Cook Area Rentals
From $240 per night (USD)VRBO
Upscale 1BR -Near Midway Airport - Free Parking & Fast CTA Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the perfect Chicago retreat at The Midway — a spacious, upscale 1-bedroom apartment on the city's South Side, i ...
From $240 per night (USD)VRBO
From $132 per night (USD)VRBO
Blueground | South Loop, washer, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...
From $132 per night (USD)VRBO
From $220 per night (USD)VRBO
Your Home Away From Home in Sauk Village
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Relax and unwind in this cozy 3-bedroom home, perfect for families, small groups, or a peaceful solo getaway. The space ...
From $220 per night (USD)VRBO
From $550 per night (USD)Expedia
Designer West Town Retreat • Game Room + Deck
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to your West Town retreat — a spacious, thoughtfully designed 3-bedroom home with two private decks, ...
From $550 per night (USD)Expedia
From $444 per night (USD)VRBO
Spacious Single Family House with Parking
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Single-family house in the heart of Chicago’s Pilsen community. This mid-century home is flooded with natural light and ...
From $444 per night (USD)VRBO
From $335 per night (USD)Expedia
The Bucktown Nook | By Transit w/ Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Unwind in this thoughtfully designed 1BR apartment, ideally located in Bucktown, one of Chicago’s most vibrant ...
From $335 per night (USD)Expedia
From $330 per night (USD)VRBO
Cozy Fully Furnished 5B4B Palos Heights Oasis
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This charming multi-level single-family home offers approximately 2,400 square feet of thoughtfully designed living spac ...
From $330 per night (USD)VRBO
From $100 per night (USD)Expedia
Delightful 2-bedroom building with AC in vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Your cozy getaway awaits in Chicago at this marvelous building. Inside, guests find two comfortable bedrooms featuring o ...
From $100 per night (USD)Expedia
From $393 per night (USD)VRBO
The Home Run: Modern 2BR Steps from Wrigley Field
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the heartbeat of Chicago in this spacious, modern 2-bedroom, 2-bathroom condo perfectly perched where the his ...
From $393 per night (USD)VRBO
From $214 per night (USD)Expedia
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 $214 per night (USD)Expedia
From $574 per night (USD)VRBO
Luxury 6BR/3BA Group Stay in McCormick, Sleeps 12
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to your luxury home in downtown Chicago! Just steps from McCormick Place, this spacious 6-bedroom, 3-bath suit ...
From $574 per night (USD)VRBO
From $243 per night (USD)Expedia
Modern 3BR BA Downtown Chicago Getaway Near McCormick
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your chic urban retreat in Chicago’s South Loop – steps from McCormick Place and surrounded by the city's bes ...
From $243 per night (USD)Expedia
From $186 per night (USD)VRBO
Luxury 2BR/2BA Suite near McCormick Place, Lakefront with Parking & Gym
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome and Experience Chicago in style at our upscale corner suite nestled in the dynamic South Loop district—just step ...
From $186 per night (USD)VRBO
From $674 per night (USD)Expedia
Luxury 6BR/4BA Suite Near McCormick with Skyline Views
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to The Luxurious Suite, your premier group getaway in Downtown Chicago’s South Loop! Perfect for business group ...
From $674 per night (USD)Expedia
From $295 per night (USD)VRBO
20th Floor Skyline 2BR Grant Park with Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in the heart of downtown Chicago, just walk away from Grant Park, in this bright and modern 2-bedroom, 2-bath high- ...
From $295 per night (USD)VRBO
From $217 per night (USD)Expedia
Modern 2BR 2BA Suite Near McCormick Place & Chicago Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Your South Loop Skyline Escape Wake up to the soft glow of sunrise over Chicago’s skyline, coffee in hand, a ...
From $217 per night (USD)Expedia
From $194 per night (USD)VRBO
Modern 2BR 2BA Near McCormick Skyline View, Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to your home away from home in the heart of Chicago’s vibrant South Loop! This spacious 2-bedroom, 2 bathroom su ...
From $194 per night (USD)VRBO
From $176 per night (USD)Expedia
Skyline 2BR 2BA in South Loop Near Museums & McCormick Place
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Modern 2-Bedroom Suite with Skyline Views in Chicago’s South Loop Welcome to your elevated stay in the heart of Chicago ...
From $176 per night (USD)Expedia
From $719 per night (USD)VRBO
Stylish 3BR Townhouse with 2 Jacuzzi and 1 private garage spot
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
About this space !!1 CAR PRIVATE GARAGE PARKING INCLUDED!! Welcome to this stylish urban home that will make you feel a ...
From $719 per night (USD)VRBO
From $630 per night (USD)Expedia
Cozy 4BR 2BA Worth Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Relax with the whole family at this peaceful place to stay. Welcome to this spacious 4-bedroom, 2-bathroom sin ...
From $630 per night (USD)Expedia
From $371 per night (USD)VRBO
Charming 5BD 2BA with spacious yard near O'hare
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: You will enjoy easy access to everything from this centrally located place near O'hare. This 5 bedroom 2 full ...
From $371 per night (USD)VRBO
From $295 per night (USD)Expedia
24th Floor 2BR Luxury Skyline Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in the heart of downtown Chicago, just walk away from Grant Park, in this bright and modern 2-bedroom, 2-bath high- ...
From $295 per night (USD)Expedia
From $295 per night (USD)VRBO
25th Floor 2BR Grant Park Suite with Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in the heart of downtown Chicago, just walk away from Grant Park, in this bright and modern 2-bedroom, 2-bath high- ...
From $295 per night (USD)VRBO
From $295 per night (USD)Expedia
Skyline 2BR Heart of Chicago Walk to Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in the heart of downtown Chicago, just walk away from Grant Park, in this bright and modern 2-bedroom, 2-bath high- ...
From $295 per night (USD)Expedia
From $295 per night (USD)VRBO
Grant Park 2BR Condo with Balcony Skyline View & Gym
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in the heart of downtown Chicago, just walk away from Grant Park, in this bright and modern 2-bedroom, 2-bath high- ...
From $295 per night (USD)VRBO
From $295 per night (USD)Expedia
21st Floor Skyline 2BR Grant Park and Field Museum
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in the heart of downtown Chicago, just walk away from Grant Park, in this bright and modern 2-bedroom, 2-bath high- ...
From $295 per night (USD)Expedia
From $105 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 $105 per night (USD)VRBO
From $101 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 sophisticated The Loop furnished studio apart ...
From $101 per night (USD)VRBO
From $127 per night (USD)VRBO
Blueground | South Loop, view, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop. It’ll be easy to simply show up and start l ...
From $127 per night (USD)VRBO
From $128 per night (USD)VRBO
Blueground | South Loop, view, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...
From $128 per night (USD)VRBO
From $171 per night (USD)VRBO
Quiet 1 Bedroom, 1 Free Parking, High Speed Wi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Kick back and relax in this stylish 1BR, 1BA condo in Lakeview, Chicago. Located on the 2nd floor, it features ...
From $171 per night (USD)VRBO
From $279 per night (USD)Expedia
2BR Garden Suite in Lakeview | Walk to Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our 2-bedroom garden suite in Lakeview, set on a quiet, tree-lined block within Chicago’s Newport Avenue Land ...
From $279 per night (USD)Expedia
From $299 per night (USD)VRBO
The City Manor Apartment 1 bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to The City Manor, tucked away on a quiet residential street in the Ravenswood neighborhood. This inviting space ...
From $299 per night (USD)VRBO
From $228 per night (USD)Expedia
Perfect 4-bedroom house with AC in delightful Chicago neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Chicago is waiting for you at this 4-bedroom house. Inside, guests find 3 queen beds and 2 twin bed, perfect for a group ...
From $228 per night (USD)Expedia
From $625 per night (USD)VRBO
5BR Family home Near O’Hare, Easy Airport & Downtown Access, Garage Parking.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Experience Chicago like a local in this 5-bedroom house. The bedrooms feature 2 full beds, 1 twin bed, and 2 double beds ...
From $625 per night (USD)VRBO
From $864 per night (USD)Expedia
Elite 4BR Art Deco suite. Garage included.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The Wrigleyville Suite is a thoughtfully designed 1,400 sq ft Art Deco 4-bedroom residence in the heart of Chicago's mos ...
From $864 per night (USD)Expedia
From $507 per night (USD)VRBO
Expertly designed 2BR Art Deco sanctuary.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the heart of Wrigleyville in this 1,400-square-foot Art Deco sanctuary, just a 1-minute walk from Wrigley Field. ...
From $507 per night (USD)VRBO
From $247 per night (USD)Expedia
Trendy and Comfortable Stay in Hyde Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Requires walking down 5 steps. Street parking is not guaranteed, we recommend using ride share apps. Experience the cha ...
From $247 per night (USD)Expedia
From $421 per night (USD)VRBO
Welcoming 3-bedroom house in vibrant Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your cozy retreat in Ukrainian Village, Chicago! This charming home features free street parking and a relaxi ...
From $421 per night (USD)VRBO
From $225 per night (USD)VRBO
Blueground | West Loop, pool, nr Union Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in West Loop. It’ll be easy to simply show up and start li ...
From $225 per night (USD)VRBO
From $197 per night (USD)VRBO
Chicago Lakefront Vacation Rental · Fire Pit Patio · Loyola Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This Chicago lakefront vacation rental sits directly across from Lake Michigan — one of the most beautifully positioned ...
From $197 per night (USD)VRBO
From $187 per night (USD)Expedia
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relax in your Cozy-Chic Garden Suite, just minutes from O’Hare & Rosemont.🌿 Enjoy a backyard, grill, free gated parking ...
From $187 per night (USD)Expedia
From $243 per night (USD)VRBO
1-bedroom apartment in charming Chicago with AC and free street parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your home away from home! This charming first-floor one-bedroom apartment offers comfort, convenience, and gr ...
From $243 per night (USD)VRBO
From $267 per night (USD)Expedia
Free parking+20 min to DT Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your home away from home in beautiful Oak Park! This bright 2 bedrooms and 2 bathrooms apartment is perfect ...
From $267 per night (USD)Expedia
From $315 per night (USD)VRBO
Welcome to this four bedroom, two bathroom apartment located in the neighborhood of Lakeview.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this four bedroom, two bathroom apartment located in the neighborhood of Lakeview. The location is fantastic. ...
From $315 per night (USD)VRBO
From $435 per night (USD)Expedia
Spacious 3-bedroom house in beautiful Chicago with AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Step into a historic Ukrainian village house in Chicago. Vintage charm meets modern comfort. Nearby restaurants, shops, ...
From $435 per night (USD)Expedia
From $239 per night (USD)VRBO
Ashland House: a roomy 3BR/2BA duplex with a rooftop deck, on the Lincoln Park border.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to Ashland House, our two-level home on the Lincoln Park and Lakeview border. It's a roomy, comfortable base wit ...
From $239 per night (USD)VRBO
From $260 per night (USD)Expedia
Free parking+20 min to downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your home away from home in beautiful Oak Park! This bright 2 bedrooms and 1 bathroom apartment is perfect fo ...
From $260 per night (USD)Expedia
From $601 per night (USD)VRBO
Modern West Loop Gem-City Views & Prime Location 1
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: ✨ Enjoy a stylish stay at this modern 4-bedroom, 4-bath retreat in the heart of Chicago 🌆. Perfect for famili ...
From $601 per night (USD)VRBO
From $526 per night (USD)Expedia
Modern West Loop Gem-City Views & Prime Location 4
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: ✨ Enjoy a stylish stay at this modern 4-bedroom, 4-bath retreat in the heart of Chicago 🌆. Perfect for familie ...
From $526 per night (USD)Expedia
From $367 per night (USD)VRBO
Modern West Loop Gem-City Views & Prime Location 2
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy a stylish stay at this modern 4-bedroom, 4-bath retreat in the heart of Chicago. Perfect for families, groups, or ...
From $367 per night (USD)VRBO
From $449 per night (USD)Expedia
Modern West Loop Gem-City Views & Prime Location 6
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy a stylish stay at this modern 4-bedroom, 4-bath retreat in the heart of Chicago. Perfect for families, groups, or ...
From $449 per night (USD)Expedia
From $309 per night (USD)VRBO
Charming 2-bedroom condo in superb Chicago with AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Stay comfortably in Chicago at this 2-bedroom condo. The bedrooms feature 1 queen bed and 1 twin bed, ensuring a pleasan ...
From $309 per night (USD)VRBO
From $544 per night (USD)Expedia
Modern West Loop Gem-City Views & Prime Location 5
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: ✨ Enjoy a stylish stay at this modern 4-bedroom, 4-bath retreat in the heart of Chicago 🌆. Perfect for famili ...
From $544 per night (USD)Expedia
From $376 per night (USD)VRBO
Spacious 5 Bed 2 bath House
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Spacious 5-bedroom home in Melrose Park, perfect for families, groups, or work crews. This comfortable 2-bath ...
From $376 per night (USD)VRBO
From $1088 per night (USD)Expedia
Beautiful Hyde Park Home 4 Bed/5 bath w/speakeasy!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Nestled in the heart of Hyde Park, this stunning vintage home exudes charm and elegance, boasting a spacious layout that ...
From $1088 per night (USD)Expedia
From $480 per night (USD)VRBO
Studio Mins Walk to DT OAK PARK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This centrally located studio is just a 5-minute walk from the iconic Frank Lloyd Wright Home and Studio, surrounded by ...
From $480 per night (USD)VRBO
From $198 per night (USD)Expedia
Welcome to your perfect city retreat in the heart of Skokie!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your Skokie adventure begins at this brilliant 3-bedroom condo. Each bedroom features a comfortable queen bed, perfect f ...
From $198 per night (USD)Expedia
From $325 per night (USD)VRBO
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)VRBO
From $502 per night (USD)Expedia
Wonderful 3-bedroom apartment in West Village, Evanston
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to The Greenleaf, a sunny 3BR top-floor apartment in a vintage building in Evanston’s fun & funky West Village. ...
From $502 per night (USD)Expedia
From $109 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 sophisticated The Loop furnished one bedroom ...
From $109 per night (USD)VRBO
From $164 per night (USD)Expedia
NEW Midterm Furnished Rental - 32+Days! - North Center Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Highly sought-after North Center / St. Ben's Location - 1 Garage Spot available for an additional $200/month fee. - Ful ...
From $164 per night (USD)Expedia
From $839 per night (USD)VRBO
3BR · Steps from McCormick · Balcony & Gym
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to your bright and spacious 3-bedroom Chicago retreat. The perfect Chicago base for families, groups o ...
From $839 per night (USD)VRBO
From $245 per night (USD)Expedia
South Loop · 3 Kings · Steps from McCormick Place
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to your bright and spacious 3-bedroom Chicago retreat. The perfect Chicago base for families, groups o ...
From $245 per night (USD)Expedia
From $246 per night (USD)VRBO
Spacious 3BR · Bronzeville/South Loop · Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to your bright and spacious 3-bedroom Chicago retreat. The perfect Chicago base for families, groups o ...
From $246 per night (USD)VRBO
From $738 per night (USD)Expedia
Comfortable Luxurious 4BR Home w/ Game Room + Master Suite
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
Welcome to your soon to be amazing memory at this newly remodeled, spacious and luxurious home! Your stay here wouldn't ...
From $738 per night (USD)Expedia
From $203 per night (USD)VRBO
Blueground | West Loop, pool, nr Chicago River
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in West Loop. It’ll be easy to simply show up and start li ...
From $203 per night (USD)VRBO
From $159 per night (USD)VRBO
Blueground | West Loop, pool, nr Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this pretty two bedroom Blueground apartment. You’ll love coming h ...
From $159 per night (USD)VRBO
From $105 per night (USD)VRBO
Blueground | Chicago Loop, rooftop, nr Millennium 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 $105 per night (USD)VRBO
From $123 per night (USD)VRBO
Blueground | Central Station, pool, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Central Station furnished one bedroo ...
From $123 per night (USD)VRBO
From $206 per night (USD)VRBO
Enchanting 4-bedroom apartment with AC in vibrant Chicago Hyde Park
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Your home away from home in Chicago with 4 bedrooms, including 2 full bed, 1 queen bed, and 1 twin bed. This wonderful a ...
From $206 per night (USD)VRBO
From $155 per night (USD)VRBO
NEW! 2bd River North Million Dollar Views! Parking Incl by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
32+ NIGHTS MIN, *1 GARAGE PARKING SPACE INCL* Experience our stunning 14th floor River North condo! With 2 bedrooms a ...
From $155 per night (USD)VRBO
From $148 per night (USD)VRBO
Spacious King 1BD • Top Floor Walkable Edgewater
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Revive your soul in this Edgewater Oasis Discover this sun-drenched 1-bedroom retreat on a quiet, tree-lined street in ...
From $148 per night (USD)VRBO
From $515 per night (USD)Expedia
Bright family home near I-90 with office, bar, EV charger, sleeps 6, no pets
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your bright and spacious suburban retreat; the perfect place to relax, work, and reconnect. Thoughtfully desi ...
From $515 per night (USD)Expedia
From $1997 per night (USD)VRBO
Historic Estate | 10 BR, Sleeps 16+, Game Room
- Bedrooms:
- 7
- Bathrooms:
- 10
- Sleeps:
- 22
Summary: This 1885 historic residence features 10 BR & 7 BA, comfortably accommodating 30+ guests across multiple tho ...
From $1997 per night (USD)VRBO
From $1125 per night (USD)Expedia
West Town Estate • 6BR, Game Room, Decks, 5Gbps
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 20
Summary: A stunning 6-bedroom, 5-bathroom private retreat combining two beautifully designed spaces within our histo ...
From $1125 per night (USD)Expedia
From $542 per night (USD)VRBO
Dwellish Rentals - Hyde Park Luxury Stay 5BR Near Lake & UChicago
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Experience Chicago luxury in this, professionally designed 5BR/3BA Hyde Park apt — perfectly located near hist ...
From $542 per night (USD)VRBO
From $376 per night (USD)Expedia
Bright & Spacious Boho Oasis: A Warm Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover a sun-drenched sanctuary that feels like a hidden gem. This isn't just a place to stay; it’s an airy, open-conc ...
From $376 per night (USD)Expedia
From $371 per night (USD)VRBO
Ranch Single Level Home near downtown Tinley Park
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Summary: Take it easy at this unique and tranquil getaway. You will enjoy easy access to everything from this centrally ...
From $371 per night (USD)VRBO
From $262 per night (USD)Expedia
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)Expedia
From $295 per night (USD)VRBO
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)VRBO
From $1010 per night (USD)Expedia
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)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 $372 per night (USD)VRBO
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)VRBO
From $665 per night (USD)Expedia
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)Expedia
From $436 per night (USD)VRBO
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)VRBO
From $234 per night (USD)Expedia
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)Expedia
From $234 per night (USD)VRBO
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)VRBO
From $186 per night (USD)Expedia
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)Expedia
From $511 per night (USD)VRBO
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)VRBO
From $466 per night (USD)Expedia
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)Expedia
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 $1589 per night (USD)Expedia
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)Expedia
From $381 per night (USD)VRBO
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)VRBO
From $397 per night (USD)Expedia
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)Expedia
From $516 per night (USD)VRBO
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)VRBO
From $255 per night (USD)Expedia
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)Expedia
From $328 per night (USD)VRBO
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)VRBO
From $142 per night (USD)Expedia
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)Expedia