Chicago Rentals
From $335 per night (USD)VRBO
Modern & Spacious Stay in Historic Bronzeville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to this spacious 3-bedroom, 2-bathroom apartment in the heart of Bronzeville! Perfect for families, fr ...
From $335 per night (USD)VRBO
From $439 per night (USD)Expedia
Modern 2-bedroom townhome in Chicago with private patio
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
Welcome to the safe and peaceful Chicago neighborhood Bucktown! This property lives like a single family home and consis ...
From $439 per night (USD)Expedia
From $486 per night (USD)VRBO
Spacious 3-bedroom apartment in cool Chicago with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this 4-bedroom Chicago retreat. This marvelous apartment features 4 queen beds, a cozy living s ...
From $486 per night (USD)VRBO
From $373 per night (USD)Expedia
LUXE Vintage Loft, 10min to Downtown, Retro Movie Theatre - 15% Discount Applied
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to a Luxury Vintage Getaway with a 24/7 dedicated team ensuring a comfortable and unforgettable stay. ✔ Central ...
From $373 per night (USD)Expedia
From $144 per night (USD)VRBO
Blueground | Lakeshore East, pool & w/d, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this spacious one bedroom Blueground apartment. You’ll love coming ...
From $144 per night (USD)VRBO
From $224 per night (USD)VRBO
Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Your new home away from home! This beautiful townhouse offers a cozy retreat with a queen bed and a full bed. Enjoy the ...
From $224 per night (USD)VRBO
From $505 per night (USD)VRBO
Spacious 4-bedroom apartment in fabulous Chicago with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
This Chicago apartment boasts 4 inviting bedrooms with queen beds. The bathroom comes equipped with a bathtub and a hair ...
From $505 per night (USD)VRBO
From $462 per night (USD)Expedia
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 14
Stay in a historic home in Old Town, within walking distance of Downtown, the Magnificent Mile, restaurants, bars, bouti ...
From $462 per night (USD)Expedia
From $291 per night (USD)VRBO
Chic 2-bedroom apartment with WiFi, AC in lovely Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay comfortably in Chicago at this 2-bedroom apartment. This charming property features 1 king bed and 1 queen bed, per ...
From $291 per night (USD)VRBO
From $416 per night (USD)VRBO
Luxury Meets Comfort: River North Rentals with Chic Style & Prime Chicago Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $416 per night (USD)VRBO
From $401 per night (USD)VRBO
Experience the Suite Life in Chicago’s Iconic Old Town – Spacious Stays Await
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $401 per night (USD)VRBO
From $300 per night (USD)VRBO
Luxury West Loop Suites: Your Chicago Stay with Modern Comfort & Resort Perks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $300 per night (USD)VRBO
From $535 per night (USD)VRBO
Live the Suite Life: Historic Old Town Chicago Stays with Modern Luxury & Style
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $535 per night (USD)VRBO
From $387 per night (USD)VRBO
Chic Stay in River North: Luxury Suites, Top Amenities, Near Arts & Nightlife!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $387 per night (USD)VRBO
From $3160 per night (USD)VRBO
Luxurious Old Town Chicago Suites – Perfect for Families & Corporate Stays
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $3160 per night (USD)VRBO
From $506 per night (USD)VRBO
Historic Charm & Modern Luxury in Chicago’s Iconic Old Town - Stay Level!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $506 per night (USD)VRBO
From $165 per night (USD)VRBO
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience Chicago like a local from this bright 3rd-floor sanctuary. Located on Damen Ave, you’re steps away from the c ...
From $165 per night (USD)VRBO
From $373 per night (USD)VRBO
Stylish River North Suites Luxe Comfort Near Chicago’s Best Shopping & Nightlife
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $373 per night (USD)VRBO
From $544 per night (USD)VRBO
Luxury West Loop Rentals: Modern Suites w/ City Views & Resort Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $544 per night (USD)VRBO
From $401 per night (USD)Expedia
Spacious 3 Bedroom 1 Bathroom Rogers Park Town House Budget-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Rogers Park Townhouse—perfect for creating lasting memories with loved ones. 3 Bed Room 1 Bathroom Townhouse in Rogers ...
From $401 per night (USD)Expedia
From $291 per night (USD)VRBO
Cozy 1 Bedroom Apt near Logan Sq Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This stylish place to stay is perfect for individuals couples or group trips. Kick back and relax in this calm, newly re ...
From $291 per night (USD)VRBO
From $265 per night (USD)Expedia
Modern Clean Private Entry Apartment • Free Street Parking • Washer & Dryer
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to our modern private lower-level apartment in Chicago, a comfortable and convenient home base for couples, fami ...
From $265 per night (USD)Expedia
From $136 per night (USD)VRBO
Modern 3BR/2BA Retreat with Deck, Grill, and 2GB Speed WiFi in Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Visiting Chicago for work, a game or a concert? Reside at this stylish sanctuary in Albany Park to complete your experie ...
From $136 per night (USD)VRBO
From $204 per night (USD)Expedia
Stylish 4BR/2BA Apartment with Office, Deck, Grill, and 2GB WiFi in Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Visiting Chicago for work, a game or a concert? Reside at this stylish sanctuary in Albany Park to complete your experie ...
From $204 per night (USD)Expedia
From $132 per night (USD)VRBO
Charming 2-bed Garden condo in beautiful Chicago + WiFi, AC, & private parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
Your cozy getaway awaits in Chicago at this enchanting condo. With 2 welcoming bedrooms featuring queen beds and 2 seren ...
From $132 per night (USD)VRBO
From $374 per night (USD)VRBO
Best Place to Unwind! 2 Family and Dog Friendly Units! Walk to Millennium Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $374 per night (USD)VRBO
From $355 per night (USD)VRBO
Look No Further! 2 Stylish King Units! Pet-Friendly, Walk to Riverwalk & Dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Explore the best of the Windy City from our luxurious River North base with pool This listing is for 2 separate rooms w ...
From $355 per night (USD)VRBO
From $162 per night (USD)VRBO
Luxurious 3 Bedroom Apartment in Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Your cozy getaway awaits in Chicago at this fabulous house. With 3 bedrooms including 2 queen beds and 1 sofa bed, this ...
From $162 per night (USD)VRBO
From $763 per night (USD)VRBO
Great Relaxing Overnight Stay! 4 Units with City View, Pets Are Welcome!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This listing is for 4 separate rooms within a hotel. The price shown in the listing covers all 4 rooms. ✦ Each room is ...
From $763 per night (USD)VRBO
From $639 per night (USD)Expedia
Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Modern Elegance Meets Historic Charm! Stunning 4-bed, 3.5-bath fully renovated home in the heart of the historic GAP dis ...
From $639 per night (USD)Expedia
From $164 per night (USD)VRBO
Midterm Furnished Rental - North Center, Chicago 2Bed 1Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Highly sought-after North Center / St. - Electric sit/stand desk with monitor & keyboard for remote work. - 1 Garage S ...
From $164 per night (USD)VRBO
From $202 per night (USD)VRBO
The Chicago Hotel Collection, Standard Double Queen with City Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Walk to Magnificent Mile, Navy Pier, parks. Near shops, dining, transit, arts. This listing is for a room within a hote ...
From $202 per night (USD)VRBO
From $100 per night (USD)VRBO
Blueground | Greektown, bbq, gym, nr Willis Tower
- 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 $100 per night (USD)VRBO
From $464 per night (USD)VRBO
Better Choice for your Vacation! 2 Relaxing Units with City View, Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $464 per night (USD)VRBO
From $382 per night (USD)VRBO
A Place You'll Surely Enjoy! 2 Relaxing Units with City View, Pet-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $382 per night (USD)VRBO
From $572 per night (USD)VRBO
Come Create Memories w/ Fun-filled Adventures at this Paradise! 3 Relaxing Units
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms. ✦ Each room is ...
From $572 per night (USD)VRBO
From $159 per night (USD)VRBO
Better Choice for your Vacation! Short Walk to River North Spots, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 235 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $159 per night (USD)VRBO
From $150 per night (USD)VRBO
Everything You Need For The Perfect Vacation! Pet-friendly Property, King Room!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 255 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $150 per night (USD)VRBO
From $712 per night (USD)VRBO
The Chicago Hotel Collection Magnificent Mile, 3 Standard King Rooms
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Walk to Magnificent Mile, Navy Pier, parks. Near shops, dining, transit, arts. This listing is for 3 separate rooms wit ...
From $712 per night (USD)VRBO
From $296 per night (USD)VRBO
Sleek Downtown Retreat by Chicago’s Mag Mile @ The Chicago Hotel Collection
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Walk to Magnificent Mile, Navy Pier, parks. Near shops, dining, transit, arts. This listing is for a room within a hote ...
From $296 per night (USD)VRBO
From $281 per night (USD)VRBO
The Chicago Hotel Collection, Mag Mile, Deluxe Double Queen - Premium Option
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Walk to Magnificent Mile, Navy Pier, parks. Near shops, dining, transit, arts. This listing is for a room within a hote ...
From $281 per night (USD)VRBO
From $202 per night (USD)VRBO
Upscale City Center Stay | Prime Locale | City Views | Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Walk to Magnificent Mile, Navy Pier, parks. Near shops, dining, transit, arts. This listing is for a room within a hote ...
From $202 per night (USD)VRBO
From $353 per night (USD)VRBO
Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Your Chicago adventure begins at this delightful 3-bedroom condo. With 3 queen beds, 2 futons, and 3 bathrooms featuring ...
From $353 per night (USD)VRBO
From $364 per night (USD)VRBO
Spacious 3-bedroom apartment near downtown, FREE PARKING
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to you home away from home! This bright and cozy space is perfectly located in Tri-Taylor neighborhood just 10mi ...
From $364 per night (USD)VRBO
From $266 per night (USD)VRBO
Suite Success • Business Class Living • Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your extended-stay retreat in the heart of Chicago’s South Loop. Whether you’re here for work, relocating to ...
From $266 per night (USD)VRBO
From $517 per night (USD)VRBO
Penthouse Paradise •Executive Elegance • Elevated Amenities • Sleeps 6
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Elevated Urban Luxury in Chicago’s South Loop: Welcome to your home away from home—a sprawling, sun-drenched ...
From $517 per night (USD)VRBO
From $261 per night (USD)VRBO
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your home away from home! This 3-bedroom, 1-bath space is designed for comfort, relaxation, and convenience. ...
From $261 per night (USD)VRBO
From $118 per night (USD)Expedia
Charming Newly Updated 3-bed Chicago Apartment. Extended Stay Discount
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our cozy home away from home which offers comfort and practicality. We are pleased to offer a fully furnished ...
From $118 per night (USD)Expedia
From $330 per night (USD)VRBO
Quiet 3-bedroom house in amazing Chicago with WiFi & AC. Near Everything!!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom house in Chicago is perfect for your escape to the Windy City. With 3 queen beds, 1.5 bathrooms featuring ...
From $330 per night (USD)VRBO
From $230 per night (USD)Expedia
Charming 2-bedroom apartment in fabulous Chicago with WiFi, Game Space
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to your perfect Chicago getaway! A stylish & spacious Chicago stay perfect for families, friends, couples & busi ...
From $230 per night (USD)Expedia
From $345 per night (USD)VRBO
3BR Spacious Apartment in Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Spacious 3BR/1BA home in vibrant Rogers Park—perfect for up to 6 guests. Enjoy 900 sq ft of bright, comfortable ...
From $345 per night (USD)VRBO
From $381 per night (USD)VRBO
Upscale 4BR Retreat: Wicker Park
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to your spacious 4-bedroom getaway in the heart of Wicker Park—Chicago’s most vibrant and eclectic nei ...
From $381 per night (USD)VRBO
From $361 per night (USD)VRBO
Spacious 4BR Near Wicker Park
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to this spacious and inviting 2-level apartment—perfect for families or groups! This bright and spacio ...
From $361 per night (USD)VRBO
From $257 per night (USD)Expedia
Paradise 1BR Apt in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Experience the perfect blend of comfort and style in this thoughtfully designed space, created to offer you a ...
From $257 per night (USD)Expedia
From $275 per night (USD)VRBO
Furnished 3BR Apt w/ Laundry
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: We've set up our 3-bedroom apartment to be as comfy and welcoming as possible—like a little home away from hom ...
From $275 per night (USD)VRBO
From $263 per night (USD)Expedia
Cozy 3BR Gem in North Center
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: This spacious and stylish 3-bedroom gem is perfect for families, groups, or business travelers seeking comfort ...
From $263 per night (USD)Expedia
From $376 per night (USD)VRBO
3BR | Complete & Well-Located Apt in Hyde Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Spacious and comfortable 3BR apartment in the heart of Hyde Park. This fully equipped and thoughtfully furnish ...
From $376 per night (USD)VRBO
From $266 per night (USD)VRBO
Sleek Style 3BR Haven - Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: A modern home that’s both stylish and practical, offering comfort and everyday ease. Spacious 3-Bedroom Lay ...
From $266 per night (USD)VRBO
From $372 per night (USD)VRBO
Modern 4BR Rogers Park Stay Near Loyola
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Gather your group and enjoy a comfortable Chicago stay just minutes from Loyola University, Lake Michigan beac ...
From $372 per night (USD)VRBO
From $665 per night (USD)Expedia
Spacious 5-bedroom house great for large groups
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Light and airy custom built home across from Humboldt Park with expansive views of the Humboldt Park pond/lake. Spacious ...
From $665 per night (USD)Expedia
From $321 per night (USD)VRBO
A chic second-floor plant-filled retreat in Chicago's Logan Square neighborhood.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the charm of this Logan Square Greystone apartment, a chic second-floor plant-filled retreat in Chicago's vib ...
From $321 per night (USD)VRBO
From $271 per night (USD)Expedia
NEW Eco Stay by UChicago, Lakefront & Hyde Park!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy comfort and sustainability in this beautifully designed South Side retreat. Located in a modern, solar-powered gre ...
From $271 per night (USD)Expedia
From $1738 per night (USD)VRBO
Exclusive Group Getaway in Vibrant West Loop
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 22
Summary: 'The Cubist' is the ultimate destination for your group's special occasion, offering four luxurious apartments ...
From $1738 per night (USD)VRBO
From $581 per night (USD)Expedia
Brand-New West Loop 3BR + City Views for Families
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Experience brand-new luxury at 'The Lyric,' a stunning 3BR in in West Loop’s vibrant Fulton District. You' ...
From $581 per night (USD)Expedia
From $401 per night (USD)VRBO
The Prestige: Designer 3BR/2BA in Prime Location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Prestige- where luxury meets comfort. This spacious 3-bed, 2-bath condo sleeps 8 (3 king beds & 1 pull-ou ...
From $401 per night (USD)VRBO
From $256 per night (USD)Expedia
Luxury Unit with Rooftop Lounge & Spectacular City Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 248 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $256 per night (USD)Expedia
From $321 per night (USD)VRBO
Come experience The Lake Shore!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come experience the Lake Shore! A corporate apartment that boast comfort, class and the PERFECT location to explore any ...
From $321 per night (USD)VRBO
From $207 per night (USD)VRBO
Charming Cozy 2BR Haven w/Crib Near Hip WickerPark
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
2B1B unit for 6 people plus a crib. Great West Wicker Park location (in coveted 60622 area code) just 0.9 miles from Dam ...
From $207 per night (USD)VRBO
From $426 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 $426 per night (USD)VRBO
From $202 per night (USD)Expedia
1 GB Wi-Fi, 1 Reserved Parking Space, Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Stay in this modern 1BR, 1BA apartment in Lakeview, Chicago, perfect for families, friends, or groups of up to ...
From $202 per night (USD)Expedia
From $300 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 la ...
From $300 per night (USD)VRBO
From $274 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 $274 per night (USD)Expedia
From $138 per night (USD)VRBO
Modern 2BR Apartment in Medical District
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy your stay in this spacious, fully furnished 2-bedroom, 1.5-bath apartment in Chicago’s Medical District. With two ...
From $138 per night (USD)VRBO
From $283 per night (USD)VRBO
2 Comfortable Suites Perfect for Families & Groups
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $283 per night (USD)VRBO
From $149 per night (USD)VRBO
O'Hare Suite Perfect for Families w/ Free Breakfast & Onsite Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $149 per night (USD)VRBO
From $278 per night (USD)VRBO
2 Clean Suites Ideal for Groups & Families + Convenient Airport Access Nearby
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $278 per night (USD)VRBO
From $149 per night (USD)VRBO
Contemporary Suite Near Rosemont Theater, w/ Free Breakfast & Onsite Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $149 per night (USD)VRBO
From $278 per night (USD)VRBO
Relax in 2 Family-Friendly Suites w/ Heated Pool & Hot Breakfast Near Airport
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $278 per night (USD)VRBO
From $149 per night (USD)VRBO
Enjoy A Clean & Quiet Suite w/ Kitchenette & Pool | Minutes from O'Hare Airport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $149 per night (USD)VRBO
From $283 per night (USD)VRBO
Experience Quiet Comfort in 2 Family-Friendly Suites w/ Pool & Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $283 per night (USD)VRBO
From $149 per night (USD)VRBO
Modern Suite w/ Free Breakfast & Onsite Pool Near Cumberland CTA Station
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our accommodations offer comfort and convenience with separate living areas and in-room amenities like a mini-fridge, mi ...
From $149 per night (USD)VRBO
From $348 per night (USD)Expedia
Wrigleyville Retreat • 1BR • Sleeps 6 • Full Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Ruby's Garden is a modern 1BR Near Wrigley Field • 1 Block from the Stadium Sleeps 6 • Full Kitchen • AC • Perfect for S ...
From $348 per night (USD)Expedia
From $428 per night (USD)VRBO
Bright 3 BR Wicker Park Loft. 5Beds + 2 parking. 4-min walk to Damen Blue Line!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your bright, design-forward home base in the heart of Wicker Park. This spacious 3-bedroom retreat sleeps gro ...
From $428 per night (USD)VRBO
From $817 per night (USD)Expedia
Beautiful, Spacious 3BR Ukrainian Village Home w/ Deck, Garage & Room for Groups
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to a spacious, beautifully furnished home in the heart of Ukrainian Village, designed for families, groups, wedd ...
From $817 per night (USD)Expedia
From $327 per night (USD)VRBO
Your Logan Square Oasis with Lush Outdoor Haven!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Catalpa Court -- located in the heart of Chicago's beautiful Logan Square neighborhood :) Bright and spaciou ...
From $327 per night (USD)VRBO
From $197 per night (USD)Expedia
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 $197 per night (USD)Expedia
From $290 per night (USD)VRBO
Spacious 2BR - 10 mins from Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your home away from home in Chicago — just 10 minutes from downtown! We’re conveniently located right by the ...
From $290 per night (USD)VRBO
From $465 per night (USD)Expedia
The Brass Key Residence
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Step into The Brass Key Residence, a thoughtfully curated vintage-inspired home filled with antique treasures, timeless ...
From $465 per night (USD)Expedia
From $1329 per night (USD)VRBO
Massive Queen Anne Mansion for your whole family to stay!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 15
This is your chance to stay in a historic Chicago mansion. This beautiful Queen Anne style mansion has an abundance of c ...
From $1329 per night (USD)VRBO
From $420 per night (USD)Expedia
Designer Loft 4E | Heart of Gold Coast/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 $422 per night (USD)VRBO
Designer Loft 3E | Heart of Gold Coast/River North
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: BRAND NEW APARTMENT IN THE HEART OF RIVER NORTH & GOLD COAST! Enjoy your designer styled unit located in Ch ...
From $422 per night (USD)VRBO
From $368 per night (USD)Expedia
Spacious Apt | 4 Queen Beds | Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Modern Chicago apartment in a quiet residential neighborhood, perfect for 8 guests. Features a full kitchen, high-speed ...
From $368 per night (USD)Expedia
From $1756 per night (USD)VRBO
Bohome Reserve: Chicago Wicker Park • Sauna • Chef's Kitchen • Outdoor Lounging
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Designer, plant-infused 4BR/3.5BA home in Wicker Park—crafted for retreat, work, and play. Unwind in the private sauna, ...
From $1756 per night (USD)VRBO
From $478 per night (USD)Expedia
Spacious 4BR; 2.5BR; en-suite;FL basement;appliances;central air& heat included!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Make yourself at home in this 4-bedroom Chicago townhome retreat. Each bedroom features a comfortable queen bed, perfect ...
From $478 per night (USD)Expedia
From $556 per night (USD)VRBO
4BR Downtown Retreat | Free Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Charming Chicago retreat in quiet Bridgeport. This modern 4-bedroom apartment, featuring queen beds, 2 full baths, and a ...
From $556 per night (USD)VRBO
From $336 per night (USD)Expedia
Ravenswood Loft - Peaceful 2-bedroom apartment in vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Charming 2BR in Ravenswood Manor! This cozy, sunlit apartment sleeps 6 and features 2 bedrooms, 1 bath, a full kitchen, ...
From $336 per night (USD)Expedia
From $416 per night (USD)VRBO
Large and conveniently located
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Chicago, enjoy what this 3-bedroom apartment has to offer. The space features one king bed and two queen beds ...
From $416 per night (USD)VRBO
From $661 per night (USD)Expedia
Stay at The Velvet Manor, a beautifully designed 3BR home just steps from Andersonville's vibrant Clark Street. Enjoy spacious living, a chef's kitchen, dedicated office, Jacuzzi tub, outdoor area, and garage parking.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Velvet Manor, a moody, designer-curated 3-bedroom retreat in the heart of Andersonville. Unwind in richly ...
From $661 per night (USD)Expedia
From $696 per night (USD)VRBO
Arcade • Theater • Gym • Office • Sleeps 15
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 15
Welcome to Giddings Chicago 985 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $696 per night (USD)VRBO
From $458 per night (USD)Expedia
Charming Historic Row Home in Lincoln Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience historic charm and modern luxury in the heart of Lincoln Park. This updated 1870s row home features a privat ...
From $458 per night (USD)Expedia