Cook Area Rentals
From $671 per night (USD)VRBO
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)VRBO
From $241 per night (USD)Expedia
Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This urban oasis is situated in a historic, tree-lined neighborhood at the intersection of Ukrainian Village and East Vi ...
From $241 per night (USD)Expedia
From $512 per night (USD)VRBO
ConerStone House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the beauty of Chicago from this marvelous 4-bedroom house. Guests will find three queen beds and one twin bed, ...
From $512 per night (USD)VRBO
From $150 per night (USD)Expedia
Marvelous 3-bedroom apartment with AC in vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this 3-bedroom apartment in Chicago. The perfect spot features a queen bed, a full bed, and a twin bed, making ...
From $150 per night (USD)Expedia
From $367 per night (USD)VRBO
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this spacious, newly remodeled retreat. With room for the whole family, comfortable bedrooms, a ...
From $367 per night (USD)VRBO
From $326 per night (USD)Expedia
Pool House- 4bd/ 2ba- in the city of Chicago
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Take a break and unwind at this peaceful oasis in Chicago. Whether you're playing games in the house or sitting by the p ...
From $326 per night (USD)Expedia
From $100 per night (USD)VRBO
Blueground | West Loop, pool, nr Union Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in West Loop. It’ll be easy to simply show up and start li ...
From $100 per night (USD)VRBO
From $246 per night (USD)Expedia
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Step into a sun-drenched, top-floor sanctuary with a private roof deck and sweeping skyline views. Whether you`re here f ...
From $246 per night (USD)Expedia
From $234 per night (USD)VRBO
Attractive Coach House Apartment for rent in Oak Park.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Discover the beauty of Oak Park from this 4-bedroom house. This adorable home offers three bathrooms, making it easy for ...
From $234 per night (USD)VRBO
From $107 per night (USD)VRBO
Blueground | West Loop, rooftop, nr Union Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful West Loop furnished one bedroom apa ...
From $107 per night (USD)VRBO
From $135 per night (USD)VRBO
Blueground | Near North, garden, nr Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Near North Side furnished one bedro ...
From $135 per night (USD)VRBO
From $175 per night (USD)VRBO
Blueground | Near North, fitness center, nr Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this pretty one bedroom Blueground apartment. You’ll love coming h ...
From $175 per night (USD)VRBO
From $133 per night (USD)VRBO
Blueground | West Loop, pool, nr United Center
- 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 $133 per night (USD)VRBO
From $764 per night (USD)Expedia
Modern 4BR Home ,Sleeps 10, 5 Beds, Free Parking Easy Access to Downtown&Lake
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to a bright, fully renovated this year, and stylish home designed for families and friends! Enjoy 4 bedrooms, 5 ...
From $764 per night (USD)Expedia
From $231 per night (USD)VRBO
Great Area Logan Square Apt Games Pets - Sleeps 5
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Escape to a fun, stylish 650 sq ft top-floor retreat in Chicago`s vibrant Avondale/Logan Square! Perfect for 4, this pri ...
From $231 per night (USD)VRBO
From $149 per night (USD)Expedia
Landing | Amazing 1BD, Yoga Studio, Rooftop Lounge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $149 per night (USD)Expedia
From $171 per night (USD)VRBO
Landing | Incredible 1BD, Gym, Rooftop Lounge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $171 per night (USD)VRBO
From $134 per night (USD)Expedia
Landing | Chic Studio, Clubhouse, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Soak up the best of River North at NEXT. Our fully-furnished homes are perfect for monthly or extended stays, featuring ...
From $134 per night (USD)Expedia
From $150 per night (USD)VRBO
Landing | Amazing 1BD, Pool, Yoga Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $150 per night (USD)VRBO
From $168 per night (USD)Expedia
Landing | Stunning 1BD, Gym, Rooftop Lounge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $168 per night (USD)Expedia
From $176 per night (USD)VRBO
Landing | Stunning 1BD, Rooftop Lounge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $176 per night (USD)VRBO
From $145 per night (USD)Expedia
Landing | Beautiful 1BD, Yoga Studio, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $145 per night (USD)Expedia
From $155 per night (USD)VRBO
Landing | Spectacular 1BD, Yoga Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $155 per night (USD)VRBO
From $179 per night (USD)Expedia
Landing | Stunning 1BD, Rooftop Lounge, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $179 per night (USD)Expedia
From $134 per night (USD)VRBO
Landing | Chic 1BD, Yoga Studio, Rooftop Lounge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $134 per night (USD)VRBO
From $178 per night (USD)Expedia
Landing | Modern 1BD in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $178 per night (USD)Expedia
From $171 per night (USD)VRBO
Landing | Amazing 1BD in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $171 per night (USD)VRBO
From $188 per night (USD)Expedia
Landing | Stunning 1BD in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $188 per night (USD)Expedia
From $164 per night (USD)VRBO
Landing | Stylish Studio in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $164 per night (USD)VRBO
From $132 per night (USD)Expedia
Landing | Incredible Studio in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $132 per night (USD)Expedia
From $172 per night (USD)VRBO
Landing | Stylish Studio in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $172 per night (USD)VRBO
From $163 per night (USD)Expedia
Landing | Modern Studio in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $163 per night (USD)Expedia
From $164 per night (USD)VRBO
Landing | Amazing Studio in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $164 per night (USD)VRBO
From $461 per night (USD)Expedia
Luxe 3BR + Patio & Parking | Sleeps 9 | Lakeview
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Summary: You'll feel it the moment you walk in — this isn't a typical rental. It's a sprawling, light-filled home on on ...
From $461 per night (USD)Expedia
From $201 per night (USD)VRBO
By Wrigley Field +Reserved Parking Space +95 Walkscore + In-Unit Laundry + Patio
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Top host approved all-new construction luxury condo in a quaint 3-unit building that sleeps 5 and offers great natural l ...
From $201 per night (USD)VRBO
From $211 per night (USD)Expedia
Flexhome West Town Spacious 2BR Duplex · Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover the best of Chicago from this spacious 2-bedroom, 2-bathroom duplex apartment. Whether you`re in town for a con ...
From $211 per night (USD)Expedia
From $282 per night (USD)VRBO
Luxury Fulton Market Condo - Prime Location Walking distance to Riverwalk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay in the heart of Chicago’s West Loop. One block from Fulton Market’s award winning restaurants, bars, and cafés. Clo ...
From $282 per night (USD)VRBO
From $148 per night (USD)Expedia
Private Covered Garage +In-Unit Laundry+ Restaurant Row+93 Walkscore + 606 Trail
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nicknamed "Midwest Headquarters of Hip" Logan Square was voted one of the coolest places in the country by Cushman & Wak ...
From $148 per night (USD)Expedia
From $206 per night (USD)VRBO
Top Rated w/Free Street Parking+ 2 King Beds 1 Single +In Unit-Laundry +1.5 Bath
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Newly renovated, Scandinavian inspired, apartment with all the amenities we have noted that guests desire in a home away ...
From $206 per night (USD)VRBO
From $407 per night (USD)Expedia
Spacious 4BR near Northwestern with King Beds + Crib
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Centrally located just 10 minutes from Northwestern University, it’s perfect for family trips, graduations, and easy acc ...
From $407 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 $403 per night (USD)VRBO
Spacious 4BR Near Chicago with Parking and Easy Train Access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your spacious 4-bedroom stay in Berwyn, perfect for families, groups, or business travelers looking for comfo ...
From $403 per night (USD)VRBO
From $428 per night (USD)VRBO
Stylish 2 Bedroom Aparment with Games and Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stylish 2BR Apartment w/ Modern Kitchen + Free Parking near Downtown Relax, play, and feel at home in this stylish 2-b ...
From $428 per night (USD)VRBO
From $310 per night (USD)Expedia
CHICAGO Portage Park Pad
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Traveling alone or with the family this apartment has the space to lounge rest or work. Located in a quite residential n ...
From $310 per night (USD)Expedia
From $129 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 spacious The Loop furnished one bedroom apart ...
From $129 per night (USD)VRBO
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)VRBO
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)VRBO
From $744 per night (USD)Expedia
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)Expedia
From $174 per night (USD)VRBO
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)VRBO
From $872 per night (USD)Expedia
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)Expedia
From $162 per night (USD)VRBO
Modern Berwyn Retreat - 15 Min to Midway - Easy Access to Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in this modern Berwyn apartment near Downtown Chicago and Midway Airport, ideal for families, couples, small groups ...
From $162 per night (USD)VRBO
From $381 per night (USD)Expedia
O’Hare 7-Bed Home | Workers & Insurance
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Your family will be close to everything when you stay at this centrally-located place. Comfortable 4BR/2BA home in Des P ...
From $381 per night (USD)Expedia
From $365 per night (USD)VRBO
Family Haven in Streamwood | Ideal for Stay Long
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 10
Welcome to your family-friendly extended-stay retreat in Streamwood! This inviting 4-bedroom, 3-bathroom home is perfect ...
From $365 per night (USD)VRBO
From $365 per night (USD)Expedia
Westchester Corporate Stay 5 Beds
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
The whole group will enjoy easy access to everything from this centrally located place. Comfortable 3BR Corporate Housi ...
From $365 per night (USD)Expedia
From $358 per night (USD)VRBO
Family 4BR Haven Near O’Hare + 2 Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to your spacious home-away-from-home featuring two separate newly renovated 2-bedroom, 1-bathroom apartments loc ...
From $358 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 $100 per night (USD)VRBO
Charming 1-bedroom apartment in enchanting Evanston with AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your cozy getaway awaits in Evanston at this amazing apartment. This welcoming space features a comfortable bedroom, hea ...
From $100 per night (USD)VRBO
From $142 per night (USD)VRBO
Modern 2B Irving Park Gem / Sleeps 5
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Spacious, newly renovated 2BR in Irving Park—perfect for families and groups up to 5. Enjoy a bright living area, full k ...
From $142 per night (USD)VRBO
From $505 per night (USD)VRBO
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)VRBO
From $152 per night (USD)Expedia
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)Expedia
From $243 per night (USD)VRBO
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)VRBO
From $235 per night (USD)Expedia
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)Expedia
From $212 per night (USD)VRBO
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)VRBO
From $527 per night (USD)VRBO
Where comfort meets lifestyle at The Townhouse of Western Springs
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Step into a slower rhythm at The Townhouse of Western Springs, where mornings begin with soft light filtering through qu ...
From $527 per night (USD)VRBO
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 $423 per night (USD)Expedia
Spacious Westchester Duplex for Group & Family
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Welcome to your stylish and ultra-comfortable home away from home in Westchester, IL. This large, modern duplex offers p ...
From $423 per night (USD)Expedia
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 $273 per night (USD)VRBO
Stunning Fully Furnished 3BR/3BA Mid-Century Modern Duplex in Historic Old Town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
WELCOME TO YOUR OLD TOWN RETREAT Step into modern Chicago living with historic charm. This exquisitely appointed 1,700 ...
From $273 per night (USD)VRBO
From $212 per night (USD)VRBO
NEW! Bright Modern 3Bed 2.5Bath Evanston Home w/Parking by AllSet Turnover
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
**Hosting 30+ Night Reservations** Welcome to our modern two story home in Evanston! With 3 bedrooms, 2.5 baths and ...
From $212 per night (USD)VRBO
From $358 per night (USD)VRBO
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)VRBO
From $212 per night (USD)VRBO
Relaxing 2BR Retreat w/ Parking Near O’Hare
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the best of Des Plaines from a prime location just about 5 minutes from O’Hare International Airport, with conv ...
From $212 per night (USD)VRBO
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 $444 per night (USD)Expedia
Spacious 4BR-2.5 bath Family-Friendly Retreat sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience a spacious retreat in a quite subdivision located right in the heart of famous suburbs Schaumburg . Location ...
From $444 per night (USD)Expedia
From $235 per night (USD)VRBO
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)VRBO
From $683 per night (USD)Expedia
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)Expedia
From $996 per night (USD)VRBO
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)VRBO
From $230 per night (USD)Expedia
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)Expedia
From $749 per night (USD)VRBO
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)VRBO
From $500 per night (USD)Expedia
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)Expedia
From $235 per night (USD)VRBO
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)VRBO
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 $276 per night (USD)VRBO
Where comfort begins- 2 bedrooms apartment, 15 min from Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Modern, stylish space near downtown Chicago with easy access to airports, shopping, dining, expressways, and public tran ...
From $276 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 $310 per night (USD)Expedia
Cozy 3BR Retreat with grill • Near O’Hare Airport
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to your comfortable 3BR retreat in Des Plaines, Illinois — a peaceful and convenient home located just 7 minutes ...
From $310 per night (USD)Expedia