR in the Heart of Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
1 mile to Wrigley! Bright and inviting 3-bedroom, 1-bath apartment in Chicago’s Edgewater neighborhood—sleeps up to 7 gu ...
From $307 per night (USD)VRBO
- From $151 per night (USD)
Expedia
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Perched in the heart of Wicker Park, this charming 3rd-floor apartment is your perfect Chicago base. Whether you`re sipp ...
From $151 per night (USD)Expedia
- From $117 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 pretty The Loop furnished one bedroom apartme ...
From $117 per night (USD)VRBO
- From $217 per night (USD)
VRBO
Private Romantic Retreat for Two • Luxury Escape
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape the ordinary and step into a curated romantic retreat designed exclusively for adult couples (25+). This is more ...
From $217 per night (USD)VRBO
- From $297 per night (USD)
VRBO
Luxury Designer Apartment 802| Gold Coast/Old Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: NEW APARTMENT IN THE HEART OF GOLD COAST and OLD TOWN! Enjoy your own luxury apartment in Chicago's Gold Co ...
From $297 per night (USD)VRBO
- From $537 per night (USD)
VRBO
NEW! Charming Andersonville Coach House | 3BR/2.5BA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
**Hosting 32+ Night Reservations** Tucked away on a quiet tree-lined street, this spacious two-story private coa ...
From $537 per night (USD)VRBO
- From $186 per night (USD)
VRBO
River North / Mag Mile, Lake and City Views, 43rd Floor Condo, Parking Included!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
In this breathtaking NE corner apartment at Huron and Wabash, every window frames the mesmerizing Chicago Skyline and La ...
From $186 per night (USD)VRBO
- From $282 per night (USD)
VRBO
Stay near Wrigley Field! Spacious 3BD Penthouse!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to your spacious Lakeview retreat just steps from Wrigley Field! Catch a Cubs game, explore the neighb ...
From $282 per night (USD)VRBO
- From $280 per night (USD)
VRBO
Lakeview 3BD 2BA Penthouse near Wrigley Field!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience the best of Chicago from this modern 3-bed, 2-bath Lakeview retreat, just steps from Wrigley Field, ...
From $280 per night (USD)VRBO
- From $308 per night (USD)
Expedia
Luxury Designer Apartment 1202|Gold Coast/Old Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: NEW APARTMENT IN THE HEART OF GOLD COAST and OLD TOWN! Enjoy your own apartment in Chicago's Gold Coast and ...
From $308 per night (USD)Expedia
- From $617 per night (USD)
VRBO
Downtown Chicago Stay with Free In & Out Parking 1
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 🏙️ For 4 Bedroom / 2 Bathroom Unit Enjoy a stylish experience at this centrally-located place! ✨🏙️ Exp ...
From $617 per night (USD)VRBO
- From $584 per night (USD)
Expedia
Downtown Chicago Stay with Free In & Out Parking 5
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 🏙️ 3 Bedroom / 2 Bathroom Version Enjoy a stylish stay in the heart of downtown Chicago! ✨🌆 Modern 848 ...
From $584 per night (USD)Expedia
- From $632 per night (USD)
VRBO
Downtown Chicago Stay with Free In & Out Parking 3
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 🏙️ 3 Bedroom / 2 Bathroom Version Enjoy a stylish stay in the heart of downtown Chicago! ✨🌆 Modern 848 ...
From $632 per night (USD)VRBO
- From $231 per night (USD)
Expedia
Stylish 2-Bedroom Condo – Easy Drive to Downtown Chicago & Midway Airport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Overview: Welcome to your perfect home-base in the Chicago area! This beautifully styled 2-bedroom, 1-bathroom condo is ...
From $231 per night (USD)Expedia
- From $718 per night (USD)
VRBO
Giant 5-Bedroom Home w/ Pool Table, 15 Min to Wrigley & Downtown
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Bring the whole crew to this spacious Irving Park home packed w/fun! Shoot pool, kick back with smart TVs in almost ever ...
From $718 per night (USD)VRBO
- From $162 per night (USD)
Expedia
Landing | Beautiful 2BD, Gym, Rooftop Lounge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay luxe in the Loop. Located in the heart of Chicago’s vibrant West Loop, Luxe on Madison is your home for a flexible ...
From $162 per night (USD)Expedia
- From $145 per night (USD)
VRBO
Landing | Stylish 1BD, 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 $145 per night (USD)VRBO
- From $296 per night (USD)
Expedia
Chicago Gem: Wrigley - Lakefront - Red Line Train
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the perfect blend of city excitement and neighborhood charm in this spacious 2-bedroom, 1-bath condo located in ...
From $296 per night (USD)Expedia
- From $440 per night (USD)
VRBO
Compatible: 3BR-2BT Ranch with Finished Basement!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in La Grange Park, enjoy what this 3-bedroom house has to offer. Each bedroom features a comfy king bed, perfect ...
From $440 per night (USD)VRBO
- From $295 per night (USD)
Expedia
29th Floor 2BR Suite with Balcony and Gym
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in a luxury 2BR 2BA high-rise in downtown Chicago near Grant Park, Millennium Park, and the Lakefront. Sleeps 8 wit ...
From $295 per night (USD)Expedia
- From $227 per night (USD)
VRBO
Landing | Beautiful 2BD, Pool, Gym
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Schaumburg’s vibrant Veridian campus, Element at Veridian puts you minutes from Woodfield Mall, top dining sp ...
From $227 per night (USD)VRBO
- From $499 per night (USD)
Expedia
Pristine Apartment with Free Street Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
The Fully Renovated Urban Retreat on Chicago Avenue Welcome to your beautifully renovated and pristine 3-bedroom upper-l ...
From $499 per night (USD)Expedia
- From $90 per night (USD)
VRBO
Blueground | Little Italy, pool, nr UIC
- 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 $90 per night (USD)VRBO
- From $137 per night (USD)
VRBO
Modern Garden Apartment w/ New Kitchen + Bathroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our newly renovated garden apartment in Irving Park! This private-entry unit features 2 cozy bedrooms, a bran ...
From $137 per night (USD)VRBO
- From $438 per night (USD)
VRBO
Westloop Spacious 4 bdrm Duplex with parking & workout area
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Centrally located duplex-down, ideal for families and groups of up to 10. Features 4 bedrooms (2 King, 2 Queen), 3 full ...
From $438 per night (USD)VRBO
- From $186 per night (USD)
Expedia
Cozy 2-bedroom apartment in peaceful Chicago with central A/C system
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to this beautiful apartment in Chicago. Guests will find two comfortable bedrooms, each featuring a queen bed, p ...
From $186 per night (USD)Expedia
- From $160 per night (USD)
VRBO
Blueground | West Town, balcony, nr Chicago River
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this spacious two bedroom Blueground apartment. You’ll love coming ...
From $160 per night (USD)VRBO
- From $147 per night (USD)
VRBO
Blueground | West Town, view, nr Chicago River
- 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 $147 per night (USD)VRBO
- From $511 per night (USD)
VRBO
6BR Apt • Workspace • Near Lakefront + Red Line
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to Columbia Chicago 654 by EscapeStays, the name guests can easily remember when planning their stay. Note: Bef ...
From $511 per night (USD)VRBO
- From $132 per night (USD)
Expedia
Terrific 1 bedroom apartment to ''Stay, Unwind. Enjoy.''
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your Chicago adventure begins at this 1-bedroom apartment. Inside, guests find a welcoming space featuring a king bed an ...
From $132 per night (USD)Expedia
- From $540 per night (USD)
VRBO
Newly remodeled 3-bedroom house in delightful Harvey, near new Wind Creek casino
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly remodeled 3 bedroom in Harvey, this marvelous house offers a comfortable retreat for guests. With three spacious b ...
From $540 per night (USD)VRBO
- From $201 per night (USD)
Expedia
Two bedroom in United States of America, Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bright, newly renovated, and finished like a designer condo, this modern 2-bedroom is built for exploring Chicago in com ...
From $201 per night (USD)Expedia
- From $452 per night (USD)
VRBO
Spacious 4-bedroom apartment in fantastic Chicago with AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your cozy getaway awaits in Chicago at this charming apartment. With four spacious bedrooms featuring three queen beds a ...
From $452 per night (USD)VRBO
- From $101 per night (USD)
VRBO
Cozy 1-bedroom garden apartment in W Lakeview/Wrigley/Roscoe Village/Fast WIFI
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Bright 1BR & 1 Bath in Prime Lakeview — great for long stays, remote work, or city trips! What You’ll Love: • Fast WiFi ...
From $101 per night (USD)VRBO
- From $252 per night (USD)
VRBO
Modern Edgewater Apartment: 2BD 2BA with Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience the charm of Chicago's Edgewater neighborhood from this modern retreat just steps from the Granvill ...
From $252 per night (USD)VRBO
- From $141 per night (USD)
VRBO
Blueground | Chicago Loop, pool, nr Millennium Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in The Loop. It’ll be easy to simply show up and start liv ...
From $141 per night (USD)VRBO
- From $294 per night (USD)
VRBO
Peaceful 3-bedroom apartment in charming Chicago Chinatown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
This 3-bedroom apartment is perfect for your escape to Chicago. Inside, guests find a wonderful mix of comfort with a qu ...
From $294 per night (USD)VRBO
- From $420 per night (USD)
Expedia
Penthouse Designer Loft 4W | GoldCoast/River North
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Summary: BRAND NEW APARTMENT IN THE HEART OF RIVER NORTH & GOLD COAST! Enjoy your designer styled unit located in Ch ...
From $420 per night (USD)Expedia
- From $379 per night (USD)
VRBO
Spacious West Loop Retreat UnitedCenter & Dining
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bright and spacious top-floor condo in a 2-unit building, on a quiet and safe residential street. Perfect for couples, ...
From $379 per night (USD)VRBO
- From $343 per night (USD)
Expedia
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
About This Space Welcome to your home away from home! This private 2-bedroom coach house offers all the comforts of home ...
From $343 per night (USD)Expedia
- From $315 per night (USD)
VRBO
Humboldt Hideaway! Spacious 3BR/1BA Apartment in the Heart of Humboldt Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to the Humboldt Hideaway! This spacious 3-bedroom, 1-bath apartment in vibrant Humboldt Park comfortably sleeps ...
From $315 per night (USD)VRBO
- From $151 per night (USD)
VRBO
Cozy 1-bedroom apartment in beautiful West Loop, in-unit laundry + pet friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cozy up in this serene space in one of Chicago's most beautiful neighborhoods, the West Loop. This superb one-bedroom is ...
From $151 per night (USD)VRBO
- From $407 per night (USD)
VRBO
Your Own Private Spa Near Chicago • Barrel Sauna + Saltwater Hot Tub • Sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Relax in your private spa stay in Arlington Heights. This remodeled home features a 6-person European barrel sauna with ...
From $407 per night (USD)VRBO
- From $120 per night (USD)
VRBO
Blueground | Fulton Market District, pool, nr Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Fulton Market District. It’ll be easy to simply show up ...
From $120 per night (USD)VRBO
- From $642 per night (USD)
VRBO
Luxury 4BR 4-Story Chicago Villa |Prime Gold Coast
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to your Chicago stay in the heart of the Gold Coast - a spacious, architect-designed townhome perfect for relaxi ...
From $642 per night (USD)VRBO
- From $533 per night (USD)
Expedia
Designer 3BR with Resort Amenities and Balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Experience iconic Chicago with a stay at a high-end and spacious 3BR apartment right in downtown with a large ...
From $533 per night (USD)Expedia
- From $148 per night (USD)
VRBO
Feel at Home while Exploring Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay comfortably in Chicago at this 2-bedroom apartment. The space features one queen bed and one twin bed, plus a cozy ...
From $148 per night (USD)VRBO
- From $170 per night (USD)
Expedia
Cozy Chicago Retreat Near All The Action
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Discover this 1-bedroom 2-flat in Chicago. The upper level space features a terrific bedroom with two Queen beds, a dinn ...
From $170 per night (USD)Expedia
- From $436 per night (USD)
VRBO
Stunning Evanston Retreat Near Northwestern University
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to this beautifully renovated Evanston brick home, just 10 minutes from Northwestern University and 30 minutes f ...
From $436 per night (USD)VRBO
- From $394 per night (USD)
VRBO
Sleek Avondale Condo Spa Bath King Bed +Queen bed +Garage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Modern meets mmm-hmm in this 2BR Avondale gem. King & queen beds? Check. Spa bath with rain shower & jets? Oh yes. Strea ...
From $394 per night (USD)VRBO
- From $279 per night (USD)
VRBO
2-BR central Oak Park flat+near FLW homes+near trains to Chicago+pets ok+parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Historic Oak Park Retreat Near Frank Lloyd Wright & Downtown Chicago with parking. This full-floor apartment occupies an ...
From $279 per night (USD)VRBO
- From $116 per night (USD)
Expedia
Stylish 2-bedroom Retreat Near UChicago & Close to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Consider this apartment your home away from home while you visit Chicago. This fabulous space features two cozy bedrooms ...
From $116 per night (USD)Expedia
- From $420 per night (USD)
VRBO
Patio • Workspace • Dog Friendly • Free Street Parking • Train Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You'll fall in love with this garden apartment that offers easy access to both the O'Hare airport & the heart of Chicago ...
From $420 per night (USD)VRBO
- From $248 per night (USD)
Expedia
Fabulous hotel suites in Chicago , 3 miles from United Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Unwind in Chicago at this perfect hotel suite. Guests enjoy a comfortable stay with one bathroom and climate control tha ...
From $248 per night (USD)Expedia
- From $307 per night (USD)
VRBO
Cul de sac jacuzzi home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your Country Club Hills adventure begins at this 3-bedroom house. Inside, guests find two twin beds and one queen bed, p ...
From $307 per night (USD)VRBO
- From $348 per night (USD)
VRBO
Chic Luxe Spa Retreat - Light Filled+King Bed+Garage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Experience top-floor luxury in this fully remodeled Avondale condo. Soak in the spa-style bath, bask in natural light fr ...
From $348 per night (USD)VRBO
- From $983 per night (USD)
VRBO
Modern 6 BR 3 Baths 11 beds Sleeps 17 Birthday
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 17
After two years of carefully restoring and renovating this beautiful home from the inside out, we’re excited to finally ...
From $983 per night (USD)VRBO
- From $531 per night (USD)
VRBO
New Luxury 3BR - Steps to Downtown and Metra
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Brand-new, light-filled 3-bedroom apartment in the heart of Brookfield, thoughtfully designed for comfort and style. Fea ...
From $531 per night (USD)VRBO
- From $230 per night (USD)
VRBO
Edgewater Gem by the Lake! 2BR with Parking & Gym
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Escape to Chicago's charming Edgewater neighborhood, where mornings begin with a stroll along the lakefront an ...
From $230 per night (USD)VRBO
- From $239 per night (USD)
VRBO
Cozy 2BD 2BA Apt! Steps to Lake with Gym & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience your ideal Chicago escape with this modern retreat in Edgewater. Start your morning with coffee bef ...
From $239 per night (USD)VRBO
- From $348 per night (USD)
VRBO
3BR Retreat Perfect for Professionals and Families in South Shore/ Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to your home away from home! This fully renovated 3-bedroom, 2-bathroom apartment offers modern comfort in the h ...
From $348 per night (USD)VRBO
- From $663 per night (USD)
Expedia
Fabulous 5-bedroom, 6 beds, 3 bath house near Ohare in Prospect Heights
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This unique place has a style of its own. It's spacious with 5 bedrooms, 3 full bathrooms, single family home that is in ...
From $663 per night (USD)Expedia
- From $1722 per night (USD)
VRBO
Spacious 4-bedroom Home - Walk to Lake Michigan, Beaches, NU Campus, and more!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Shack on Judson | Walk to Northwestern, Lake Michigan, Downtown Evanston and more Welcome to Shack on Judson, a spaciou ...
From $1722 per night (USD)VRBO
- From $268 per night (USD)
Expedia
Peaceful King+Queen - 2BR+2BA - WFH Apt - Near: Northwestern-Chicago-Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy this beautiful, newly renovated 2-bedroom 2-bathroom apartment in Evanston’s arts district. Walk to shops, cafes, ...
From $268 per night (USD)Expedia
- From $519 per night (USD)
VRBO
Downtown Chicago Stay with Free In & Out Parking-2
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 🏙️ For 4 Bedroom / 2 Bathroom Unit Enjoy a stylish experience at this centrally-located place! ✨🏙️ Exp ...
From $519 per night (USD)VRBO
- From $360 per night (USD)
Expedia
3-bedroom apartment in adorable Chicago with AC for your stay
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the beauty of Chicago from this 3-bedroom apartment. The fabulous space features one king bed and two queen bed ...
From $360 per night (USD)Expedia
- From $321 per night (USD)
VRBO
Inviting & Serene: A Book Lover’s Haven
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our newly updated 3-bedroom, 2-bath home! Thoughtfully designed to create a restful, welcoming atmosphere. En ...
From $321 per night (USD)VRBO
- From $174 per night (USD)
Expedia
The Langley Luxe Modern style unit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Langley Luxe Chicago is waiting for you at this 2-bedroom apartment. Inside, guests find two queen beds that promise ...
From $174 per night (USD)Expedia
- From $202 per night (USD)
VRBO
Studio King Hotel Suite – Sports Illustrated Resorts Chicago, Downtown Loop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience the vibrant heart of downtown Chicago at the Sports Illustrated Resorts Chicago – Studio King in the Loop. Th ...
From $202 per night (USD)VRBO
- From $224 per night (USD)
VRBO
Studio Hotel Suite: 2 Dbl Beds-Sports Illustrated Resorts Chicago, Downtown Loop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in the heart of downtown Chicago at the Sports Illustrated Resorts Chicago Studio with 2 beds – Sleeps 4. This mode ...
From $224 per night (USD)VRBO




































































































