Chicago Rentals
From $111 per night (USD)VRBO
Luxury 1BR Condo – Views, Comfort, & Style
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your home away from home—an upscale, sun-filled 1-bedroom condo located on the 41st floor in the heart of Chi ...
From $111 per night (USD)VRBO
From $251 per night (USD)Expedia
2BR Brownstone 7-minutes to Event Centers, Downtown, & Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Garden Oasis — your cozy home base in a historic Chicago Brownstone! Live like a local just minutes from ...
From $251 per night (USD)Expedia
From $853 per night (USD)VRBO
Entire Home in Historic Logan Square with private backyard, parking available.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Kick back & relax in this calm & stylish space! Perfect for families & large groups. I built and designed my home it's b ...
From $853 per night (USD)VRBO
From $343 per night (USD)Expedia
Sunny & Spacious Bucktown 3Bd/2Ba w/Laundry
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful Condo Quality Fully Furnished and Renovated space for monthly rental. A super spacious 3 bedroom, 2 bath apa ...
From $343 per night (USD)Expedia
From $317 per night (USD)VRBO
2 Spacious Rooms with 2 Queen Beds Near Magnificent Mile
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
With walkable access to shopping, theaters, and public transport, La Quinta Downtown is ideal for family visits or frien ...
From $317 per night (USD)VRBO
From $177 per night (USD)VRBO
1 Mi to Blue Line: Pet-Friendly Unit in Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Fenced Yard w/ Grill | 1 Mi to Logan Square Planning a Windy City getaway? Book this 2-bedroom, 1-bath Chicago vacation ...
From $177 per night (USD)VRBO
From $557 per night (USD)VRBO
Chic Vintage Stay w/ Private Balcony – Walk to Argyle Redline, Lake, Dining
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Step into vintage charm at Maison Winona, a 1908 Prairie School stunner by Chicago architect Frederick Schock, in the he ...
From $557 per night (USD)VRBO
From $191 per night (USD)VRBO
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience the charm of Chicago in our thoughtfully designed 2-bedroom garden apartment, located in the heart of vibrant ...
From $191 per night (USD)VRBO
From $221 per night (USD)VRBO
Mid-Century Gem in Avondale - 2BR - Office - Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This newly renovated bright and airy 2-bedroom, 1-bath apartment with a dedicated office space is nestled in the heart o ...
From $221 per night (USD)VRBO
From $210 per night (USD)Expedia
Lincoln Square Sunny 3BR-1Bath Condo – Family-Friendly, Walk to Everything!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Designer 3BR-1Bath Retreat | Private Patio | Private Garage | Luxe Kitchen | Lincoln Square Welcome to your stylish hom ...
From $210 per night (USD)Expedia
From $636 per night (USD)VRBO
The Green Oasis- 4bdrm 3bath Condo- 11 mins from DTWN
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Modern, spacious, newly renovated condo located in a quiet residential Washington Park neighborhood. 6 mins away from Ra ...
From $636 per night (USD)VRBO
From $125 per night (USD)VRBO
2 Mi to South Shore Beach: Unit w/ Balcony & Yard!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
2 Mi to UChicago | Outdoor Dining Settle in and stay awhile — make this 3-bedroom, 1-bath vacation rental your Chi-town ...
From $125 per night (USD)VRBO
From $516 per night (USD)VRBO
Spacious 4-bedroom house in charming Chicago with Game room and outdoor dining
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the beauty of Chicago from this 4-bedroom house. With 2 queen beds and 2 twin beds, this phenomenal property of ...
From $516 per night (USD)VRBO
From $843 per night (USD)Expedia
Spacious & Stylish Home with Garage + Rooftop Deck. 10 min Walk to Train.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 13
Stay comfortably in Chicago at this 3-bedroom house. With 1 king bed, 3 queen beds, and 3 twin beds, this phenomenal pro ...
From $843 per night (USD)Expedia
From $134 per night (USD)VRBO
Blueground | West Town, washer, nr Chicago River
- 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 $134 per night (USD)VRBO
From $81 per night (USD)Expedia
Blueground | West Town, pets allowed, nr 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 $81 per night (USD)Expedia
From $139 per night (USD)VRBO
Blueground | Rush & Division, balcony, nr Lake Shore Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $139 per night (USD)VRBO
From $768 per night (USD)Expedia
Luxurious Cozy 4BR 4-Story Gold Coast Villa with Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to your perfect Chicago getaway at 111 W Elm St — where classic elegance meets modern comfort in the heart of th ...
From $768 per night (USD)Expedia
From $235 per night (USD)VRBO
City Studio Escape Bright, Sleek & Modern
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury space is meticulously designed for ...
From $235 per night (USD)VRBO
From $314 per night (USD)Expedia
Stay, Relax & Explore Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
Unwind in a serene, upscale space where comfort meets elegance. This modern Chicago escape features refined finishes, pl ...
From $314 per night (USD)Expedia
From $278 per night (USD)VRBO
Boulevard Stays | 5 Minutes to Magnificent Mile and River North
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience chic comfort in this modern River North retreat—just 5 minutes from the Magnificent Mile, CTA, top d ...
From $278 per night (USD)VRBO
From $376 per night (USD)Expedia
Spacious Pilsen 4 Bed 4 Bath Family Retreat
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to your stylish home away from home in the vibrant Pilsen neighborhood! This newly listed 4-bedroom, 2- ...
From $376 per night (USD)Expedia
From $283 per night (USD)VRBO
Soaring ceilings, city views and private rooftop deck!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the heart of Lakeview, between Lincoln and Southport, you will be wowed by the 17-foot ceilings and city view ...
From $283 per night (USD)VRBO
From $163 per night (USD)VRBO
Charming Garden Flat w/ King Bed
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our charming garden flat in Chicago! This private-entry unit features 2 bedrooms—one w/ a king bed—a renovate ...
From $163 per night (USD)VRBO
From $1133 per night (USD)VRBO
Massive Avondale Home, Sleeps 15 people, 4 King Beds, Rooftop Deck, & Garage
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 15
Experience Chicago from the comfort of this massive 4500 sq ft home. 6 bedrooms and 6 bathrooms, TWO kitchens, private r ...
From $1133 per night (USD)VRBO
From $161 per night (USD)Expedia
3bed/2bath Penthouse style Apt. W/ fitness room & office 14 min to DT Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to our Mediterranean inspired penthouse style apartment in Historic Hyde Park Chicago. This tranquil & elegant re ...
From $161 per night (USD)Expedia
From $249 per night (USD)VRBO
Chicago Citrus Charm 2BR WestTown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Step into this vibrant and stylish two bedroom apartment, perfectly located just minutes from downtown Chicago! Designed ...
From $249 per night (USD)VRBO
From $278 per night (USD)Expedia
Logan Duplex - Sleeps 14 - 2 Ba
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 14
**WILL BE FULLY FURNISHED BY 8/15/2025** Spacious 1500 sq fT duplex - 3 BR 2 BA In the heart of beautiful and fun Logan ...
From $278 per night (USD)Expedia
From $125 per night (USD)VRBO
Downtown Living: Walkable, Modern Chicago Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Remote Work Ready | Willis Tower View | On-Site Market Stay in the Loop — where every meeting, meal, and museum is just ...
From $125 per night (USD)VRBO
From $197 per night (USD)Expedia
Stylish 1BR in Bronzeville Near Downtown Cozy Stay w/ Free Wifi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This 1-bedroom condo is perfect for your escape to Chicago. The fabulous heating and AC will keep you comfortable throug ...
From $197 per night (USD)Expedia
From $559 per night (USD)VRBO
NEW! Spacious 3-Bed West Loop Townhouse, 1 Car Garage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Immerse yourself in this stylish 3 bed, 2.5 bath luxury townhouse in Chicago's vibrant West Loop. You're steps away fro ...
From $559 per night (USD)VRBO
From $125 per night (USD)Expedia
Chicago's Leafy Street Hideaway - 1 Bedroom Condo with a Side of Sass
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Vintage charm meets modern upgrades in this remodeled 1BR apartment. High ceilings, original hardwoods, and a kitchen wi ...
From $125 per night (USD)Expedia
From $243 per night (USD)VRBO
Chic Chicago Spa Retreat – Luxe & Light-Filled
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience top-floor luxury in this fully remodeled Avondale condo. Soak in the spa-style bath, bask in natural light fr ...
From $243 per night (USD)VRBO
From $321 per night (USD)Expedia
Casa Wolfram 20 Minutes from Downtown In The Heart of Logan Sqaure
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Chic 2 bedroom in the heart of Logan Square. A unique retreat thoughtfully designed. Every corner is curated with style ...
From $321 per night (USD)Expedia
From $595 per night (USD)VRBO
Newly Renovated 2BR Unit Near DePaul University
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Unwind in the bustling city of Chicago at this superb apartment. With 2 enchanting queen bedrooms and a cozy living room ...
From $595 per night (USD)VRBO
From $284 per night (USD)Expedia
Sleek Avondale Condo -- King and Queen + Spa Bath + Garage + Sass
- 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 $284 per night (USD)Expedia
From $340 per night (USD)VRBO
Bright 3BR Retreat Near McCormick + Museum Campus
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The State Suite — a modern, artfully designed 3-bedroom, 1-bath apartment perfect for everyone! Just minutes ...
From $340 per night (USD)VRBO
From $141 per night (USD)Expedia
Stylish 3-BR Humboldt Park Retreat, Walk to Parks/Transit
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Mid‑century charm in a light-filled 3-bedroom Chicago apartment. Located on a tree‑lined street just steps from the 606 ...
From $141 per night (USD)Expedia
From $180 per night (USD)VRBO
Flexhome West Town 2BR Apt T1
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The space: The apartment comfortably sleeps 4 and has flexible seating areas so you can work or relax at your convenienc ...
From $180 per night (USD)VRBO
From $553 per night (USD)Expedia
Beach Side in the City - Chicago
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Consider this apartment your home away from home while you visit Chicago. This amazing property boasts 5 bedrooms with a ...
From $553 per night (USD)Expedia
From $131 per night (USD)VRBO
Stylish 3-bedroom apartment in Humboldt Park with AC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a peaceful stay at this 3-bedroom apartment in Chicago. The bedrooms feature 1 king bed and 2 queen beds, perfect ...
From $131 per night (USD)VRBO
From $125 per night (USD)Expedia
Scott House of Woodlawn - Incredible 3-bedroom house in Chicago; AC and extras
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Your Chicago adventure begins at this 3-bedroom house. With 1 king bed, 1 queen bed, and 1 sofa bed, guests will find co ...
From $125 per night (USD)Expedia
From $155 per night (USD)VRBO
Cozy Studio In Lakeview, Near Wrigley field
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lakeview is a great location with a mixed residential and business feel. This newly redecorated studio is larger than mo ...
From $155 per night (USD)VRBO
From $391 per night (USD)Expedia
Spacious 3BDR Luxury Penthouse 10 min from Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stylish 3BD/2BA penthouse with high ceilings, oversized windows, stainless steel appliances, quartz countertops, in-unit ...
From $391 per night (USD)Expedia
From $215 per night (USD)VRBO
2- Bdrm Apt Desert Themed w/AC in Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this delightful apartment in picturesque Chicago. This cozy space features 2 bedrooms with a queen and 2 twin ...
From $215 per night (USD)VRBO
From $164 per night (USD)Expedia
New Private Apartment - Pilsen Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This completely remodeled private 1 br apartment in a quiet corner of East Pilsen. Centrally located close to downtown, ...
From $164 per night (USD)Expedia
From $159 per night (USD)VRBO
Luxury 1BD residence w/parking. Gated and safe. 15 mins from O’Hara
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
(Located in River Grove not chicago. That is an error. ) With a minimalist vibe, your stay will be a emotionally enriche ...
From $159 per night (USD)VRBO
From $250 per night (USD)Expedia
Archways at the Lincoln Park Zoo 2bed/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in a historic 1920s renovated hotel, this apartment retains charming Art Deco arches that add a touch of history ...
From $250 per night (USD)Expedia
From $282 per night (USD)VRBO
Lovely Garden Set up is Perfect for Your Morning Coffee or a Drink After Some Great Blues Music at Kingston Mines by AllSet Turnover
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This perfectly located 2 BD/2 BA unit is waiting for you to call it home for your trip to gorgeous Lincoln Park! Make y ...
From $282 per night (USD)VRBO
From $175 per night (USD)Expedia
Furnished 2-Bed, 1.5-Bath Home – Old Irving Park – Perfect for Longer Stays!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 1
Looking for a cozy, fully furnished home base in Chicago without the platform mark-ups? This charming single-family hous ...
From $175 per night (USD)Expedia
From $597 per night (USD)VRBO
Flexhome West Town 2BR Apt T1
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The space: The apartment comfortably sleeps 4 and has flexible seating areas so you can work or relax at your convenienc ...
From $597 per night (USD)VRBO
From $153 per night (USD)Expedia
Enjoy a stylish experience at this centrally-located place
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a stylish experience at this centrally-located place. Welcome to your private attic retreat near the heart of Loga ...
From $153 per night (USD)Expedia
From $138 per night (USD)VRBO
Pet Friendly Queen Unit! Near Chicago Attractions!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
With a great location in a trendy neighborhood near shopping, dining, and attractions, this is the perfect spot for your ...
From $138 per night (USD)VRBO
From $175 per night (USD)VRBO
Modern Queen Stay! Pet Friendly Accommodation w/ Gym Access | Chicago Riverwalk!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $175 per night (USD)VRBO
From $823 per night (USD)VRBO
Spacious 2-bedroom apartment with AC in vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this superb apartment in picturesque Chicago. With 2 cozy bedrooms, heating, AC, a hair dryer, and an iron, gu ...
From $823 per night (USD)VRBO
From $636 per night (USD)Expedia
Fabulous 2-bedroom apartment with AC in Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this apartment in picturesque Chicago. This cozy retreat features 2 bedrooms with a king and queen bed, a well ...
From $636 per night (USD)Expedia
From $407 per night (USD)VRBO
Luxury 3 bedroom in Chicago, minutes from downtown and steps from Lake Michigan
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the perfect blend of style, comfort, and convenience in this beautifully remodeled 3-bedroom, 2.5-bathroom home ...
From $407 per night (USD)VRBO
From $401 per night (USD)Expedia
Hancock Lookout Steps to Beach and Transit includes CHI Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Wake up in Chicago’s Gold Coast with stunning views of Lake Michigan and the Hancock Tower. This top-floor high-rise apa ...
From $401 per night (USD)Expedia
From $145 per night (USD)VRBO
Cozy 2BR + Office - Park Views, Backyard, & BBQ!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Welcome to your home away from home in Logan Square! Step into this delightful 2-BR, 1-BA retreat in a friendly neighbo ...
From $145 per night (USD)VRBO
From $344 per night (USD)VRBO
1BR Apt l Sentral Michigan Ave l Walk to Museums & Parks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience downtown Chicago with ease from this modern one-bedroom apartment at Sentral Michigan Avenue. Enjoy home-cook ...
From $344 per night (USD)VRBO
From $444 per night (USD)VRBO
Sentral Michigan Ave l 2BR Apt l Ideal for Family or Friends
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located just steps from Lake Michigan and Grant Park, this two-bedroom unit offers spacious comfort in the middle of it ...
From $444 per night (USD)VRBO
From $366 per night (USD)VRBO
Sentral Michigan Ave l 1BR + Den l Flexible Work & Stay Space
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Settle into your Chicago home away from home with this 1-bedroom apartment plus den in the heart of the South Loop. Idea ...
From $366 per night (USD)VRBO
From $507 per night (USD)VRBO
Premium 2BR l Sentral Michigan Ave l View, Pool & Near Lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect for more extended stays or group trips, this premium two-bedroom unit offers expansive city or lake views, plus ...
From $507 per night (USD)VRBO
From $296 per night (USD)Expedia
Studio Apt l Sentral Michigan Ave l City Views & Full Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay in the vibrant South Loop at Sentral Michigan Avenue, where city energy meets lakefront relaxation. This stylish st ...
From $296 per night (USD)Expedia
From $507 per night (USD)VRBO
Sentral Michigan Ave l 2BR Premium l Modern & Walk Everywhere
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect for more extended stays or group trips, this premium two-bedroom unit offers expansive city or lake views, plus ...
From $507 per night (USD)VRBO
From $296 per night (USD)VRBO
Sentral Michigan Ave l Studio Apt l Steps to Downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 506 sq. ft, equipped with complimentary toiletries, kitchen w ...
From $296 per night (USD)VRBO
From $408 per night (USD)VRBO
Sentral Michigan Ave l Premium 1BR l Upscale South Loop Stay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy elevated city living in this premium one-bedroom apartment with sweeping views of Lake Michigan or downtown. Moder ...
From $408 per night (USD)VRBO
From $444 per night (USD)VRBO
2BR Apt l Sentral Michigan Ave l Walk to Lake & Museums
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located just steps from Lake Michigan and Grant Park, this two-bedroom unit offers spacious comfort in the middle of it ...
From $444 per night (USD)VRBO
From $366 per night (USD)VRBO
1BR + Den l Sentral Michigan Ave l Near Grant Park & Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Settle into your Chicago home away from home with this 1-bedroom apartment plus den in the heart of the South Loop. Idea ...
From $366 per night (USD)VRBO
From $408 per night (USD)VRBO
Premium 1BR l Sentral Michigan Ave l Lake View & Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy elevated city living in this premium one-bedroom apartment with sweeping views of Lake Michigan or downtown. Moder ...
From $408 per night (USD)VRBO
From $344 per night (USD)VRBO
Sentral Michigan Ave l 1BR Apt l Sleek Space in South Loop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience downtown Chicago with ease from this modern one-bedroom apartment at Sentral Michigan Avenue. Enjoy home-cook ...
From $344 per night (USD)VRBO
From $618 per night (USD)Expedia
New! Beautiful 7BD Home - Sleeps 15 + 2 Car Garage
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 15
Discover roomy comfort and historic charm in our fully renovated Chicago‑style bungalow in North Mayfair. With seven bed ...
From $618 per night (USD)Expedia
From $719 per night (USD)VRBO
Spectacular Gold Coast Villa Near Beach w/ Parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Gold Coast Villa Retreat — a stunning, fully renovated private home designed for families, groups, and bu ...
From $719 per night (USD)VRBO
From $50 per night (USD)Expedia
Private Room in Stylish West Humboldt Park Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Enjoy a comfortable private room in a quiet 3-bedroom condo, perfect for solo travelers or business guests. The room fea ...
From $50 per night (USD)Expedia
From $1026 per night (USD)VRBO
Charming 2-bedroom apartment in fabulous Chicago with AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Chicago like a local in this 2-bedroom apartment. Marvelous and quaint, this cozy space offers a bathroom wit ...
From $1026 per night (USD)VRBO
From $126 per night (USD)Expedia
Logan Square Loft — Writer’s Retreat Near Blue Line & Cafés
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay in the heart of Logan Square at Writer’s Retreat Loft — a bright, creative apartment just steps from the California ...
From $126 per night (USD)Expedia
From $330 per night (USD)VRBO
4-bedroom house in brilliant Chicago with AC, WiFi. Enjoy your stay.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Discover this enchanting 4-bedroom gem in Chicago. This gorgeous apartment boasts 2 full beds, 1 queen bed, and 1 bunk b ...
From $330 per night (USD)VRBO
From $172 per night (USD)Expedia
Welcoming 2-bedroom apartment with AC in vibrant Chicago Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Get ready to relax in this cozy and artistic 2 bedroom 1 bath apartment on a quiet tree-lined street in Chicago's Edgewa ...
From $172 per night (USD)Expedia
From $301 per night (USD)VRBO
Gilean Urban Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience sophisticated urban living at the Gilean Urban Retreat, an MGM property nestled in Chicago's historic Bronzev ...
From $301 per night (USD)VRBO
From $222 per night (USD)Expedia
Spacious 2BR - 10 mins from Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your home away from home in Chicago’s Near West Side neighborhood—just 10 minutes from downtown! This spaci ...
From $222 per night (USD)Expedia
From $370 per night (USD)VRBO
Downtown Chicago Retreat 2BD/2BA Views+Gym+Rooftop
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 4
Summary: Experience the best of downtown Chicago in this sleek 2-bedroom River West apartment with bold black-and-gold a ...
From $370 per night (USD)VRBO
From $1374 per night (USD)Expedia
Designer Combo 2E & 2W | Heart of Gold Coast/ River North
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 20
Summary: BRAND NEW APARTMENTS IN THE HEART OF RIVER NORTH & GOLD COAST! Enjoy your designer styled units located in Chi ...
From $1374 per night (USD)Expedia
From $1365 per night (USD)VRBO
Luxury 9 BR, Villa Mins from Downtown and the Lake.
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 12
Welcome to your perfect getaway! This newly remodeled 9-bedroom, 6.5-bathroom villa offers a blend of modern elegance an ...
From $1365 per night (USD)VRBO
From $954 per night (USD)Expedia
Sleeps 22 • Modern Multi-Unit • Gym • Workspaces
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 22
👉 Reserve all 4 units with a total of 6 bedrooms in the heart of Chicago. Each space combines modern style with comfort ...
From $954 per night (USD)Expedia
From $174 per night (USD)VRBO
Lower level luxury
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover Chicago like a true local in this stylish 2-bedroom lower-level retreat. Perfect for small groups, this tranqui ...
From $174 per night (USD)VRBO
From $285 per night (USD)Expedia
Fully furnished, modern short-term stay home near Obama Presidential Library.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This Chicago corporate apartment boasts 2 inviting bedrooms, one with a queen bed and the other with two twin beds. The ...
From $285 per night (USD)Expedia
From $112 per night (USD)VRBO
Blueground | Greektown, rooftop, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...
From $112 per night (USD)VRBO
From $103 per night (USD)Expedia
Stylish & Comfy Stay • Close to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stylish & Comfy Stay • Close to Downtown ★☆ ABOUT OUR HOME ☆★ Located in the heart of Chicago’s Brighton Park neighborh ...
From $103 per night (USD)Expedia
From $110 per night (USD)VRBO
Chic & Cozy Chicago Stay • Close to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Chic & Cozy Chicago Stay • Close to Downtown ★☆ ABOUT OUR HOME ☆★ Nestled in a prime Chicago neighborhood, this home of ...
From $110 per night (USD)VRBO
From $151 per night (USD)Expedia
Delightful 4-bedroom apartment in Chicago with AC
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
Discover the beauty of Chicago from this 4-bedroom apartment. Each bedroom features a cozy queen bed, perfect for a good ...
From $151 per night (USD)Expedia
From $195 per night (USD)VRBO
Location! Location! Cozy 2bd entire apartment with free parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this cozy apartment in Chicago. This rental features 2 cozy bedrooms with queen beds, a bathroom with a batht ...
From $195 per night (USD)VRBO
From $231 per night (USD)Expedia
Clean & Equipped 2BR Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Clean, well-furnished 2-bedroom with everything in place. The Space: Our place has a cozy living room, a full ...
From $231 per night (USD)Expedia
From $954 per night (USD)VRBO
Lucky Green - A Bold 9BR/5BA w/ Parking by Wrigley
- Bedrooms:
- 5
- Bathrooms:
- 9
- Sleeps:
- 19
This 9BR/5BA space is a 7-minute walk from Wrigley Field and perfect for large groups. 3 living rooms, 3 kitchens, and t ...
From $954 per night (USD)VRBO
From $166 per night (USD)Expedia
Beautiful condo with AC in vibrant Chicago\n10 mins to beach. 10 mins to downtown
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Consider this condo your home away from home while you visit Chicago. This wonderful property features 2 bedrooms with a ...
From $166 per night (USD)Expedia
From $139 per night (USD)VRBO
Unforgettable fully furnished three bedroom, one bathroom in Edgewater
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Get ready to relax in this 3-bedroom condo in Chicago. This delightful property offers guests a serene atmosphere to unw ...
From $139 per night (USD)VRBO
From $147 per night (USD)Expedia
Urban Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Consider this house your home away from home while you visit Chicago. This quaint property features 2 bedrooms with a ki ...
From $147 per night (USD)Expedia
From $298 per night (USD)VRBO
private 3 bedroom garden apartment in Lincoln square Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Stay comfortably in Chicago at this 3-bedroom fully furnished apartment. located in a safe neigborhood The space feature ...
From $298 per night (USD)VRBO
From $256 per night (USD)Expedia
1 GB Wi-Fi | Reserved Parking | Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: The pictures are from another apartment we have in this building. The design, furniture and layout of the apart ...
From $256 per night (USD)Expedia
From $182 per night (USD)VRBO
Cozy Condo, Sleeps 2!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Stay in the heart of Old Town, Chicago at this stylish 1-bedroom, 1-bathroom condo with a king bed, in-unit lau ...
From $182 per night (USD)VRBO
From $368 per night (USD)Expedia
Stylish Sleeps 6 1 Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stay in this modern 2BR, 1BA apartment in Lakeview, Chicago, perfect for families, friends, or groups of up to ...
From $368 per night (USD)Expedia