Chicago Rentals
From $262 per night (USD)VRBO
Modern Chicago 3BR Stay, 5 min to United Center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Minutes from Downtown Chicago and the Medical District, this West Side retreat puts you near the city’s premier attracti ...
From $262 per night (USD)VRBO
From $295 per night (USD)Expedia
Chicago Skyline 2BR - 6 Min to Millennium Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from Chicago’s vibrant South Loop and Grant Park, this city retreat offers the perfect blend of comfort, style, an ...
From $295 per night (USD)Expedia
From $1010 per night (USD)VRBO
The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
The Dakin Estate is a refined two-level 4BR Art Deco duplex in Wrigleyville, blending elevated design, comfort, and ente ...
From $1010 per night (USD)VRBO
From $372 per night (USD)Expedia
Near Lake and Museum • Modern • Game Area
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to 76th Chicago 535 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. Stylish ...
From $372 per night (USD)Expedia
From $665 per night (USD)VRBO
Spacious 5-bedroom building with WiFi, AC in beautiful Chicago
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 9
Make yourself at home in this superb 6-bedroom Chicago retreat. With amenities like a washing machine, WiFi, and AC, gue ...
From $665 per night (USD)VRBO
From $436 per night (USD)Expedia
Family-Friendly Home with Style & Space
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your Chicago getaway! This residence blends mid-century charm with modern updates, offering a warm and inviti ...
From $436 per night (USD)Expedia
From $234 per night (USD)VRBO
Modern 3BR Chicago Home - 10 Min to Wicker Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience city living in Noble Square, just minutes from downtown Chicago, renowned dining, nightlife, shopping, and ic ...
From $234 per night (USD)VRBO
From $234 per night (USD)Expedia
Modern 3BR Chicago Retreat, 7 Min to Fulton Market
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Experience this modern 3BR luxury home just minutes from West Loop, Downtown Chicago, and the city’s best dining, shoppi ...
From $234 per night (USD)Expedia
From $186 per night (USD)VRBO
Chicago Edgewater 3BR - 9 Min Walk to Loyola
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stay in Chicago’s charming Edgewater neighborhood, just minutes from Loyola University, Lake Michigan beaches and transi ...
From $186 per night (USD)VRBO
From $511 per night (USD)Expedia
Newly renovated, Chic, Spacious & Bright 1-bedroom apt in Lincoln Park!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Discover the best of Chicago from this charming one-bedroom (king) apartment! It is newly updated, bright and spacious. ...
From $511 per night (USD)Expedia
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 $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 $838 per night (USD)VRBO
Sleeps 18 • 8BR • Game Room • Gym • Theater
- Bedrooms:
- 3
- Bathrooms:
- 8
- Sleeps:
- 18
Welcome to Central Chicago 515 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ No ...
From $838 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 $486 per night (USD)VRBO
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)VRBO
From $749 per night (USD)Expedia
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)Expedia
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)Expedia
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)Expedia
From $202 per night (USD)VRBO
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)VRBO
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 $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 $123 per night (USD)VRBO
Blueground | South Loop, view, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in South Loop. It’ll be easy to simply show up and start living ...
From $123 per night (USD)VRBO
From $311 per night (USD)VRBO
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)VRBO
From $274 per night (USD)Expedia
Spacious 3BR 10 Min to Wicker Park & Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stay comfortably in this welcoming Chicago home in the heart of Humboldt Park. Perfectly positioned near local restauran ...
From $274 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 $325 per night (USD)Expedia
Luxury home + Huge yard in Avondale Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Emerald Oasis— a stylish 2-bed, 1-bath retreat on a rare double lot in Avondale, voted the 5th coolest neighb ...
From $325 per night (USD)Expedia
From $267 per night (USD)VRBO
Urban Chicago 3BR Retreat, 5 min to West Loop
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Minutes from the United Center and the Medical District, this West Side retreat offers easy access to Chicago’s top dini ...
From $267 per night (USD)VRBO
From $318 per night (USD)Expedia
Stylish 3-Bedroom Family Retreat-Walk to Transit-Quiet Tree-Lined Street
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Experience the best of both worlds in our spacious 3-bedroom home perfectly situated in a serene, tree-lined neighborhoo ...
From $318 per night (USD)Expedia
From $466 per night (USD)VRBO
Modern Home Near Downtown Chicago - Bronzeville
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This spacious, modern entire home is ideally located near McCormick Place and downtown Chicago — perfect for conferences ...
From $466 per night (USD)VRBO
From $111 per night (USD)VRBO
Blueground | Chicago Loop, rooftop, nr Millennium Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in The Loop. It’ll be easy to simply show up and start liv ...
From $111 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 $286 per night (USD)VRBO
Beautiful Bollywood 3 Bed Gem near Loyola University/Rogers Park/Lake Michigan
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your fresh, spacious, and effortless stay in the heart of Chicago’s vibrant Devon Avenue district! Located ab ...
From $286 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 $1032 per night (USD)VRBO
Downtown Chicago Stay with Free In & Out Parking 4
- 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 $1032 per night (USD)VRBO
From $464 per night (USD)Expedia
Downtown Chicago Stay with Free In & Out Parking 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: ✨ 2 Bedroom / 1 Bathroom Unit ✨ Enjoy a stylish experience at this centrally located place! 🏙️ Spacious ...
From $464 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 $718 per night (USD)Expedia
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)Expedia
From $162 per night (USD)VRBO
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)VRBO
From $145 per night (USD)Expedia
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)Expedia
From $296 per night (USD)VRBO
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)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 $201 per night (USD)VRBO
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)VRBO
From $452 per night (USD)Expedia
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)Expedia
From $295 per night (USD)VRBO
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)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 $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 $115 per night (USD)VRBO
Blueground | West Loop Gate, pool, nr Union Station
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this sophisticated studio Blueground apartment. You’ll love coming ...
From $115 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 $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)Expedia
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)Expedia
From $533 per night (USD)VRBO
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)VRBO
From $315 per night (USD)Expedia
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)Expedia
From $170 per night (USD)VRBO
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)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 $248 per night (USD)VRBO
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)VRBO
From $983 per night (USD)Expedia
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)Expedia
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 $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 $114 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 cozy The Loop furnished one bedroom apartment ...
From $114 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
From $337 per night (USD)VRBO
One Bedroom Hotel Suite – Sports Illustrated Resorts Chicago, Downtown Loop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience the heart of downtown Chicago at the Sports Illustrated Resorts Chicago – One Bedroom in the Loop. This bouti ...
From $337 per night (USD)VRBO
From $720 per night (USD)Expedia
Beautiful Home - Great for Groups, Parking & Food
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 18
This is a large historic Chicago home home that sleeps 18 and is perfect for large family or group stays. 6 bedrooms and ...
From $720 per night (USD)Expedia
From $346 per night (USD)VRBO
Paradise Lounge 3bd apartment in Central Chicago with AC & Balcony
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to this enchanting apartment in picturesque Chicago. With three queen beds, The whole group will enjoy easy acces ...
From $346 per night (USD)VRBO
From $105 per night (USD)VRBO
Blueground | South Loop, city view, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in South Loop with views over the city. It’ll be easy to s ...
From $105 per night (USD)VRBO
From $197 per night (USD)VRBO
1 Block to Red Line Station: Walkable Chicago Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Off-Street Parking | Work From Home Friendly | Easy Hwy Access Immerse yourself in the charm and excitement of the Wind ...
From $197 per night (USD)VRBO
From $198 per night (USD)Expedia
Modern 2BR Avondale with Free Parking Near CTA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stylish and spacious 2-bedroom Avondale apartment with hardwood floors, a modern kitchen, bright living area, spa-style ...
From $198 per night (USD)Expedia
From $1037 per night (USD)VRBO
ENVITAE Hotel, 4BR Luxury Modern Apartments
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury space is meticulously designed fo ...
From $1037 per night (USD)VRBO
From $696 per night (USD)Expedia
4 Bedroom Penthouse Loft in Heart of Wicker Park
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Neighborhood highlights The loft is located in Wicker Park, a highly desirable commercial area in Chicago. The neighborh ...
From $696 per night (USD)Expedia
From $274 per night (USD)VRBO
McCormick Place Modern Suite for 4, with Optional Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Wake Up to City Views in the Heart of Chicago Designed for your comfort and connection, this modern South Loop 1BR Suit ...
From $274 per night (USD)VRBO
From $175 per night (USD)VRBO
Blueground | The Loop, pool, nr Millennium Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this stylish The Loop furnished two bedroom apartm ...
From $175 per night (USD)VRBO
From $384 per night (USD)VRBO
Spacious 4BR West Loop Retreat w/Optional Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Experience comfortable city living in this home near Downtown Chicago. Featuring hardwood floors, stainless steel applia ...
From $384 per night (USD)VRBO
From $234 per night (USD)Expedia
Stylish brand new 3BR Near West Loop/Fulton Market
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your stylish Chicago retreat — a bright, modern 3-bedroom home designed for comfort, convenience, and memorab ...
From $234 per night (USD)Expedia
From $129 per night (USD)VRBO
3BR Vintage Apt • Patio • Walk to McKinley Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in a spacious 3-bedroom apartment on the 1st floor of a charming vintage home in McKinley Park. Perfect for familie ...
From $129 per night (USD)VRBO
From $247 per night (USD)Expedia
Cozy 1BR in Bridgeport w/free street parking/ McCormick/Chinatown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Consider this cozy apartment your home away from home while you visit Chicago! Located on the second floor of a charming ...
From $247 per night (USD)Expedia