Chicago Rentals
From $109 per night (USD)VRBO
Blueground | Chicago Loop, pool, nr Millennium 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 $109 per night (USD)VRBO
From $808 per night (USD)Expedia
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to our bright and modern 4-bedroom corporate suite in the heart of Chicago. Designed for both comfort ...
From $808 per night (USD)Expedia
From $744 per night (USD)VRBO
Modern 3BR Apartment Near North Ave Shops
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to your bright and spacious 3-bedroom Chicago retreat. Enjoy an open living area, fully equipped kitch ...
From $744 per night (USD)VRBO
From $174 per night (USD)Expedia
Cozy 2-bedroom condo near O'Hare/Train/Pet OK/Balcony
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Enjoy this home away from home! * Convenient location – Close to the airport with easy access to downtown, just a short ...
From $174 per night (USD)Expedia
From $872 per night (USD)VRBO
Charming 5-bedroom Jefferson Park Bungalow near O’Hare
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Consider this bungalow your home away from home while you visit Chicago. This marvelous retreat features five spacious b ...
From $872 per night (USD)VRBO
From $590 per night (USD)Expedia
Huge 4BR+4BTH Penthouse in West Town Hotspot!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your perfect Chicago home base w/Free Parking! Stay in a newer construction 4 Bedroom / 4 Full Bathroom Pent ...
From $590 per night (USD)Expedia
From $119 per night (USD)VRBO
Blueground | Chicago Loop, pool, nr Millennium Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $119 per night (USD)VRBO
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 stylish The Loop furnished one bedroom apartm ...
From $117 per night (USD)VRBO
From $106 per night (USD)VRBO
Blueground | Little Italy, pool, nr National Museum of Mexican Art
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Little Italy. It’ll be easy to simply show up and start ...
From $106 per night (USD)VRBO
From $103 per night (USD)VRBO
Blueground | Chicago Loop, pool, nr Millennium Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in The Loop. It’ll be easy to simply show up and start living i ...
From $103 per night (USD)VRBO
From $126 per night (USD)VRBO
Blueground | Edgewater, fitness center, nr Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Edgewater. It’ll be easy to simply show up and start li ...
From $126 per night (USD)VRBO
From $166 per night (USD)VRBO
Blueground | Central Station, pool, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Central Station furnished two bedro ...
From $166 per night (USD)VRBO
From $105 per night (USD)VRBO
Blueground | West Loop Gate, pool, nr Union Station
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish West Loop Gate furnished one bedroom ...
From $105 per night (USD)VRBO
From $96 per night (USD)VRBO
Blueground | West Loop, pool, nr Union Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in West Loop Gate. It’ll be easy to simply show up and start li ...
From $96 per night (USD)VRBO
From $270 per night (USD)VRBO
Studio Near Wrigley • Sleeps 4 • Games + Fireplace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Waveland Chicago 544 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $270 per night (USD)VRBO
From $180 per night (USD)Expedia
Adorable 1-bedroom building with AC in beautiful Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Make yourself at home in this 1-bedroom Chicago retreat. This adorable building offers a cool space where guests can rel ...
From $180 per night (USD)Expedia
From $155 per night (USD)VRBO
Welcoming 2-bedroom building with AC in vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Chicago, enjoy what this 2-bedroom building has to offer. The quaint space features one queen bed, perfect fo ...
From $155 per night (USD)VRBO
From $671 per night (USD)Expedia
Spacious 5-bedroom house in charming Chicago on a quiet secluded block.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Consider this house your home away from home while you visit Chicago. This superb property features five bedrooms, inclu ...
From $671 per night (USD)Expedia
From $550 per night (USD)VRBO
Huge 5BR Heart of Fulton Market, Duplex of dreams
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to your spacious duplex located in the Heart of Fulton Market, one of Chicago’s most exciting and sought-after n ...
From $550 per night (USD)VRBO
From $186 per night (USD)Expedia
South Loop 2BR Oasis w/ Patio & Gym Near McCormick Place and Soldier Field
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a modern 2-bedroom corner suite in Chicago’s highly sought-after South Loop, just a short walk from McCormick ...
From $186 per night (USD)Expedia
From $403 per night (USD)VRBO
NEW! Stylish 3BD/2.5BTH w/parking! United Center!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Book your next Windy City getaway at this 3-bed, 2.5-bath Chicago vacation rental. Perfect for families or friends, this ...
From $403 per night (USD)VRBO
From $505 per night (USD)Expedia
Serene 2-bedroom condo with AC in vibrant Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in Chicago, this delightful condo offers guests a comfortable stay with two cozy bedrooms featuring a queen bed ...
From $505 per night (USD)Expedia
From $152 per night (USD)VRBO
Cozy 2-bedroom apartment on top floor in the heart of Ukrainian Village with AC.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This memorable apartment is the perfect, charming home base for your trip to Chicago. In the heart of Ukrainian Village, ...
From $152 per night (USD)VRBO
From $243 per night (USD)Expedia
Chicago Stay Near Midway Airport & Orange Line
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Windy City Nest, a cozy 1-bedroom retreat in Archer Heights, Chicago. Enjoy a clean, modern space designed fo ...
From $243 per night (USD)Expedia
From $235 per night (USD)VRBO
River North Stay | 1 Unit | Near Chicago Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Chicago's vibrant River North neighborhood, this hotel offers easy access to downtown attractions such as the ...
From $235 per night (USD)VRBO
From $212 per night (USD)Expedia
Spacious 1BR - Free Parking, Golf & Midway Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
More Space. Free Parking. Unbeatable Location. Skip the cramped city stays — this spacious 1-bedroom Chicago apartment ...
From $212 per night (USD)Expedia
From $382 per night (USD)VRBO
Minutes to Wrigley - Games Arcades - Patio - Sleeps 12
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 12
1000 sq feet 2nd floor unit 3BR 1BA In the heart of beautiful, fun, and safe Lakeview East/Wrigley Located minutes from ...
From $382 per night (USD)VRBO
From $253 per night (USD)VRBO
Chicago Boutique Hideaway • Private Deck, Fire Pit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: A rare private outdoor deck with fire pit—your own cozy escape. Tucked away behind a historic Chicago home, ...
From $253 per night (USD)VRBO
From $328 per night (USD)VRBO
Boutique Retreat • Private Patio + Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to Maison Jardin Soleil! A historic home built in 1885 and recently updated for timeless charm and m ...
From $328 per night (USD)VRBO
From $235 per night (USD)Expedia
Prime Location! Near Millennium Park, Shedd Aquarium, Willis Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for a room within a hotel. ...
From $235 per night (USD)Expedia
From $683 per night (USD)VRBO
2 Spacious Units Close to Navy Pier! Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Set in the River North neighborhood of Chicago, this property offers easy access to popular Chicago attractions, restaur ...
From $683 per night (USD)VRBO
From $996 per night (USD)Expedia
Group Vacation! 4 Comfortable Units, Rooftop Deck
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for 4 separate rooms withi ...
From $996 per night (USD)Expedia
From $230 per night (USD)VRBO
River North Stay | 1 Unit | Near Chicago Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in Chicago's River North neighborhood, this hotel offers easy access to popular attractions like the Magnificent ...
From $230 per night (USD)VRBO
From $749 per night (USD)Expedia
Recharge & Relax! Three Comfortable Units for Group Travel Near Willis Tower
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for 3 separate rooms withi ...
From $749 per night (USD)Expedia
From $500 per night (USD)VRBO
Vacation Day Is Always A Great Idea! Two Great Units, Close to Willis Tower
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for 2 separate rooms withi ...
From $500 per night (USD)VRBO
From $235 per night (USD)Expedia
Perfect Destination! Onsite Bar and Restaurant, Close to Shedd Aquarium
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for a room within a hotel. ...
From $235 per night (USD)Expedia
From $145 per night (USD)VRBO
Blueground | Cabrini-Green, pool, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Cabrini-Green furnished one bedroom apar ...
From $145 per night (USD)VRBO
From $133 per night (USD)Expedia
3 Bedroom Chicago Apartment w/ Large Kitchen & In-Unit Laundry
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Unwind in Chicago at this delightful apartment. With 3 bedrooms featuring a king bed, heating, in-unit laundry, and wind ...
From $133 per night (USD)Expedia
From $777 per night (USD)VRBO
3BR Art Deco retreat with garage.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This thoughtfully designed 1,400 sq ft residence is just a 1-minute walk from Wrigley Field. Blending historic character ...
From $777 per night (USD)VRBO
From $171 per night (USD)VRBO
Blueground | Rush & Division, rooftop, nr Lakefront
- 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 $171 per night (USD)VRBO
From $118 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 beautiful Central Station furnished one bedro ...
From $118 per night (USD)VRBO
From $299 per night (USD)Expedia
Spacious Modern 3BR • Top‑Floor + Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Recharge in Your Edgewater Oasis Spacious modern top‑floor 3BR with a private street‑facing deck and an enclosed sunroom ...
From $299 per night (USD)Expedia
From $109 per night (USD)VRBO
Luxury Furnished Garden Unit in North Park. Stylish, Modern & Peaceful
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This property is available for 32+ day stays only (mid-term rental)! Kick back and relax in this calm, stylish space. Th ...
From $109 per night (USD)VRBO
From $766 per night (USD)Expedia
Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to affluential Bronzeville neighborhood. Bronzeville jazz room is a luxury living space. Designed for small grou ...
From $766 per night (USD)Expedia
From $468 per night (USD)VRBO
1 Free Parking, Gym, Balcony, Sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Stunning 3 bedroom West Loop apartment with 1 Garage Parking Space, Private Balcony with 1 king bed, 2 full be ...
From $468 per night (USD)VRBO
From $234 per night (USD)Expedia
Spacious 3BR Near United Center & Medical District
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your stylish Chicago home designed for comfort, convenience, and easy city access. This modern 3-bedroom, 2-b ...
From $234 per night (USD)Expedia
From $126 per night (USD)VRBO
Bright & Quiet 2 Bd Nest / 1st FL Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Our peaceful apartment is the perfect home base for your trip to Chicago. Guests will find two comfortable bedrooms, fea ...
From $126 per night (USD)VRBO
From $240 per night (USD)Expedia
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)Expedia
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 $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 $100 per night (USD)VRBO
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)VRBO
From $393 per night (USD)Expedia
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)Expedia
From $214 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 $214 per night (USD)VRBO
From $574 per night (USD)Expedia
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)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 $719 per night (USD)Expedia
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)Expedia
From $295 per night (USD)VRBO
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)VRBO
From $295 per night (USD)Expedia
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)Expedia
From $295 per night (USD)VRBO
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)VRBO
From $295 per night (USD)Expedia
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)Expedia
From $295 per night (USD)VRBO
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)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 $358 per night (USD)Expedia
Lincoln Park Apt: Walk to Beach, Shops & Dining!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Escape to this charming 1-bedroom, 2-bath vacation rental in the heart of Lincoln Park! Located near top attractions lik ...
From $358 per night (USD)Expedia
From $1216 per night (USD)VRBO
Steps to Lake & Beach! Multi-Level Oakland Haven
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
3 Mi to McCormick Place & Museum Campus | 4 Mi to Downtown | Fire Pit + BBQ | Basketball Court Experience the perfect b ...
From $1216 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 $197 per night (USD)Expedia
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)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 $315 per night (USD)Expedia
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)Expedia
From $435 per night (USD)VRBO
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)VRBO
From $239 per night (USD)Expedia
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)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 $367 per night (USD)Expedia
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)Expedia
From $449 per night (USD)VRBO
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)VRBO
From $309 per night (USD)Expedia
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)Expedia
From $544 per night (USD)VRBO
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)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 $164 per night (USD)VRBO
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)VRBO
From $839 per night (USD)Expedia
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)Expedia
From $245 per night (USD)VRBO
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)VRBO
From $246 per night (USD)Expedia
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)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 $206 per night (USD)Expedia
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)Expedia
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)Expedia
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)Expedia