Cook Area Rentals
From $582 per night (USD)VRBO
Chic River North Retreat: Luxe Suites, Stunning Views, Steps from Chicago Life!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $582 per night (USD)VRBO
From $2557 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 $2557 per night (USD)VRBO
From $435 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 $435 per night (USD)VRBO
From $654 per night (USD)VRBO
Experience Chic Chicago Living in Old Town – Spacious Suites & Luxe Amenities
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $654 per night (USD)VRBO
From $859 per night (USD)VRBO
Stylish River North Suites: Luxury Living Near Chicago’s Best Shopping&Nightlife
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $859 per night (USD)VRBO
From $200 per night (USD)Expedia
5 Mi to Dtwn: Ukrainian Village Apartment!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Walk to Restaurants | Sleek Furnishings Make the most of your next Windy City adventure when you book this updated Chic ...
From $200 per night (USD)Expedia
From $112 per night (USD)VRBO
Blueground | South Loop, pool & w/d, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this bright South Loop furnished one bedroom apart ...
From $112 per night (USD)VRBO
From $374 per night (USD)Expedia
House with garage, outdoor dining and basement bar
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Escape to this superb house in picturesque Chicago. With 4 queen beds spread across 4 bedrooms and 3 bathrooms equipped ...
From $374 per night (USD)Expedia
From $83 per night (USD)VRBO
Comfy 2-bedroom apartment with WiFi, in historic Chicago neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Your home away from home in Chicago with 2 bedrooms and 1 bathroom. This nice apartment features 1 queen bed, 2 full bed ...
From $83 per night (USD)VRBO
From $420 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 $420 per night (USD)VRBO
From $167 per night (USD)VRBO
Cozy 2b2ba: 15 min Bus Downtown, 7min to UChicago, Bike to Lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Cozy Study: Bronzeville 2b/2ba perfect for remote workers, students, visitors & tourists! Spacious, cozy ...
From $167 per night (USD)VRBO
From $128 per night (USD)Expedia
Blueground | West Loop, gym & bbq, nr Willis Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in West Loop Gate with views over the city. It’ll be easy ...
From $128 per night (USD)Expedia
From $907 per night (USD)VRBO
Experience Chic Old Town Living: Spacious Suites, Top Amenities & Iconic Locale
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $907 per night (USD)VRBO
From $668 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 $668 per night (USD)VRBO
From $228 per night (USD)VRBO
Flexhome Ukrainian Village 2BR D2
- Bedrooms:
- 1
- 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 $228 per night (USD)VRBO
From $281 per night (USD)Expedia
Charming 3-bedroom townhome with Central AC and WiFi in lovely Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to this cool townhome in Chicago. This fabulous rental features 3 bedrooms - one with a queen bed and two with t ...
From $281 per night (USD)Expedia
From $503 per night (USD)VRBO
4BR Home with Game Room: Chicago Leisure Escape
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This playful Chicago hideaway mixes retro charm with cozy comfort. Fire up the arcade, challenge your crew to pool or fo ...
From $503 per night (USD)VRBO
From $184 per night (USD)Expedia
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 $184 per night (USD)Expedia
From $247 per night (USD)VRBO
Two Bedroom - Tranquil Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our enchanting 2-bedroom, 1-bathroom haven nestled in the vibrant heart of Wrightwood, Chicago. Ideal for fam ...
From $247 per night (USD)VRBO
From $655 per night (USD)Expedia
Peaceful Oasis - Captivating Six-Bedroom Escape
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Discover the charm of Wrightwood, Chicago, from the comfort of our enchanting 6-bedroom, 3-bathroom rental haven. You wi ...
From $655 per night (USD)Expedia
From $456 per night (USD)VRBO
Andersonville Charming 3 Bedroom/2 Bath House with Family Room plus Yard & Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in Andersonville - voted the 2nd best neighborhood in the world in 2021 by Time Out - this fully FURNISHED singl ...
From $456 per night (USD)VRBO
From $236 per night (USD)Expedia
3BR Oasis, Gym, Workspace, Quiet Location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
✨ The place is really nice she just set it up so all the furniture is brand new and also there's a treadmill and some gy ...
From $236 per night (USD)Expedia
From $282 per night (USD)VRBO
New Modern 3BR, Gym, Workspace, Quiet Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
✨Clean and comfortable space. Accurate description. Safe street. Would love to stay again! ✨ 📢 Welcome to the perfect ...
From $282 per night (USD)VRBO
From $130 per night (USD)Expedia
Charming Chicago 3-bed / 1 Bath Apartment. Extend 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 $130 per night (USD)Expedia
From $302 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 $302 per night (USD)VRBO
From $701 per night (USD)Expedia
Hot Tub & Sauna: Hoffman Estates Villa in Elgin!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Pets Welcome w/ Fee | 2 Kitchens | Cookout Ready | Quiet 80 Acres This tranquil retreat offers rustic luxury with plent ...
From $701 per night (USD)Expedia
From $125 per night (USD)VRBO
Spacious Skokie Retreat - 2BR/2BA - Mins to Chicago, mall & Train
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your home away from home in Skokie! This stylish and spacious 2-bedroom, 2-bathroom condo is perfect for fami ...
From $125 per night (USD)VRBO
From $161 per night (USD)Expedia
Charming 2-bedroom apartment in enchanting Chicago with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Make yourself at home in this 2-bedroom Chicago retreat. This excellent apartment features 2 queen beds, a cozy living r ...
From $161 per night (USD)Expedia
From $265 per night (USD)VRBO
Central Haven Escape: Stylish 3BR With Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Unwind in our cozy and modern 3-bedroom retreat, perfect for relaxing after exploring the city. Two bedrooms feature plu ...
From $265 per night (USD)VRBO
From $183 per night (USD)Expedia
Be our guest in Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover this fabulous 2-bedroom gem in Chicago. This soothing apartment features 1 king bed and 1 queen bed, a cozy bat ...
From $183 per night (USD)Expedia
From $335 per night (USD)VRBO
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Get ready to relax in this lovely 2-bedroom house in Hazel Crest. This welcoming property features 1 king bed, 1 queen b ...
From $335 per night (USD)VRBO
Click For PricingExpedia
Charming 1-bedroom apartment in brilliant Berwyn with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Make yourself at home in this enchanting 1-bedroom Berwyn retreat. This cozy apartment features a peaceful queen bed in ...
Click For PricingExpedia
From $402 per night (USD)VRBO
Spacious 4BR Home. Your Cozy Home Away from Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Spacious & Stylish 4-Bedroom Retreat | Perfect for Families & Groups Welcome to your perfect Chicago getaway! This bea ...
From $402 per night (USD)VRBO
From $182 per night (USD)Expedia
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 $182 per night (USD)Expedia
From $173 per night (USD)VRBO
Peaceful One Bedroom Home near Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: This peaceful one-bedroom home in Forest Park, IL, offers a serene retreat with convenient access to Chicago. L ...
From $173 per night (USD)VRBO
From $211 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 $211 per night (USD)Expedia
From $612 per night (USD)VRBO
Stylish 3BR Apt Near Wrigley Field & Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Your cozy getaway awaits in Chicago at this superb apartment. With 3 bedrooms including 1 full bed and 2 queen beds, thi ...
From $612 per night (USD)VRBO
From $325 per night (USD)VRBO
Spacious 2BR Family-Friendly Stay, 4 Queen Beds + 2 Baths, Parking & Laundry.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Relax and unwind in this cozy Evanston retreat. This spacious 2-bedroom apartment features 4 queen beds (2 in each room) ...
From $325 per night (USD)VRBO
From $1052 per night (USD)VRBO
7BR Apartment City Escape Near Cubs + Laundry Ready
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 16
Lakeview blends charm, excitement, and history—perfect for baseball fans and city lovers alike. Wrigley Field, home of t ...
From $1052 per night (USD)VRBO
From $173 per night (USD)Expedia
Cozy studio in Andersonville Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This newly constructed studio offers a stylish, modern space just steps from Clark Street—home to some of the best resta ...
From $173 per night (USD)Expedia
From $119 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 $119 per night (USD)VRBO
From $540 per night (USD)VRBO
Best Place to Unwind! 2 Family and Dog Friendly Units! Walk to Millennium Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $540 per night (USD)VRBO
From $708 per night (USD)VRBO
Relax & Explore! 3 King Units, Steps from Riverfront, Pet-Friendly Property!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $708 per night (USD)VRBO
From $1080 per night (USD)VRBO
Four Cozy Queen Rooms! Perfect for Family & Friends, Pets Are Welcome!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $1080 per night (USD)VRBO
From $810 per night (USD)VRBO
3 Comfortable Units! Pet-friendly Property! Near Riverwalk & Chicago Attractions
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $810 per night (USD)VRBO
From $472 per night (USD)VRBO
Look No Further! 2 Stylish King Units! Pet-Friendly, Walk to Riverwalk & Dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $472 per night (USD)VRBO
From $431 per night (USD)VRBO
McCormick Cozy 3Bedroom with Optional Parking for 8 guests
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
• MESSAGE US for SPECIAL RATES • State street location • Minutes walk to McCormick Convention Center • 4K Roku HDTVs in ...
From $431 per night (USD)VRBO
From $207 per night (USD)Expedia
NEW Private West Loop 1br with Backyard near Green Line and CTA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This place is a true hidden gem. I’ve lived in Chicago for over two decades and travel often, so when I designed this sp ...
From $207 per night (USD)Expedia
From $226 per night (USD)VRBO
NEW! Vintage 3 Bed Condo in Chicagolands Trendy Berwyn by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this lovely three-bedroom hidden gem in Berwyn, just minutes away from Chicago and everything the city has to ...
From $226 per night (USD)VRBO
From $233 per night (USD)Expedia
NEW! 3 Bed Vintage Condo in Chicagolands Trendy Berwyn by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Start your adventures in this lovely three-bedroom hidden gem in Berwyn, just minutes away from Chicago and everything ...
From $233 per night (USD)Expedia
From $201 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 $201 per night (USD)VRBO
From $1410 per night (USD)VRBO
Great Relaxing Overnight Stay! 4 Units with City View, Pets Are Welcome!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $1410 per night (USD)VRBO
From $262 per night (USD)VRBO
Serene 3-bedroom apartment in Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to our stunning retreat, perfect for families or friends seeking a stylish getaway. This beautifully designed un ...
From $262 per night (USD)VRBO
From $561 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 $561 per night (USD)Expedia
From $160 per night (USD)VRBO
2 Mi to Wind Creek Casino: Quaint Homewood Haven
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Dog Friendly w/ Fee | Close to Golf, Dining & Shopping | 30 Mi to Chicago Whether you're visiting loved ones, hitting t ...
From $160 per night (USD)VRBO
From $156 per night (USD)Expedia
Your Perfect Schaumburg Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Have fun with the whole family at this beautifully remodeled home that offers a perfect blend of luxury and convenience. ...
From $156 per night (USD)Expedia
From $170 per night (USD)VRBO
New Listing /20% Discount 32+/ Fast Wi-Fi / 1 Parking Spot!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Highly sought-after North Center / St. Ben's Location -1 Garage Spot INCLUDED!! - Fully furnished unit with everything ...
From $170 per night (USD)VRBO
From $465 per night (USD)Expedia
Ideal Spot Just Minutes from O’Hare Airport | LCP Collection
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience a welcoming blend of comfort and ease in this inviting 3-bedroom getaway, conveniently situated only ...
From $465 per night (USD)Expedia
From $420 per night (USD)VRBO
3-bedroom apartment in Chicago Medical District, 5 mins from United Center
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably in Chicago at this 3-bedroom apartment. Each bedroom features a cozy queen bed, perfect for a good nigh ...
From $420 per night (USD)VRBO
From $443 per night (USD)Expedia
Spacious 3BR in South Loop Near McCormick - Optional Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The State Suite — a modern, artfully designed 3-bedroom, 2-bath apartment perfect for everyone! Just minutes ...
From $443 per night (USD)Expedia
From $108 per night (USD)VRBO
Charming 2-bedroom apartment in Roscoe Village/Free Washer/Dryer/WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This 2-bedroom, 1-bath home in Roscoe Village offers full-size beds in each bedroom, sleek vinyl flooring throughout, fr ...
From $108 per night (USD)VRBO
From $394 per night (USD)Expedia
Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This 5-bedroom bungalow in Berwyn is perfect for your escape to a tranquil setting. With 3 queen beds and 2 futons, gues ...
From $394 per night (USD)Expedia
From $160 per night (USD)VRBO
Elegant & Stylish 1 Bed & 1 Bath Apartment ~25 Minutes from Downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
A Chic & Tranquil Gem! Escape the hustle and bustle in our modern and serene basement apartment. This beautifully design ...
From $160 per night (USD)VRBO
From $2611 per night (USD)Expedia
Modern- Smart Home in Wicker Park
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Come enjoy and relax in this calm, modern, stylish space located in Wicker Park. This plant filled oasis in the city i ...
From $2611 per night (USD)Expedia
From $122 per night (USD)VRBO
1 Mi to Garfield Park Conservatory: Modern Apt!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Dedicated Workspace | 6 Mi to Downtown Chicago Get ready to explore top Chicago attractions when you retreat to this br ...
From $122 per night (USD)VRBO
From $140 per night (USD)Expedia
Vintage 1-br apartment with AC, WiFi in charming, safe, quiet Berwyn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy the quiet and safety of Berwyn, IL, in a Mid-Century-styled, PRIVATE 1-bedroom apt in a classic, brick, 1929 2-fla ...
From $140 per night (USD)Expedia
From $69 per night (USD)VRBO
The Chicago Hotel Collection, Standard Double Queen with City Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $69 per night (USD)VRBO
From $103 per night (USD)VRBO
2 Bedroom Furnished Apartment with W/D Heart of Logan Square by Blueline train
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Home sits on private safe sought-after street block. This fully furnished 2-bedroom 1 bath apartment has a recently reno ...
From $103 per night (USD)VRBO
From $618 per night (USD)VRBO
Luxury Designer Penthouse NW | Pool | Gold Coast
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center o ...
From $618 per night (USD)VRBO
From $1505 per night (USD)VRBO
Making The Best Memories Along The Way! 4 Units with City View, Pets Are Welcome
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $1505 per night (USD)VRBO
From $753 per night (USD)VRBO
Better Choice for your Vacation! 2 Relaxing Units with City View, Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $753 per night (USD)VRBO
From $1129 per night (USD)VRBO
Everything You Need For The Perfect Vacation! 3 Relaxing Units, Pets Are Welcome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $1129 per night (USD)VRBO
From $711 per night (USD)VRBO
A Place You'll Surely Enjoy! 2 Relaxing Units with City View, Pet-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $711 per night (USD)VRBO
From $1066 per night (USD)VRBO
Come Create Memories w/ Fun-filled Adventures at this Paradise! 3 Relaxing Units
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $1066 per night (USD)VRBO
From $202 per night (USD)VRBO
Better Choice for your Vacation! Short Walk to River North Spots, Pets Allowed!
- 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 $202 per night (USD)VRBO
From $209 per night (USD)VRBO
Everything You Need For The Perfect Vacation! Pet-friendly Property, King Room!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $209 per night (USD)VRBO
From $87 per night (USD)VRBO
Blueground | Gold Coast, AC, nr Hancock Center
- 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 $87 per night (USD)VRBO
From $372 per night (USD)VRBO
The Chicago Hotel Collection Magnificent Mile, 3 Standard King Rooms
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $372 per night (USD)VRBO
From $207 per night (USD)VRBO
Sleek Downtown Retreat by Chicago’s Mag Mile @ The Chicago Hotel Collection
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $207 per night (USD)VRBO
From $134 per night (USD)VRBO
The Chicago Hotel Collection, Mag Mile, Deluxe Double Queen - Premium Option
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $134 per night (USD)VRBO
From $69 per night (USD)VRBO
Upscale City Center Stay | Prime Locale | City Views | Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $69 per night (USD)VRBO
From $124 per night (USD)Expedia
Modern Condo - Lux Upgraded Unit - No Pet Fees!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kick back and relax in this beautifully designed, top 1% reviewed 1-bedroom condo. This open-floor-plan Owner’s Unit off ...
From $124 per night (USD)Expedia
From $211 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 $211 per night (USD)VRBO
From $147 per night (USD)Expedia
Blueground | Greektown, bbq, gym, nr Willis Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Greektown. It’ll be easy to simply show up and start li ...
From $147 per night (USD)Expedia
From $159 per night (USD)VRBO
Prime Location Wicker Park Studio Close to Shops & Dining
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Modern Comforts: Prime Wicker Park Studio, close to shops & dining in Chicago, offers a comfortable apartment with free ...
From $159 per night (USD)VRBO
From $385 per night (USD)VRBO
Spacious 4-bedroom house in amazing Des Plaines with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
This Des Plaines house boasts 4 inviting bedrooms, including 1 king bed, 2 queen beds, 1 bunk bed, and 1 futon. With 2 b ...
From $385 per night (USD)VRBO
From $331 per night (USD)VRBO
Family Haven-Prime location ideal for long stays
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
WELCOME to our inviting retreat❗️❗️ "Discover a haven of comfort and convenience in the heart of Streamwood, perfect fo ...
From $331 per night (USD)VRBO
From $623 per night (USD)Expedia
Family Friendly 2 Bedroom Full Kitchen Free Laundry Work Space 1 FREE Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Nestled in the heart of Chicago, this charming apartment boasts 2 cozy bedrooms with queen beds, perfect for a small gro ...
From $623 per night (USD)Expedia
From $108 per night (USD)VRBO
Charming 1-bedroom apartment with WiFi, AC in Glenview, great school district
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover this 1-bedroom gem in Glenview. This pleasant apartment offers WiFi, coin laundry, and more for your convenienc ...
From $108 per night (USD)VRBO
From $285 per night (USD)Expedia
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 $285 per night (USD)Expedia
From $348 per night (USD)VRBO
Spacious apartment in awesome Chicago with WiFi, AC- 4 Bedrooms
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to Kam Suites, your ideal retreat in Chicago! This spacious apartment comfortably sleeps ten guests, with one co ...
From $348 per night (USD)VRBO
From $447 per night (USD)VRBO
Charming Hinsdale Home with Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Discover this marvelous 4-bedroom gem in Hinsdale. This cool house features 3 queen beds, WiFi, AC, a washing machine, h ...
From $447 per night (USD)VRBO
From $487 per night (USD)VRBO
\"Spacious 2BR Retreat with Office, Stunning Backyard & Grill in Hanover Park\"
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to The Hanover Hideaway, a stylish 2-bedroom retreat in Hanover Park that offers the perfect mix of comfort, con ...
From $487 per night (USD)VRBO
From $225 per night (USD)Expedia
The Family Retreat, The Family Retreat Oasis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A spacious 4-bedroom, 2-bathroom house ideal for larger groups or families. Situated just outside Chicago, in Calumet Ci ...
From $225 per night (USD)Expedia
From $416 per night (USD)VRBO
Charming 2-bedroom apartment in fabulous Westchester with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Your home away from home in Westchester with 2 bedrooms. This awesome apartment features 1 full bed, 1 bunk bed, a cozy ...
From $416 per night (USD)VRBO
From $221 per night (USD)Expedia
Clean home in quiet neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Relax alone or with family at this peaceful place in very quiet neighborhood. Single family house with 1600 sq ft ,it ha ...
From $221 per night (USD)Expedia
From $421 per night (USD)VRBO
The Urban Family Retreat
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Welcome to your ideal getaway located on the vibrant southeast side of Chicago. This spacious property comfortably sleep ...
From $421 per night (USD)VRBO
From $320 per night (USD)Expedia
Blueground | South Loop, pool & gym, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy South Loop furnished one bedroom apartme ...
From $320 per night (USD)Expedia
From $327 per night (USD)VRBO
Blueground | South Loop, pool & gym, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop with high floor views over the city. It’ll b ...
From $327 per night (USD)VRBO
From $124 per night (USD)Expedia
Blueground | Fulton Market, gym & AC, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Fulton Market District with views over the city. It’ll ...
From $124 per night (USD)Expedia