Cook Area Rentals
From $650 per night (USD)VRBO
Comfortable and cozy 4BA, 2BA Home in Worth
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Relax with the whole family at this peaceful place to stay. Welcome to this spacious 4-bedroom, 2-bathroom single-family ...
From $650 per night (USD)VRBO
From $355 per night (USD)Expedia
Newgard Nest I Walk to Loyola, Beaches & CTA l Bright 2nd FL Apt w/ Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Peaceful 2nd-floor, 3-bedroom apartment in Rogers Park near Loyola University and the lake. Ideal for families, visiting ...
From $355 per night (USD)Expedia
From $271 per night (USD)VRBO
Brand new 1 Bedroom Apartment in La Grange close to Metra
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cheerful and inviting, this one-bedroom, second-floor suite offers a comfortable and welcoming retreat for couples, smal ...
From $271 per night (USD)VRBO
From $391 per night (USD)VRBO
Brand new 3 BR apartment, downtown La Grange close to Metra
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Sunny and stylish three-bedroom, second-floor suite that blends easy elegance with everyday function. With a spacious li ...
From $391 per night (USD)VRBO
From $368 per night (USD)VRBO
Brand new 2 BR Apt in downtown La Grange close to Metra!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Spacious and thoughtfully designed, this vibrant two-bedroom, second-floor suite is an ideal choice for families or grou ...
From $368 per night (USD)VRBO
From $376 per night (USD)VRBO
Brand new 2BR Apartment in downtown La Grange close to Metra
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy, light, and effortlessly charming, this two-bedroom, second-floor suite offers a welcoming retreat for couples, sma ...
From $376 per night (USD)VRBO
From $202 per night (USD)VRBO
Stylish 1BR/1BA Near Lake in Rogers Park + Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Rogers Park is Chicago’s northernmost lakefront neighborhood, known for its beaches, parks, and tree-lined streets lined ...
From $202 per night (USD)VRBO
From $191 per night (USD)Expedia
Pilsen Gem Near the Loop and Chinatown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in our cozy private one-bedroom coach house with a comfy living room, sofa bed, kitchenette, and full bathroom. Ups ...
From $191 per night (USD)Expedia
From $804 per night (USD)VRBO
Grand 5,500 sq ft Pilsen home, 5BR, sleeps 11, near downtown
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Luxe 5BR Pilsen Home, Chef's Kitchen, Sleeps 11 One of Pilsen's most striking homes. Four floors of open space with 12- ...
From $804 per night (USD)VRBO
From $663 per night (USD)Expedia
Spacious 3BR 2BA Haven City Views Steps to MagMile
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Welcome to The Haven — a sunlit 3BR retreat in the heart of The Loop with skyline views and steps-from-the-par ...
From $663 per night (USD)Expedia
From $1539 per night (USD)VRBO
Luxury PH: Panoramic Views + Prime Location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: Temporary housing doesn't have to feel temporary. The Sol, a 4-bedroom penthouse on the 23rd floor in the Chic ...
From $1539 per night (USD)VRBO
From $218 per night (USD)Expedia
✨ Beautiful 2BR Apartment with Laundry
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax and unwind in this stylish and comfortable 2-bedroom apartment in Chicago, thoughtfully designed to offer the perf ...
From $218 per night (USD)Expedia
From $407 per night (USD)VRBO
Central Evanston Private 1st Floor Roomy Apt
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Discover this updated, private 1st-floor apartment in central Evanston, ideal for short stays or extended visits. Perfec ...
From $407 per night (USD)VRBO
From $450 per night (USD)Expedia
Spacious 5BD 2BA House / Melrose Park
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Your cozy getaway awaits in Melrose Park at this charming house. With five bedrooms featuring two king beds and three fu ...
From $450 per night (USD)Expedia
From $305 per night (USD)VRBO
Location Jackpot! Minutes to Downtown, McCormick & Chinatown-free parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
## Location Jackpot! Minutes to Downtown, McCormick Place & Chinatown Looking for the perfect blend of city excitement a ...
From $305 per night (USD)VRBO
From $274 per night (USD)Expedia
Historic Family Home | Walk to U Chicago, Obama Center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in a refined bohemian retreat just steps from the University of Chicago and one mile from the Obama Presidential Ce ...
From $274 per night (USD)Expedia
From $260 per night (USD)VRBO
Oak Park 4BD 2BA / PentHouse
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Discover this 4-bedroom gem in Oak Park. This quaint apartment features two king beds, one full bed, and a twin bed, per ...
From $260 per night (USD)VRBO
From $371 per night (USD)Expedia
Modern 3BD 1BA house - Tinley Park
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 5
Stay comfortably in Tinley Park at this 3-bedroom house. The space features two queen beds and one twin bed, perfect for ...
From $371 per night (USD)Expedia
From $388 per night (USD)VRBO
Cozy 3BR-6BA Entire Home in Schaumburg. Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your ideal home-away-from-home in Schaumburg, Illinois! This spacious and thoughtfully designed 3-bedroom ret ...
From $388 per night (USD)VRBO
From $246 per night (USD)VRBO
Welcome to our 2-Bed Apartment in West Town for 7!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: Experience Chicago from the heart of vibrant West Town. Start your morning with coffee in a bright, open livin ...
From $246 per night (USD)VRBO
From $266 per night (USD)VRBO
Homewood Haven 3BR Near Chicago & Metra Stration
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our spacious and comfortable 3-bedroom,1.5 bath home in the charming village of Homewood, Illinois—perfect fo ...
From $266 per night (USD)VRBO
From $795 per night (USD)Expedia
Spacious 3-bedroom apartment in lovely Chicago with FREE Garage Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this apartment in picturesque Chicago. This delightful space features three comfortable bedrooms and a well-ap ...
From $795 per night (USD)Expedia
From $289 per night (USD)VRBO
West Town Gem: 3-Bedroom Spacious Apartment
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to your home away from home in Chicago's charming West Town neighborhood. Start your morning with the ...
From $289 per night (USD)VRBO
From $626 per night (USD)Expedia
Gold Coast Gem
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the heart of Chicago, where River North meets the storied Gold Coast, one of the city’s most walkable neighborho ...
From $626 per night (USD)Expedia
From $258 per night (USD)VRBO
Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
• Stylish 2-bedroom, 1-bath retreat in Oak Park—just minutes from Downtown Chicago • Primary bedroom: king bed, dual ov ...
From $258 per night (USD)VRBO
From $543 per night (USD)Expedia
Charming 5BD 2BA with spacious yard near O'hare
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
You will enjoy easy access to everything from this centrally located place near O'hare. This 5 bedroom 2 full bath, ope ...
From $543 per night (USD)Expedia
From $212 per night (USD)VRBO
Modern 1BR Near Midway - CTA Train - Golf Nearby
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Skip the cramped hotel room. This spacious, modern 1-bedroom near Chicago Midway Airport gives you the room to breathe, ...
From $212 per night (USD)VRBO
From $295 per night (USD)Expedia
Skyline 24th Floor Near Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in a luxury 2-bedroom, 2-bath high-rise suite in downtown Chicago near Grant Park, Millennium Park, and the Lakefro ...
From $295 per night (USD)Expedia
From $403 per night (USD)VRBO
Spacious 5-bedroom house in Des Plaines, convenient to everything
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
This 3,500 sq ft. house in Des Plaines offers plenty of space for guests to relax and unwind. With five bedrooms featuri ...
From $403 per night (USD)VRBO
From $705 per night (USD)Expedia
Envitae Hotel, 4BR Modern Sleek Apartment
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury space is meticulously designed fo ...
From $705 per night (USD)Expedia
From $240 per night (USD)VRBO
Cozy Estate in charming Willow Springs 20 minutes from Downtown and Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 9
Welcome to this pleasant cozy estate in Willow Springs. Unwind with the whole family in this serene spot. It’s just a bl ...
From $240 per night (USD)VRBO
From $359 per night (USD)Expedia
Skyline Luxury 19th Floor Retreat Near Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in a luxury 2-bedroom, 2-bath high-rise suite in downtown Chicago near Grant Park, Millennium Park, and the Lakefro ...
From $359 per night (USD)Expedia
From $295 per night (USD)VRBO
Luxury 21st floor Skyline Views near Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in a luxury 2-bedroom, 2-bath high-rise suite in downtown Chicago near Grant Park, Millennium Park, and the Lakefro ...
From $295 per night (USD)VRBO
From $431 per night (USD)VRBO
Why pay for a hotel room when you can have a 3 bedroom house?
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Calumet City house boasts 3 inviting bedrooms, including 3 queen beds and a cozy sofa bed. Guests can unwind in the ...
From $431 per night (USD)VRBO
From $1228 per night (USD)VRBO
McCormick Meetup - Prime Location - Sleeps 16
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Spacious Chicago Retreat for Large Groups, Business Travel & Extended Stays Welcome to your home away from home in Ch ...
From $1228 per night (USD)VRBO
From $272 per night (USD)Expedia
Modern 1BR w/ Workspace near O'Hare
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to River Chicago 563 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Note ...
From $272 per night (USD)Expedia
From $365 per night (USD)VRBO
1BR Near O'Hare • Balcony • Workspace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to River Chicago 506 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Note ...
From $365 per night (USD)VRBO
From $233 per night (USD)VRBO
West Town Lookout • Spacious • Modern • Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Step into a bright, open-concept home where oversized windows flood the space with natural light and high ceilings creat ...
From $233 per night (USD)VRBO
From $897 per night (USD)VRBO
Luxury Oasis in the Heart of the City with Incredible Private Roof Deck & Patio
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning designer 3 bedroom-3 bathroom home in Chicago's trendy Ukrainian Village—minutes from the Loop & steps to the t ...
From $897 per night (USD)VRBO
From $496 per night (USD)Expedia
Luxury 4br duplex Lakefront Living Without the Downtown Price
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this adorable apartment in picturesque Chicago. With four cozy bedrooms—three featuring queen beds and one wit ...
From $496 per night (USD)Expedia
From $125 per night (USD)VRBO
2-bedroom walkable 2 BLOCKS University of Chicago & President Obama Center Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Welcome to this FULLY FURNISHED charming condo in Woodlawn. Walking distance to LAKEFRONT, New President Obama Library C ...
From $125 per night (USD)VRBO
From $269 per night (USD)VRBO
2-bedroom house. Unit 2 Walkout Basement
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to this spacious, private, and very clean 2-bedroom, 2-bathroom unit 2 in the Elgin/Streamwood area, convenientl ...
From $269 per night (USD)VRBO
From $344 per night (USD)VRBO
5 Minutes to Wrigley + Sauna + Games + Free Garage Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Cute 700 sqft ground floor unit 2BR 2BA In the heart of beautiful and fun Lakeview, minutes from Wrigleyville and Montro ...
From $344 per night (USD)VRBO
From $375 per night (USD)VRBO
Elegance: 4BR - 2 BT NEW Modern Ranch w/ 2 Living Rooms
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Unwind in Arlington Heights at this enchanting house. This is a ranch home with a finished basement! With four comfortab ...
From $375 per night (USD)VRBO
From $170 per night (USD)VRBO
2-bedroom house on a quiet, tree-lined street with modern amenities throughout
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
A Comfortable Chicago Home Base — Pet-Friendly & Work-Ready Welcome to your Chicago home away from home, set in a quiet ...
From $170 per night (USD)VRBO
From $301 per night (USD)Expedia
Chicago Home with gym - 15 min to O’Hare & Rosemont
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to my home! This is my primary residence, thoughtfully prepared for guests while I'm away. The home features thr ...
From $301 per night (USD)Expedia
From $401 per night (USD)VRBO
NEW! Ukrainian Village 2 BD/2BA - Steps from Division!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind in my bright, airy 2BR/2BA garden condo on a quiet tree-lined block in popular Ukrainian Village. The home featu ...
From $401 per night (USD)VRBO
From $158 per night (USD)VRBO
West Loop Living • New Furniture • Garage Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your home away from home in the heart of Chicago's West Loop. This thoughtfully furnished high-rise condo com ...
From $158 per night (USD)VRBO
From $232 per night (USD)VRBO
Vibrant, walkable Andersonville Gem-easy access to Wrigley, venues and Downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this apartment in picturesque Chicago. With 3 comfortable bedrooms featuring 2 queen beds and 1 king bed, gues ...
From $232 per night (USD)VRBO
From $1112 per night (USD)Expedia
The Beverly Hills of Chicago Luxury Stay
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to your luxury home away from home in the "Beverly Hills of Chicago." Thoughtfully designed for families, friend ...
From $1112 per night (USD)Expedia
From $330 per night (USD)VRBO
Modern Design 3 BDR Apartment
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover your stylish retreat in Avondale! This beautifully appointed 3-bedroom apartment seamlessly blends modern luxur ...
From $330 per night (USD)VRBO
From $524 per night (USD)VRBO
Shorter Walk To Wrigley Than A Home Run
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This unit is a shorter walk to Wrigley Stadium than a home run. Catty-corner to Wrigley Field, you'll be at the center ...
From $524 per night (USD)VRBO
From $568 per night (USD)VRBO
Modern& Spacious 2BR with Garage Parking in Chicago's Prime Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in Chicago, this marvelous apartment offers guests a comfortable retreat with two cozy bedrooms and a well-appoi ...
From $568 per night (USD)VRBO
From $578 per night (USD)Expedia
Spacious 1BR apartment in welcoming Chicago with Garage Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Get ready to relax in this 1-bedroom apartment in Chicago. The space offers a peaceful retreat with cozy heating and air ...
From $578 per night (USD)Expedia
From $891 per night (USD)VRBO
Logan Sq 4BR Duplex • Garage • Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Perched on the entire third floor of a classic Chicago brick building, this private 4-bedroom, 2-bath duplex gives your ...
From $891 per night (USD)VRBO
From $224 per night (USD)Expedia
Stylish Midway Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our Chicago home! This comfortable 2-bedroom retreat is perfect for families, couples, business travelers, or ...
From $224 per night (USD)Expedia
From $68 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Near North Side furnished studio apa ...
From $68 per night (USD)VRBO
From $150 per night (USD)Expedia
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Near North Side. It’ll be easy to simply show up and st ...
From $150 per night (USD)Expedia
From $89 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this bright Near North Side furnished studio apart ...
From $89 per night (USD)VRBO
From $75 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in Near North Side. It’ll be easy to simply show up and start l ...
From $75 per night (USD)VRBO
From $156 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Near North Side furnished one bedroom ap ...
From $156 per night (USD)VRBO
From $98 per night (USD)Expedia
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Near North Side furnished one bedroo ...
From $98 per night (USD)Expedia
From $154 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Tribune Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Near North Side. It’ll be easy to simply show up and st ...
From $154 per night (USD)VRBO
From $155 per night (USD)Expedia
Blueground | Near North Side, rooftop, nr Chicago River
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this charming one bedroom Blueground apartment. You’ll love coming ...
From $155 per night (USD)Expedia
From $98 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Chicago River
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this pretty studio Blueground apartment. You’ll love coming home t ...
From $98 per night (USD)VRBO
From $172 per night (USD)Expedia
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Near North Side. It’ll be easy to simply show up and st ...
From $172 per night (USD)Expedia
From $73 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Near North Side furnished studio apart ...
From $73 per night (USD)VRBO
From $77 per night (USD)Expedia
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Near North Side furnished one bedroom ...
From $77 per night (USD)Expedia
From $151 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Near North Side furnished two b ...
From $151 per night (USD)VRBO
From $149 per night (USD)Expedia
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this beautiful two bedroom Blueground apartment. You’ll love comin ...
From $149 per night (USD)Expedia
From $621 per night (USD)VRBO
Modern& Spacious 2BR in Prime Location with 1 Parking Spot
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your home in the heart of Chicago's iconic Lincoln Park neighborhood! This beautifully appointed 1-bedroom ap ...
From $621 per night (USD)VRBO
From $474 per night (USD)Expedia
2 br, 2 bt, UChicago Coachman's Guesthouse
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This 2 bedroom, 2 full bath, stand alone UChicago Coachman's House sleeps 5 comfortably. Less than 1/2 mile to the UChic ...
From $474 per night (USD)Expedia
From $129 per night (USD)VRBO
Peaceful 3-bedroom apartment with AC in vibrant Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this marvelous apartment in Chicago. With three comfortable bedrooms and two bathrooms, guests have plenty of ...
From $129 per night (USD)VRBO
From $178 per night (USD)VRBO
Great Amenities Onsite! Pool, Private Parking, Free Breakfast, Close to Legoland
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Stay close to George Clayson House Museum and Legoland Discovery Center! This listing is for a room within a hotel. ✦ ...
From $178 per night (USD)VRBO
From $108 per night (USD)VRBO
Cozy Stay in Chicago/ 2 Bedroom/ Up to 4 People/32+ Days Stay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Looking for a cozy, convenient place to stay in Chicago? This charming apartment in Roger’s Park is the perfect. This fu ...
From $108 per night (USD)VRBO
From $205 per night (USD)VRBO
Peaceful Norwood Nest- elevated comfort! Walkable, near O'Hare
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Chicago is waiting for you! Enjoy our newly remodeled impeccably clean, cozy and peaceful 1-bedroom supreme comfort in t ...
From $205 per night (USD)VRBO
From $101 per night (USD)VRBO
2-bedroom apartment in Downtown Skokie AC,Walk to train shoppings restaurants!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This Skokie apartment boasts 2 inviting bedrooms, each furnished with a comfortable queen bed. The fantastic bathroom fe ...
From $101 per night (USD)VRBO
From $348 per night (USD)Expedia
Luxury King Bed • Remodeled Safe Chicago Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to River Chicago 362 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ✨ What ...
From $348 per night (USD)Expedia
From $419 per night (USD)VRBO
Spacious 4BR house in lovely Bellwood Near O'Hare for all occasions
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Make yourself at home in this 4-bedroom Bellwood house. The adorable space features a master suite with two queen beds, ...
From $419 per night (USD)VRBO
From $228 per night (USD)Expedia
Cozy 1-Bedroom House in Tranquil Skokie With Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your cozy, sun-filled hideaway—perfect for families, couples, professionals, or small groups seeking both com ...
From $228 per night (USD)Expedia
From $284 per night (USD)VRBO
Chicago Haven simple comfort with a touch of style
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Chicago Haven blends modern comfort with a welcoming, home-like atmosphere-ideal for solo travelers, professionals and f ...
From $284 per night (USD)VRBO
From $986 per night (USD)Expedia
Gold Coast Pristine 5BR - 3.5BA - Patio - Parking
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Free Garage Parking!! Experience the best of Chicago in this stunning multi-level Gold Coast residence. Perfect for gro ...
From $986 per night (USD)Expedia
From $313 per night (USD)VRBO
Charming 3BR Home With 2 Parking Spot, Near Transit & Shopping,
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This memorable house is the perfect home base for your trip to Skokie. Guests will find three king bedrooms that offer p ...
From $313 per night (USD)VRBO
From $226 per night (USD)Expedia
Bright and Spacious 2-Bedroom Skokie Home – With 2 Parking Spots
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in Skokie, this charming 2-bedroom house offers the perfect retreat for guests seeking comfort and style. Both s ...
From $226 per night (USD)Expedia
From $234 per night (USD)VRBO
Modern 2-Bedroom House with Free Parking and Convenient Location,
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your stylish Skokie stay—a cozy and practical 2-bedroom getaway designed with both comfort and convenience in ...
From $234 per night (USD)VRBO
From $606 per night (USD)VRBO
Luxury Penthouse COMBO 07/04 Terrace | River North
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Enjoy the combination of your luxury two-story designer styled apartment located in River North - the city's c ...
From $606 per night (USD)VRBO
From $661 per night (USD)VRBO
Luxury Penthouse COMBO 07/02 Terrace | River North
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
Summary: Enjoy the combination of your luxury designer styled apartment located in River North - the city's center of n ...
From $661 per night (USD)VRBO
From $131 per night (USD)VRBO
Affordable and Convenient Room with King-Size Bed – Ideal for Relaxing Stays
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our rooms offer comfort and convenience with plush beds, free Wi-Fi, flat-screen TVs, and private bathrooms. Just 1.8 mi ...
From $131 per night (USD)VRBO
From $131 per night (USD)VRBO
Plan Your Stay in a Peaceful Room w/ King Bed Near Midway International Airport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our rooms offer comfort and convenience with plush beds, free Wi-Fi, flat-screen TVs, and private bathrooms. Just 1.8 mi ...
From $131 per night (USD)VRBO
From $144 per night (USD)VRBO
Affordable Stay Near Midway Airport – King-Size Comfort + Convenient Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our rooms offer comfort and convenience with plush beds, free Wi-Fi, flat-screen TVs, and private bathrooms. Just 1.8 mi ...
From $144 per night (USD)VRBO
From $144 per night (USD)VRBO
Budget-Friendly King Room Perfect for a Relaxing Getaway near Soldier Field
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our rooms offer comfort and convenience with plush beds, free Wi-Fi, flat-screen TVs, and private bathrooms. Just 1.8 mi ...
From $144 per night (USD)VRBO
From $129 per night (USD)Expedia
Entire Apartment Next to Wrigley Field.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Spacious 2-Bedroom Apartment Steps from Wrigley Field Enjoy the best of Chicago from this stylish and spacious 2-bedroo ...
From $129 per night (USD)Expedia
From $112 per night (USD)VRBO
Warm Modern 2BR • Walkable Roscoe Village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A calm, furnished 2BR in a classic 1912 two-flat in Roscoe Village. Original stained glass, built-ins, wood floors, dini ...
From $112 per night (USD)VRBO
From $334 per night (USD)Expedia
Casa Arlington, cozy, updated, close to all shopping.Home away from home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Make yourself at home in this 3-bedroom Arlington Heights house. The space features 2 queen beds and 1 full bed, perfect ...
From $334 per night (USD)Expedia
From $382 per night (USD)VRBO
Calling all Cubs Fans: Beautiful 4-bedroom condo across from Wrigley Field
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
This 4-bedroom condo is perfect for your escape to Wrigleyville in Chicago. The lovely space features a king bed, two qu ...
From $382 per night (USD)VRBO
From $297 per night (USD)Expedia
Dreamy South Loop Getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your cloud-like escape in Chicago's South Loop. This bright, spacious retreat is designed for comfort, featur ...
From $297 per night (USD)Expedia
From $610 per night (USD)VRBO
Spacious 4-bedroom townhome in fantastic Bronzeville Chicago Neighborhood
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Stay in this beautiful 4BR, 3.5BA greystone in historic Bronzeville—just a few doors from the former home of Bo Diddley, ...
From $610 per night (USD)VRBO
From $531 per night (USD)Expedia
Spacious 5-bedroom house in Chicago with AC Near Obama Center & UChicago
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to your spacious Chicago home away from home! This beautifully furnished 5-bedroom, 2.5-bath home is perfect for ...
From $531 per night (USD)Expedia
From $331 per night (USD)VRBO
Fabulous 4-bedroom house with Inground Pool! On quiet cul-de-sac.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Make yourself at home in this 4-bedroom Glenview house. The space features a king bed, queen bed, full bed, and twin bed ...
From $331 per night (USD)VRBO
From $237 per night (USD)Expedia
The Nook • Vintage Flat Near Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $237 per night (USD)Expedia