Cook Area Rentals
From $247 per night (USD)VRBO
Cozy 1BR in Bridgeport w/free street parking/ McCormick/Chinatown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Consider this cozy apartment your home away from home while you visit Chicago! Located on the second floor of a charming ...
From $247 per night (USD)VRBO
From $355 per night (USD)Expedia
Luxury Penthouse Loft w/Terrace 507 | River North
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: BRAND NEW PENTHOUSE DUPLEX LOFT IN THE HEART OF RIVER NORTH WITH PRIVATE TERRACE! Enjoy your luxury two-sto ...
From $355 per night (USD)Expedia
From $307 per night (USD)VRBO
Luxury Penthouse Loft w/Terrace 504 | River North
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: BRAND NEWPENTHOUSE DUPLEX LOFT IN THE HEART OF RIVER NORTH WITH PRIVATE TERRACE! Enjoy your luxury two-sto ...
From $307 per night (USD)VRBO
From $366 per night (USD)Expedia
Luxury Designer Loft 202 | River North
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: BRAND NEW LOFT IN THE HEART OF RIVER NORTH! Enjoy your luxury designer styled loft located in Chicago's cen ...
From $366 per night (USD)Expedia
From $355 per night (USD)VRBO
Luxury Designer Loft 302 | River North
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: BRAND NEW LOFT IN THE HEART OF RIVER NORTH! Enjoy your luxury designer styled loft located in Chicago's cen ...
From $355 per night (USD)VRBO
From $355 per night (USD)Expedia
Luxury Designer Loft 402 | River North
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: BRAND NEW LOFT IN THE HEART OF RIVER NORTH! Enjoy your luxury designer styled loft located in Chicago's cen ...
From $355 per night (USD)Expedia
From $355 per night (USD)VRBO
Luxury Designer Penthouse Loft 502 | River North
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: BRAND NEW PENTHOUSE LOFT IN THE HEART OF RIVER NORTH! Enjoy your luxury designer styled loft located in Chi ...
From $355 per night (USD)VRBO
From $311 per night (USD)Expedia
3-bedroom apartment in lovely Chicago with AC and comfort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Nestled in Chicago, this wonderful ground unit apartment offers a comfortable stay for guests seeking a home away from h ...
From $311 per night (USD)Expedia
From $126 per night (USD)VRBO
Peaceful 1-bedroom apartment with AC in vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the beauty of Chicago from this 1-bedroom apartment. Guests enjoy a peaceful living room with a queen bed, perf ...
From $126 per night (USD)VRBO
From $295 per night (USD)Expedia
Chicago 2BR 27th Floor Skyline Views - 5 Min walk Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Wake up in this modern Chicago suite designed for modern urban living in the heart of downtown. Elevated high above the ...
From $295 per night (USD)Expedia
From $306 per night (USD)VRBO
Corporate apartment with 2 bedrooms and fantastic view of lake and skyline
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Located in Chicago, this corporate apartment is a cool retreat for travelers. With two bedrooms, including one cozy quee ...
From $306 per night (USD)VRBO
From $80 per night (USD)VRBO
Value-Friendly Room w/ Free Parking Perfect for Road Trips | Close to O’Hare
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located minutes from O'Hare Airport, our inviting rooms blend comfort and convenience. Enjoy a king-sized bed, free Wi-F ...
From $80 per night (USD)VRBO
From $80 per night (USD)VRBO
Affordable Room Perfect for Short Layovers w/ Free Parking & Easy Highway Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located minutes from O'Hare Airport, our inviting rooms blend comfort and convenience. Enjoy a king-sized bed, free Wi-F ...
From $80 per night (USD)VRBO
From $343 per night (USD)Expedia
Family-Friendly 4BR Skokie Home - Garage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this fully furnished 4-bedroom, 2-bath home in Skokie, ideal for families, groups, and extended stays. The ma ...
From $343 per night (USD)Expedia
From $211 per night (USD)VRBO
Spacious & Clean 1.5 Story Apartment with Parking - Easy Access to City+ Airport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in this spacious 2-bedroom Forest Park apartment near Downtown Chicago and Midway Airport, ideal for families, frie ...
From $211 per night (USD)VRBO
From $184 per night (USD)Expedia
Spacious Apartment w/Game Table for 7 near City + Airport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Stay in a spacious first-floor Berwyn apartment near Downtown Chicago and Midway Airport, ideal for families, groups, ev ...
From $184 per night (USD)Expedia
From $174 per night (USD)VRBO
Elegant and Family Friendly Apt w/Parking and Easy Access to City and Airports
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Stay in an elegant 2-bedroom Forest Park apartment near Downtown Chicago and Midway Airport, ideal for families, friends ...
From $174 per night (USD)VRBO
From $147 per night (USD)Expedia
Cozy and Charming Forest Park Apt with Parking - Easy Access to City + Airports
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in a thoughtfully designed Forest Park apartment near Downtown Chicago and Midway Airport, ideal for families, smal ...
From $147 per night (USD)Expedia
From $167 per night (USD)VRBO
Galactic Getaway - 15 Min to Midway - Easy Access to Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Stay in this modern 2-bedroom Berwyn apartment near Downtown Chicago and Midway Airport, ideal for families, friends, sm ...
From $167 per night (USD)VRBO
From $143 per night (USD)Expedia
Serene Oak Park Apartment with Crib - Easy Access to Downtown and Airport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in this serene 1-bedroom Oak Park apartment near Downtown Chicago and Midway Airport, ideal for couples, small fami ...
From $143 per night (USD)Expedia
From $147 per night (USD)VRBO
Stylish Berwyn Retreat - 15 Min to Midway - Easy Access to Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stay in this modern 2-bedroom Berwyn apartment near Downtown Chicago and Midway Airport, ideal for couples, families, sm ...
From $147 per night (USD)VRBO
From $161 per night (USD)Expedia
Modern and Lux 2BD for 4 Near City and Airport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stay in this modern 2-bedroom Berwyn apartment near Downtown Chicago and Midway Airport, ideal for families, couples, sm ...
From $161 per night (USD)Expedia
From $158 per night (USD)VRBO
Stylish and Relaxing Apt w/Parking and Easy Access to City and Airports
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Stay in a stylish 1-bedroom Forest Park apartment near Downtown Chicago and Midway Airport, ideal for families, small gr ...
From $158 per night (USD)VRBO
From $149 per night (USD)Expedia
Cozy and Stylish Oak Park Apartment - Easy Access to Chicago and Airport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay in a stylish 1-bedroom apartment in Oak Park. Perfect for couples, small families, small groups, business travelers ...
From $149 per night (USD)Expedia
From $104 per night (USD)VRBO
Private Room Healthcare Pros Welcome 15 Min to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 6
- Sleeps:
- 2
Clean, comfortable private room in Chicago's Bridgeport neighborhood — just 15 minutes from the Medical District and Do ...
From $104 per night (USD)VRBO
From $234 per night (USD)Expedia
Bright 2BR Retreat near McCormick & Museum Campus
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Wake up to Chicago’s glittering skyline from your private 2BR, 2BA suite right on iconic Michigan Avenue. Sip your morni ...
From $234 per night (USD)Expedia
From $235 per night (USD)VRBO
Hyde Park University of Chicago Penthouse 3 bedroom/2 bathroom + gym & office
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Chicago is waiting for you at this 3-bedroom apartment. Each bedroom features a king bed, offering guests a tremendous a ...
From $235 per night (USD)VRBO
From $87 per night (USD)Expedia
The Jewels, 2 bed/2 bath, UChicago 2mi, Parking, DTWN 15mi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to ABODE6535: The Jewels Suite. This apartment is named after Chicago's popular grocery store chain and its resi ...
From $87 per night (USD)Expedia
From $974 per night (USD)VRBO
Near Zoo and Beach • Reading Nook + Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the best of Chicago from this newly renovated 3-bedroom apartment in the heart of Lincoln Park. Just minutes ...
From $974 per night (USD)VRBO
From $83 per night (USD)Expedia
King Bed Non-Smoking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Comfortable Accommodations: Des Plaines Motel By OYO O'Hare Airport Chicago in Des Plaines offers air-conditioned rooms ...
From $83 per night (USD)Expedia
From $594 per night (USD)VRBO
Discover the Heart of Chicago from Our Modern 3 Bed/ 2.5 Bath Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to a stylish stay in this modern, charming, family-friendly home just minutes from picturesque downtown Chicago. ...
From $594 per night (USD)VRBO
From $137 per night (USD)Expedia
King bedroom apartment with workspace, AC, Parking, Laundry/by Arlington Heights
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This fully furnished King bedroom apartment has a fully stocked kitchen for way prep and a workspace for remote workers ...
From $137 per night (USD)Expedia
From $258 per night (USD)VRBO
Spacious 3BR Suite with Skyline Views Near McCormick
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome and Experience the best of Chicago in this modern, high-rise 3-bedroom, 2-bathroom suite — located in the vibran ...
From $258 per night (USD)VRBO
From $474 per night (USD)Expedia
West Loop Condo w/Parking + Gym - Walk to Fulton Market
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your Chicago home base in one of the city’s most sought-after neighborhoods. This stylish condo blends comfor ...
From $474 per night (USD)Expedia
From $453 per night (USD)VRBO
Townhome 3 bedroom 2 bath with Parking - near McCormick Place , Chinatown Sox
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our new townhome offering in Chinatown. This 3-story home has 4 queen beds to accommodate 8+ guests. An outdo ...
From $453 per night (USD)VRBO
From $828 per night (USD)Expedia
Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to your home away from home in peaceful Westchester, IL! This professionally managed 5-bedroom, 2-bath ...
From $828 per night (USD)Expedia
From $199 per night (USD)VRBO
Modern 2BR/2BA Corner Suite Near McCormick Place
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your modern 2-bedroom, 2-bathroom corner suite offers unbeatable convenience and comfort, located just steps ...
From $199 per night (USD)VRBO
From $276 per night (USD)Expedia
Nice 4-bedroom apartment near everything
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 12
Discover this 4-bedroom apartment in Chicago. The space features a king bed, two queen beds, and a full bed, comfortably ...
From $276 per night (USD)Expedia
From $482 per night (USD)VRBO
23PL - 4 Bedroom/2 Bath - Chinatown, McCormick Place
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to our humble home. A beautiful two levels that combined to offer 4+ bedrooms, 2 baths, 2 living rooms, 2 dining ...
From $482 per night (USD)VRBO
From $617 per night (USD)VRBO
New! 10-min to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Stay in style at this newly remodeled 4 Bedrooms (2 per floor) and 2 Full Bathrooms (1 per floor) retreat in O ...
From $617 per night (USD)VRBO
From $741 per night (USD)VRBO
Elevated Gem - Sleeps 12 - 20 mins to Downtown Chicago
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Welcome to a beautifully designed 5-bedroom, 3-bath home nestled in the heart of Oak Park, IL — where charm, c ...
From $741 per night (USD)VRBO
From $465 per night (USD)Expedia
Boho City Escape | Parking + Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy a Boho City Escape designed for comfort, style, and easy Chicago living. This bright 2-bed, 2-bath stay features c ...
From $465 per night (USD)Expedia
From $409 per night (USD)VRBO
Modern Zen Retreat mins from Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this modern boho retreat in the heart of Ukrainian Village. Thoughtfully designed with botanical accents, natu ...
From $409 per night (USD)VRBO
From $262 per night (USD)Expedia
2-bedroom apartment in pleasant Oak Lawn with AC comfort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Chicago Ridge at this delightful apartment. With two comfortable bedrooms and two bathrooms, guests find plent ...
From $262 per night (USD)Expedia
From $276 per night (USD)VRBO
2 bedroom 1.5 in Boystown a short walk to Wrigley Field, close to everything
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience Chicago like a local in this 2-bedroom apartment. One room has a queen bed with a small offshoot room with a ...
From $276 per night (USD)VRBO
From $331 per night (USD)Expedia
Private Hot Tub & Patio! Chicagoland Extended Stay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Wood-Burning Fireplace (Wood Provided) | Washer & Dryer | Easy I-80 Access Make the Chicago suburbs your home away from ...
From $331 per night (USD)Expedia
From $340 per night (USD)VRBO
Ranch Cozy Home close to O'Hare
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this enchanting house in River Grove. With four cozy bedrooms featuring full beds, guests can enjoy plenty of ...
From $340 per night (USD)VRBO
From $346 per night (USD)Expedia
Spacious & Renovated 3BR/2BA Full Kitchen. Steps from McCormick Place & the Loop
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your spacious, sun-drenched, freshly renovated retreat in a quiet, family-friendly Chicago neighborhood. Bri ...
From $346 per night (USD)Expedia
From $118 per night (USD)VRBO
Blueground | Fulton River District, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Fulton River District furnished one ...
From $118 per night (USD)VRBO
From $110 per night (USD)VRBO
Blueground | Fulton River District, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Fulton River District furnished one be ...
From $110 per night (USD)VRBO
From $191 per night (USD)VRBO
Modern 2BR Suite w/ Skyline View Near McCormick Place & Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your elevated stay in the heart of Chicago’s vibrant South Loop! This bright and modern 2-BR, 2-BA suite is l ...
From $191 per night (USD)VRBO
From $475 per night (USD)Expedia
Charming 3-bedroom bungalow 15 min south of Chicago ,15 min from Obama Center
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Chicago, enjoy what this 3-bedroom bungalow has to offer. This amazing space features two bathrooms and keeps ...
From $475 per night (USD)Expedia
From $1019 per night (USD)VRBO
Premier 5BR Art Deco duplex with garage.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to the Wrigleyville Art Deco Executive Duplex, a spacious 5-bedroom, two-story retreat designed for memorable gr ...
From $1019 per night (USD)VRBO
From $2001 per night (USD)Expedia
Premier 9BR Art Deco manor with garage.
- Bedrooms:
- 4
- Bathrooms:
- 9
- Sleeps:
- 22
Welcome to The Addison Art Deco Manor Estate, a 4,200 sq ft private 9-bedroom residence just steps from Wrigley Field. D ...
From $2001 per night (USD)Expedia
From $196 per night (USD)VRBO
Charming Cozy Compact Studio- free street Parking- McCormick-Chinatown-RateField
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Compact Studio Near McCormick, Chinatown & Sox Stadium This 1st-floor compact studio (approx. 200–250 sq. ft.) offers a ...
From $196 per night (USD)VRBO
From $233 per night (USD)Expedia
4-bedroom apartment in fabulous Chicago with AC for your stay
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
This memorable apartment is the perfect home base for your trip to Chicago. With four comfortable bedrooms featuring two ...
From $233 per night (USD)Expedia
From $301 per night (USD)VRBO
Spacious Des Plaines Home - Near Airport, Casino & Arena
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Your family or group will be close to everything when you stay at this ideally located and fully furnished home in Des P ...
From $301 per night (USD)VRBO
From $513 per night (USD)Expedia
4BR Retreat w/ Theater, Arcade, Gym and Firepit
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to Mobile Chicago 934 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Not ...
From $513 per night (USD)Expedia
From $622 per night (USD)VRBO
4 BR • Theater Room • Gym • Walk to Lincoln Park!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Saint Paul Chicago 293 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ ...
From $622 per night (USD)VRBO
From $401 per night (USD)Expedia
Private Gym and Workspace • 3BR in Quiet Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to Osage Chicago 461 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Note ...
From $401 per night (USD)Expedia
From $511 per night (USD)VRBO
Stylish 3BR Apt | Gym and Workspace | Near O’Hare
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Osage Chicago 805 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Note ...
From $511 per night (USD)VRBO
From $650 per night (USD)Expedia
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)Expedia
From $355 per night (USD)VRBO
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)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 $430 per night (USD)Expedia
Spacious 5-bed 2-bath house - Berwyn
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Nestled in Berwyn, this quaint house offers plenty of space with five bedrooms, including two king beds, one full bed, a ...
From $430 per night (USD)Expedia
From $450 per night (USD)VRBO
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)VRBO
From $305 per night (USD)Expedia
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)Expedia
From $274 per night (USD)VRBO
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)VRBO
From $260 per night (USD)Expedia
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)Expedia
From $371 per night (USD)VRBO
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)VRBO
From $266 per night (USD)Expedia
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)Expedia
From $795 per night (USD)VRBO
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)VRBO
From $596 per night (USD)Expedia
Fabulous 3-bedroom townhome with AC in vibrant Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Get ready to relax in this 3-bedroom townhome in Chicago. The space features one king bed and two queen beds, perfect fo ...
From $596 per night (USD)Expedia
From $626 per night (USD)VRBO
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)VRBO
From $258 per night (USD)Expedia
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)Expedia
From $543 per night (USD)VRBO
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)VRBO
From $212 per night (USD)Expedia
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)Expedia
From $295 per night (USD)VRBO
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)VRBO
From $403 per night (USD)Expedia
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)Expedia
From $705 per night (USD)VRBO
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)VRBO
From $240 per night (USD)Expedia
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)Expedia
From $359 per night (USD)VRBO
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)VRBO
From $295 per night (USD)Expedia
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)Expedia
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 $295 per night (USD)Expedia
18th floor 2BR Grant Park Suite with Balcony, Gym
- 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)Expedia
From $496 per night (USD)VRBO
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)VRBO
From $125 per night (USD)Expedia
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)Expedia
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 $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 $232 per night (USD)Expedia
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)Expedia
From $1112 per night (USD)VRBO
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)VRBO
From $568 per night (USD)Expedia
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)Expedia